a colleague is hitting on me and I don’t know how to respond

by Alison Green on November 22, 2017

A reader writes:

I work for a mid-sized association. As such we are run by our members, anything we do comes through our committees, these are made up by our most devoted members. I’ve been at the association for about a year now and have attended multiple of these committee meetings. It’s not unusual for our staff to have drinks/dinner/etc. with members after meetings. That’s where my problem starts.

I made friends with a member, Jim. Jim is on the younger side of our members, probably mid-30’s. During our summer meetings, he asked what I was up to after meetings, and I just happened to be meeting some friends not far from where he was staying (these were in my hometown), so I invited him along not thinking much of it. It seemed fine. There were a couple of weird comments made during meetings, but I shook them off. I didn’t know him that well and I was sure it was innocent.

Fall meetings rolled around, and I was traveling to them, he messaged asking me the first night what was going on and I invited him along for drinks with a few colleagues and a members. No big deal. Didn’t really interact with him, he was talking to one of the higher-ups from my association. He apologized for not talking to me, but it really didn’t bother me. I was chatting to other people.

The next night, he texted again asking what I was up to, I was at dinner with a couple of colleagues and considering calling it an early night. This is the text conversation that followed:

Him: Didn’t we call it an early night yesterday? haha We could grab a couple beers/tequlia (not both) or get a six pack over here. I’m not looking to rage or anything.
Me: I really think I’m going to go watch tv in bed haha
Him: lol, no worries! I’d invite you over to do just that (Couch obvi), but I don’t have cable at the place.

I’m a little uncomfortable here. I realize he added in the couch part, but it still doesn’t seem right. I knew for a fact that he had an entire house through airbnb to himself. I responded, I was just going to call it a night.

He must have realized it was slightly off, because the next day after my meeting he pulled me aside to apologize. Claimed he was super tired and didn’t realize what he said until that morning. I laughed it off, it was fine, whatever. I left after that to do some touristy things with a coworker before our late flight. When the texts rolled in again.

Him: How’s sight seeing?
Me: Not bad at the American History Museum
Him: Awesome! Wanna do something dumb tonight? (You’re like) “not particularly?”
Me: huh? My flights at 8
Him: Change it? Watch the game here. I haven’t stayed up for an entire game in this series.
Me: Nah, I’d rather stick with my plans, I’m pretty ready to get home

I’m not sure once again if I’m reading into it or not.

It’s been a couple of weeks, since this all went down, I went on vacation almost right after this and tried not to think about it. I’ll be seeing him again in a couple months at our big event.

I’m just not sure how to address it. Am I overthinking it? Maybe it was all innocent and I’m being a bit narcissistic thinking anything more of it. Damn Millennials always thinking so highly of themselves (I’m 24).

Just looking for an idea of what to do. I don’t want to report it to my boss. I report directly to a VP here. It wasn’t totally appropriate, but he’s a beloved member here, and people see him going far with the association. I’d hate to ruin his reputation, especially if it’s all in my head.

It’s not all in your head. It sounds like he’s hitting on you.

This isn’t about you thinking too highly of yourself. It reads very much like he’s coming on to you. I mean, in the most generous reading, he’s at a minimum trying to get to know you socially in a non-work way. In a less generous reading, he’s ignoring your polite signals of non-interest and trying to override them.

It’s true that from his side, he could be figuring that you’re friends, and you invited him out a couple of times — albeit with a group — and that he’s only now starting to get the “nah, I’m not up for hanging out” messages. (Although that answer could change depending on the contents of other text messages and those “couple of weird comments” from earlier.) But at this point, if he really cared about the signals you’re sending, he’d read them as polite expressions of non-interest. Continuing to push anyway is at best rude, and at worst potentially creepy. We won’t know where it falls on that spectrum until we see how he acts when you make your desire for him to stop clearer — but for the record, a good guy would have already picked up on it.

At this point, I’d do two, and possibly three, things:

1. Stop responding to his text messages. If you feel like you can’t do that without being rude to someone who you have to be polite to for professional reasons, then respond much, much later — like a couple of days later — and even then you don’t have to respond to all of them. You should also consider saying, “Hey Jim! The best way to reach me is at my work email. I mainly use my phone for personal stuff.”

2. It’s possible that that will take care of it — that the drop in responsiveness on your side will make him get the message that this isn’t happening. But if it doesn’t, then get more direct. As in: “It was great to hang out with you and other members at the meeting in Ottawa, but I’d like to keep our relationship professional. Thanks for understanding!”

If he’s a decent dude, this will take care of it. He might be a little embarrassed, but he will hear you loud and clear and will stop. If he’s not a decent dude, he will continue — and at that point you’ll move on to step #3.

3. If a clear statement of non-interest from you doesn’t stop his behavior, then at that point you should loop in your boss and/or HR. This doesn’t have to be a huge deal. You can just say something like, “Jim Bumbridge has been asking me out. I told him very directly that I preferred to keep the relationship professional, and he hasn’t stopped.”

This wouldn’t be about ruining his reputation. It would be about the fact that someone who you have to deal with for work has continued to push for dates after you told him to stop, and needs to be shut down. In fact, your employer has a legal obligation to keep you and other employees from being sexually harassed by members, and you’d be doing them a favor by letting them know what’s happening. If he really is going to go far with the association, as you suspect, then it’s all the more important that this is addressed and handled now, rather than letting the problem get worse as he gains importance and power.

But first try clearly telling him you’re not interested and see if that solves it. If he’s a decent guy, it will. And if he’s not a decent guy, that’s all the more reason to speak up.

(Frankly, there’s also an argument for looping in your employer even if step #2 does fix the problem, in case he’s doing this to multiple people in your organization or does it to other people in the future.  If he has a pattern of using his professional access to hit on women who feel obligated to be polite to him, that’s something your organization needs to know about and shut down.)

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  1. Escapee from Corporate Management*

    Great advice from Allison. I hope #1 or 2 gets the message across. One other suggestion: use only business language and media in your communications with Cecil. Texts with “LOL” and “haha” send a signal of friendship. Emails saying “I am not available to meet with you at that time” of “That is not part of my plan for the evening” send a message that you are interacting as a business colleague, not as a potential date.

    1. Fortitude Jones*

      Texts with “LOL” and “haha” send a signal of friendship.

      This. When I’m blowing people off, I don’t use any kind of emoticons/emojis/abbreviations/etc. that would give the impression I’m kidding.

      2. LBK*

        Eh, I do since I think it keeps things polite and softens the awkwardness of telling someone you don’t want to hang out, but it does sometimes have the undesirable effect of coming off as responding flirtatiously in kind to people who aren’t great at getting or respecting hints.

      3. Emi.*

        My exception to this is The Ha Ha Shutdown: when someone sends you jokey flirt-texts you don’t want, you respond “Ha ha ha ha ha ha ha” (no punctuation, and too many “ha”s for normal text-laughing).

    3. Princess Consuela Banana Hammock*

      Agreed. I’m not blaming OP because they were behaving totally fine and in a friendly (but not inappropriate) way. But I would deploy Alison’s advice #1 and #2 together, and switch back to a more formal tone. This may be moot if OP stops responding to texts (stop responding to texts, OP), but it’s a good reminder for email, etc.

      1. Escapee from Corporate Management*

        I see this happen in so many situations beyond the one OP describes. For someone in their early 20’s, using “haha” means “I’m being friendly”. For someone older, “haha” means “don’t take me seriously”. Emojis often carry the same message. When mentoring members of the ‘texting generation”, my advice has been that until you know your audience, use business language if you want to be taken seriously in a business setting.

        1. oranges & lemons*

          I’m not sure that it would typically be an issue with this sort of friendly relationship, except that it gives Jim plausible deniability that the OP isn’t really turning him down.

          1. SarcasticFringehead*

            I’ve seen at least one (and I’m sure there are many more) harasser claim that he honestly thought a coworker was totally into him because she sent a heart-eyes emoji in a thank-you text. That’s not to say the harassment was her fault, at all, but as you said, it gave him plausible deniability (and of course he kept the texts, so they came out in discovery).

            1. Anonymoose*

              Those hearty eyed emojis are stupid anyway. The only person I know that uses it is my mom when she tells me she loves me over text. And even then I internally eye roll.

          2. Anonymoose*

            And since they’re both of the texting generation, I’m not sure that rule applies in this instance necessarily – but in order to rebuff a professional suitor, yes, going back to biz language only is spot on.

      2. Specialk9*

        I’m not blaming OP at all, but encouraging her to be more aware of unintentional signals. Inviting a random male co-worker to go out with one’s personal friends is not a casual thing – it indicates something on the range of ‘I’d like to be real friends with you’ to ‘I’d like to get sexy with you’ to ‘be my boyfriend – meet my friends, next my parents’. It’s ambiguous in intensity, but very clearly over the line from casual co-workers to having a personal relationship of some kind. Him interpreting her intentions is really understandable. As a woman, I don’t invite random guy co-workers to hang with my non-work buddies. (Actually I’m pretty private, so don’t invite any random work friends into my inner circle until we’re solid friends first.) But especially not guys, because it’s a signal, and will be interpreted that way by lots of people.

        Imagine him going back to his friends, like you’re going to AAM, for help interpreting. “So she invited me out with co-workers, which doesn’t necessarily mean anything, but she also invited me to be introduced to her non-work friends, which does mean something, right? And she texts me a lot, so I’m not reading this wrong, right? She’s into me? What should I do next?”

        I think that because the signal was unintentionally interested (in either friendship or romance), she needs to find ways to show disinterest – work friend zone him. But using words, not just hinting, because frankly she’s not great so far at predicting how others interpret her actions so words are safer.

        1. Green Goose*

          For a person in their early-mid twenties I think it isn’t that uncommon to be friendlier with coworkers and invite them out. It’s a more open time of life, “the more the merrier”, which is similar to the college experience that can bleed over into the first phase of work-life.
          In my experience of post-college/early career (and not uncommon in my friend group) I would invite coworkers that I got along with (but had no interest in) out with friends when I was younger and single. I’m in my 30s now and married, and I don’t do that anymore and don’t see it happening a lot anymore with coworkers who are around my age.
          There is a 10ish year age gap between the OP and Jim, so I can see where the OP originally invited Jim in a “the more the merrier” way that might be common in her life style/group of friends. Jim misinterpreted the invite. This might be projecting but at 24, if I invited a 35ish year old coworker out to hangout with friends, the age gap would have been significant enough to me that I would have in no way considered the possibility of the other person seeing it as a date.

          1. Specialk9*

            It’s a good point about the 20s being more open. (So good lesson learned – older people read things in!)

            I’m coming back to say that, since OP explained down thread that he openly *has a serious live-in girlfriend* that I can totally see OP thinking it was ok to cross that line. “Usually, inviting just him to hang with my social friends could be misinterpreted, but he has a serious girlfriend so he won’t think I’m making a move. It’ll be fine.”

          2. Anonymoose*

            Hello, are we forgetting that generationally they’re the same? Just because he’s in his mid thirties doesn’t mean he’s decrepit. Sheesh!

            1. Specialk9*

              She says she’s in her 20s, 24 exactly. I’m in my 30s and feel like I’m much much older, based on slang used. :D. This stuff changes fast!

        2. Artemesia*

          This. The guy is not yet out of line as he has been flirted with and invited to socialize with her; she just needs to give a very clear ‘not interested’ message and Alison suggested several. Hitting on someone in the workplace is not harassment or inappropriate (unless it is for reasons of hierarchy or other conflict of interest or involves married people); the line is ‘does he take ‘no’ for an answer’ and thus a clear needs to be given .

    4. Birch*

      Yep, this. Also as AAM says,

      You should also consider saying, “Hey Jim! The best way to reach me is at my work email. I mainly use my phone for personal stuff.”

      I would even go further and say “I only use my phone for personal stuff.” And make it clear that the previous texts were so Jim could find the group at a social work function, not to continue messaging OP whenever he feels like it. It’s disappointing when people can’t accept friendly a semi-social relationship based on a mutual workplace, but sometimes you have to draw that boundary and stick to it 100%. Also one final point: regardless of how you met this guy, someone you barely know asking to “hang out” in a private space is NOT SAFE. If he cared about your feelings, he would ask you to meet in public. That’s a huge red flag for his character.

      1. Elder Dog*

        Saying you only use your phone for personal stuff is saying that you were considering this a personal relationship, and now you’re not, and may well lead to his trying to fix that or explain himself. I’d stick to Alison’s script here. (re: life lessons learned the hard way)

        2. Birch*

          I meant that OP would gently correct this behavior, to say “I see why you were contacting me on this number because it was the only way you could find this work event, but I prefer to keep it only for my personal contacts, so I would prefer you to contact me solely through my work email.”

          I’ve done this and found it to be pretty effective, although you might have to block the number and definitely stop replying to the texts. Bottom line is that it’s OK to say “stop contacting me this way.”

    5. Lumen*

      This. You know how people say that using a period to end a text message comes across as ‘cold’ (or even ‘rude’)? I think that is bonkers and oversensitive, for what it’s worth. However, our urge to make even rejection seem warm and friendly can lead to a lot of textual confusion. Keeping it simple, straightforward, and leaving out any ‘softening’ things like emojis or LOLs will help get your point across that you’re trying to shut this down.

      1. Cassie*

        Punctuation is rude? I really did not know this was a thing. I guess it’s good that I seldom communicate via text!

        1. many bells down*

          I think the idea is that it gives the impression of a very blunt statement, whereas leaving off the period seems more … open? Friendlier?
          “I can’t make it to your party, sorry.”
          “i can’t make it to your party sorry”

          The first one is seen as deliberately declining the invite (I don’t want to come) while the second one reads as “I would have come but I can’t”.

          1. AcademiaNut*

            See, I would read the first as “I know how to use punctuation properly and care about doing so.” and the second says “I can’t be even bothered writing a proper sentence to turn down your invitation.”

            But I’m not much of a texter, and badly punctuated, uncapitalized writing irritates me.

            1. Zahra*

              I pretty much think the same thing. If you can’t be bothered to use capitalization and punctuation, making your texts harder to read by the same token, I’m going to judge. Negatively. It’s not the end of the world, but it’s a small check in the minus column.

              1. Klaxons*

                It’s a deliberate choice, though. Think of it as a subdialect of English, designed to convey tone in an otherwise toneless medium. Abstaining from capitalized letters is a way of suggesting a casual tone; we also sometimes capitalize random letters or words to emphasize them. The differences among “No”, “no”, and “no.” are pretty huge within context; acronyms like “lol” and “lmao” are used to add tone also. Insisting on “proper” capitalization and punctuation can, in some contexts, come across as smug and rude, cold and distant, or overly formal. (I say “or” because these may or may not overlap.)

                In fact, there are punctuation marks “text-speakers” may use regularly that aren’t even in use in “proper” English. /This/, *this*, or -this- might suggest emphasis, since italics aren’t usually applicable in text messages; or even tildes like ~this~ could suggest a distinctly mocking emphasis. Example: apparently i’m a ~bad person now because i didn’t like mad max

                so texting a peer like this would make sense. like it may seem toneless and blunt to you but there are Rules ok this isnt Lingual Anarchy over here lmao

                You may find it harder to read, but I think it often makes it a lot easier to understand. You can’t always tell what somebody means when you can’t see their face or hear their voice, but designing visual cues into the language certainly makes it easier. Of the friends I have who text me in all lowercase letters and runon sentences, there is somebody with a master’s degree, a chemical biologist, and two teachers. That’s just how we write to each other, in some circles. It doesn’t mean they’re not bothering to communicate well with me; nor does it mean they’re incapable of following grammatical rules in appropriate contexts. I think being able to switch dialects of English on a dime, dependent on who you’re talking to, is an excellent skill to have; and it’s a skill that many of today’s young people taught themselves and developed together through use. Isn’t that cool?

                To take it back to the LW’s conundrum, however, it may in fact behoove her to switch to a more formal tone with this man in particular, in light of his apparent tendency to read too much into her social invitations.

                1. S*

                  Yup yup yup

                  I am perfectly capable of punctuating but with friends, I adopt the friendlier tone — we’ve made fun of our friend who constantly punctuates properly because it sounds so formal in a casual text.

                  https://www.nytimes.com/2016/06/10/world/europe/period-full-stop-point-whatever-its-called-millennials-arent-using-it.html

                  http://nymag.com/selectall/2016/06/the-period-isnt-dead-but-it-is-niche-now.html

                  https://www.thecut.com/2016/08/why-ending-a-text-with-a-period-makes-you-a-bad-person.html

            2. Pomona Sprout*

              AcademiaNut, I’m with you. To me, a sentence without punctuauion at the end doesn’t look “friendlier”–it just looks sloppier!

            3. Fiennes*

              Punctuation isn’t some eternal rule of virtue for language; it’s something we use to make our writing more clearly understood. If you put a period on the end of a text that leads the recipient to interpret that text being more curt/negative/angry than you meant it to be, *that’s* incorrect punctuation. If leaving out the period is what communicates the correct meaning/tone to the most people, then that’s correct.

              1. NorthernSoutherner*

                Former English teacher here and totally agree, Fiennes. Or is it ‘totes’ lol. I actually even feel the same way about email. Here and there I might add an exclamation point, just to make sure the recipient takes my message in the friendly way I intend. Of course, reading over an email once, I realized it sounded like I was shouting my way through, so I’ve modified that.

                But with texting, it’s a whole new language as far as I’m concerned. Punctuation be damned! : )

          1. Chickaletta*

            Huh. Turns out I’ve been sending the wrong signal at random times without even realizing. Now I’m going to have to scroll through all my text messages.

            Yay for modern living inciting paranoia in yet one more way.

          3. Pomona Sprout*

            I’m thinking this must be a generational thing? It would never occur to me NOT to use punctuation st the of sentence, in a text or otherwise. Also, I am an old fart. Pershaps these two things are not a mere coicidence!

    6. Else*

      Yeah, this is really helpful at pulling back because most people are easily able to read that message and will match your increased formality with the same. Some people of good will still need a more explicit statement – anybody with issues reading social cues may not read this for what it is – but generally speaking, this really helps at resetting your relationship and its parameters. Of course, if he’s a jerk, or pushy, you’ll need to be more explicitly rejecting, and that may end it, or if it doesn’t – HR!

  2. straws*

    I might switch 1 & 2. Maybe I’m more of a direct person, but I feel like calling him out and making your preference clear would be a good first step. If he doesn’t respect that very clear boundary, then try #1 to distance yourself. Move on to #3 if he pushes back in any way for either of the first 2 steps. If he’s really just that oblivious, being blunt & clear and allowing him to see what he’s doing and have the chance to stop/correct the behavior is a kindness.

    1. Ihmmy*

      Same. Given there’s been a history of high responsiveness to texts, it might be best to directly address it and then add in the texting distance

    2. Shadow*

      Agreed. Lots of people don’t take silence as an answer. They’ll just rationalize that the person must be busy so they’ll keep trying. Better to be direct (politely) up front. That way there’s no ambiguity about the silence.

      You’ve already given hints and they haven’t worked. More hints won’t do it- be direct.

      1. Koko*

        Yes, it’s one of the common logical fallacies that people make – weighing positive (present) information more highly than negative (absent) information.

        On your end, you’re going through a thought process where you consciously decide not to respond, so to you it feels like you’ve done something.

        But on the other person’s end, it often is seen as a lack of data. They are just waiting for more data.

        So you’re friendly to them: Positive datapoint. She likes me!

        Then you go silent, take a long time to answer messages: Absence of data. No further information to conclude.

        When you finally do answer or next time you see him, you are again polite and pleasant or laugh off his earlier transgressions to smooth things socially: Positive datapoint! She likes me!

        We tend to view silence as a gap between datapoints rather than a datapoint itself.

    3. JulieBulie*

      Agree. It might be more humane, and more to the point it avoids any delay in getting to #3 (and strengthens your complaint to HR) if that becomes necessary.

      I had a similar experience, years ago, with a coworker I barely knew. At first I thought he was just lonely and looking for someone to talk to, but eventually found that based on our extremely brief interactions (all initiated by him, after I had already said that I wasn’t looking for a relationship), he considered me to be his girlfriend.

      I explained it to him with apples and said I would go to HR if he didn’t back off. He rebutted this with a long, crazy screed, then “pre-emptively” contacted HR himself, which didn’t help him at all when they saw some of the creepy shit in the last email he had sent me. He was put on probation or something, and soon after was let go for another boundary-defying incident (trying to organize a mutiny against management).

      In retrospect, I see that it was a mistake for me to give him the benefit of the doubt when he started calling me at home after I told him I wasn’t looking for a relationship. If someone ignores a clear “no” once, he or she will probably ignore it a second time. So it’s best not to delay that first clear “no.”

      1. Specialk9*

        You explained it to him with apples? I’m imagining this: “Well Jim, I’m the honeycrisp apple here, and you’re the Macintosh apple. But see, apples can either grow naturally, or be grafted onto a flourishing tree. But, well, neither have happened for us and realistically, not gonna happen. I’m sure you understand. (Big juicy bite) Ok, nice talking with you.”

        1. JulieBulie*

          LOL.
          More like, “Wakeen has six apples. Jane doesn’t want any of them. How many apples does Wakeen have left?”

          2. The Supreme Troll*

            I was imagining an explanation a whole lot more inappropriate…but I’m not going to write it here!

    4. Thlayli*

      Absolutely. OP hasn’t actually given him any clear rejection at all. It’s all been I’m too tired/have a plane to catch. How is he supposed to know they are just excuses and not the real reason? If I ask someone to do something on a particular day and their response is I’m busy that day, I take it to mean another day would work. If you aren’t interested just tell him that with actual words.

      Also, I’m not too keen on Alison’s statement that “a good guy” would have got the message by now. A socially aware guy would have got the message, but socially aware does not equal good. There are plenty of socially aware people who are not nice and plenty of perfectly nice people who do not read social cues well and are not very socially aware. its entirely possible this is a perfectly nice guy who’s just not good at social cues and is taking her statements that she’s just too tired/busy to meet up as true statements. Not being good at reading between the lines doesn’t make him a bad guy.

      If OP tells him with actual words that she is not interested in him eg “I’m not attracted to you”/ “I don’t want to date you” (with no emojis or smilys or lols or qualifiers – an actual clear statement with no mixed messages) and after that he still tries to pursue her, THEN you can say he’s not “a good guy”. But he’s not necessarily a bad guy just because he’s not very good at reading social cues.

      1. Thlayli*

        I have since seen below that apparently this guy has a girlfriend. So obviously he is not a nice guy because he was trying to have an affair.

      2. Akcipitrokulo*

        Yeah – below suggests other data that he isn’t a good guy! But worth saying “I may be misreading some signals, but I’d like to make it plain I am not interested in a romantic relationship of any kind with you. Sorry if this is not what you intended to say.”

        Gives him the out of “oh no, just socialising with colleagues, all above board!”

        And then if he doesn’t stop, throw the book at him.

  3. Such as it is*

    He’s definitely hitting on her. But, here’s the thing, I don’t know that I blame him. Understanding that it’s super uncomfortable to reject advances, being gentle or subtle or kind, can sometimes be hard to read. I’m not saying OP should have knocked him over the head with rejection, but I do think being less friendly and less responsive would have nipped this thing in the bud much sooner. All good suggestions. But, I don’t see a reason to suspect (yet) that he’s not a decent person and would stop the attention as soon as its obvious OP is not interested.

    1. Cheddarcheese*

      She wasn’t sure he was hitting on her. It’s hard to less friendly and less responsive when you aren’t sure if someone is just being friendly or if they’re trying to pursue you romantically. If you decide they’re hitting on you and it turns out they’re not, being less friendly can have professional repercussions.

      1. Such as it is*

        I’m of the school where responding LOL/hahaha/any emoji opens the door to a more casual, friendly acquaintenance than a professional one. So, using said language with a professional colleague can indicate one is open to a more informal relationship. I’m not saying she has to be rude. Dial back the casual. Allison’s suggestions on how to respond are perfectly reasonable and shouldn’t have repercussions.

      2. MK*

        I disagree. If being less friendly is going to have professional consequences, it’s not going to matter if it happens before you made sure the other person is hitting on you or after. Being less friendly does not mean unfriendly, just strictly professional.

        I believe I was spared this kind of pestering in large part because I am a naturally reserved sort of person. And, yes, it sucks that women who by nature are more warm in their manner might have to squash that part of their personality in the office.

        1. FiveWheels*

          I too have never really experienced this* and it may be due to my being reserved as well. In fact, socially my “I dislike you but tolerate you” signals are apparently almost indistinguishable from my “I’m madly in love!” signals! If you’re less reserved and more naturally friendly, it’s a difficult line to walk.

          * the exception is a client who repeatedly tried to proposition me. I didn’t feel in any way harassed though, it was sad more than anything else.

      3. Kelly L.*

        Yep. And then you have the subgroup of jerk who will push boundaries and push boundaries until you finally say “I’m not interested,” and then the jerk responds with “What, you thought I was hitting on you? No way! (insert description of exactly how ugly they’ve suddenly decided you are).”

        1. Trig*

          Yeaaaah, I feel like this guy has been hitting on her with juuuuust the right amount of plausible deniability that this could well be his reaction (with or without the vitriol).

          OP, if that’s how it plays out, don’t let it fluster or embarass you, and don’t second guess your gut feel that he totally was hitting on you. I’d guess his interactions were purposely vague so he could go for it if accepted or save face if rejected. It’s not necessarily (though possibly) malicious, but a blase “ok, great, glad we’ve sorted that out then” without embarassment or apologies is fine, no need to win the point of whether he was or was not hitting on you.

      4. oldbiddy*

        I have a lot of experience in casually hanging out with groups of friends/coworkers/people at conferences. Inviting someone to come hang out with you and your coworkers at a conference is pretty normal and has no romantic connotations. Indeed, finding one or two people I know at a conference and then going to dinner or drinks with a bunch of their friends or colleagues is my #1 introvert networking strategy. But if I ask someone what they’re up to that evening and find out they’re not going out, I don’t try to get them to change their minds, I simply move on and see if there are any other groups of people I can go hang out with. I also don’t try to escalate it into hanging out one on one.
        To me, it seems like he is being just vague enough so he can deny that it was anything other than friendship. After the first time that she was blunt abut not wanting to get together, most people would’ve read the signs and backed down a bit. He did so briefly, but then repeated the process the next day.

    2. Snark*

      Yup. He’s not asking for massages or being icky, and hey, way to be a baseline decent human being, Jim! But he’s most definitely making a move on a younger woman who’s displayed interest in spending time with him in social, drinky occasions, and I think if the interest is not actually reciprocated, she needs to be compassionately clear about that.

      I’m not sure what (if anything) to tell her about how to act with younger, reasonably attractive male members (hurr hurr) moving forward, because it’s actually reasonable that she might invite a work associate to a work-related social event, and she should feel free to. But I think if a guy (or whomever!) is being decent and aboveboard, they’re at least owed a kind rejection without ambiguity.

      1. Luna*

        He is only owed a kind, unambiguous rejection if he is giving her unambiguous messages about what he wants. He isn’t. Asking a young work associate to “Come hang at my place, spend the night! (but on the couch, OF COURSE, I’m not that creepy kind of guy lol!!). She is right to be confused about his intentions, he is deliberately sending mixed signals so that he doesn’t get clearly rejected without ambiguity. That’s not being aboveboard.

        1. Else*

          Yeah – there’s nothing wrong with him trying once or twice to find out if she’d like to hang out with him one-on-one instead of just in a group, if he’s careful and tactful. This isn’t actually either of those things. Making joking comments about joining him in bed (which is exactly what he did, by denying it) or whining about changing her plans to stay with him are way too much and definitely on the inept or creepy side without an existing relationship, which there is clearly not. If he’d asked if she’d like to meet him alone for drinks in the bar, or go out for a one-on-one dinner and made it clear that he was interested, it would not have been creepy so long as he took her refusal well. Both of those are in public places and don’t involve her making major changes to what else she’s doing.

          1. Specialk9*

            I don’t get a creepy vibe, I get the hopeful vibe, in response to what seem like romantic signals from OP. Inviting a guy from work to go out with my friends seems like trying to start something romantic, it’s hard not to interpret it that way. He’s trying to make the next step happen, and she hasn’t actually given clear ‘no’ signals to counter the strong ‘yes’ signal. It’s one of those things about dating, it’s really really hard to interpret the tea leaves, especially for those of us who are socially awkward. He’s not yet being creepy, and *thinking* about kinda-hinting isn’t fair – it’s no kind of signal. Use yours words, OP, kindly. If you can’t handle using direct words – and I’m picking up that you’re a hinter – then start mentioning the person you’re dating in casual ways.

            1. Danger: Gumption Ahead*

              IT wasn’t a group of friends. It was a group that worked for/are members of the same association the LW works for and he is a member of. Big difference

              1. Specialk9*

                There were two times (unless you’re OP and know something not in the letter). The first time was with social friends, in her home town. The second time was with related professional socializing, with co-workers and members.

                If the OP *hadn’t* introduced a guy from work to meet her childhood friends in a purely social setting, I would think that he was in the wrong for thinking she was interested. But for OP not to be aware that inviting a male co-worker (and only one) to meet her non-work friends might seem like a signal of interest… That’s odd to me. Of course he thinks she’s interested!

            2. Agent Diane*

              Sorry, it’s very easy to not read “come join my friends for a drink” as “romantic”. It’s social, end of. I’ve done it when I’ve pre-existing plans with friends and then found a lone colleague I get on with is at a loose end. It’s avoiding the awkwards of “let’s have dinner together” by having “want to join us for dinner?” instead.

              This may be a UK/US cultural difference.

              1. Specialk9*

                You’re right, I think in the UK, going drinking is a much more routine thing. Going for a pint isn’t a big thing, as I understand it. “Getting a drink” in the US is a very date activity. Going for a drink in a group is not date-y, but it tends to be more of an inner circle thing, so inviting him seems like pulling him into her social set and introducing him to her personal friends. All signals of interest, whether as friend or romantic, beyond the professional coworker.

                I wouldn’t do it, and if I did it, I’d understand if he thought my doing so was making a move.

                1. Turtle Candle*

                  Huh, I’m in the US (West Coast) and “hey, we’re getting some beers, wanna join us?” after a day of meetings or a conference or something is perfectly normal. It’s a pleasantry I’d extend to someone who was chatting at the end of the meeting and doesn’t indicate anything date-y or inner-circle-y.

                2. Specialk9*

                  Turtle Candle, ok, good point, there is also an exception for co-workers going out together, that can totally be casual. But saying about a group of colleagues “hey we’re going to beers, wanna come?” is hugely different from saying to a single colleague (a woman to a man) “hey I’m going out with my childhood friends, wanna come?” THAT is the part that was the unintentional signal of interest.

                3. Specialk9*

                  “Single” here meaning only one person, not relational statut. Though I’m assuming/hoping he’s also unpartnered.

                4. Agent Diane*

                  That is definitely not how it would read here – and from others’ replies it’s not a universal social norm in the US. But it does help explain so of the responses here which suggest OP did something to attract the Schrodinger Creepbag.

                  And yes, adding a lone colleague to a group “going for a drink” over here is not a “I’m into you, please hit on me in increasingly icky ways” move.

                5. Akcipitrokulo*

                  I’d totally ask a colleague at a loose end to come join us if we were heading pub-wards! That’s … polite?

              2. blackcat*

                I have done exactly this at a conference in my hometown area. But it was entirely a “OMG I think my colleague will love my friends, and he’s about to move to this city! I should help him find friends!”

                I not only introduced the guy to his current friend group that night, I also introduced him to his fiancee. I’m quite sure he only interpreted my “lets get drinks with my friends” as “I think you’ll like my friends.”

                Everyone involved in this story is from the US, so I don’t think this is just a UK/US split. Maybe an age thing? Or maybe he knew I wasn’t interested because I’m married?

                2. Specialk9*

                  Hmm, interesting. I’m really *certain* of the signal this sends, but it sounds like it’s a more ambiguous situation for other people. Helpful feedback for me!

                4. Turtle Candle*

                  I think this must be a regional or industry or cultural difference or SOMETHING, because I’m equally sure that when I’ve seen this it as been platonic and not a signal.

          2. oldbiddy*

            I agree with you. He’s inviting her on what Dr NerdLove calls “Schrodinger Dates” – it’s simultaneously a date and not a date. He gets the benefit of being able to save his ego if she tells him she’s not interested (either during the date or if she turns down the invitation). It can be harmless if it’s just two people hanging out and figuring out if they’re interested in each other as more than friends, but his refusal to pick up on the signs that she’s not interested is very creepy.

            1. blackcat*

              Thank you for introducing me to this term. I went on a Schrodinger Date in college. It was the worst. When I declared it “not a date,” he made a face like I had killed a cat.

            2. ClownBaby*

              I love this. Well…I hate being on a Schrodinger Date…but I absolutely love that there is a term for it. It’s a lose-lose situation for (most often) the woman. If I say I’m not interested, the guy will say I am full of myself and it wasn’t a date. If I don’t say anything, and then I eventually learn it “was” a date, I get called a tease for leading the guy on and get told that I “should’ve known better.”

              I think Jim in OP’s letter hasn’t done anything ‘wrong’ but is toeing a line. A more direct response from OP should get the message across…even if it ends with her being called an overconfident tease :( . Hopefully he will get the hint quickly if the OP implement’s AAM’s advice (especially option 2). Being upfront is hard, but most often it is the best way to get things done!

            3. Tiny Soprano*

              I have the deepest, fieriest loathing for Schrodinger’s Dates, and I am very suspicious that LW would end up on a few if she hangs out with this guy again. IME they come from people who are pretty sure you’d say no if they asked you directly so they… like, try and stealth their way into a date? Because that totally works? Either way it’s pretty skeevy.

            4. Renee*

              Yes, I’m with you here. I’m more than a little annoyed with people taking LW to task about not being direct, when this guy has been anything but direct. If he just asked her out, she could say no. She’s trying to be polite to a business colleague, but he’s being a weasel. If he’s approaching this indirectly to test the waters, then he should be receptive to her responding indirectly to avoid being rude.

        2. InfrequentCommenter*

          This seems like an overly malicious way of reading into it. Couldn’t the guy just genuinely enjoy her company and be ok with thing going either way (staying platonic or progressing forward) and that the reason for the mixed signals?

          1. Safetykats*

            Would you ask someone who was just a casual, platonic friend to change their travel plans to spend another evening with you? I wouldn’t. I think that’s a clear signal that Jim has no appropriate social boundaries, or already considers the “relationship” to be much more than it is.

            I would advise OP to go directly to HR with the text messages. Going to HR doesn’t mean you’re filing a formal complaint – but giving them a heads-up about this guy could be really important of things escalate when OP shuts him down, and if he’s behaving this way with others (both of which are more than likely). The conversation with HR can be posed as asking for advice, as opposed to intervention – although my advice would be intervention soon. These kinds of guys often don’t take no for an answer easily or well, and they are more likely to take it at all from someone perceived as an authority figure.

            In the meantime, please don’t be alone with him. It doesn’t sound like you intend to watch a game with him or do dinner one-on-one, but please don’t even share a cab, or end up as the last two people at a function. It’s hard to know where clueless turns to creepy turns to dangerous, but for me this guy is seriously suspect.

            1. InfrequentCommenter*

              No I wouldn’t ask a platonic friend to change their flight plans. I know others that would and not think much about it tho. For some people travel/flights aren’t seen as a big deal especially if your young, without family commitments, live by an airport where flights are less expensive. I also wouldn’t invite a male coworker out repeatedly and send “haha” and “lol” txts then assume he’s a predator when he simply invites me over a few times. If I didn’t want to be invited over and thought he was wanting more it would be “sorry not interested”. End of situation. No need to go to HR or even let anyone else know because I’m an adult with a voice of my own.

            2. Akcipitrokulo*

              Um… yes?

              Not if it would cost them money, and would depend on how much I liked their company and if there were a special reason to stay on, but yeah.

          2. oldbiddy*

            He was a bit too persistent/didn’t read the signs well. If he asked her every night if she wanted to hang out and she said ‘no, thanks’ and he left it at that, I’d figure he might be interested but could go either way.

        3. Natalie*

          I really don’t think unambiguous responses are something people can deserve or not, but also who cares? The OP should do what they believe will be *most effective* at getting him to leave her alone, and not worry about some kind of parity in their interactions.

          Personally, I would probably take the approach of telling Jim that I don’t want to develop personal relationships with members, since that covers both friendship and dating, and then stop responding to his texts or redirect him to work topics.

        5. Snark*

          Well, and given new information from LW, I’m totally off-base here and giving him the benefit of doubt where none is appropriate, so I retract my post.

        6. Indie*

          Yeah, I am the kind who will call out the vaguester with an extremely blunt ‘I.am.not.interested.’ to model courage but it’s super annoying to be cast in that role. The role of ‘the person who risks talking about their hunches and feelings’ should automatically go to the person who potentially has something to gain.

        7. neverjaunty*

          Exactly. It’s not as though he said “hey, would you like to go on a date?”

          But of course it’s her job to be the one to straighten the situation out, because emotional labor is for girls. *eyeroll*

      2. LBK*

        Hmm, I think going from hanging out with someone in a group of coworkers to asking them to hang out at your place alone is a pretty big escalation; at the very least I’d say you need to invite someone to hang out one-on-one in neutral territory first. And asking someone to change their flight so they can do that? Eek. Little weird.

        The self-deprecation of him asking her over assuming she’ll probably say no gets my hackles up a little too. My gut says that’s something a person who doesn’t take rejection well would say. He’s not, like, sexually harassing her, but my Spidey sense is tingling in the same way OP’s seems to be re: treating this situation sensitively.

        1. CS Rep By Day, Writer By Night*

          “I think going from hanging out with someone in a group of coworkers to asking them to hang out at your place alone is a pretty big escalation”

          Yep, this was the red flag for me. There’s just something extremely presumptuous about it that has all of my spidey-senses tingling.

          1. Specialk9*

            It’s not really. She made an indication of interest (come meet my non work childhood friends), he asked her over to watch something. It’s the dance of unwritten romantic signals.

            The part that I’m actually agreeing with, after reading other comments, is that his telling her to reschedule her flight to come over was somewhere between socially awkward (bad joke trying to seem cool) to concerning (as a possible sign of a boundary violator). Worth keeping an eye on.

            I just hesitate to jump on this guy yet. I think OP needs to communicate in line with Alison’s advice, and if he still is being pushy, then he is in the wrong. I just feel like it’s early days in this situation.

            2. The Supreme Troll*

              Specialk9, I agree with everything you’ve been saying. I think the OP was absolutely correct in asking Alison for advice (and Alison has given the OP great points to use in her conversations with him); but please, let’s not make the coworker to be a monster.

            3. Someone else*

              It didn’t read like she said “come meet my non work childhood friends”. I thought it was more like he asked “hey doing anything after this meeting-we’re-in-right-now ends” and she said “actually I have plans with (buncha people) but if you want to join, sure?” which I can see how could be misread as somewhat interested, but it’s a lot more ambiguous than “come meet my childhood friends” and her subsequent behaviour was much more clearly “no thanks”. Still both their actions, at that early stage, were ambiguous, thus they both had buckets of plausible deniability on that occasion, but her actions throughout the story strike me as swinging between “neutral friendly” and “no thank you”, whereas his swing between “friendly” to “creepy boundary stepper”.

        2. Oranges*

          The self depreciation is a way that she can reassure him that of course she doesn’t think he’s a loser. He might not be doing it consciously because it’s something we all do to a greater or lesser extent. But a pattern of such behaviour is… not good.

          A single rain drop doesn’t mean a flood. But there can be no flood without them.

        4. Djuna*

          My Spidey senses were tingling right from “Didn’t we call it an early night yesterday?”
          If he uses “we” in that context, it’s a strong sign he thinks there’s an “us” – and he needs to be disabused of that notion.

          The other texts just build on that, and he knows he’s overstepping if he apologized for some of it – but then to approach OP again? I’d be even more direct, “It seems like every time you text me, you have to apologize afterwards for something you’ve texted. I’d like to avoid that awkwardness and keep our professional relationship intact. Please don’t text me like that anymore.”

          It may be blunt, but sometimes a blunt instrument does the job best.

          1. Bess*

            Yeah, that was where the hairs on the back of my neck stood up.

            It might be an example of “forced teaming”? Newer concept for me but you create a “we” immediately to facilitate (premature) trust. At best it’s a sign of manipulation and ulterior motive.

            1. Karyn*

              I was just going to make the “Forced teaming” comment. The Gift of Fear is a phenomenal book, and taught me a lot about how to watch for those kind of things.

              1. RVA Cat*

                Yes that’s straight up forced teaming. Didn’t the rapist who got in by carrying groceries say “we’ve got a hungry cat in there”?

                1. Karyn*

                  Yes! That story scared the crap out of me, but then it made me realize how often I’ve come across that kind of behavior that, while it ended up being more annoying than dangerous, I’ve let slide. I’ve gotten much more aware of my environment and interactions with people because of that book.

    3. Bess*

      I disagree. He’s contradicting her and being pushy in the examples we have. Directing her to come over even when she’s said she’s tired–TELLING her to change her flight? This is someone who is not taking no for an answer and is actually not listening to what she’s communicating. Boundary testing like this is done consciously by people who are trying to see what they can get by being pushy.

      The idea that she should have been less friendly to somehow stop this is really kind of messed up. She’s required to be polite and professional to a coworker, and there’s actually a lot of creepy dudes (especially in work settings) who know women can’t be cold or distant without suffering professional consequences for it (and honestly this is an expectation for specifically women in every area of life). These creepers operate under a veneer of plausible deniability and use the ambiguity to their advantage, to keep people off guard and guessing and open to more boundary testing.

      1. Such as it is*

        The idea that she should be less friendly is actually not messed up, it’s part of human interaction. You don’t want to do something, you directly tell that person. The fact that she’s friendly with a colleague is not the issue. The fact that she’s now uncomfortable with their level of friendliness is the issue and in order to end that, she needs to not be friendly. I completely disagree with the idea that this guy is somehow a creeper because he’s interested in her. If we want people to respect our boundaries than we need to tell them what those boundaries are. It is unfair to assume that because you think she politely declined his advances that his perception was that she was simply not available that time.

        1. Bess*

          He’s not creepy because he’s interested in her. He’s creepy because he’s contradicting her and attempting to change her answers to his questions.

          You were saying she should have been less friendly earlier to “nip it in the bud.” But she’d only had subtle signs before and wasn’t sure he was interested. You’re basically putting the onus on LW to fix a situation when really, the one at fault here is someone who continues to receive polite “no”s and in the moment tries to change them to “yes”s.

          1. Such as it is*

            Ok, so if she was unsure that he was interested, isn’t safe to assume that he was unsure whether she was interested? The issue here is that LW is the one who is not interested and so yes, the onus is on her to tell him so. There is no fault here. For either of them. She doesn’t have to “fix the situation,” she needs to be more direct about it. He didn’t receive a polite “no” he received reasons why she couldn’t meet him/hang out with him. Not everyone is capable of reading subtle social cues. This is not her fault, but if she’s not willing to be direct, she will suffer more of the same.

            1. Bess*

              Do you think that someone who responds to an acquaintance who says “I can’t, I am tired/have a flight,” with “come over in spite of what you just told me” or “change your flight to come over to my house all by yourself!” is respectfully testing the waters, or listening to her at all?

              Do you really think this guy would be receptive to a simple “no, thank you”? Because based on the examples given, I think he’d ask for reasons and keep arguing about it.

              1. Such as it is*

                I think he’s flirting with her. Badly. And yes, i do think if she told him no, he would stop pursuing her. And if he doesn’t then she would have due course to escalate it to her manager.

                1. neverjaunty*

                  Good grid. When she told him no to an invitation, he argued with her. I’m really not getting everyone bending themselves into pretzels to scold the OP about what a clearly nice dude this co-worker is.

              2. Susana*

                Well, “no, thank you” would be more direct than what she was saying. She was giving reasons… which kind of made it sound like she would if she could, but can’t. Again, I know it’s hard – we’ve all given some version of “I can’t go Friday night; I’m washing my hair,” because it’s kinder than saying. “I’m just not interested.” But you can see why he holds out hope. He’s not being creepy or predatory here – he’s just clinging to the positive signals she sends instead of being shot down by the negative ones. So she just needs to find a way to make her lack of intentions toward him clear. I think Alison’s ideas are perfect.

                1. Turkey*

                  This is utter cow manure, and I am sick of giving people – epsecially guys – a pass on it. The English language uses soft no’s, okay? It a linguistic quirk, ot’s also cultural, it goes back literally centuries: the engligh language uses soft no’s. All the time. For literally everything.

                  And we can read soft no’s just fine whenever we don’t really care about the outcome. In fact, we can read them so well, and do it so routinely, that we can tell a soft no is coming from the apologetic facial expressions and tone of voice before someone has even finished the soft excuses part of the sentence and got to the soft ‘but no’ at the end.

                  Hard no’s are seen as rude and even aggressive. A blunt no is such an aggressive move, verbally, it can start a fight all by itself.

                  He’s not ‘holding out hope’ because he can’t understand a basic feature of the enlgish language that he’s heard everyday, probably multiple times a day, ever since he was a child. He’s ‘clinging to the positive signals’ and refusing to hear or respect her perfectly clear and obvious soft no’s becaus he’s being a jerk.

                3. Julia*

                  I always thought that when someone declines an invitation and doesn’t make a counter-invitation, they’re not interested. E.g.:
                  Person 1: Wanna hang out tonight?
                  Person 2: I’m super tired, so no thanks.
                  → not interested

                  Person 1: Wanna hang out tonight?
                  Person 2: I’m super tired, so how about tomorrow?
                  → could be interested

              3. Former Employee*

                The thing is, I’ve had friends who would do that because they tended to be somewhat self-centered and would ask me to change plans just to hang out with them or some similar, low level activity (not like change your plans so we can go to a once in a lifetime event).

                I’m not willing to say it’s that big a deal that he asked, but it is up to her to “just say no”.

              4. Susana*

                But Bess.. she keeps giving excuses why she “can’t” see him, rather than just declining. I agree that he’s interpreting things in the most positive way fir his own wishes, but this is not a case of some stalker hassling a woman who has shown zero interest in any kind of relationship. She has indeed indicated a willingness to have a *social* relationship, and he wants it to be romantic. She needs to let him know that’s not an option.

            2. Liane*

              In what English dialect in *any* English-speaking area does, “How about changing your flight plans” mean “Gee, I am not sure if you are interested in me, so I am now asking plainly”?

              1. JulieBulie*

                I think the correct translation (in all English dialects) is, “I haven’t given any thought to whether you are interested in me or not; I am interested in you, so go ahead and change that flight, that would be great.”

                1. Koko*

                  Reminds me of my younger days, I was having a rough week and went out dancing with some girlfriends. A guy came up to me and pointed to his friend and said he wanted to dance with me. I said no thank you. His response was, “But he really wants to dance with you!”

                  As if restating what his friend wanted was a persuasive argument.

                2. JulieBulie*

                  Koko: I have a certain coworker who, on being told “no” when asking for a frankly unreasonable work-related favor, would follow up with “but it would really help me out a lot.”

                  Eventually he was told not to do that anymore; I’m not sure if he understood why it pissed people off.

            3. Luna*

              But he isn’t being direct! He is trying to get her to come to his home, but also saying it’s just to casually hang out. He isn’t being direct that the real reason he seems to want her to come to his house is to hook up. His intentions might seem obvious to us, but I can easily see someone younger, who thinks this man can be trusted because they work together, being confused and not fully aware of what his real intentions are.

            4. Oranges*

              Why can’t the guy do that though? Seriously? Why can’t HE ask her if she’s interested in perusing a romantic relationship with him?

              Also, soft nos are a thing. My rule of thumb is if the guy can hear a soft no other places he doesn’t suddenly become deaf to them because pants-feels. He might be in denial but he knows that she’s saying no.

              FYI: Most English speakers don’t actually say “no”; we employ the soft no.
              Example: “Want to get some coffee with me sometime?”
              Replies:
              “I would love to but…” (No)
              “S..ure… Let um.. let me check with….” (Don’t wanna)

              So if they can hear it normally they don’t get a pass if suddenly they’re “confused” and it was a “miscommunication”.

          2. Allison*

            Some men are creeps in that they “creep” over women’s boundaries under the guise of friendliness, and they often so it so slowly and gradually that their target doesn’t realize how close he’s gotten until he’s right up in her space, wondering why she won’t bang him.

            “Wanna hang out sometime?” is the mating call of a dude who wants to make a move but doesn’t want to get rejected, so he maintains plausible deniability (“oh I just wanted to hang out, it’s not a date or anything) up until the moment she’s comfortable with him and he’s had enough liquid courage to suddenly ram his tongue down her throat, giving her no time to defend herself.

      2. seejay*

        100% this. There’s friendly and then there’s way too pushy. He was friendly to a point, then he pushed some things that went way too far into creeper zone. My hackles went up at a few things he said. :/

      3. Not a Real Giraffe*

        Yeah, perhaps I am a snarky person, but I would have responded to the “Change it?” text with, “did you really just advise me to change my flight home so I could sit on a couch with you and watch a televised game?” It’s comments like these that people will respond “oh I was joking, c’mon” too, but you know they sent it in the hopes that you’d take them up on their insane and inconvenient plan to spend time together.

        OP, I completely get the friendly tone and use of lol/haha to soften a rejection, but you will have to be much, much clearer with this guy. He sees your disinterest as a schedule conflict, not what it is, which is a rejection.

        2. Laura*

          “did you really just advise me to change my flight home so I could sit on a couch with you and watch a televised game?”

          That’s exactly what I would have written!

      4. Princess Consuela Banana Hammock*

        I agree with Bess. I get the blurred lines logic, but in this case, I don’t think OP blurred lines at all. When he asked about going out, she brought him to work-related gatherings with groups of people. When he pushed her to hang out one on one, she clearly rebuffed him.

        He’s relying on plausible deniability, and if he’s in any way a decent person, he’ll back off once OP deploys suggestion #2. ideally he’d be self-aware enough to get it by now, but subtlety doesn’t often work with folks who demand that you change your flight to entertain them.

        Also, going out with members after hours and in groups is really normal and somewhat expected when you work for associations. Let’s not blame OP for doing her job.

        2. LBK*

          100% agree. I don’t think he’s being oblivious about the implicit lines the OP has drawn in their relationship (that it’s a hang-out-with-coworkers thing, not a come-over-alone thing). I think he understands those lines perfectly and is taking advantage of the fact that the OP hasn’t been explicit about them yet to test the boundaries. Plausible deniability is exactly right – he’s being ambiguous on purpose so that if the OP does flat out reject him, he’s left the door open to say “Oh, no, I totally didn’t mean like that!” and gaslight the OP into feeling like the weirdo who was misunderstanding what were *obviously* meant as friendly overtures, not come-ons.

        3. JB (not in Houston)*

          This this this. The OP hasn’t done anything wrong. The problem is with Jim, who is using a super common tactic to give himself plausible deniability.

          1. Alice*

            OP hasn’t done anything wrong at all. But if she wants the current situation to change, she’ll probably need to say what she wants clearly — using something like Alison’s second suggestion. Maybe he’ll gaslight her and be rude, or maybe he’ll be reasonable and professional. I hope the latter happens, and if the former happens then bring in HR and the VP right away.
            But the current situation is untenable for OP, and listening to us on this board say that he’s a jerk isn’t going to fix it.
            I hope OP finds a good resolution — ideally with him behaving professionally, and if not, then through a professional response by management and HR.

      5. Birch*

        Yeah I was gonna say, all his suggestions involve OP being alone with him in his space and drinking. That’s way into icky territory even before we get to telling OP to change their flight.

        1. RVA Cat*

          Yes. Sorry to say, but if I were the OP I would keep a sharp eye on my drink if I was out with him again….

          1. Snorks*

            Sorry, it’s ridiculous to jump to that conclusion.
            He asked her out (sort of). He has been a little over the top for sure but to say he’s not a rapist is going way too far.

            1. Birch*

              He didn’t ask her out, he asked her to come drink beer “or” tequila in his room. Huge difference.

              1. Snorks*

                That is asking someone out? He asked her out on a date (again, sort of). The date just happens to be in his room.
                It’s still a huge lap to go from there to rapist.

      6. Susana*

        He’s not being creepy, and she’s not really made it very clear she’s not interested. Kind of the opposite – she’s invited him out several times with friends and colleagues (which no, does not mean she wants to date him, but also is beyond any requirement to be polite to co-workers). She’s texted him in a non-professional way. In her mind, she’d keeping this friendly/not romantic. In his mind, she’s signaling she could be interested. She just needs to find a kind way to let him know she’s not interested. I get it we’ve all been there; you want to be clear but also not hurt someone’s feelings. But he’s not been wildly out of line here.

        1. JB (not in Houston)*

          I don’t get this “nonprofessional way.” I would use “ha ha” and LOL and other informal language in a text to my boss, and he would never get the idea that I’m suggesting our relationship is anything but professional. Yes, it’s not “professional” in the sense that it’s informal and is therefore the language equivalent of wearing shorts and flip-flops to work, but it’s still “professional” in the way that even offices wear you can wear whatever are expected to conduct themselves like professionals. The informality of her language is not the problem here.

          Nothing in the language she’s shared with us signals that she could be interested, unless you believe that anything less direct than “I am definitely not interested in you” signals that someone could be interested. But that’s not how language works (although studies show that men have a hard time understanding soft “no”s–but ONLY in the context of women turning them down–meaning, men understand how language works when they want to).

          1. LBK*

            Agreed with your first paragraph. I mean, just generally speaking, most people don’t talk to their coworkers in a strict formal manner even while in the office, unless you’re in an important meeting or something with clients/bigwigs around. Using text speak in a text to infer someone is into you is a pretty big stretch. Not to assume too much, but I wonder if the people who are saying she was too casual are big texters – if saying “lol” means someone likes me I have a whole phone full of apparent suitors!

          2. Escapee from Corporate Management*

            Sorry, I disagree. I am not in my 20’s, so my peer group does not use “LOL” and “haha” unless they are personal friends making a joke. What seems informal but professional to one group seems unprofessional to many people who are 35+. Given that Jim is in his 30’s, he may very well see this use of “text speak” as signs that the relationship has moved from business to a personal one. That doesn’t excuse his complete lack of ability to get the message, of course, nor diminish the inherent creepiness of asking someone you barely know to change her flight.

            1. Cheddarcheese*

              I’m 36 and regularly communicate with text speak and know what it means. It’s not some mythical language that only 20-somethings understand.

              1. Specialk9*

                No but it’s silly to pretend there aren’t generational trends with language. I am friends with a guy in his early 20s, who teases me about how my texting is sooo formal because I know how to spell, and use punctuation. (I find it odd, because Swype is the one doing my spelling. Though, true, the commas and periods are on me.) But yeah, I write “before” not b4… Because we’re not paying by the character, dude, it’s not the 1850s on a telegraph.

                2. SS Express*

                  There definitely are generational trends with language, but in my experience they’re the other way around. Most people I know in their 20s use full sentences with capitals and punctuation when they text and email. It’s the 40+ crowd who use “txt spk” abbreviations and leave out punctuation. I imagine the people who are doing it can’t type/text very quickly and want to save time, find capitalising and punctuating too fiddly, don’t know how to use/aren’t comfortable with predictive text and autocorrect, and possibly in some cases are doing what they think young people do.

                  And I mostly only use “lol” in (informal, obviously) emails with my non-millenial coworkers because they all use it.

                3. Static*

                  Completely agree with SS Express, in my experience it’s very much the older crowd (mid forties and upwards) who tend to use txt spk, and younger people who send texts using full English language! It’s actually way harder to message in txt speak with the current generation of smart phones which have autocorrect and the qwerty keyboard, whereas with the older style phones it was a pain to write in full sentences due to having to hit the number 2 three times for a single ‘c’ for example. I always assumed it was because older people are probably more likely to still be using older phones and less into updating to newer smart phones so their texting style never evolved.

        2. A.*

          I think he is wildly out of line. She should be able to go to work without being hit on or having to reject someone. I’ve had coworkers ask me out before but I’ve never had a coworker invite me over to his house alone at night to hang out. I would feel so uncomfortable if someone I worked with crossed that boundary. If a man I did not know well invited me to his house, I would just ignore the text. No need to be polite or spare feelings. But Jim is banking on the fact that they have to work together so she has to be polite to him. Add to that, she is much younger than him and likely not as experienced in the work world. He is a creep.

          1. Sarah*

            I agree here. It’s one thing to ask a coworker out if you’re really clear that’s what you’re doing and make it VERY clear that you will keep things professional if they’re not interested. It’s quite another to invite a younger coworker over to your house, alone, at night, and include alcohol in the invitation. (!) That’s not a date, or at least definitely not a first date.

            1. Starbuck*

              Yeah, that’s a hookup invitation. Super awkward to go from presumed casual acquaintance, to that.

        3. Princess Consuela Banana Hammock*

          What would make this “wildly out of line” and “creepy” to you? (I’m asking genuinely—not trying to be snarky or aggressive.)

          1. A*

            Because we have to work together. I have to remain civil. I am a captive audience so to speak. I am at work to work. I don’t want my coworkers hitting me up for sex. It is uncomfortable and icky. Plus say I go and he makes a pass at me or crosses a line, will I have to answer for why I was even there in the first place? It’s not fair to place her in that position.

            1. Susana*

              He hasn’t asked her for sex. He invited her over and she said no – probably would have been better if were an out-and-out no instead of something that could give him hope. Look, people meet at work and date and even marry. She’s not a child; she’s in her 20s and he’s in his 30s. Not a crazy age difference and it’s pretty patronizing to suggest she’s a naive delicate flower who can only date people her parents arrange for her, with chaperone. She’s not interested, so she should make that clear. If he does press her for dates after that, then yeah, an issue for HR. We’ve all had to deal with people who were interested in us in a way we did not share. It does not make us victims.

    4. MissGirl*

      Yeah, I’m not sure she’s been that clear in her refusals that she’s not interested. That’s probably because she wasn’t sure he was interested in her and didn’t want to read too much and the awkwardness of rejection.

      Now that she knows, if he asks her out again, she needs to be very clear she’s not interested. Don’t offer excuses like the plane ride because that implies she would be interested at another time.

      Give home the chance to back off

      2. MillersSpring*

        “Don’t offer excuses like the plane ride because that implies she would be interested at another time.”

        Big YES to this.

        1. Luna*

          I really don’t see this as an excuse- she cannot explicitly reject him if he will not explicitly ask her on a date. Why is it all on OP to be the only one to clear up these “mixed signals”?

          1. JulieBulie*

            How long do you think OP should wait for Jim to clear up his mixed signals? His current strategy is protecting him from rejection. If OP is tired of it, a passive approach will not help.

          2. Not a Real Giraffe*

            Because right now, the OP is the one who has the issue with the “mixed signals.” Jim is perfectly content to keep doing what he’s doing, but it’s a problem for the OP — so the OP has to be the one to address it.

            I like the suggestion somewhere else in the thread to offer up a possible misreading of the situation, “not sure if I’ve misinterpreted things here but…” as a way to explicitly reject someone who has not explicitly asked you out.

          3. Specialk9*

            Because she *gave* the mixed signals? She gave him yes signals but secretly is thinking no signals.

        2. LBK*

          I’ve heard diametrically opposed arguments on this topic. Some people make your argument, that giving an excuse implies they just need to try again later. But on the flipside, some people argue that giving excuses keeps the situation de-escalated, and that blunt rejections are what often make situations worse. YMMV – seems like it really depends on the guy you’re talking to.

            1. LBK*

              I mean, the easiest solution would be for people (especially men) who get rejected to just accept that they’ve been rejected and not take it as a challenge, regardless of the method of delivery.

              1. neverjaunty*

                It would. Unfortunately, the OP has no control over whether Jim is going to suddenly flip to “gawd, how stuck-up of you to assume I was interested in you!” – and given his behavior up till that point, he’s not exactly broadcasting maturity and a willingness to accept a clear no.

      3. ThatGirl*

        True but there’s also this subtle dance many women feel we have to do, to be politely disinterested but still friendly, because we’ve been conditioned to do it. And many men don’t know how to take a soft no for an answer, so it leads to all this draaaaama over “mixed signals”.

        Ideally of course we’d be able to just flat out say “sorry not interested” but throughout history that has led to men being violent a-holes so I understand the difficulty there.

        1. medium of ballpoint*

          +1. We’re dealing with Schrodinger’s Jerk here. Will he take a soft no well? Signs point to no, since he’s been ignoring her soft nos. That would certainly make me hesitant to give him a harder no if I were in her shoes so I can understand her reticence. There’s also a strange undercurrent in the comments that she’s somehow responsible for making the rejection palatable and not awkward for him. If Jim wants to hit on someone, he runs the risk of rejection. It’s not OP’s job to make that a comfortable experience for him.

          3. MizA*

            Another +1.

            It’s not her responsibility to temper her “no” in a language he’ll (choose to) understand. It’s his responsibility to realize anything but an enthusiastic “yes” is his cue to back off.

            1. Specialk9*

              Yeah but so much of this stuff is unwritten and unspoken, and relies on subtle cues.

              Years ago, I finally asked out my crush, who accepted then cancelled so I assumed was rejecting me… But months later learned he thought he was just saying no for that night and thought I’d ask again. (Uh nope, supply of courage depleted.)

              I spent most of my teens and twenties in frustrated confusion as to whether I was friends or *more* with guys, and later found out it was about half and half. (Current me could have used direct language or initiated something, but I was too unsure and scared of rejection then.)

              So maybe I’m identifying too much with this guy. But dating is hugely ambiguous, and it’s so hard to read the signals.

              1. neverjaunty*

                Current Jim, like current Specialk9, could unambiguously ask the OP out instead of doing this plausible-deniability crap. It’s really not fair to give him a pass on being vague and pushy.

      4. Elizabeth H.*

        I disagree – I think even if you ARE sure someone is interested in you you can still give a “soft refusal” and most people will get the message.
        On the converse, I’ve gone on some online dates recently and because I’m really busy and dating isn’t a big priority, it’s frequently incredibly difficult to find a time to meet up with someone I want to see again (this has happened with a couple different people). Each time I have reiterated my clear interest in meeting up again and explained contingencies (like “my brother is visiting all next week, I won’t be free except 9pm thursday”). A lot of people pick up on the absence of that type of clarity. In my experience as a single late-20’s woman, most guys genuinely get the message, and I’ve also “received” that type of message. Everyone varies in how direct they are willing to be off the bat but I feel like the majority of people employ and react to more of a “soft rejection” where if you want to not see someone in a dating way, you either reply days later or never reply to a message, turn down a meetup suggestion without proposing an alternate date or stating you’re still interested, etc. It becomes a problem if someone persists after one or two rounds of this but the OP doesn’t seem to be at this stage yet.

      5. hbc*

        Why does she have to be clear in her refusals of his interest when he hasn’t been clear in his expression of his interest?

          1. Bess*

            But he is the one who developed it to that point…lol. She didn’t “let” anything develop by simply existing and being friendly to a colleague.

            1. Such as it is*

              Hi Bess – you and I are just going to fundamentally disagree on this. I’m not saying she encouraged his interest or “let” it develop. I’m saying that his interest developed and she’s not interested. Ergo, she should tell him she’s not interested, so that he knows it’s not going to develop into anything more.

              1. LBK*

                I’m not saying she encouraged his interest or “let” it develop.

                I mean…that is literally word for word what you said:

                But why let it develop to a point where he is clear about his interest if she’s not interested?

                Your earlier comment seemed to say that she should have cut this off earlier, which I think is what Bess is disagreeing with (and I disagree as well).

                1. Such as it is*

                  I’m not going to get into an argument about what you think I meant. I’ll just state it plainly so there’s no confusion.
                  1)I literally place no blame on the OP for the situation
                  1) I would recommend if you think someone is interested in you and you are not interested, it is best to limit contact and not engage with them
                  2) People are confusing and don’t always think like we think they will
                  3) I am of the opinion that he is socially/emotionally immature and has not picked up on the social cues that she is not interested
                  4) I may be wrong.
                  5) If so, then she would have every reason and the empirical information she needs to go to her supervisors and let them know.

                2. LBK*

                  Okay, but don’t get miffed when you say something, someone quotes you, and then you immediately say you didn’t say it when your original comment is still there for all to see in plain text. If you chose your words wrong, so be it, but I don’t think it’s on others to assume you meant something other than what you wrote.

                3. Such as it is*

                  No worries… not miffed. Just clarifying. I didn’t chose my words wrong. But, it is interesting what you assume I mean.

                4. LBK*

                  How am I to assume any other interpretation of this comment?

                  But why let it develop to a point where he is clear about his interest if she’s not interested?

                  Who is the subject of this sentence that is taking the action of letting it develop if not the OP? You are clearly saying the OP allowed it to get this far.

                5. Such as it is*

                  It was a hypothetical question in response to the previous comment asking why she had to be clear when he wasn’t clear about his intentions. I was literally asking how would it be helpful for her to wait until his intentions were clear, particularly if she wasn’t interested. I was not saying she had encouraged his attentions, I was saying it would be better to say something now then to wait and see when there was a real possibility his interest would just grow further, thereby making the situation even worse. In other words: Why let it develop to a point where he is clear about his interest if she’s not interested?

                6. Specialk9*

                  LBK, for heaven’s sake, you’re doing some really unpleasant nit-picking out a fellow commenter. Please stop, it’s not kind, and that’s why most of us hang out here.

                7. LBK*

                  Because until such a point as he’s direct about his interest, there’s nothing for her to directly reject. And it’s been explained in many other comments why being direct when she hasn’t yet received an explicit expression of his interest could turn out badly for her, so there’s valid reasons to tread lightly. Mainly because at the point where he’s still intentionally being ambiguous, it gives him an out to respond to her rejection by saying “Oh, I wasn’t interested in you like that” and puts him in the position of turning the discomfort of the situation back on the OP. That is precisely why people make ambiguous advances instead of direct ones.

                  That could be particularly bad for the OP since he’s a well-liked work colleague. It is not as simple as “be clear about your lack of interest before it gets to the level of the other person being clear about their interest” – even in a social situation due to the risk of escalation, but especially in a work situation where there’s a power dynamic at play that could affect your career.

                  I don’t think I’m nitpicking word choice – I’m disagreeing with the sentiment as a whole. If that sentiment is only one sentence I don’t have a lot to go on.

                8. Such as it is*

                  I understand and appreciate the argument. I wasn’t looking to debate it further with you, because if you read through this conversation, it’s pretty obvious we disagree. I was only explaining what my sentence meant, since you had a difficult time with it and thought I was blaming the victim for encouraging his behavior.

          2. Natalie*

            I totally agree that it’s obnoxious but this happens a lot in interpersonal relationships. Throwing our hands up and sighing “I shouldn’t have to do this” doesn’t change the fact that we may actually have to do it.

            Jim isn’t the one that wrote in here. The only person we can suggest action to is the letter writer.

          3. IN A FRIGGIN' RELATIONSHIP?!?*

            FYI the OP mentions that the guy has a (live-in?) girlfriend in a thread below, and had made a point of telling her that fact. Does that change your judgment of the behavior of the OP?

              2. IN A FRIGGIN' RELATIONSHIP?!?*

                I know there’s a lot of replies, so if you want to jump to the LW’s statement re: the girlfriend, it’s in a thread that is started by someone named LoV.

        3. O*

          This. I hate being put in this position. So uncomfortable. And, as I’ve gotten on in years and been in safer spaces to take communications risks, I’ve found it empowering to push back on the dynamic itself. As in, “I seem to be getting signals that you’re interested in me.” Pause. See how they respond. And *then* state clearly that I am not interested.

        4. Dlique*

          This completely. There are ways he could even be clear without actually saying, “I am interested in pursuing you romantically” – he’s approaching her in this gray area intentionally because it’s so defensible. ‘I never asked her out, I just told her that hypothetically I would’ve invited her to watch TV alone with me in my airBnB if I’d had the utilities.’ This pretty effectively removes OP’s power to refuse, because it’s not an actual invite, but it’s also pushing the boundaries outside of professional so that he can point to it and say, ‘she didn’t say no!’ Maybe he really is a perfectly decent human being, but his behavior is inappropriate and it’s *not* OP’s fault for not reacting to him “correctly”. The age difference also brings in a power dynamic that is not helping!

          1. Birch*

            Yeah and also, she didn’t mention any classic “good” romantic signals. Has he complimented her at all? Has he struck up a conversation about her interests? Suggested books or movies she might like? Said “hey, it’s been so great meeting with you, would you like to chat some more over a coffee?” We can’t know, but what we do know is that he told her to make an expensive last minute decision to spend the night on his couch. Gross. What is up with dudes doing this plausible-deniability type flirting that just involves giving borderline sexual suggestions and then saying they were jokes? It’s not funny. It’s not attractive. It just makes women feel uncomfortable. Dudes, stop doing this.

        5. Jesmlet*

          It’s just a standoff where they’re seeing who can tolerate the ambiguity longer. If I was OP, I’d just bite the bullet, be direct and have the uncomfortable conversation (#2).

        6. InfrequentCommenter*

          Because she’s the one that wants the advances to stop. The easiest and most logical way for that to happen is for her to simply state state that. End of problems in most cases unless they guy is a creep/jerk but so far we have no reason to believe he is.

        7. NorCalPM*

          Why does she have to be clear in her refusals? Because she wants him to stop texting her about meetups in which she’s not interested. She wants him to just stop it already.

          Indicating that she’s interested only in strictly professional communication about strict professional topics is a good way to get him to stop sending her personal texts.

          When I’ve been in LW’s situation, my goal was to get the guy to knock it off. I was invariably successful and never suffered any career repercussions myself. Just wrap yourself in the cloak of professional invulnerability. One exception: a stalker who had mental health issues. I wasn’t his only “stalkee.” But that’s a whole ‘nother ballgame.

      6. Anon one time only*

        I like the Captain Awkward standard for this kind of situation, where after two refused invites, you back off and if the other person really wants to spend time with you in that manner, they will initiate. We’re at 2 and there’s definitely a pattern. Plus I imagine the social group invites from OP will stop now as well which should be another indicator.

        1. Elizabeth West*

          Yep, that’s what I did. I asked, he said yes, I checked back to arrange a time, and he demurred, so I said okey dokey. No response after that means/meant I’m not interested. Was I disappointed? Yeah, but it was probably for the best. I’d rather spend my time with someone who really wants to be there.

    5. MommyMD*

      Yes. Friendliness and hanging out socially can be misinterpreted. Now is the time to really cool down the responses and just ignore most of them. If he persists, then he’s a jerk.

    6. hbc*

      No, “definitely hitting on” is “Would you like to go on a date with me?” Or “I’m starting to think about you as more than a colleague and friend. Any chance you’re thinking that way too?” When hitting on is definite, it gives an opportunity for a definite yes or no.

      Those who choose to hide behind plausible deniability (and I am one of them) owe it to the other person to take the rejection of the figleaf as a rejection of the subtext as well. Putting the responsibility on her to figure out “couch obvs” doesn’t mean “friends sometimes crash on couches” but “I hope to join you on said couch” is unfair.

      1. Ask a Manager* Post author

        Those who choose to hide behind plausible deniability (and I am one of them) owe it to the other person to take the rejection of the figleaf as a rejection of the subtext as well.

        I really like this sentence.

        3. Liane*

          As Carolyn Hax would say, “Needlepoint/cross-stitch that on a sampler!” Better yet, loom it into a large tapestry.

      2. Such as it is*

        I agree that if he is being coy about his advances than he should have a better handle on her coy replies. But, just because one is hiding behind plausible deniability doesn’t mean they have the emotional/social intelligence to understand subtle cues.

        Though I do find it interesting that most of the arguments regarding my comment are about how I’m putting the responsibility on her. I’m not sure why empowering the LW to speak her mind more directly is such an issue. Or why it would appear as though I’m giving this guy a pass because I think she should be more direct. When we have relationships with other people – be it colleagues, friends, family – it is a dual responsibility to interact with them in ways that correspond with the relationship. Sometimes that relationship is a little fuzzy, sometimes our perception of a relationship is a little fuzzy. Because people are all different. So instead of letting a situation develop where fuzzy turns into uncomfortable, I am advocating for her to be more direct. That’s all. That’s it. Take it as you will.

        1. Lily Rowan*

          It’s because being more direct can have negative repercussions for her. She’s a fairly junior employee, he’s a beloved member of the association. Our society has taught women that clearly rejecting a man is dangerous in so many ways, I don’t blame her at all for being hesitant.

          1. Elizabeth West*

            Yes. Way back when I worked in a factory cafeteria, one of the workers asked me out. We had chatted in a non-flirty friendly manner, and I guess he interpreted that as interest. He asked me while he was in line at lunch, with me at the other register, with a ton of people behind him–so I’d say yes and not embarrass him, maybe?

            I said no thank you as kindly as I could. He then yelled at me. In front of everyone. The other workers were appalled. Can you imagine what could have happened if he’d gotten me alone to ask me and I’d refused? There were a ton of places in that building he could have done something awful without being seen. I don’t like to think about it. He never spoke to me again, and I hope it was because someone called him out on it, though I never found out for sure.

            It’s way past time society stopped tolerating this kind of thing.

        2. LBK*

          But, just because one is hiding behind plausible deniability doesn’t mean they have the emotional/social intelligence to understand subtle cues.

          I hate this explanation. Men who can’t understand social cues are a tiiiiiiiiiiny minority of the men who do this. Most are perfectly capable of understanding social cues and just choose to disregard them because the ambiguity gives them plausible deniability to pretend like they didn’t realize what they were doing, or that they didn’t understand what the woman was doing.

          So instead of letting a situation develop where fuzzy turns into uncomfortable, I am advocating for her to be more direct.

          But this does give the guy a pass because it basically says if she wants to stop being uncomfortable, it’s on her to be direct about the situation. There’s no way the guy is going to do it as long as he can keep riding the wave of ambiguity and pushing the boundaries.

          1. Koko*

            I also tend to think that even if we go with this very charitable explanation that there are all these bumbling men out there who are just clueless when it comes to social signals…

            …then the only way to fix that social problem is for men who bumble around to experience harsh consequences for doing so. Excusing the behavior because they’re so bumbling just ensures that the world continues to be a safe place for men to bumble around, no matter how many women they bumble into over time.

            Which means that whether they’re truly bumbling or just pretending to be doesn’t matter. We are a society of bumble enablers. They should be told in no uncertain terms that their behavior is unacceptable. They will figure it out when and only when forced to by consequences.

            1. Allison*

              Right, we need to remove the bumpers and let them get some gutter balls so they’re forced to learn to bowl better.

              1. Cheddarcheese*

                Yeah, but there are some men who, when you remove the bumpers, don’t learn to bowl better and instead just pick up the ball and throw it at people’s heads. And you often can’t tell learners from throwers apart.

                1. Koko*

                  Yep, which is sadly why it’s important that men in particular stop making excuses for other men. Because men are the ones best positioned to effectively deliver actual negative consequences to other men. Men getting away with the clueless act has a lot more to do with other men who defend their cluelessness than it does whether women call them on their crap or not.

        3. hbc*

          “But, just because one is hiding behind plausible deniability doesn’t mean they have the emotional/social intelligence to understand subtle cues.”

          Sorry, but this is bull. The fact that he knows to hide his cues behind plausible deniability means that he recognizes that overt passes aren’t acceptable. He’s expecting her to pick up the subtext, therefore he’s aware that subtext exists, and he should be looking for it.

          Also, most men who Just Don’t Understaaaaaand negative signals from women they’re romantically interested in pick up those signals perfectly well in other contexts. The rare exceptions are not the ones doing the coy “We’ll hang out as just friends, wink wink, oh there’s something in my eye.” This is a choice he’s making to ignore the answer he’s gotten.

        4. Luna*

          You call it empowerment, we call it a burden. Potato/potato. Which one it is depends on the OP’s personality and position.

          I would also argue that the fuzzy advances can often be more uncomfortable than direct ones. Asking the OP to come to his house alone is super uncomfortable. Pulling her aside at a public event and politely asking her if she would be interested on going on a date next time he is in town, and politely taking “no” in stride if that is her response, is way more comfortable IMO.

          1. Allison*

            It’s emotional labor. He doesn’t have to reveal his feelings, but she has to carefully tell him she suspects he wants something more than friendship and she wants him to know she doesn’t feel that way.

            3. neverjaunty*

              Bingo. And then he can vent his hurt feelings about the rejection by attacking her for “misreading” him.

        5. InfrequentCommenter*

          This!!! As a 27 y/o female I don’t understand why anyone would not encourage her to do this. Other comments imply it’s because he could retaliate but we have no reason to believe he would at this point. If I’m the future there was reason to believe he was going to do negative things to her because she declined his advances that’s a whole other conversation. I don’t understand why that would be the automatic defaul assumption tho.

          1. LBK*

            Other comments imply it’s because he could retaliate but we have no reason to believe he would at this point.

            I mean, we have a massive amount of stories from women who have had guys escalate after rejection to go on. And yeah, #notallmen or whatever but these interactions have every single hallmark of the guys in those stories. If you don’t want to be treated like a creepy dude, maybe don’t do all the stuff creepy dudes always do?

            Lucky you if you’ve never had a rejection go badly, I guess, but I think you’re the outlier.

            1. InfrequentCommenter*

              I agree we have a massive amount of stories where retaliation happens. I’ve had losers not take it well when their advances were declined. There’s also average Joe’s that get turned down everyday and do not retaliate against anyone but those aren’t stories we hear as much about because they end up being nonevents. The default should be to assume you’re going to be victimized when their isn’t a reason to believe it’s a more likely outcome. I feel like it’s just as likely this guy is a bit socially awkward/non-direct personality wise. I see no reason to believe a kind, direct statement of not being interested wouldn’t but the whole thing to rest. Of course if that doesn’t work I would advocate OP loop others in, etc., etc. but I don’t think any of the advances have been that predatory as of now.

              2. Cheddarcheese*

                You also don’t hear the stories of the millions of people who safely cross the street without looking. It doesn’t mean you shouldn’t cross the street without looking. I pretty much assume any time I cross the street without looking, I’m going to get hit by a car, so I look.

                My default in life pretty much is “If I don’t pay very close attention here and take caution, I may get hurt”.

                1. InfrequentCommenter*

                  Being cautious is one thing. If we were to use you analogy tho the thread would be assuming you would get hit crossing the street and need an ambulance on standby just in case.

          2. JamieS*

            I think it has to do with people interjecting their own experiences into it. Personally I’m a 20 something female who’s never been harmed by a man in any capacity. I’ve never been attacked by a guy, never had a guy try to intimidate me, never had a guy abuse me, never had a guy not immediately stop the second I said no or otherwise indicated “no”. In other words, while I logically know most men probably could harm me if they chose, I don’t fear men and really have no reason to. For women who have been given reason to fear men I can easily see why they would see strong potential for retaliation and would be hesitant to directly shoot him down because of it.

            To be clear, I maintain my opinion that saying something like Alison’s script when he asked her out to drinks (if not even earlier) would have been the best course of action and that she should pursue that course of action now. However I also think as far as danger (real or perceived) a woman saying ‘Thanks but I want to keep my professional relationships professional.’ is a lot less risky than saying ‘No I’m not interested in going out with you.’ since, IMO, the second one is much more likely to be taken as a slight against his manhood.

      4. Allison*

        “When hitting on is definite, it gives an opportunity for a definite yes or no.”

        THIS!

        There have been times where guys have been playing the game Jim is playing, edging closer and closer and being super friendly, maybe not realizing how obvious his agenda is but doing a super job maintaining plausible deniability so that I would look like an ass if I said “look, I’m not into you.” I’d need an actual “hey, wanna go out sometime?” or “hey, I have feelings for you” for me to actually shut this guy down, and by keeping things vague, he’s preventing me from giving him the clear rejection I WANT to give him because all the attention he’s giving me is making me super uncomfortable and I want it to stop already! And he may actually be doing that on purpose! It’s like that person walking slowly in the middle of the sidewalk, and slowly ambling to the side here and there but never moving over enough to give you room to pass. Maddening.

    7. JamieS*

      I think being less friendly and responsive would just be continuing to expect him to pick up on hints. A polite direct rejection is, IMO, the best way to go.

    8. Liz2*

      There’s no blaming anyone. If OP were a male, everything they had done would be seen as standard hang out with coworkers social norm. Only once the other person persisted and made it more than just drinks/hang do you realize you need to push some brakes.

    9. oranges & lemons*

      I do think the bar should be higher for work relationships though–a decent Jim would I think be more sensitive to the possibility that the OP is uncomfortable being less friendly because of their work connection, and back off faster.

  4. CC*

    Reading this is kind of heartbreaking—I thought the same thing when I was younger, “oh I must be reading too much into it” and “oh I don’t want to ruin his reputation.” Don’t worry about his reputation. If he cared about the consequences, he would have shied away after you politely declined the first time. Also the fact that he’s about 10 years older is disconcerning as well. Anyway, the point is you’re not hurting him—you’re helping him by showing this kind of behavior is not ok, as well as the company, and other women.

    1. medium of ballpoint*

      Agreed. A lot of people are missing the power dynamic here, and Jim’s power over OP means the onus is on him to be responsive to her cues.

      1. ragazza*

        Yes–exactly. Also the reason many women don’t want to give an outright “no” is because some guys get mad when they’re rejected, and she has to work with this guy. It could end up being uncomfortable for her or even have professional consequences.

        1. Oranges*

          Also because we don’t DO hard nos in our lives. We all do the soft no (okay, my FIRST soft Minnesotan no might not be heard to a.. New Yorker because regional differences but c’mon).

          Have you ever said to an invitation from a friend “No I’d rather play video games than hang out with you tonight” or do you do a “Sorry, but….(plausible excuse)”. Sometimes I lie, sometimes I just fudge the truth eg: “Sorry but I’m peopled out” (I have said this).

          It’s a way to salve the other person’s ego because no one likes to be rejected. It’s the little white lies that make us able to get along in a group without huge amounts of conflict. Just you know, the usual amount.

          1. JamieS*

            Well I don’t think you need to finish the sentence with ‘than hang out with you tonight’ since that’s just rude but I don’t see anything wrong with saying you’d rather stay in and play video games. That’s what I’d do and I don’t think a friend would become angry because you told them you didn’t feel like hanging out.

            Actually, for the sake of honesty, I don’t actually play video games but I’ve definitely told someone (okay several someones) I’d rather stay home by myself and watch Youtube videos while eating raw cookie dough.

      2. Shadow*

        Wait it’s on him to interpret hints he may not even recognize? How frustrating to keep giving what you think aren’t hints that you have no way of knowing are ever received.

        2. MsSolo*

          If “would you like to come over to my place alone and drink alcohol with me and sleep over but on the couch because plausible deniability haha” is a hint, I can only imagine being direct involves getting his genitals out. There’s some idea here he’s being subtle. He’s not. He’s being very, very blatant and throwing in some lols to shield himself from repercussions.

    2. InfrequentCommenter*

      Why is ruining his reputation even coming into play here tho? She hasn’t even told him she not interested yet but somehow there is a reason to think eventually the whole situation would need to be made public? I can’t help but think if this was my brother/cousin/any other male I care about it would see really odd that someone would need to make a huge deal about being asked to their home after casually hanging out and texting a few times? It seems that the thread is jumping to concluding this guy is a standard jerk/creep/power tripping frat boy but we have no evidence of that. A simple “thanks for the invites but I’m not looking to be more then work friends” could end the whole thing.

      1. Panda Bandit*

        We have evidence. He has a live-in girlfriend. Some of the things he said, like commanding her to change her flight, are total jerk moves.

        1. Specialk9*

          The live in girlfriend part was not in the original letter, which most of us were responding to. It really does change things.

        2. Susana*

          The live in girlfriend we didn’t know about (and btw, that would not be a deal-break for some women. Not me, but some women). And he did not demand she change her flight – he asked her to. Maybe the guy’s a creep, maybe not. But we won’t know until she makes it far more clear she’s no way, no how interested. She has to stop texting him – especially very friendly texts – and she should not be inviting him to join her and her friend after work.

  5. Snark*

    “Him: Awesome! Wanna do something dumb tonight?”

    “I’m not sure once again if I’m reading into it or not.”

    I…..oh boy. There’s nothing to even read into there. That is completely unambiguous hitting-on. He is asking you to come over for sexy times. We’re directly in “Netflix and chill?” territory. If nothing else, please start trusting yourself and your sense of the obvious a little bit more, and stop talking yourself out of it when you notice something obvious.

    Now, I don’t actually think he’s in the wrong at all here, because he seems to be doing it in a gentlemanly fashion and no potted plants have been defiled. I don’t think he’s even off base in interpreting your behavior towards him as an indication of possible reciprocated interest. I think a simple, “I’d like to keep our relationship professional” is totally fine, and my impression is that he will honor that.

    1. Jerry Vandesic*

      +1

      The suggestion of saying “I’d like to keep our relationship professional” is direct and perfectly on target. Until that happens, all the rest is just speculation.

      1. NorCalPM*

        Yes! “I’d like to keep our relationship professional” is the right approach. It includes the phrase “keep our relationship,” so it’s not a total shut-down. It just re-directs things towards that end (professional) and no place else, which is what she wants and which is totally legit. If the guy keeps pestering you after you’ve sent that message, then you’ve got something to escalate.

        1. Specialk9*

          I didn’t actually know that “doing something dumb” was sexual. I just kind of found it a weird awkward statement. Maybe I’m too old to evaluate this conversation properly.

          1. Tealeaves*

            Snark hit the nail on the head here. But even if it’s not Netflix and chill territory, “dumb” can never mean anything good. Probably involving alcohol or pranks. Seriously, what else could you be suggesting with that? Staying up all night to discuss the conference? At the bare minimum, it’s asking OP to jump to a highly personal level of friendship. And the way he casually asked you to change your flight for him just so that you can hang out, yeesh. That just reeks of a college kid maturity level. Huge red flag. I’d stop inviting him out for anything. Also like what Alison said, don’t reply him straightaway if he contacts you on your personal phone. Remove him from your personal circle and space.

            1. Susana*

              I thought “dumb” meant frivolous. But it doesn’t matter anyway. He seems sort of immature, on top of anything else. I agree that “I’d really like to keep our relationship professional” is the way to go. Direct. And no excuses that might make him think “no” is just “not tonight.”

    2. CaliCali*

      Totally agreed. Whether due to some (rightful) hesitancy or acknowledgement of the professional relationship, he’s clearly leaving you an out every time he has a proposal, and you’ve taken it. You’ve been friendly and inclusive, he’s hoping for it to be a bit more, but you’re not, and it’s all completely OK. If you firmly set that boundary and he tries to cross it, that’s another matter, but as of now, I think you benefit yourself by acknowledging “yes, he’s hitting on me, but no, I don’t want it to go further,” and setting the boundary thusly. And a person in their mid-30s should have been around that block a few times and handle it well.

      1. Birch*

        Not trying to nitpick your language here, but I find it…. interesting…. that the concept of “leaving someone an out” is even a thing in making suggestions about dating. As if the default is to go along with what he wants. It just emphasizes the power differential. IMO his suggestions are already crossing boundaries as they’ve all involved her being alone in his space, drinking, and he even told her to change her flight. He’s not asking if she wants to get coffee–that would be a completely different situation! He’s demanding private time with her and the cutesy way he’s self-denigrating in the second exchange makes it even creepier. And I don’t think this stuff gets any easier to handle because you always have to judge whether this is-he-being-creepy-or-am-I-overreacting situation might escalate into retribution if you outright reject him or stalking if you try to soften the rejection.

        1. CaliCali*

          So re: an out, I guess I was referring to making plans in general — like if I’m asking a friend for coffee but know it might be a hard thing for them to swing, or if they’ve got social anxiety, whatever, I’ll say I’m “leaving them an out” if I make a pretty soft request and then say “and if you can’t, no worries!” But that being said, you make a good point. If it was asking her out, it’d be one thing. He’s asking her over, and that has a different subtext. And now that we know he’s got a live-in girlfriend, it’s clear he’s just setting up plausible deniability to cover his tracks.

        2. Jennifer Thneed*

          > > And a person in their mid-30s should have been around that block a few times and handle it well.

          > And I don’t think this stuff gets any easier to handle […]

          I think that CaliCali was saying that Jim, as someone in his mid-30’s, should be able to take friendly rejection well. The OP tells us that she’s 24.

    3. Snark*

      And now LW has posted here disclosing that the guy has a live-in girlfriend, so maybe disregard that entire last paragraph. Guy’s a creeper, ref throws a red flag, nope nope nope.

  6. Wannabe Disney Princess*

    Oooookay. The first exchange could maybe, MAAAAAAAAAYBE, be brushed off as trying to get to know you if you’re feeling generous. But in the second one…asking you to change your flight? Dude. No. Unless you’re my long distance boyfriend, there is no way I’m trying to change my flight the same day. That would be enough to make me shut it down right there. At this point, personally, I’d roll steps 1 & 2 together. If he doesn’t stop after that? Definitely loop in your boss.

        2. medium of ballpoint*

          I’m seconding the red flag. If it’s a joke, it’s a pushy and uncomfortable one. If it’s serious, then he’s pretty arrogant if he thinks an evening on his couch is worth the cost of changing a plane ticket, particularly given OP hasn’t shown any interest in him. Pushing a boundary like that is often an exploratory move that signals other boundary crossings, not a single jokey event.

          1. Snark*

            “particularly given OP hasn’t shown any interest in him”

            I don’t think that’s a given at all. She hasn’t felt any interest towards him, but repeated invitations to hang out socially do give the impression that a person might be interested. And clearly he’s under that impression, as he apologized for not spending more time talking to her.

            Is he pushing a boundary? Maybe. Just about any romantic or sexual overture towards someone you don’t know well is pushing a boundary, though. Was it kinda borderline? Very much, which is why I think the yellow caution flag is warranted. A dude who misreads an opening and goes charging through as if he got the red carpet is probably a little entitled, might be a little pushy, might be pretty clueless. But red flag? That pops up if he gets shitty about a professional, unambiguous rejection.

            1. Birch*

              He’s not inviting her to hang out socially though, he’s inviting her to drink in his space. It’s weird because it’s clearly not an invitation to a date or even just hanging out platonically but to a hookup. She never invited him anywhere alone, but with colleagues. That’s pretty clear that she has no desire to get to know him personally.

              1. Snark*

                Well, now that we know he’s actually got a live-in girlfriend, I agree. But I entirely disagree that an invitation out with colleagues is a clear indication of zero interest in getting to know someone personally. It’s not an unambiguous indication of interest, certainly, but it doesn’t communicate no interest whatsoever, either. That said, he was well out of line to ask her for anything more than “Hey, would you like to have dinner with me sometime in the next few weeks?”

                1. Elizabeth West*

                  Hmmm nope, if someone asked me to come over to their place to drink, girlfriend or not, I’d assume they wanted to hook up. And to change my flight? Fuck no. That’s pushy as hell, even as a joke. FLAG FLAG FLAG FLAGGITY FLAG FLAG.

                  I usually agree with you, Snark, but I think you’re way off on this one. Though I may be looking at it through the lens of someone who was raped this EXACT WAY because I gave someone the benefit of the doubt.

                2. Koko*

                  The problem is that he’s skipping steps. They have only seen each other in group settings. You just don’t go from that to drinking alone in a private home. It’s very presumptuous and has a very clear meaning. I used to be open about my marijuana use on my dating profile and I got messages from guys asking me to come smoke with them. Hell. No. I actually started writing in my profile that you should only message me “if you know what an appropriate first date is (hint: it’s not at your house).”

                3. Tealeaves*

                  Paraphrasing but AAM said something about social events outside of work are not professional once alcohol is involved. And in a private space? Alone??? That’s alarm bells going off.

              3. Specialk9*

                “She never invited him anywhere alone, but with colleagues. ”

                Before hanging out with co-workers, she invited him to go out with her non-work childhood friends. It really is a signal. Though if he was open about having a live in girlfriend, I actually get her thinking “oh this would be an issue, but he has a serious girlfriend so he won’t think I’m making a move.”

                1. Totally Minnie*

                  It doesn’t matter that they were her friends from outside work. The point is that she has never once spent any time with this man alone in a social setting. Going from “drinks with a big group of other people” to “come to my house alone for implied future sexytimes” is skipping quite a few steps, and many a reasonable woman will be weirded out by that level of escalation.

              4. Oranges*

                Eeeeeh. I can see (sans GF) Snark’s point and your point. I think however that this is what boundary pushers do. Snark’s boundaries are different than yours. Which is fine.

                Personally, I think it was a red flag only because of the sea of all the other little bad colored flags that were waving. Also, because in my area subtext is more commonly used which changes the communication. If I’m talking to someone from a different region I try to become more explicit about if things.

                My theory is that it keeps all of us from murdering each other during the long winters.

            2. medium of ballpoint*

              “She hasn’t felt any interest towards him, but repeated invitations to hang out socially do give the impression that a person might be interested.”

              Do you see what you’re saying here? You’re saying that a woman asking a man to spend social time as part of a group they mutually belong to, is an expression of romantic interest. That leaves zero room for women to be friends with men, or have a mentoring relationship, or get to know each other outside the office without potentially signalling that clothes are coming off. That’s a problem.

              1. Snark*

                I’m not saying that at all. But if someone repeatedly invites you to attend social, drinking occasions, that does at least communicate a receptiveness to connecting socially. And it would not be inappropriate to – after a few of those, and if you were both single and there was some chemistry, and they seemed to be interested – ask the person if they were interested in joining you for dinner or something. And if you misread the situation and there’s no interest, and they say, “Oh, thanks, but I’d like to keep things on a professional footing,” you say, “Of course. So, I’m really excited to see what the outreach committee comes up with for the yearly fundraiser,” and that’s the end of it. And a solid 85 or 90 times out of a hundred, even making the ask for dinner would be misreading the situation badly, and those are the situations when a decent person allows friendships, mentorships, and professional acquaintances to take root without any subtext.

                What he did, now that we understand the situation in fullness, was totally inappropriate. But there are times when it’s appropriate reasonable , in context, to interpret repeated invitations as indications of at least potential interest.

                1. Fact & Fiction*

                  Replying to SpecialK9 assuming your comment was the me (dratted nesting sometimes, ha): I mean…I personally feel that inviting a colleague out to socialize with friends if you happen to be from the town where both colleagues are staying for meetings is clearly a polite, mostly work-related gesture of kindness that should STILL not be automatically interpreted as overt interest because it involves a female and male colleague. Unless the inviter clearly states something to that effect. People, women included, should be able to invite people of all genders somewhere without it automatically indicating some sort of romantic interest. Just my opinion though.

                2. neverjaunty*

                  Yeah, so, a totally-different-behaving-Jim would be an entirely separate letter. That would be the letter where, after hanging out with the LW at group events, Jim asked her out directly.

                  That’s not what’s happening here. ‘Come over to my place and get drunk but there’s a couch haha!’ and ‘you have to catch a plane? change it!’ is Not That.

              2. Fact & Fiction*

                Yes! Just because a woman invites a _work_ colleague to _work-related_ activities does not automatically mean she wants the smexy times with said man. If this man had “honorable” intentions toward the colleague, he should 1. Spend time getting to know her and 2. Extend a no-pressure direct date invite to her. His actual behavior reveals he has no such honorable intentions.

                Not to mention, that he is older, more work experienced and senior also means there is a power dynamic that he should actually NOT pursue a romantic (or what seems more likely by things like his let’s do something dumb lol comment, sexual) relationship with this colleague. Period.

                MAYBE if the younger colleague clearly indicated “Hey I’m interested in X are you? But even then…

                I’m just so tired of the default assumption being of COURSE a woman is automatically interested if she doesn’t say “NO!” How about colleagues assume women never want to be groped or see their junk in the workplace until and only if directly asked? (Given all the work harassment reports that are only now seeing the light of media day.)

                2. A.*

                  Thank you. This response is perfect. Just because we grab drinks as a group does not mean I want to come over late night. It is veering into “I can not socialize with members of the opposite sex at work because it could lead to sex” territory.

                3. Specialk9*

                  Look, agreed about work events. But she first invited him to hang with her non work friends, in a purely social occasion. *then* She kept it to work socializing. It really is different.

                4. Oranges*

                  Replying to A because nesting:

                  Also how would that translate to gay people? Or non-binary? (These sorts of questions/hypotheticals amuse me greatly….)

                  This is one of the few benefits of being gay… society expects us to be friends with females so the BS of “No friends you might be attracted to” passes us by (usually). And if I’m getting hit on by a guy either a) he doesn’t know OR b) he’s a SUPER creep.

                  Gotta find the silver linings somewhere….

          2. Bess*

            Flaming red flag for me, too. He is clearly hearing “not tonight” and basically says “yes tonight” every time. This is entitlement and boundary testing, not “innocent socially unaware dude who still isn’t sure if she’s not interested.” Because in that scenario he’d at least be like “okay not tonight, what about tomorrow?”

      2. Snark*

        Totally conceded, y’all. And now LW has posted here disclosing that the guy has a live-in girlfriend, so maybe disregard everything I posted here? Or maybe don’t, and give me a smack upside the head, since I apparently need that? You all called it about 9000x better than me.

        2. Princess Consuela Banana Hammock*

          It’s ok, Snark. I was genuinely curious because you’re usually a great ally on these issues, and it was strange to see a bunch of women saying “RED FLAG RED FLAG” while you were saying, “Naw, yellow.” Thanks for clarifying and updating!

          1. Fact & Fiction*

            I agree. I think that sadly, some of these things you only develop the proper spidey sense for by having experienced/discusses with enough women who have experienced these things often enough. And even then, it’s easy to sometimes doubt yourself…

          2. Specialk9*

            I’m a woman with very developed creep sensors, and still thought that based on the original letter, it was yellow flags only.

            1. Oranges*

              I think we all have different social cues. Personally, I was seeing red flags because of how we roll in MN.

              Also Snark thanks for debating us. I WANT to debate you when we think different things. It helps ME define what I believe because I have to put words around it.

              Thanks also for being awesome enough to own that you were wrong in this case. Being wrong in public isn’t fun but you respected us enough to do so.

        3. Lissa*

          I am a woman and saw it as a yellow flag could be creep could be awkward situation as well! Having experienced both types in my younger daus. Though never from a colleague at least. Which I suppose could be what darkens the flag to Red here vs a nonwork situation

          1. Lindsay J*

            Same here.

            But I know I am A. kind of oblivious to social cues in general and B. Wasn’t really socialized? I guess is the correct word – I wasn’t brought up with the sense of caution or the sense that I need to be delicate and friendly at all times – like a lot of woman so my level of threat assessment is off compared to the mainstream – so this is probably just an extension of that.

    4. Elizabeth H.*

      It sort of depends on the social circle. I can envision some scenarios in which it’d be a jokey comment, moreso if for example the comment was made at a party or gathering that both people were already at. It’s the kind of thing that I’d be comfortable just registering that the dude was interested in me and seemed pretty into partying, but deflecting.

    5. Snark*

      Honestly? This guy. I was at a scientific conference for a week, and had spent some time socializing with a woman who presented right after me in the same breakout session. We went for drinks, there was that certain buzz in the air, she said with some regret that she needed to get back to her room because her flight was early, and I said, “If you don’t need to be back for anything specific, why not bump it back?” And she thought a bit, stepped out to make a call, and stayed.

      1. Wannabe Disney Princess*

        There’s a difference, though. She said she regretted having to leave early. She was already open to staying. Nothing in the LW’s reply suggests that. He asks if she wants to doe something and she said what time her flight left. A minor difference, yes, but a key one.

        2. Snark*

          There is a difference, yes, but the original post wasn’t that nuanced. The rhetorical question was asked, “Who the heck asks someone they barely knew to change their flight,” and I answered. In context, it was not only appropriate but appreciated. And I – I think and hope – have a pretty well-tuned sense of context and propriety, so I actually read the room right.

          1. 42*

            1) The OP makes no mention of feeling ‘a buzz in the air’ as you and your companion apparently did.
            2) You and your companion were already sharing drinks for the evening, you didn’t text her when she was already out with colleagues (without you) and spring this request on her apropos of nothing.

            Huge difference.

            1. Basia, also a Fed*

              Yes, but Snark isn’t responding to the OP. He’s responding to Katniss’ “Who the heck asks someone they barely know to CHANGE THEIR FLIGHT to hang out?!” His response makes perfect sense in this context.

          2. Malibu Stacey*

            Maybe change it to, “Who the heck texts back ‘Change your flight’ to someone they barely know” if it’s bothering you?

          3. oranges & lemons*

            I think you’re inclined to give this guy the benefit of the doubt because you can easily see the non-creepy interpretation of his actions–but when weighing potential creepiness of a relative stranger, these ambiguously creepy gestures have to be weighed pretty heavily.

            1. Snark*

              Yeah, and now that the LW has informed us he’s already attached, I’m letting this line of argument die a quick and unlamented death.

      2. Malibu Stacey*

        That’s different – 1) she was already hanging out with you, 2) it was a face-to-face conversation where syntax, body language, etc. can be conveyed, and 3) she specifically brought up regretting having to take an early flight.

            1. Snark*

              Sure. Which is why I said above, I think this dude gets a yellow flag, slow the car down, debris on track. He’s being pushy, and he needs an immediate unambiguous letdown, because nooope. But the request alone is not categorically unthinkable. Context still matters.

              1. Malibu Stacey*

                Well, you also said he was being “gentlemanly”, which . . . no. I would say presumptuous at best.

                2. Malibu Stacey*

                  @ Snark, it definitely makes sense why he’d be so bold re: changing the flight . . . it’s probably a lot easier for him to cheat on the road than at home.

              3. Princess Consuela Banana Hammock*

                But also you weren’t telling your colleague to change her flight so she could hang out with you in your room on your couch to watch a game. His “change your flight” command seems to be at a higher “boundary-crossing” level than your conversation in-person with your colleague.

              4. Snark*

                I’m cutting this argument loose entirely and retracting it, because new information paints him in a vastly worse light, so please disregard.

      3. Camellia*

        You say, “…there was that certain buzz in the air,…”

        I call that chemistry and you both picked up on it. There was no chemistry at all here and the OP knows that, but the guy either doesn’t or is ignoring it.

      4. Snark*

        And now LW has posted here disclosing that the guy has a live-in girlfriend, so I’d like to retract everything I posted here, because it has no bearing. Feel free to smack the Snark.

  8. Many Emails*

    I have to take exception to the second part of #2. If he were a decent dude, then either he never would have crossed the line in the first place, or he would have been direct and asked her out for real.

  9. KHB*

    If you’re worried about seeming narcissistic or that he’ll come back at you with “How dare you think I was interested in you that way, don’t flatter yourself,” a well placed “I don’t know if I’m reading this wrong” can go a long way. As in, “I don’t know if I’m reading this wrong, but I want to make clear that I’m not interested in anything more than a professional relationship.” If he replies with “Haha, of course you’re reading it wrong,” you can say “Great! I’m glad to hear it.” Declare your uncertainty like you’re going through customs, and it’ll be hard for him to use it against you.

  10. Susana*

    I think “hitting on her” is a tad judgmental – makes him sound like a predator, and he’s just trying to advance a relationship to another level. It’s not like she’s given him NO indication she’d be interested – has invited him out with friends several times and answered his texts in a non-professional way. Yes, this is awkward, but he hasn’t made a physical pass or gross sexual comment. I do think OP needs to make it clear – just something that says, I’ve enjoyed meeting up after work, but I want to be clear that I really just want a friendly professional relationship. I really don;t think he’s done anything wrong, though. No coercion here, and he’s not her supervisor. Just be clear before it gets more awkward.

    1. stefanielaine*

      I have never considered “hitting on” to have a predatory or coercive aspect. Curious whether others might hear it differently, but to me it’s just a term that means he’s trying to create a social relationship of some kind with her.

      2. Jennifer Thneed*

        For me, “hitting on” means the social relationship in question is specifically sexual.

        People “hit on” someone they want to “hook up” with. And while the gentleman in Barbershop used the phrase “hook me up” to mean, “okay white boy, give me a haircut if you think you’re so good”, that’s not quite the same phrase. “Hook up” might not go past sloppy kissing, but it’s certainly sexual.

      3. JamieS*

        To me it depends on how it’s said, for instance “Jim’s hitting on me” compared to “Jim won’t stop hitting on me”, but in general I don’t find it to have a predatory or coercive aspect.

      4. Susana*

        Ah. I guess I tend to use the expression, “trying to chat me up” or something. Hitting on, to me, has always meant very aggressive behavior, though not criminally so. Semantics, I guess!

    2. Myrin*

      Isn’t “to hit on” just a snyonym of “to flirt with”? I’m honestly asking because I’m not a native speaker but I’ve never really gotten the impression that “hitting on” has negative connotations, maybe just more blatant ones (like, flirting is more “elegant” compared to it)?

        1. NYCWeez*

          In my social circles, “hit on” is always used to mean “unwanted advances” and is definitely a negative term. My friends would say a guy was “flirty” or “into them” if the attraction is mutual.

        2. The Supreme Troll*

          I kind of see it that way too, an intention that, in the eyes of a lot of people, wouldn’t be seen as evil or nefarious. There is a very good chance that the coworker has romantic intentions, and wants to follow through on those because (in his view…at least what I think), he doesn’t to let a great opportunity slip by. But it is quite normal to feel that way and to want to act on that in a friendly, civil way.

      2. CAA*

        I don’t think you’re going to get consensus from native English speakers on the connotations of “to hit on”. It’s slang, which is notorious for changing its meanings over time and across age groups. I’m quite sure that my mother would interpret it differently (and more negatively) than my daughter would.

      3. nonegiven*

        Isn’t ‘hitting on’ a step past flirting? People flirt all the time without actual personal interest. ‘Hitting on’ is a clear signal of non professional interest.

        1. Hrovitnir*

          Yeah, I see “hitting on” as flirting with [clear, to some degree] intent. Whether it’s creepy or not depends on the context; to me it’s not inherent in the action. I guess it’s disturbingly commonly a creepy thing though. :/

    3. Elizabeth H.*

      It doesn’t have any kind of negative or predatorial valence to me! I think it’s a pretty neutral phrase, I would use it to describe my own behavior. To me it just means “interacting with in a way that manifests your interest in the person.” (I’m a native English speaker, woman)

    4. MillersSpring*

      I consider “hit on” to have the same meaning as “flirt,” albeit with a more one-sided connotation. I’ve heard “hit on” since the 70s. (Note: I’m a native speaker with many years of experience as a copywriter and editor.)

    6. Princess Consuela Banana Hammock*

      i don’t know anyone who uses “hit on” as an inherently predatory phrase. If someone hits on you, you canlike or dislike it, but either way, they’re flirting with you with the goal of getting a date or intimate encounter.the phras is t predatory; the context could be.

    7. Anonymous Educator*

      Clearly, Susana and I are in the minority here. FYI: Susana, you aren’t the only one who thinks the phrase hitting on her has a slight predatory connotation.

      2. Susana*

        I’m starting to feel really middle-aged! Also, I have to *stop* saying to both men and women, want to hook up this weekend? Because to me that means going to the movies, not having casual sex.

    8. Observer*

      Hitting on is not coercive, so the term is being used appropriately. But he really HAS given some evidence of either being highly socially clueless or seriously boundary pushing.

      Jumping from social invitations to group outings with professional acquaintances to “come sleep on my couch instead of your bed” is a fairly big move. And asking her to move her flight?! That’s NOT a normal or reasonable response to the messages she’s sent.

    9. LBK*

      It’s not like she’s given him NO indication she’d be interested – has invited him out with friends several times and answered his texts in a non-professional way.

      Assuming a coworker who has a friendly conversation with you is into you sounds like a recipe for disaster. Most people are cordial and friendly to colleagues due to having a vested interest in getting along with them, even colleagues they actually hate. Suggesting anything beyond a formal business email = flirtation doesn’t sound correct to me at all.

  11. JamieS*

    So basically a man expressed interest in OP, OP’s not interested but has communicated that by giving “hints” and making excuses instead of just telling him, and (not surprisingly to me) he hasn’t picked up on those hints. This isn’t complicated. Just tell him you aren’t interested in clear plain language.

    At that point if he continues to push, loop in your manager (or an appropriate higher up) and report him for harassment.

    1. Shiara*

      The thing is he… hasn’t really expressed interest in the OP. Not explicitly. The subtext is clearly there, especially when you add everything up together, but he’s not giving her a direct expression of interest for her to give a direct declining of interest back to. And he’s deliberately tossing in stuff like (couch obv) to obscure it. So it’s obnoxiously unfair that he’s allowed to lay out his interest in the subtext, but isn’t expected to pick up on her rejection unless she makes it explicit. (I really like how hbc put it in an above comment)

      Annoyingly, getting explicit about “I would like to maintain a professional relationship with you” is OP’s best path forward. But if “just telling” was that easy, he could have been the one to do it in the first place.

      1. InfrequentCommenter*

        “And he’s deliberately tossing in stuff like (couch obv) to obscure it.” Why is him adding this seen as being sly? Why can’t it be that he would just be inviting her over and is expressing that instead of the bed they could watch tv/movies on the couch? I would take it as he’s clearly making it obvious that he doesn’t expect the situation to become overly sexual.

        1. Elizabeth West*

          I wouldn’t.

          “Well the bed would be more comfortable. There’s a tv in there–let’s go lie down.” Or “We were watching tv and I just got this vibe so it just kind of happened.”

          This is triggering me SO MUCH so I’m going to have to step away from this post, y’all. You’re not seeing clear and present flags here. I’m just–I can’t. Gotta go.

        3. Oranges*

          Yeah, see… no. The couch is plausible deniability. 100%. It’s so he can go “I obviously didn’t mean it like THAT” when it’s kinda obvious he DID.

          Why I say he did: If you change the LW to… lets say the Rock (or any other male who you find “empowered”). Suddenly this becomes kinda weird no? Like if this was only about friendship the dude is trying TOO HARD and ramping up the intimacy TOO MUCH by about 10,000,000.

          So, the mention of the couch is most likely a manipulation tactic about how he’s “safe”. This means if this was successful (and he’s a predator (signs point to maybe)) he has her a) possibly/probably intoxicated b) in a space he controls c) thinking he’s okay d) in a tableau where she’s powerless to press charges should anything happen. NOT GOOD. I’m not gonna risk the next 1-6 years of my life (counting in therapy, PTSD etc) on that.

          Also, you know what? A normal dude only interested in friendship would mention the couch too! So it’s not the single behavior. It’s the behavior in context with the 0-60mph intimacy and the boundary testing that we’re responding to.

          1. InfrequentCommenter*

            Well the question is about declining the invites. She shouldn’t go if she doesn’t want to. All she has to do is say “thanks for the invite but I try and keep work/personal friendships more separate. Not interested anything more.” End of story.
            I also take offense to the part that “he has her intoxicated”. People do. It get intoxicated if they choose not to consume alchol. She’s not a child and to emply she dose the have a choice I’m the matter of consumption really undermines her.

            1. Oranges*

              Yeah, see predators actually use alcohol to incapacitate their victims and since she’s young she might not know that. Most older people don’t know that. Sexual predators either a) use intoxicants or b) prey on people they know or c) both. The ones that use force and prey on (non-marginalized) strangers usually get caught because their victims are believed.

              Let’s break down how this could go: she goes to his house. Says “having a drink is okay” and has ONE (if he’s a predator it’ll be double strength probably). Then he pressures her to have another and she’s buzzed maybe? And it’s WORK to keep on saying no. So fine another one. She is now pretty drunk. She can offer almost no resistance and because she was drunk and didn’t ‘fight’ the old chestnut of “Regret the Morning After” will rear it’s ugly head.

              Other way: She goes and doesn’t drink because reasons, he pressures her but she remains firm. If he does anything he’s now in a much more tenuous position since she’s not drunk because of our social narritives. After all girls who drink aren’t “nice girls” [subtext: only nice girls deserve protection]. which is a black hole of effed up). AND because he knows she defends her boundaries and isn’t good prey.

              Last way: She goes and turns down the drink. He pressures her and it’s so much easier to just… have a drink. She does. Return to the adventure in the first paragraph only this time he’s more confident he won’t get caught because she could be badgered into regenning on her “no” which makes her less likely to press charges (Because she’s been socialized to ignore her wants for what others want and it’s stuck. So it’ll be harder for her to go against the tide if she wants to report him.)

            2. Oranges*

              PS. Original Question: Why is him adding this seen as being sly? Why can’t it be that he would just be inviting her over and is expressing that instead of the bed they could watch tv/movies on the couch? I would take it as he’s clearly making it obvious that he doesn’t expect the situation to become overly sexual.

              I tried–in a rambling way–to explain how predators operate and why the mention of the couch isn’t good. It’s a way to lower her defenses in a place where that’s probably a very bad idea.

      2. JamieS*

        Well at this point he could’ve texted “IT’S MOUNTIN’ TIME!” and been less obvious but even before his romantic intent was clear he still expressed clear interest in a more personal relationship. To me the crux of the issue is a colleague wants a more personal/less professional relationship and OP wants to keep it friendly but professional.

        This is a pretty common occurrence that I think should more or less be handled the same regardless of whether romantic intentions are suspected. Obviously if Jim continued to push the substance of the HR complaint would change compared to if he was just expressing interest in friendship but I don’t think OP needs clear romantic intention before it’s appropriate to set a boundary on it being a professional relationship.

    2. EBStarr*

      It’s interesting that you put it in this way, that he “expressed interest” but she has only communicated by giving “hints.” Because he *hasn’t* actually literally expressed interest in her, he’s just invited her to hang out in ways that could plausibly not be romantic. By any rational standard, the OP has been better at using her words to communicate her lack of interest than he has been at using words to indicate his interest.

      Seems like women are always expected to respond with an *explicit* “I’m not interested,” even when the man never said in “clear plain language” that he was interested. Yet when it comes to the man’s behavior people are all too quick to leap to his defense with, “Well how could he have known, you were so unclear!” even when she’s actually said no to multiple invitations in a row.

      1. JamieS*

        Oh my word choice was quite deliberate. I expressed it that way because he expressed clear and obvious interest in a personal relationship even though he wasn’t explicit about the nature of the personal relationship. That’s a point against him but it doesn’t change my opinion on how it should have ideally been handled. OP clearly doesn’t want any kind of personal relationship and I think it would’ve been best to clearly state that from the get go whether or not there’s a romantic undercurrent.

        Also, I know this is probably unfair, but yes I do think if you aren’t interested in something and/or something/someone is bothering you it’s best to make it expressly clear even if the other person isn’t being as clear.

    3. LBK*

      It’s interesting that you feel comfortable clearly interpreting his invitations as signals that he’s interested in her, but you don’t think her rejections of those invitations can be clearly interpreted as her not being interested in him.

      1. JamieS*

        Yes I do interpret inviting someone out to drinks on a nonprofessional capacity or suggesting they “do something dumb” to be a clear indication the inviter wants a more personal relationship and “I think I’ll watch TV instead” to be a not clear indication of not being interested.

        As I said above this probably isn’t fair but yes if something is bothering you I think the onus is on you to be direct and say something. Otherwise you’re the one who’s going to continue to be in a position you don’t want. This holds true whether it’s a romantic situation or if it’s a situation where you’re upset that a coworker routinely interrupts you or a situation where you’re a manager and your employee is doing something you don’t like. Speak up!

        1. LBK*

          Yes I do interpret inviting someone out to drinks on a nonprofessional capacity or suggesting they “do something dumb” to be a clear indication the inviter wants a more personal relationship and “I think I’ll watch TV instead” to be a not clear indication of not being interested.

          I mean…this just feels blatantly contradictory. He asks if she wants to do something one on one, she says no. Regardless of the wording, if the first can be interpreted as “I’m interested in you, are you interested in me?” how can the second not be interpreted as “No, I am not interested in you”?

          1. JamieS*

            We might have to agree to disagree on this but I don’t think they’re contradictory at all. I say that mostly because of the inherent differences between extending an invitation and being the invitee. I think a person can make it obvious they are interested in pursuing a more intimate relationship (rather that be romantic, friendship, or something else) by issuing specific invitations such as asking someone over to hang out or asking them out for drinks alone. However I don’t think gently turning down specific invitations as they come makes it clear you’re not interested in pursuing that relationship. Well at some point it’d become clear to most people but I don’t think an individual rejection makes it clear but I do think an individual advance can make intentions clear. By rejection I mean turning down the specific invitation not making a general “I’m not interested” statement.

            Lets shift the lens a bit away from romantic overtures since that tends to muddy the waters for people. For example, lets say someone you know casually but aren’t close friends with asks you if you want to grab some drinks tonight (assume it’s obvious there’s no romantic intent). To me, that would be a clear sign they’re trying to advance the relationship. OTOH, if you turned down that specific invitation I think it’d be an overreaction to interpret that as you never ever wanting to hang out with this person one on one or otherwise pursue a closer friendship.

            I know this is a bit different in that he’s making romantic overtures. However I think the concept is essentially still the same.

          2. Tau*

            Agreed. In fact, I have social skills difficulties (due to autism) and I would not have picked up on the sexual connotation in Jim’s texts. It’s clear now that people have pointed it out but I read the post going “hmm, sounds legit, maybe the ‘change your flight’ thing is a joke?”. If I’d been in the OP’s position, I could have gotten into serious trouble. I actually did get into serious trouble in a similar situation when I was younger.

            On the other hand, the OP’s responses read as a very standard soft refusal to me, and a basic rule of relationships is that after a few refusals you stop trying to advance intimacy and leave the ball in the other person’s court. I worked that one out as a teenager.

            From my perspective, she is not the one who’s been vague and indirect about her intentions.

            1. Marthooh*

              Thank you! I’m so tired of reading that poor Jim is probably socially awkward, and can’t pick up on subtle social cues, and the onus is on the LW to figure it all out and make everything crystal clear.

  12. Justin*

    He may or may not be a bad guy, but I think, as said above, if you make it crystal, explicitly clear, “I just want to make sure that you understand I want to keep our relationship strictly professional,” you’ll find out pretty fast if he’s going to respect your wishes or not.

    1. Justin*

      But also: if he’s really interested, he should stop being wink-and-hint-and-tee-hee about it and say so (not that she would be interested, but so that this plausible deniability nonsense game can stop).

      In this case, though, he needs to stahp. And absolutely so once she tells him what has been suggested.

      Your instincts are on point. When I had much worse self-esteem I was into this dumb “well if I don’t ask her out she can’t reject me aha! I have solved it” thing (but thankfully, not with anyone in a professional capacity).

      1. Fortitude Jones*

        He may be doing it this way because they’re in a professional capacity. If, as her colleague, he comes right out and asks her out and she says no, he may believe there would be some ensuing awkwardness he’d rather avoid either on his part or hers. If they weren’t coworkers, he may have taken the direct approach – we may never know.

        1. KHB*

          I don’t know that their professional relationship is all that relevant here – I’ve seen all sorts of people take this approach in all sorts of contexts. The idea is that if he never directly asks, he can never be told “no.”

  13. Blue Eagle*

    It doesn’t surprise me that he kept texting you as your responses to him were lukewarm and not clear. My suggestion is to respond more clearly that you want to keep your work life and professional life separate. Dodging the issue by saying you want to stay in or you don’t want to change your plans does not send a clear message of NO. If your answer is no, I’m not interested at all, then say that (i.e. no, I’m not interested in getting together outside of work functions. I prefer to keep my personal life and professional life separate). This needs to be your first step and only escalate if he continues to pursue it.

    1. Ask a Manager* Post author

      I think, though, that this is the crux of why this is hard. Especially in work situations, the hope is always that you can remain warm and not cause any awkwardness for the other person, and that they’ll still get the message.* And often they do! But when they don’t, you need to be prepared to do the stuff I talked about in the answer. But it’s not inherently wrong that she wasn’t crystal clear from the get-go.

      * Doubly true because women are often penalized if they’re not at least somewhat warm in these situations.

      1. Elizabeth H.*

        Agree. I don’t really feel like she was “dodging the issue,” or like it’s necessary to be so direct even when you have a purely social and not at all professional relationship. If the guy was someone she had met at a party or through friends and exchanged numbers with, or even a guy she had met on Tinder and gone out for a drink with once, I would still consider their exchanges pretty reasonable on both parties’ side and that he would be likely to pick up on it and stop messaging her after this last round. After one or two deflections most guys get the message.

      2. JamieS*

        I think you can be warm, tactful, and polite while still clearly telling someone you aren’t interested in a more personal relationship whether it be romantic or just as friends.

        As far as OP not being wrong I tend to disagree on that. Not wrong as in OP is at fault and is in the wrong but wrong as in a direct polite would’ve been the best course of action.

        1. Lily Rowan*

          And I feel like she 100% did that (was warm, tactful, and polite while still clearly telling someone you aren’t interested in a more personal relationship) every time he said, “What are you doing tonight?” and she said “Come hang out with the team!” and then didn’t really talk to him out.

          That is not actually that hard to read.

          1. JamieS*

            No inviting someone out to drinks with a group and then talking to others in the group isn’t an indication you’re not interested in a more personal relationship. At most it’s an indication you’re a social butterfly. Neither is “I think I’ll stay in bed and watch TV. Haha!” or “my flight leaves at 8.” Although IMO that whole last interaction was odd.

            A clear reject is something like Alison’s script. Basically something that directly says “I enjoy your company in a professional capacity but only in a professional capacity”

          2. Emi.*

            Yeah, I once let a romantically interested classmate tag along to a party because I couldn’t figure out how to shake him politely, and once we got there I flirted briefly with every boy there except him (including one who turned out to be a seminarian). It wasn’t exactly my proudest moment, but he stopped pursuing me.

      3. LBK*

        I mean, we need look no further than the flood of news stories from women who have been expected to cover up actual sexual assault in order to preserve their careers. No wonder women are hesitant to do something as seemingly simple as tell a coworker they’re not interested in him.

      4. Tau*

        I wouldn’t say it’s just women, really? There’s a post linked further up which talks about how indirect refusals are actually the normative way of communicating refusals in our society; directly saying “no, I’m not interested, go away” is a violation of social norms and seen as rude. Generally speaking, you want to avoid violating social norms in a rude way when talking to a coworker. Especially when said coworker has managed to stay within social norms via plausible deniability so far.

        Which is to say – it’s completely understandable that she wasn’t direct so far, and it sucks that the coworker has put her in this position. I’m of the opinion that you have no business hitting on someone in a situation that constrains their ability to be rude (e.g.: coworker relationship) if you’re going to ignore soft refusals.

        1. LBK*

          I agree that soft refusals are the social norm on both ends of the gender spectrum, but because there’s still a strong expectation that the man will be the pursuer and men also hold more positions of power than women, I think women end up having to do a disproportionate amount of soft rejection.

    2. hbc*

      But she’s not interested in keeping her personal and professional life separate. She hangs out with work people a fair amount, from what I can tell from the letter.

      That’s what makes this so insidious–she’s pretty much stuck rejecting his non-advance (and risking him being all “It was just TV with a work buddy! I explicitly said couch!”), lying to him and changing her work approach, being distant in a way that’s kind of non-collegial, or continuously turning down invites to hang out in the room where his bed is.

      1. TootsNYC*

        drinks with several people from your work? That’s professional, and maybe personal. Both.

        Going to his place to watch sports, by herself, in the evening? That’s personal, and not at all professional.

  14. Unexpected Dragon*

    This whole scenario falls into the “plausible deniability hit-on”. It’s definitely there, but indirect enough to leave him the change to do some variation of “haha, no, just trying to be friends” thing. I would also lead with option #2, as it’s more direct. I can see him doing a whole attempt to brush it off as the OP exaggerating, which actually makes this really easy! If he claims he wasn’t, you can always follow up with a “oh, good, so it’ll be super easy to be strictly professional going forward then.”

    1. Queen of Cans & Jars*

      “oh, good, so it’ll be super easy to be strictly professional going forward then.”

      This is a great response!!

  15. I'll say it*

    ANYTHING that changes the professional trajectory of your relationship with this person is A BAD THING. I don’t know if people fully comprehend that even “I don’t blame him” and “at least it wasn’t…” statements make these situations so much worse. Now the OP has to carry the burden of not only having to reject (or put in his place) this guy, but being worried about doing it. And watching what she says – to him, and now to every male. This kind of thing seems like it can be overlooked, but it can’t. It just can’t. Men (and women) need to stop overreaching. It’s damaging. I’m talking from a lot of experience.

    1. Snark*

      “Now the OP has to carry the burden of not only having to reject (or put in his place) this guy,”

      I don’t see how rejecting him “puts him in his place,” because I don’t see how he’s been improper, in context. But what I really don’t get is how rejecting someone you’re not interested in is a “burden” or some kind of imposition. Lacking telepathy, how else is one supposed to communicate that interest isn’t reciprocated?

      “but being worried about doing it. And watching what she says – to him, and now to every male.”

      I don’t think she has to worry about it – beyond being courteous and professional in how she rejects him. And I don’t think she has to watch what she says, even. Grownups can make overtures and have them rejected and be adults about it. If he’s a petulant child about it, that’s its own problem, but like I said, lacking telepathy, it’s not a bug that adults have to use their words, but a feature.

      “Men (and women) need to stop overreaching.”

      How is it “overreach” to pursue a romantic connection with someone you’re initially connected to in a professional capacity and who ostensibly shown signs of reciprocated interest?

      1. Health Insurance Nerd*

        I agree. Some of these responses are so over the top. A man shows interest, does some texty-flirting, and is instantly classified as a creepy predator who won’t take no for an answer, and will ruin the LWs professional reputation once she officially rejects him.

        (and I write this comment as a woman who is married to someone I met at work- so I dunno, maybe I am biased!)

        1. Detective Amy Santiago*

          Probably because so many of us have seen this kind of situation escalate quickly in the past.

          Sure, it’s possible that this guy is not a jerk and will back off once the OP makes it clear she isn’t interested, but it’s also possible that he’s not and there’s nothing wrong with cautioning OP about that.

      2. Snark*

        And now LW has posted here disclosing that the guy has a live-in girlfriend, so I retract everything I posted here, at least as applies to this situation.

        1. Health Insurance Nerd*

          Whoa- just saw that. I’ll retract my comment as it applies to this letter, but I still do feel like the tendency to immediately jump to the worst possible conclusion about who someone is does apply in so many of these cases. I think a small part of me still wants to believe that most people are good (even though I’m continually proven wrong!).

          1. Jennifer Thneed*

            I think that most people ARE good, by their own estimation. It’s tricky to learn to see your own behavior from the outside and realize that someone else might have a different and equally valid opinion. (And then to realize that their opinion might be more valid than yours in a certain setting – that’s a pretty major epiphany. And can lead to shame, which can lead to doubling-down, sadly.)

            So. It’s tricky. I also think it’s a basic skill of adulthood. (I *also* think it’s related to how most people can’t edit their own writing. Because they can’t stop being aware of what they know well, and just read it as a stranger would. But I know I’m biased here.)

          2. Oranges*

            It’s not that. Most people are good. But when that happens usually those people don’t write into advice columns. They do the awkward dance and it’s all… awkwardy but they get over it.

            Usually LWs are people who can see something is “off” and the commentariate (is that even a word?) is responding to that. We can see the sea of little red flags that we’ve had to.

            Just like I would believe a PoC if they told me this cop I was interacting with was a racist even though I DIDN”T SEE IT when I was talking to the cop. I would believe they’ve had more experience in picking up the cues because they’ve had to. And if it was a chorus of them? Why would I even try to doubt?

            Please believe women when we say “Possible Creeper”.

            1. Oranges*

              Sorry, didn’t see you were female HIN. I’m gonna guess you’ve not run across many creepers who acted like this? Or that this is normal operating procedure where you are? Because my spidey sense was tingling. And you know what, even now I might be wrong and he might be an awkward idiot.

              But… I don’t think so based upon both the fact that I can read situations very well (Yay hypervigilence!) and multiple other women are saying the same thing.

  16. Granger*

    He’s definitely hitting on you and he’s definitely not getting the polite messages. It’s super awkward, but HE is the one making it awkward. He KNOWS you don’t want this – these exchanges are clear, you are politely rebuffing him. As someone his age who had this happen at your age, my next step (with my life experience now!) would be to send a kind but firm message to allow him to back out of this gracefully. No more hinting.

    This might get push back from him – “Oh you’re misinterpreting me”, “Oh I didn’t mean it like that”, “Oh you’re so full of yourself, I wasn’t even.” These responses all mean he’s not respecting you and he isn’t safe to be around. Anything that means “message received and understood” is a good sign.

    I would also like to get this on the record somehow – after doing this, perhaps a quick email to your boss saying “heads up, this happened, I was uncomfortable and told him so clearly, I’ll let you know if anything untoward happens.” She doesn’t need to do anything, but you’ve laid the potential sexual harassment out for her so she can protect you and the organisation just in case.

    1. TootsNYC*

      “he’s definitely not getting the polite messages”

      I would say he’s definitely trying to not hear those messages.

  17. Murphy*

    It definitely sounds like he’s hitting you, and purposely trying to keep it vague. Like he’s gauging your reactions to see if you’re interested, so he doesn’t have to come right out and say it.

  18. Akcipitrokulo*

    Yeah, he’s leading up to asking you out… he’s trying to find out where the lines are with you. It’s doing both of you a favour to let him – nicely – know where they are.

    Being honest will either mean he’s a bit disappointed, gets over it and goes back to being a co-worker with whom you get on well (which is probable), or he doesn’t accept your lines, in which case HR is perfectly reasonable as he’s not being a decent person.

    1. Akcipitrokulo*

      To be clear… nice does not mean indirect. Nice means assuming no bad intentions and politely and *firmly* stating your lines.

  19. Observer*

    OP, please follow Alison’s advice. He is DEFINITELY crossing a line here.

    Don’t use softening language. Do be clear, even if it feels rude. And DO NOT invite him out again, even to events / meetings with colleagues. Either he is clueless and will misunderstand. Or he knows what he is doing and is going to use this as an excuse. Either way, you don’t owe him any invitations, and you should not give him any chances to misunderstand or “misunderstand”. Also, don’t share your plans with him. “What are you doing this evening?” either gets no response or “I have plans.” If he pushes (and make no mistake, it’s pushing), and asks “What?” “Oh, stuff” or something vague like that. If this stuff keeps up, please share that with the higher ups.

    If you are right that he has a future with the association, this is ESPECIALLY important. Either he needs to learn that he cannot do this stuff, or he needs to NOT progress. I know that you don’t want to “ruin his career”. But, if he’s doing this stuff and won’t stop, his career NEEDS to be stopped. Because the higher up the ladder he goes the more opportunities he has, and greater the abuse he will commit, unless he stops NOW. This is not minor stuff.

    Please keep in mind that this is NOT YOU “ruining his career”. If this happens it will be HE that ruined his career.

    1. Snark*

      I agree with basically everything you’re saying, right up until you insinuate that this is abusive behavior. And I think it’s always best to err on the right side of that line, but I really don’t see how he’s being flagrantly transgressive here.

      1. Observer*

        I said it’s abusive if he pushes back and doesn’t take no for an answer. And, IF he won’t take no for an answer, he needs to be stopped. Either by teaching him an important lesson (ie this is NOT ok) or by stopping his progression.

          1. Snark*

            And lo! The guy is actually a shit and has a live-in GF, so never mind my benefit of the doubt. Observer, your instincts were dead-on, and I totally concede.

            1. MsSolo*

              I think ti’s kinda interesting that him having a live in girlfriend removes your ability to give him benefit of the doubt. Like, even if he’s throwing in the plausible deniability to defend himself from the girlfriend, instead of rejection, he’s still doing it because his priority is getting what he wants with the minimum of risk, and isn’t taking into account what either woman wants. He doesn’t hear “no”s he doesn’t want to hear, and arranges his life so that he hears the fewest “no”s possible – that’s an issue whether he’s single, coupled, poly or just interacting with other humans in general. I think the people who were seeing red flags aren’t surprised that he’s in a relationship, but it doesn’t change the colour of those flags.

    2. TootsNYC*

      Actually, if he doesn’t get the message that this is inappropriate, and he needs to stop, then the ASSOCIATION will be harmed.

      It’s not about his career.
      And that’s why I think you should bring it up to your managers, and do so in the context of Harvey Weinstein and others, and the fallout that the organizations are experiencing because they didn’t deal with that problem early on.

      Point out that this guy is skirting close to the line, and that there is still time to stop him from creating trouble for the organization. You’re the canary in the coal mine, and you’re happy to leave it at that, but for the sake of the organization, it’s important that they heed the warning. And it will benefit him as well.
      Because if he learns, great. If he doesn’t, they can prevent his problem from becoming THEIR problem.

      1. Observer*

        Which is an additional reason why the OP shouldn’t feel like she needs to worry about his future and career.

  20. whatsinaname*

    He’s interested, but it also isn’t clear (to him) that’s she’s not (yet). I agree that all that’s probably needed is a quick “hey I’m sorry if you got the wrong idea, but I want to keep things professional” type text, if he even texts her again since it seems to have been a few weeks without contact. It definitely needs to be nipped in the bud if she’s not interested, but I don’t think he’s completely stepped outside the bounds (since people do actually end up befriending or romantically involved with coworkers/business associates all the time in a non-problematic non-sexual harassment type of way), he’s just been testing the waters and needs a clear no. And then of course if that doesn’t stop it, it should be escalated…but I don’t get the impression Jim is a bad guy, just needs a clearer message.

  21. LoV*

    Speaking as a man, I think that a direct approach (#2) is best, it’s also more fair to the guy too. Sure, getting rejected sucks but it’s better to know. You sulk about it for a bit and then get over it.

    Also, I wouldn’t blame any guy for being indirect. One, it’s a good way to get to know someone to see if you do want to date them or if you’d be a good match. Two, asking someone out is a social risk and it makes sense to see if there is anything there first before risking directly asking someone out.

    In any case, good luck to the OP.

        1. LoV*

          Of course it’s ok for her to be indirect if that’s what she wants, but there’s a risk he might not get the hint.

          I’m not saying she was wrong in her initial responses at all. However considering the situation and what the OP wants to happen, being direct now seems like the best course of action.

          1. Katie the Fed*

            There’s also a risk that he’ll deny being interested in her, accuse her of being stuck up and self centered, and behave like an asshole.

    2. LW*

      I guess the other part that I didn’t mention and I realize it’s a small thing but, he had previously introduced me to his live-in gf, and had brought her up then as well. So maybe that put another line there in my mind, that made me question the interaction.

      2. Snark*

        ………….that is a very much not-small thing, to the point that I now wish I were able to delete about 80% of my posts in this thread. That is, in fact, quite the big thing, and it would have changed Alison’s answer and a lot of responses, like mine, that tended to give him the benefit of the doubt.

        1. Andy*

          this is huge. he is terrible. you must stay away from this person I think and protect yourself professionally.

        3. O*

          Yeah. I think work power dynamic + age power dynamic + he’s attempting to cheat on his partner punt this into the Tell HR + Tell The VP category. Not just to protect you and protect others you work with and protect the organization, but this is probably not the character of person that the organization wants going far for them.

          2. Alice*

            Wait, would you feel like you had to go to HR and the VP if you discovered that someone else in your office was cheating or not exclusive with their partner?

            I mean, by all means, if OP tells him “From now on let’s keep our relationship professional only” and he reacts any way that’s not professional, sure, go to HR. But I don’t want to work somewhere where my boss and HR are interested in cheating on partners.

            1. TootsNYC*

              it’s not that he’s cheating.
              It’s that he’s trying to create a MUCH more intimate relationship with someone who doesn’t have the same ability to push back.

        4. LW*

          I say small thing, because previously bringing up a gf, I’ve gotten the response of, “well it’s not a wife and people push those lines all the time.”

          4. KHB*

            Whether she’s his girlfriend or his wife, some people have relationships that are openly non-monogamous. And other people are cheating cheaters who cheat. I don’t think you need to concern yourself with how he conducts himself in his other relationship(s) – just with making sure that your own relationship with him stays as professional as you want it to be. I think most of the advice you’ve gotten here still works.

            1. Elizabeth H.*

              Oh yeah! As someone who has been online dating recently being openly non-monogamous seems more popular these days, I forgot about that option. It doesn’t change the advice at all though. Agree that there is no need to speculate or concern yourself w/his other relationships.

            2. O*

              This is not the behavior of someone who is openly *and ethically* non-monogamous, regardless of what agreements might or might not be with his girlfriend.

              Telling someone you have a live-in girlfriend and then hitting on them, unless you have already (truthfully) told them you are in an open relationship, is not cool.

              1. KHB*

                I don’t necessarily disagree, but the question here isn’t “How cool is Jim?” but rather “What should the LW do next?” And I still think it makes sense for her to give him one crystal-clear “Please stop – this is not what I want” before escalating. I’m not sure what HR can reasonably do about the situation as it stands right now.

            3. O*

              Ah, meant to elaborate — I meant that his other relationship became relevant *to LW* and *to the situation* when he named it and then hit on LW. He’s basically asking her to be a party to cheating, which is super-unethical, and also unquestionably inappropriate in a work setting. Whereas without that factor, there’s a lot more fuzziness to the situation.

              1. Samalam*

                Honestly I think Beyond just weather someone’s personal relationships and how they conduct them are the purview of HR, we have to consider whether or not HR would actually consider their interaction thus far to be morally unscrupulous— without a clear statement of disinterest/desire to keep things professional. It is my opinion that for her own protection, OP still needs to take that step before reporting the situation to HR, because I don’t think the company is going to view this as behavior that is worthy of anything more than a warning unless there’s proof he has gone against a clear statement of disinterest.

          5. Elizabeth H.*

            I can see that being potentially relevant if it wasn’t a serious relationship but it is. Even if you were really into hanging out with him as a friend, or even if you were interested in him also, and would have wanted to go watch TV or get drinks or something again, it’s not appropriate to invite a woman for a drink/to your place at night/express interest in one-on-one hangout unless you are already really good platonic friends. So yes, with the information that he’s in a serious relationship, and you and he are (friendly-ish) colleagues but not friends, his invitations to hangout one-on-one, late at night, at the place he’s staying are obviously inappropriate. Because this demonstrates his willingness to be inappropriate (which I wasn’t convinced his overtures were, before) I would speculate that he would be less likely than I previously thought to stop texting you in response to soft rejection, and that it’d probably be good to practice a more direct response like “Hey, I’m not up for hanging out just the two of us and I want to keep our interactions in the professional context.” which is still pretty soft but says what you mean. If he asks you why or pesters you about it then you can be even more direct and say that you want to keep it professional and please don’t text you again.

            1. Elizabeth H.*

              Sorry, I should have been clearer, “it’s not appropriate to invite a woman for a drink/to your place at night/one-on-one datelike hangout unless you are already really good platonic friends when you ARE WORK COLLEAGUES and didn’t meet in a dating context.”

          6. Rosie*

            … whoever said that to you is garbage and should be ashamed of themselves. His partner is not a small thing. Go to HR. This man is not your friend and never was, but you didn’t know that at first. With this text evidence, now you do. You haven’t done anything wrong here. He has.

            1. Elizabeth H.*

              That’s incredibly harsh and such a huge generalization. People break up all the time, including when they meet someone they are more interested in. Anyway, the OP, and we, are not in the position of speculating on this guy’s relationship and morals, and while quite arguably being creepy, I don’t think Jim has done anything HR-worthy. If he harasses her, then yes, but his actions haven’t risen to the level of harassment, completely regardless of what we or anyone else thinks about the ethics of hitting on women when you are in a serious relationship.

              1. Natalie*

                Pretty sure Rosie means whoever had the “not a wife” line. Suggesting that it’s okay to pursue someone in a relationship just because that relationship is not marriage IS garbage and that person should be ashamed of themselves.

              2. neverjaunty*

                People divorce all the time, including when they meet someone they are more interested in.

                The sentiment that’s bothering people is ‘who cares if you betray your partner’s trust, it’s not like there’s paperwork involved’.

          7. Malibu Stacey*

            Apparently those people have never got an angry facebook at 12:30 AM from the live-in GF because her boyfriend asked YOU out.

          8. Snark*

            Yeah, creepy, icky, bad people push those lines all the time, I guess, but that doesn’t make it any less of a reasonable deal-breaker and indictment of his character. That makes it WORSE.

          9. JulieBulie*

            “people push those lines all the time”
            I.e., some people do not respect the boundaries of others… which is really what this letter is all about.

          10. Natalie*

            Uh… dafuq? That ain’t normal at all. Whomever is giving you that response is 100% not someone you should get advice from or ever, ever date unless you like being cheated on.

          11. GG Two shoes*

            people say that? Gross.

            LW, I’m glad you commented. I work in, I’m guessing, a similar field (we are an assn. with member, bi-annual conferences/meetings, etc.). I can completely see how if a member came to me with these things I would treat if differently than, say, a coworker or client. I also know as a young gal, that finding other young folks to hang out with at these meetings can be hard- at least in my experience. I can see why you would be hesitant to accidentally burn a bridge. Saying all that, I think Allison’s advice is sound and you would be right to say her two talking points above. Best of luck!

          12. Matilda Jefferies*

            Ugh, I’m Ugh, I’m so sorry that anyone said that to you. I have to wonder who that person was (Jim himself, maybe?), and what their actual agenda was, because someone hitting on you when they have a live-in partner is really not a “small thing.” It’s a BFD, regardless of whether they’re married or not.

            So basically, anyone who told you that it doesn’t matter that he’s trying to get together with you even though he has a girlfriend, is lying. If it was Jim who said this, his motives are pretty obvious, and he can go to hell. If it was someone else, it’s likely that they’re trying to excuse their own behaviour in this area.

            Either way, I’m sorry that people have tried to shut you down when you have expressed concerns like this. Whoever those people are, and however they fit into your life, please know that they are not to be trusted. Your concerns are valid, and you were right to bring them up.

          13. Oranges*

            Listen, if you want to sleep with other people besides your GF that’s great… as long as she knows. Informed consent is… kinda important.

            To me it’s like a someone asking “Is there wheat in this cake”. You wouldn’t lie to them because that would be taking away their agency.

            And you know, maybe the person is a celiac(?) and really wants the heck out of that cake and is willing (and able) to go through the fun of whatever reaction they have to gluten. Or maybe they’re allergic and would go into scary non-breathing times. Or maybe they just are watching how much flour they consume for an experiment. It doesn’t matter. What matters is me giving them the info so THEY CAN DECIDE.

            When you lie* then you are taking away knowledge they need. And usually for selfish reasons.

            *Sometimes you need to lie because safety, society, etc. This is not one of those times.

          14. Laura*

            LW: people who give you the “it’s not a wife” line are making your life very easy, because now you know you can’t trust them at all.

          15. Tealeaves*

            Omg he’s gaslighting you and you don’t even know. Now he’s created so much ambiguity that you keep questioning yourself about whether you’re overreacting or being oversensitive. “He’s just like that. It’s a culture clash. He doesn’t mean it.” YES HE MEANS IT.

        5. LBK*

          I gotta say, I don’t understand how this is such a big change in the situation for you…when you were willing to give him the benefit of the doubt before, was it because you thought there was a chance he might genuinely just want to be friends? Or because you thought he might genuinely be completely oblivious to how human interaction usually works?

          1. medium of ballpoint*

            Agreed. I’m seeing a lot of commenters saying “I thought he was just another Bumbling Clueless Guy, in which case OP is overreacting and should just be clear with him,” and after finding out about the girlfriend saying, “Okay, this isn’t Bumbling Clueless Guy, this is Deliberately Trying to Cheat Guy, and that changes everything!” But I think a lot of (presumably) women, all along, were saying, “He isn’t Bumbling Clueless Guy and I’m not sure exactly what kind of guy he is, but he’s definitely some variation on Sketchy, Creepy Guy.” Trying to Cheat Guy is a subcategory of Sketchy, Creepy Guy and *that’s what people were picking up on along.* I hope folks will keep that in mind the next time they run into a situation like this and consider trusting the majority intuition.

          2. Myrin*

            I feel like I’m missing an inside joke (only it’s not a joke) tbh because I don’t get how a girlfriend’s existence is relevant here at all.
            (If anything, it could lead people to give this guy more of a benefit of the doubt, saying that if he has a gf surely he can’t have intentions towards anyone else, which is a line of thinking I’m firmly against but I see relatively often.)

            1. LBK*

              That is exactly my thought – I’m very confused how people who were seeing ambiguity to his behavior before think being unavailable makes trying to hang out ostensibly as friends *more* creepy, not less (which it theoretically should, if we are giving the benefit of the doubt to this guy and taking him at his word).

              1. alana*

                Because the ambiguity wasn’t whether he wanted to be friends or more than friends. It was whether he was just missing signals (bad) or deliberately missing them (very, very bad). The baseline assumption was that he wanted to date her and was using a plausible-deniability approach — “Netflix and chill” is a cliche for a reason — not that she was genuinely misinterpreting platonic interest.

                The things he was doing were absolutely flirtatious and probably (given the age gap, the professional context, and the refusal to take no for an answer) creepy, and knowing he has a GF eliminates the “probably.”

            2. Ask a Manager* Post author

              I agree. The existence of the girlfriend doesn’t change the advice for the OP. It makes the guy look more like a jerk, but it’s not any kind of additional evidence that he’s hitting on her (he already clearly was).

            3. JamieS*

              Agreed. Maybe it’s my own jadedness speaking but in situations where someone on the road is suspected to be hitting on a colleague (or anyone really) my assumption is they’re looking for some road nooky. Having a serious romantic partner waiting at home doesn’t change that. Now if it was discovered Jim had a live-in boyfriend that might change my viewpoint.

      3. Birch*

        This is just another plausible deniability tactic. In your letter, every time he suggested something that could be construed as more than “just friends,” he put this cute little parenthesis in to make sure you knew he was thinking you could have taken it that way, and to reassure you of his intentions. He’s been very careful. Did he ask if you wanted to hang out in public or do an activity you might be interested in? Because when guys actually want you to feel safe and to make friends, they don’t ask you to drink beer/tequila in their room.

      5. IN A FRIGGIN' RELATIONSHIP?!?*

        Yeah, I feel like that changes A LOT of things in regards to how we’re interpreting both your behavior and his behavior (yours = much more easy to identify with; his = ewwwww icky icky icky). Maybe Alison should add a little clarification to the original post?

      6. paul*

        and this is why context matters in judging actions. This takes it from (to me) tone deaf but very possibly entirely innocent to yikes.

      7. Princess Consuela Banana Hammock*

        OP, this guy is making my blood boil. He is being objectively creepy. Your gut isn’t wrong on this.

      8. Akcipitrokulo*

        Yeah, that takes it from possibly innocent testing waters to being a creep.

        TBH it’s the same advice… politely and firmly draw your lines followed by chat to HR if he doesn’t back off… but internal dialogue can be very different!

        It’s also more likely he will ignore your line – which is harassment and HR should know.

        One “I want to have only a professional relationship” is plenty for him to get the message and back off.

        1. Snark*

          I feel like as soon as I read that, it was like that picture where it looks like a young girl one moment and an old woman the next. It’s like, oh. OH.

      10. LeisureSuitLarry*

        LW, if you think this is a “small thing” I would really like to know what you think is a big thing in this situation. That’s some pertinent information to leave out and it changes a whole lot of the internet jury’s mind on Jim.

      12. alana*

        Yes, that’s a big deal, and here’s why. If he weren’t in a committed relationship, the situation as explained sounds like a pretty run-of-the-mill awkward scenario when you meet someone outside of an explicit dating-centric context. You hung out, he had a good time, he wanted to hang out/ do more, you did not. He’s definitely been immature and arguably unprofessional — and he should have picked up on your soft no if he was going to do that kind of plausible deniability approach — but jury’s out on how much of a creep he is until you actually say, hey, I’m not interested.

        The ages of the people involved were one red flag here — if you were two 24-year-olds, I’d be much more likely to buy that kind of “hey, wanna hang out?” plausible deniability approach, but by your mid-30s you should really know how to ask someone out for a drink, and that’s a fairly large age gap given your ages. (“Mid-30s” isn’t super precise — as a 30-year-old, I’d find a 31- or 32-year-old dating a 24-year-old to be maybe a little unusual but not all that weird. A 37-year-old and a 24-year-old? That raises my eyebrows hard.)

        A second red flag was the professional power dynamic — you don’t work in the same office and he’s not your boss, so he might have thought he wasn’t doing anything wrong. But any time you’re not on exactly the same line as the org chart, there’s a power dynamic to keep in mind, and as the more powerful person, it’s his responsibility to be sensitive to it and make sure he’s not making you uncomfortable.

        So. Older, more established guy hitting on younger, less established woman in a professional setting and not taking no for an answer — but you’re maybe 10 years apart, he’s not your boss, you haven’t said a flat no. There’s a tiny veneer of plausible deniability.

        But older, more established guy WITH A PARTNER hitting on a younger, less established woman and not taking no for an answer? Nope. This is not a dude who just lacks emotional intelligence or situational awareness. This is creepster territory. He is not genuinely interested in finding somebody to date (or mess around with), met someone he liked in a work setting, and is failing to get the message. He is someone who is out to push boundaries and act inappropriately. He no longer gets the benefit of the doubt.

        Tell him, if he texts you again, that you’re not interested. Screenshot and save the texts. Tell your boss and tell HR, and tell them in a way that leaves a paper trail. You are not overreacting, you are not full of yourself, you are smart enough to know bad news and a forest of red flags when you see them approaching.

    3. lawyer*

      Yeah, I have been in this position so many times, and I understand why men use the indirect approach, but then the woman bears the burden of being direct to shut it down. If men are going to use the indirect approach, they need to accept an indirect refusal, and err on the side of assuming disinterest.

      Also, I cannot tell you how many times I’ve gotten a really nasty negative response when I did cut through the soft pedaling and say, “hey, I’m having fun hanging out, but I see you as a friend – not a potential boyfriend – and want to make sure we’re on the same page.” I *wish* what I’d mostly experienced was men sulking. Instead I’ve gotten everything from the tearful multiple texts/calls/emails for weeks response to the calling-me-a-slut (because I *don’t* want to sleep with you…the lack of logic burns) to the showing-up-outside-my-classes response. And I think what I’ve experienced has been less severe than many women.

      1. KHB*

        “the calling-me-a-slut (because I *don’t* want to sleep with you…the lack of logic burns)”

        I’ve gotten this too, and after a lot of thought, I think I understand it. It’s wrapped up in the virgin/wh-re dichotomy – either a woman is pure as the driven snow or else she owes her body to any man who expresses a passing interest in her. If you’re a sexual being at all (as most of us are), you’re squarely in the latter category, which means you’ve done him a grave injustice by not acquiescing to his demands.

        This is, of course, complete horsepuckey. But if you’re looking for logic, there it is.

  22. i'maskingamanager*

    Up to now it has been a misunderstood communication between them. I don’t think what the guy is doing is any different than lots of other guys do when they are interested in somebody and trying to figure out if that person is interested in them. The situation has now gotten to the point that the OP is uncomfortable and doesn’t want it to continue. So it’s time for the OP to make herself clear. I don’t think HR needs to get involved unless Jim doesn’t stop after being told to. Then it is an HR issue.

  23. FirstTimeCaller*

    For me, this line was the most disturbing: “Claimed he was super tired and didn’t realize what he said until that morning.” Is he trying to say he blacked out and didn’t remember the text exchange? Or he knew he had crossed a line, was embarrassed, and tried the age- old excuse “oh I was super tired”. Either way, his behavior is odd. Asking you to change your flight so you could hang and watch the baseball game? Mmmmm no thanks. Good luck! Please keep us updated!

  24. boop the first*

    If only people would stop looking for romantic partners at the workplace.
    And while we’re at it, let’s leave alone strangers who are trapped on public transit.
    And strangers who are trapped at THEIR customer-facing workplaces.

    1. MilkMoon (UK)*

      Oh god, the last two especially. The amount of men who take advantage of women in customer service rolls (f2f and on the phone) is staggering. I’ve spent my entire working life having to ‘laugh off’ disgusting men using the fact I’m a captive and fire-able audience to massage their egos.

      1. CorruptedbyCoffee*

        I work in a front-facing position and deal with people from all walks of life. The other day, a man at least 20 years older than I am called me “honey.” I was irritated, but he was older and I was at work, and he was the customer. So, I told him “have a nice day,” and turned away. He actually leaned over the counter and said “you’ll notice I called you honey. Because I love women.”

        I replied “actually, I’d prefer my name.”

        He replied “if my wife was standing here, I’d still call you honey, right in front of her. Because I love women. I love ALL women.”

        It’s amazing what men say to customer service workers.

        1. MilkMoon (UK)*

          Ew, I’m sorry :( Unfortunately I’m sure you have many more tales to tell, as I do. When I worked in retail there was a regular customer who used to lean over the counter and try to comb our (mine and s female colleague’s) hair -_____-

          I’m glad I’m on the other end of a phone these days, at least I can grimace all I like and hang-up If needs be.

    2. A.*

      Places I’ve been hit on…at the site of a car accident when I was t-boned by a drunk driver, while said drunk driver was being cut out of the car, in a hospital’s ICU unit while visiting a sick family member, during an interview by the interviewer, at the courthouse by a defendant wearing handcuff, by a security guard at my building and the list goes on and on. It is especially tricky when it is someone you have to see on a regular basis (such as a coworker or supervisor) but it is never appreciated.

      1. MilkMoon (UK)*

        & then women get called ‘bitches’ as we get older because we grow tired of this rubbish and stop ‘playing nicely’.

  25. Boo*

    I’ve only recently as a woman in my 30s discovered the joy of realising I don’t have to respond to iffy emails/texts. It’s a great non-confrontational way of getting the message across that you will only take part in professional conversations. Sympathies, OP – I had a lot of this stuff in my teens/20s and it was always so difficult putting a lot of emotional labour into crafting professional yet direct yet not rude/presumptuous responses to plausibly deniable come-ons, particularly as I’m naturally a pretty blunt person. Such a waste of time.

  26. Myrin*

    OP, if I’m reading this correctly, you only ever see Jim at these meetings, right? (About) four times a year, is that correct? And he has only ever reached out to you in the context of these meetings? (As in, when you were actually physically close due to a meeting happening.)

    I’m asking this because it seems to me like he is a bit of an “opportunity flirter”, meaning you’re on his mind when you’ve just seen each other anyway but not much beyond that. That is a good thing! Because of that, it should be quite easy to employ Alison’s #1, just become slower and slower at responding – if he hasn’t actually contacted you in the months between your meetings, I can see this issue resolving itself if you become more unavailabe.

  27. Nita*

    Yes, he’s hitting on you. It does look like there were some crossed wires though. To some people, being invited to a social event when not strictly required / texting about anything on a personal phone / texting about non-work things suggests personal interest. Clearly to you, these things suggest nothing beyond being polite. You’ve got to be clear with him that you are not romantically interested in him and did not mean to come across that way. If he’s a decent human being, he will probably be a bit embarrassed, and will stop pestering you. If he does not get the hint, there is always HR… and you should probably avoid inviting him anywhere that’s optional.

  28. Student*

    OP – I advocate for the clear, harder reject because it means things will cool off faster.

    However, if you can’t push yourself to do that in the face of his plausible-deniability-solicitation, then there is a tried and true method for getting a very clear message to him: the fake boyfriend. You shouldn’t have to resort to this, but it is very effective at solving exactly this problem.

    He asks you out for drinks on business travel? “Can’t, busy chatting with my boyfriend, hope you have fun though!”

    He invites you for evening plans? “No thanks, I’m looking forward to catching up with my boyfriend.”

    He says something flirty? Bring up your boyfriend and how great or interesting he is. The topic change does not need to be subtle.

    This is tried-and-true signaling for adults on business travel who suspect they are getting hit on, but it’s been left a little ambiguous and you still have to work with these people. Sending the message of “I have a significant other that is the joy of my life,” need not be 100% honest to successfully convey to your business partner that you are not open to anything sexual with the business partner. Works reasonably well for men and women alike.

    1. caryatis*

      I don’t agree. OP clearly needs to practice the skill of saying no, and saying no without reference to another man.

        1. NorCalPM*

          He has clearly asked a question, though. Come over and watch movies in my room, on the couch (where you can spend the night. Seriously? LOL). Reschedule your flight to watch a baseball game with me (Seriously? LOL).

          To both of those questions, my answer would be short and sweet. “No thanks.” Same answer to all such questions. And then add the line about wanting to keep the relationship professional. That should put paid to his nonsense. If it doesn’t, then escalate.

      2. OlympiasEpiriot*

        Absolutely. Don’t perpetuate the problem with the another-man’s-property thing.

        He should listen to her because of her agency over her time.

        1. FirstTimeCaller*

          Yeah, I’m going to respectfully disagree with the “I have a boyfriend” line. It deflects the issue that SHE isn’t interested, and her wishes should be listened to. Also, she shouldn’t have to lie to get him to back off. A straightforward approach is always better then the dance around/false excuses.

          1. Student*

            I agree it’s not ideal from a feminist empowerment angle.

            However, this isn’t exactly a watershed feminist empowerment moment. He’s not taking her hints.

            She, of her own agency, doesn’t sound keen on outright, directly rejecting him. I understand her thinking here. There is a real cost to her being direct when he isn’t, and we shouldn’t ignore that.

            From personal experience, I’ve found that guys don’t always take even a very direct rejection seriously or graciously. They usually back off much more often and pleasantly if I present myself as lovingly attached to some other guy – as “happily taken property”. Again, that’s deeply non-ideal from a feminist standpoint. However, in my opinion, that actual problem is squarely on the generic-men’s side: if a lower proportion of men responded like utter glassbowls to an impersonal and direct rejection, I’d use it more often. It doesn’t do me any actual harm to present myself, truly or falsely, as happily coupled to get a guy to stop hitting on me – I know it is a lie, and I can deploy it selectively to protect myself as desired and dispense with it if I am actually interested in someone.

            1. OlympiasEpiriot*

              …and then one day you get to deal with a really insistent guy who notices you are always w/o said imaginary boyfriend and starts bugging you about that.

              Just a whole lot easier in the long run to be consistent and make guys take a no when you mean no.

              1. LBK*

                But I think the point is that you can’t force anyone to take no for an answer, so sometimes to get out of a situation, you have to give the version of no that’s going to have the best chance of getting them to leave you alone.

                For a colleague that you’ll continue to see, the “I’m taken” lie probably isn’t the best option because it’s a hard illusion to maintain over time, and even if it’s true, there’s more likelihood that the guy you said it to will still be around if at some point that relationship ends. But a rando at a bar that you’ll probably never see again? I think getting him off your back by saying you’re taken is perfectly fine. I’d feel much more comfortable saying that than telling a stranger whose behavior you can’t predict to their face that you’re not interested.

                1. NorCalPM*

                  Well, maybe you can’t. Although I’ve never had any problem – except for one psycho stalker – not stop bugging me when I made it clear, in a polite and professional way, that they needed to stop.

                  But you know who can? HR can. The association can. Sounds as if this guy has something to lose. Think he wants to lose it? I’ll bet he doesn’t. Unless the guy is unhinged, he can be made to see the light.

                2. OlympiasEpiriot*

                  Alright, ymmv. Personally, the rando at the bar is even a bigger problem. Then I get the “Well, where is he, why are you here without him?”

                  And then, what if I flirt with a guy I do like at same bar? Unless that ‘rando’ left, there’s an opportunity for a problem. Then what about that scene? Now I’ve got one known a$$hole who I have lied to, one unknown quantity who maybe I wanted to play with, and a whole bar-full of unknowns who will be treated to the show.

                  My personal experience is that it doesn’t consistently have the wanted effect and I’m better off being straightforward.

                3. Tiny Soprano*

                  I had a friend at uni who started wearing a ring on her wedding finger simply because it was the easiest way for her to safely ward off the endless stream of creepers.

    2. JulieBulie*

      Considering that Jim has a GF, I don’t think OP’s theoretical BF will make much difference, unless they go out on a double-date.

    4. Tealeaves*

      It won’t work in this context because they have to see each other often. Also, he’s mentioned that he’s open to pushing boundaries. The convo would likely go like this: “Your boyfriend won’t mind.” “Hey, ditch your boyfriend tonight and come hang out with me instead.” The fake boyfriend is just an excuse in the end, like saying you have to walk your imaginary dog every time people ask you out. It’s exhausting to keep up for OP. And because he knows so many people in her association, the lie would quickly unravel.

  29. caryatis*

    He’s definitely hitting on you, but it’s not necessarily wrong to hit on people you work with. OP, say no, much more clearly than you have (I like Alison’s line about using work email), and move on.

  30. chica (not a guy I promise)*

    Sooooo much overthinking here. Why so much angst? Of course he’s interested. He is not getting the subtle hints that OP was just being friendly and is not interested. Just shut him down. Kindly. Don’t answer his texts right away if you don’t want to shut him down directly (later you answer and say, oh I must have missed that text). Or respond by saying you have other plans that night (none of his beezwax what they are). no emoji, no haha, no lol. Next time you are there just be polite & friendly and don’t ask him to an after party. If he asks you to hang out later (on or off his couch, seriously WTH?!? yuck) just say no thanks. Or you can take the direct approach and proactively tell him you think he’s gotten the wrong idea and that you’re not interested in him. He will likely protest that OF COURSE he wasn’t interested in you he was just being friendly!!! (insert eye rolling here). whatever. don’t waste your emotional angst on him. If he doesn’t give up after you have clearly told him you are not interested then that’s when he veers into creepy and you get your boss/HR involved. But seriously, just because a guy is hitting on you that you are not into, doesn’t mean he’s creepy. I guarantee that if you were into this guy, all those lines would have been cute, butterfly-inducing. And who knows, maybe that’s worked for him before? So assume good intentions until he really veers into creepy territory.

  31. OlympiasEpiriot*

    A useful thing for me is that I have as bright a line as possible between work and personal even to the point of having two cellphones. For some this might be onerous; but, I have found it good for me. It also keeps me from making errors that might ultimately be harmless, but could be misconstrued by the wrong people.

    Just a tangentially related hint.

  32. nnn*

    The “thinking too highly of yourself” comment made me think of a response that is useful in some contexts. (OP’s best placed to determine if this would be of use to her):

    “If you keep saying things like that, it might give people the impression that you’re hitting on me. You wouldn’t want them to think you’re that unprofessional!”

  33. Elder Dog*

    Not suggesting doing this, but years and years ago, this would have been a situation where before the next conference where OP would see Jim, she’d borrow her mother’s engagement ring and not say anything to him at all unless he brought it up. It was a subtle move, but also allowed the man in question to save face and dial things back to “only friends” under his own power, thus preserving his ego and the friendly interaction.

    For what it’s worth, I don’t see Jim’s invitations as being terribly creepy, just lonely and he clearly thought the OP was more interested in him than she is. I think a lot of that came from her inviting him to more social events he might not otherwise have been included in. She seemed to be introducing him to her friends. That’s something people who are interested in a romantic relationship often do. He just mis-read what was going on.

    1. Detective Amy Santiago*

      I hate that advice. Women should not have to pretend they are involved with another person in order to maintain their personal boundaries.

      1. Elder Dog*

        The ring thing? That was advice from 50 years ago. Like I said, I wasn’t suggesting it as something LW should consider doing now.

        1. Tiny Soprano*

          But seriously I had a friend who’s done the ring thing in the last ten years. It worked and most importantly, it kept her safe. It’s wrong and gross that many people still take the word of a small piece of jewellery over that of a living human being though, I agree.

          1. Happy*

            Unfortunately, certain types of jobs/ situations make sporting a wedding ring even more likely to get hit on. In my twenties (20+ years ago), I was bartending and a guy looking to cheat would see a married woman as a safer bet to not have problems with later.
            Years later I noticed I got hit on more with a ring than not.
            For whatever reason, nice guys have never been direct with me but creeps still like to creep, directly or indirectly.

    2. Elder Dog*

      Just saw OP’s followup under “LW”. I take it back. It is creepy, and LW needs to be clear the next time he asks her what she’s doing. “What’cha doing?” “Out with friends.” “I’m lonesome. Can I tag along?’ “Sorry, personal friends. Not work related.”

    3. Akcipitrokulo*

      Definitely not a good way of handling it. The situation needs clear and direct boundary drawing, not muddying the waters and feeling as if you’re tricking people.

      Added to that that she should be respected as herslef, not someone’s appendage, and the awkwardness of having to carry on the deception if asked or congratulated…

      All round not a plan!

  34. Janelle*

    Ok so he’s hitting on you. And? So what? Are you, an adult, really in need of advice to just not continue talking to him? I’m really lost as to why this was even posted.

    1. Detective Amy Santiago*

      … this is an unnecessarily harsh comment.

      Women have to be careful how they respond to men who hit on them for a myriad of reasons, especially when the workplace angle adds another layer to the whole thing.

    3. Ask a Manager* Post author

      Hey, this is really harsh and violates the commenting rules. I’m leaving it up because I want to respond to you and I want to leave up the responses of the others who also responded.

      If you don’t understand why this can feel tricky and not straightforward, please read the many comments here explaining exactly that.

    4. FirstTimeCaller*

      Because they work together and they’re professionals. He isn’t just some guy at a bar, they’re colleagues.

    5. Akcipitrokulo*

      Yeah… not OK. You may be in a position where this wouldn’t be an issue for you. That’s great and I’m happy for you (no sarcasm).

      Not everyone is you. This is a perfectly reasonable ask.

    6. Karyn*

      It’s not helpful to suggest that she just stop talking to him. This didn’t happen in a bar where she could just leave and come back a different night when he’s not there. She’s in a workplace environment and will, at the very least, have to see and interact with him in the office on a fairly regular basis. Given the fact that she’s junior and he’s a respected member of the office, I can certainly see why OP needed advice on how to handle this, and perspective as to when to escalate it to HR.

  35. IN A FRIGGIN' RELATIONSHIP?!?*

    OP: I don’t think anyone has said it outright, but there are some vibes here of “you may have been leading him on,” and if you ARE feeling that way, I just want to say: it doesn’t freaking matter. ANYONE is allowed to stop being interested in someone. You don’t need to justify it. You’re dating someone and now want to not date them? Cool, end the relationship. You were testing the waters to see if there was an attraction and now you aren’t attracted? Cool, let’s end the casualness. You wanted to hang out as friends but now don’t see friend potential? Cool, let’s only interact at work.

    I’m trying to say: if you feel like you could’ve/should’ve/ought’ve done something different – it doesn’t matter. You still have the right to change your behavior today or have a difficult conversation right now, and that is TOTALLY OKAY. What you did or didn’t do yesterday does NOT effect what you are allowed to do today. Isn’t that what most of the AAM posts are anyways? “My coworker makes your mom jokes and I laugh because I don’t know what else to do” – okay, ask him to stop making your mom jokes and it DOES NOT MATTER that you laughed at them for the previous month. YOU ARE ALLOWED to change the nuance of the relationship at any point.

    1. NorCalPM*

      Thank you. Couldn’t agree more! I get soooooooooooo sick of variations on the “she was asking for it” line. It’s such a crock.

    2. Matilda Jefferies*

      Yes, yes, yes. Don’t get into a big debate about what you said or did or didn’t say or didn’t do, that led him to think you were interested in him. None of that matters. The point is, you’re not interested in him NOW, and therefore he needs to back off – end of discussion. Good luck, I know this is a tricky one.

    3. Tuna surprise*

      ^^^ THIIIIISSSSS!!!! ^^^^

      I would like this whole comment embroidered on a pillowcase, please and thank you.

      A big pillowcase, big enough to fit over the metaphorical anvil I want to put inside it to whack the creeps who don’t get it.

      Also, this is a great comment and you should feel great about yourself

  36. Bookworm*

    I’m sympathetic, OP. I was in a similar situation when I was 22. I was lucky (nothing bad happened) because of a combination of me being genuinely oblivious + busy trying to sort out my post-college self, I tend to be blunt/honest and he had been made aware that this was not okay/he was already on thin ice for other stuff (also I was not the first). You said you had been with the organization for about a year. Have you made other friends there? Even if you’re not quite ready to speak to a higher-up it may help if you know of a possible ally or at least another person who may have been the target of Jim’s attention.

    In retrospect I didn’t realize/I didn’t know. It wasn’t until I had spoken to someone else who was involved in another incident with him (long story) that helped me put some of his comments into context. At the very least you may find you aren’t alone or have someone in your corner. Good luck. I hope you update us if you can and I hope he backs off.

  37. Snark*

    And so, now that we know from LW that the guy has a live-in girlfriend and he wasn’t being flirty and “hey, live a little” but pushing for her to facilitate his cheating on the road, I find myself rereading the thread and wondering how blistering blue barnacles I gave this smarmy, icky little asshat the benefit of the doubt. What the hell, Snark? I identified with the guy! I got to know my wife when she – a contractor – joined my coworkers and I for a happy hour! I’ve asked a girl who was obviously interested in me to bump back her (no-fee, Southwest airlines) flight to spend the evening together! Let’s not jump to conclu-OH WAIT HAHA HE’S ACTUALLY A GARBAGE PERSON NVM

    In case anybody wonder how these garbage-ass people carve out the social space to do this kind of bullshit, for years and decades on end, this is how. I say this not to self-flagellate – though I will be whipping myself across the shoulders with juniper branches presently – but to point out how even the well-intentioned benefit of reasonable doubt, even by allies, can shelter these garbage-ass dudes, and what a problem that is.

        1. Andy*

          Kind of? I realize that it may seem counterproductive, but if HE can see it he can be it! If my son can see other white dudes speaking sense and see other white dudes listening to women, POC, everyone with respect and responding thoughtfully, and (gasp) acknowledging his misreads, etc. maybe he can learn how to do it without some of the boomeranging I see out of other white americans.
          I support you, Snark.

    3. CaliCali*

      I think honestly any of us who have kind of identified with a work-flirting situation (good or bad) read it a bit through our own lenses. Someone unattached who finds someone attractive and wants to feel out how someone else feels? Not inherently bad. Someone who IS attached who is trying to test the waters? Bad. I’m a woman and I didn’t pick up on it either, but I also tend to err a little too far on the benefit-of-the-doubt giving side overall. And perhaps in an Occam’s-razor type of scenario, I did attribute to awkwardness/hesitancy that which could be explained by creeperdom.

    4. LBK*

      I mean, nice of you to come around now that there’s an additional fact added to the story, but it is a little frustrating that an avalanche of people (mostly women) saying “this is exactly how creepy dudes operate” didn’t convince you. The creepy guy won’t always have a girlfriend that makes the situation more clear; this is the kind of situation women have to navigate all the damn time with no concrete points of rejection like an existing girlfriend to anchor on.

      1. Snark*

        No question. In fairness, I did still think that the subtext was sexual and that a rejection was warranted, but….yeah. What can I say? Sometimes the way a certain scenario is framed makes it hard to reframe, and that’s a cognitive trap we’ve all fallen into.

      2. LizB*

        Agreed. Snark, I love your comments, but (to borrow your optical illusion metaphor from above) when a bunch of women are saying “Based on my experience, this picture shows an old woman, not a young girl,” maybe take that as your cue to reconsider how your own experience is coloring your perspective.

        2. Birch*

          YES, this. I think one of the biggest problems with this era of figuring out how to sort out the actual creepers from the innocent mistakes is that we given men the benefit of the doubt for their intentions (which we have zero knowledge about). Can we try just giving women the benefit of the doubt for the feelings they’re actually telling us?

    5. LeisureSuitLarry*

      Dammit! I was all set to post something about giving the guy the benefit of the doubt, and then I saw this comment.

    6. Health Insurance Nerd*

      You responded to the information provided in the letter, as did I. More details coming to light after the fact changes the entire perspective, but that does not make you wrong for giving him the benefit of the doubt, which is what I did as well.

      More information was disclosed, you adjusted your perspective, and here we are :)

      1. Oranges*

        You responded to the info in the letter as seen through your own life. SO DID WE and you told us our perspective was over-reacting. No, over-reacting would have been calling 911 or going straight to HR after one incident. We were being cautious because he was putting out “creeper signals”.

        See… Snark I’m actually not being that hard on because he said “I was le dumb. My bad” You on the other hand don’t appear to get why you “giving him the benefit of the doubt” over a sea of (mostly)women saying otherwise is a problem.

        Analogy/Story time: you go to Australia and they say: “Mate, snakes that look like this [insert picture here] can be very dangerous. There are some other snakes that can look like it but if you look closely enough you can USUALLY tell the difference.”

        You go out in the field with him and lo and behold there be a snake! You with your very limited knowledge want to give the snake the benefit of the doubt. The guide says “Nah mate, that one looks poisonous”. Would you let someone walk up to it? Would you be concerned if they said it bit them? Would you deny them medical treatment because that snake obvs wasn’t poisonous? Stop covering for the snake, trust the guides with the specialized knowledge.

        I think the story got away from me…. they usually do…

        1. Oranges*

          Sorry. I was pretty angry. You DO have a point that the pendulum can swing the other way too far. Because I’m guilty of that but if a chorus is agreeing with me then yeah. I’m actually jealous that most snake where you live aren’t poisonous but after getting bit so hard twice I have a bias and I’m much more likely to err on “it be dangerous” than not.

          I have researched how predators operate and what the warning signs are so being told that I’m over cautious got under my skin. My bad.

    7. BlueSedum*

      Even if he were single… enjoying an informal and more personal conversation with a woman in a public place, hearing her express regret that she had to leave so soon, and softly suggesting that she change her flight in order to spend more time doing something she already indicated that she wanted to do doesn’t really sound all that comparable to directing someone who isn’t already hanging out with the guy informally and hasn’t indicated she wanted to change her flight so that she could come over to the guy’s room and hang out privately. It’s a bit of a bummer that you only recognized the discrepancy once you discovered he was also a cheater.

    8. Student*

      The key warning signal you missed is when there’s no reciprocity in interactions, such that there is escalating one-sided demands/requests.

      His actions – with no other context – are not necessarily problematic.

      His actions – in the context of her actions and responses – were pretty bad.

      We had this context even before his girlfriend entered into the picture. But you focused on his actions and ignored hers, probably because you identified with his actions a bit and didn’t identify with hers. All the women easily identify with hers and not his, because this happens to pretty much all of us at least once in our lives.

      If somebody you might like asks you to hang out in a group, public setting, you don’t escalate straight to “hang out alone in private with me” unless you are at least a bit of a jerk. You can either attempt to reciprocate equally with a public-group thing, or you can ask for one step up in intimacy at a time, but not more than that – you’d properly escalate for something like a public one-on-one, or a private group event. Going for more than that, private one-on-one, is a lot of intimacy escalation at once, and if you’re going to do it you ought to have your eyes open to rejection.

      Then, when she responds to an invite with disinterest or unavailability that may be indirect rejection or may be plausible real conflict – you don’t escalate intimacy. If you want to ask again, you ask for something that’s back on firm ground you know you’re both comfortable with, so you can reassess whether you’re both interested mutually. He could’ve asked a group of colleagues out for bowling or happy hour or something. He didn’t – he tried for even more intimacy than he’d tried for in his rejected request, by asking her to not only spend one-on-one time with him in private, but also ask her to cancel significant existing plans for him and stating he was thinking about something doing “something dumb”. That right there is a substantial escalation in request for intimacy and in pressure, and it’s wrong and creepy largely because it was a response to her trying to ease off the relationship.

      If someone sees you pulling away and decides to up the stakes, that’s the creepy bit. It’s what makes a creep. It has to do with how the women responded previously and the level of established relationship – not just the man’s actions in a vacuum. We don’t hate and fear being hit on in and of itself, we hate when we pull away and the guy responds by trying to pull us back even harder.

      2. Snark*

        And the thing I’m wondering is….why did I ignore that context? The way you frame it here….I mean, obvious creeper status, even without knowing he’s got a girlfriend and is looking for an NSA side fling. Just obvious. It bears some introspection to figure out why I insisted on filtering that through rosy lenses, even when others weren’t. I mean, I think and hope that I would not miss that context in the situation myself, and that’s not how I operate, but I’m not sure why I misread that situation so badly.

        1. Andy*

          we all see things through the lens of our own experience and you’ve navigated superficially similar waters without being creepy so you were inclined to give this person the benefit of the doubt. try not to be super-bashing on yourself for it.

        2. Tuna surprise*

          To be fair to you and almost everyone else commenting here, our culture glosses over and even romanticises the worst kind of creepy-dude behaviour. A significant number of Hollywood’s so called rom-coms present stuff like legal-definition criminal stalking as ‘Aww, look how much he loves her! He broke into her house, opened all her mail, and actively sabotaged her at work! <3<3<3'

          I mean, when you could turn about 80% of our 'love stories' into horror movies by changing nothing but the backing music on the soundtrack, our culture has a problem that's bigger than any one individual, you know?

          (You've Got Mail, I'm looking at you. That movie creeped me out more effectively than any dozen horror movies I've seen.)

          1. Birch*

            Wait, what’s wrong with You’ve Got Mail? I mean he definitely should have told her who he was after he found out who she was, but at that point he had a lot of respect for her and knew she would hate him if she knew who he was.

        3. Bess*

          Snark, I wrote and deleted a few comments on your yellow flag/red flag thing, because I was interested in your position, but didn’t want to seem like I was looking for an argument or demanding an answer from you.

          So for me, in a dating context (or an unwanted advances at work context), yellow flags don’t exist for me anymore, because I’ve never seen a yellow flag that didn’t pretty quickly advance to a red flag.

          This is weird for me, because I’m typically a Pollyanna type who assumes everyone is BFFs and is looking out for others’ best interests. But maybe that’s made me susceptible enough to this type of thing in the past that now I’m vigilant about it and watch for precursors. And it’s tough because abusive people actually look for and target others who are open to giving the benefit of the doubt, and use that to manipulate them into all kinds of messed up situations.

          Separately, there’s also that weird “misogyny bomb” I’m always watching for, where a woman says something entirely normal and a nearby male EXPLODES about the crap that women do that he’s clearly been ruminating on his whole life and chooses to make you answer for in the moment.
          Example 1: A company-wide party at a previous job arranged an after party at a bar where all the lady servers wore very revealing clothing. I told a group of work acquaintances that this made me uncomfortable, and a dude in the circle I didn’t even know WENT OFF about how women are ridiculous and actually want to dress like *slur* to take advantage of men and men have the right to leer at whoever they want and women want to have their cake and eat it too and I could not possibly object to going to a place like this for a work event, like…he was really mad, and erupted in a work setting about something so reasonable, and I had no idea how to respond.
          Example 2: I was out on a first date with a dude and he got us a round of $4 beers. Later he asked if I wanted another and I said “sure,” and then he shouted at me, out of nowhere, accusing me of “milking it”? And thankfully we were in a public place where I could immediately leave without him following me.
          I have more stories, but the point is it can even happen “at random” and it’s angry and hostile specifically toward you, a woman, on behalf of all men, and it’s frightening. And that leads me to be hyper-vigilant with men I don’t know well (and honestly, in some cases with those I do know) and always be looking for signs they might erupt.

          So it’s sad, but I only see red flags now, particularly when it comes to anything that looks like entitlement or pressuring or repeatedly disregarding someone’s stated preferences until they give a more desired answer.

        4. Student*

          It’s obvious to me.

          You did the same actions (or close enough), but with better results. From the fact that you got better results, I can assume with some safety that the woman’s context response in your case was much more positive.

          You saw that we were condemning his actions, and you responded by defending his actions because they are also your actions.

          It’s really, really difficult to spell out why largely-identical actions are wrong in one context and right in another. I spent entirely too much time on that post trying to spell out what specifically made the guy give off “creepy” vibes to me immediately, but I’m glad I did because now I have a better, more solid frame for these interactions in my own life.

          It’s also sometimes the case that badgering someone to do something they don’t want to do pays off. I hate even writing that out, because the adult in me screams “Just because it works doesn’t make it right.” Now that I’m an old fogy, I realize that it’s the wrong approach to override somebody’s clearly-stated boundary (no matter how “wrong” you think that boundary is). If there’s a positive outcome to be had, you can get there by other means than badgering and ignoring what the person tells you. And it’s better, long-term, to miss that potentially good outcome than to run roughshod over someone. Younger me did not get that.

          Younger me sometimes blatantly ignored what other people wanted when she thought she knew better – and got a good outcome often enough to reinforce this behavior for a very long time. I’m ashamed of many of these, and I ought to be ashamed of all of them. It’s a good thing I’m female, and it’s more due to luck and gender roles than anything else that I never tried this in initiating a romantic relationship. If I’d been a guy, there’s a good chance I would’ve been a creepy, overbearing one. Coming to terms with that realization is painful.

          1. Oranges*

            Amen to that. I was convinced in my early 20’s that relationships would happen if I just wanted them hard enough and went after people (usually my friends). It never did work thank gods. I love that you analyzed it.

            Snark? Everything she said here is truth. You saw this guy through your actions and layered on your subtext; you ignored the subtext we all saw. This is human. You owning your ooops is awesome.

        5. neverjaunty*

          And the thing I’m wondering is….why did I ignore that context?

          Bluntly? Because, as you said, you identified with Jim. You put dudely ‘yeah, I been there’ over listening to women on the other side of someone like Jim. And you didn’t listen to women telling you Jim was a tool because, when we identify with a person, an attack on that person feels a little like an attack on us.

      6. Elizabeth H.*

        If somebody you might like asks you to hang out in a group, public setting, you don’t escalate straight to “hang out alone in private with me” unless you are at least a bit of a jerk. You can either attempt to reciprocate equally with a public-group thing, or you can ask for one step up in intimacy at a time, but not more than that – you’d properly escalate for something like a public one-on-one, or a private group event. Going for more than that, private one-on-one, is a lot of intimacy escalation at once, and if you’re going to do it you ought to have your eyes open to rejection.

        I really disagree! I think this is so overly cautious. If I meet someone at a party and we’re really hitting it off, or if I meet someone in a public social setting and invite him to come along to a party with me, and after that he asks me if I want to come over to his place, I’m not going to think he’s a jerk, but I’m probably going to think he wants to hook up with me. Maybe I want to hook up with him and I’m pleased he asked me. If I don’t want to go, I’d tell him I can’t or would prefer to stay in or whatever. The only difference in the situation is that meeting someone as a work colleague, even if you invite them to a social setting, you’re supposed to have a more distant and strictly professional relationship. That’s why the Jim in this story is more potentially a creep. It DOESN’T make someone inherently a jerk if they invite you to hang out privately one-on-one. It makes you kind of forward, which might be off-putting to some people, but I’ve done it and had it done to me and I’m sure others have too. Not everyone wants to wait three dates or expects that from others, and that’s fine.
        Once again, this situation is different because they are work colleagues and so you are expected to maintain more professional distance. But as a general rule, I don’t think it is invariably morally wrong to be that forward.

    9. NorCalPM*

      It’s tough to understand how the wildebeest feels when you’ve always been the lion (even a very nice, smart, savvy, empathetic lion). You simply don’t develop the same bone-deep instincts. You don’t have to. Most of us do. Sometimes our lives depend on it.

    11. chi type*

      See if this posts since I took the R word out to avoid moderation…

      This is something I see over and over from non-creep guys in my life.
      They’re not predators and they can compare it to a time they did something sorta-kinda similar and a woman was interested. So they have a hard time believing it when women say “no, that guy’s a creep, trust us”. And the guy seems fine to them because of course he hides the creepy around men. So they all start thinking women are just oversensitive and anything they say is going to get them fired and witch-hunted and blah, blah, blah.
      It’s almost cute that they’re so naive that they can’t believe creeps exist. ALMOST CUTE but not really.
      I understand you can’t always see it guys but this is really simple. JUST BELIEVE WOMEN.
      That’s all we are asking of you. That’s what fighting r&*^ culture means.
      Sorry, Snark, to spew that on you. It may have been festering lately. :P

    12. Jennifer Thneed*

      Hey Snark, thank you. I was following your points, and you WERE being super-clear that the guy was doing things wrong, but you were also doing all things other people here have stated so well, about reading your own history into someone else’s actions.

      And then you came here and sat right up front and copped to it all, and showed that you’ve learned a New Thing. And my guess, based entirely on reading your fairly-anonymous writings on this here internet blog, is that you really will absorb this information deeply.

      The next thing you get to do (lucky guy!) is share this new understanding with other men you know. (Signal-boost the women! Do you ever let some kinds of “jokes” slide? You can stop doing that.) So many of us will thank you.

  39. Shadow*

    I know aam read it as he’s not picking up your cues, but have you ever thought he probably thinks you’re not picking up his? That’s the way I read it.

  40. N.J.*

    I know we are giving the OP advice here, so I do agree with Alison’s suggestions on how to address this directly with Jim, but I want to challenge some of the themes I’m seeing emerge in the comments section in regards to the OP’s conduct and responsibility in this situation. It is not the moral responsibility of the person with lesser power in a situation like this to perform all the damn emotional labor and political navigation to turn Jim down and still maintain positive outcomes for everyone. In this situation, as a heterosexual woman being pursued by a heterosexual man, the societal, social and business power dynamic is structured in his favor. He, as the person in the position of privilege, has the moral responsibility to not assume that friendly overtures, (and inviting a work acquaintance out to group events is that and nothing more) are equal to the possibility of romantic interest. Doubly so in a work environment. This theme of saying that the OP hasn’t been clear in her rejections or has been too “soft” or informal with emojis and text speak is a reflection of a widespread societal attitude that the “victim” of some form of harassment or discrimination has to be worthy, according to preset societal norms, to be able to express a grievance.

    It’s the attitude you can see in which members of a minority group often have to take on a certain role to be assumed right when expressing a grievance. For example, if you are a black man shot by the police, you have to be the right kind of black man for what happened to be wrong (not have a criminal history, obedient to police and not defiant etc.) instead of assuming that the police have the moral obligation to approach situations with the utmost care for individual life and a proactive attitude about questioning their own biases. Or when we now see the scores of of allegations of sexual misconduct against entertainment and political figures and question the legitimacy or veracity of complaints because they are being made decades later or weren’t reported etc.

    I’m not saying that the OP’s situation is as grave as the ones above or that anyone in the comments section is consciously trying to belittle her experience, or even that this is a full blown case of what I described, but I wanted to stress that the OP did nothing wrong in giving “soft” rejection signals or in being friendly in the first place-she is stuck in the performative role required by society, which commenters here have touched on, in which women are required to be warm, to be friendly, to be indirect, lest we remind someone that we are people who have value and don’t exist to be ego massagers, friendly team players, nurturing, caring and sex objects for everyone else’s gratification. And now we tell her “be direct”, “since you weren’t direct nothing Jim did has been wrong or creepy”, “assume that he is just hard at picking up social cues” etc.

    Following Alison’s advice and being direct and creating distance are the best courses of action, but let’s not assume that there are no consequences to women when they choose to step outside the box society likes to put them in.

    1. Shadow*

      No one said she did anything wrong by giving hints. Just that it wasn’t working so she should ratchet it up. I would bet most commenters here think she did exactly what she should do as a first step. It’s just time to move up to step 2

      1. LadyKelvin*

        Actually many (maybe not most) commenters were saying the exact opposite, that she should have shut him down immediately and it is her fault that he didn’t pick up on her soft no’s. But I totally agree with N.J. and having been in this situation too many times to count I am glad that N.J. was able to articulate it so much better than I ever could have.

      2. N.J.*

        Well, Blue Eagle’s comment comes to mind, as do the lengthy discussions upthread about whether soft nos are enough, about how some people fear rejection or can’t pick up social cues, whether or not to give this guy the benefit of the doubt, the discussions as to whether using informal texts is too friendly, etc. To me that means folks are replicating albeit the societal views that I discussed above and I think it’s important to call out thos dynamics when we can. It doesn’t mean that anyone who didn’t agree with the OP using soft nos was displaying full blown sexist attitudes or anything, it means that there is an undercurrent here that is shaped by the attitudes I pointed out. I’m certainly not the only one who picked up on this undercurrent. In a frigging relationship picked up on the vibe in their 12:36 comment, medium of ballpoint picked up on it 11:42, for example.

        1. Jules the 3rd*

          +1000 . Thinking about it from this viewpoint, you get to the Creepy Guy vibe without having to get more info like the gf. Thinking like this is one way women avoid Schroedinger’s Harasser.

          OP, welcome to the world of being a woman in a workplace and the emotional labor of how to limit harassment.
          – If he wants to meet privately and socially 1 on 1, he’s hoping for sex. He won’t admit it, and will try to turn it back on you if you call him out directly.
          – If he is more than 5 years older than you, or a customer of your org, or an employee who’s been there longer, or a manger, there’s a power differential.
          – Being strictly professional can be a defense. Soft nos, hard nos, documentation, help are *all* legitimate responses. You get to figure out what works best for you, in your situation.
          – It sucks that you have to do this figuring out.
          – TRUST YOUR GUT. You were RIGHT about this. There’s a reason you were right.

          Alison gives you good advice on what the next level of soft no looks like (slowing responses), what a hard no looks like, etc.

          I’m really blunt so I usually skip the soft no’s, and go straight to, ‘hey, I need this to stay at a professional level’ but I am not you, and you need to do what is most comfortable for you.

    3. Alice*

      Of course she didn’t do anything wrong. But since she asked for advice about what to do next, lots of us are giving it. And since “wait for the guy to start doing his own emotional labor” doesn’t seem like it will get the result OP wants, we’re telling her “be direct, and escalate to management if Jim responds in a creepy way.”

      No one (I hope) is saying “OP was too soft, so it’s her fault.” Some are saying “so far, your responses have been too soft to achieve your goal of having a professional-not-personal relationship with this guy.”

      If the guy in a situation like this writes in, then we will give him advice about being sensitive to his privilege and the pressure that his “target” experiences.

      1. N.J.*

        Yes, direct is best, but it’s important to point out the undercurrents here. The undercurrents may be why she took a “soft” approach in the first place. She’s in a damned if you do, damned if you don’t type of situation. If she approached it with a hard reject from the beginning there was a likelihood she would be penalized in some way for the directness. She approached it “softly” and will now need to be direct to change the situation. I guess the pattern for me is that she did what women are often socialized and forced (by societal expectations and power differentials) to do and there is some risk inherent in now breaking that script and being direct, even though that is the only recourse left and Gould have been ok to do from the start. I wanted to go on record as noting the inherent difficulties and our responsibility as a society to break this programming and to say that the OP didn’t do anything wrong, whether anyone directly called that out or did so obliquely.

        1. Shadow*

          You’re missing the point. How hard or soft you initially respond is a personal thing. It’s like discipline. the first step you take is largely determined by what you feel should get it done. and if your action doesn’t work you take progressively more serious steps. That’s all everyone’s saying

          1. N.J.*

            I reselect that personal style has something to do with this and do agree that direct works, especuakkt if you can’t get results with softer approaches. That doesn’t mean we ignore the societal context here, that’s all.

    4. Oranges*

      We’re all wading in this toxic sludge so please to wipe feet off before coming into the house.

      We’re gonna pick it up. Can’t help it. But that doesn’t mean I want toxic mud all over my house….

  41. BlueSedum*

    FYI, predators purposefully target women under the age of 25 because they know that a) younger women are less likely to feel comfortable directly rejecting them b) younger women are much less likely to make a fuss and alert other people/the authorities if the predator doesn’t back off, and c) are less likely to be explicitly aware of the social norms that would allow one to feel confident in detecting when something is off and creepy and not-ok and not simply a miscommunication. Just throwin’ that out there.

    1. The Rat-Catcher*

      This is truth. There are so many interactions I wasn’t sure about at the time that I can look back now and say “Yup, that was weird.”

    2. CaliCali*

      There are so many things I wish I could go back and say to my 25-year-old self, namely that YES YOU’RE RIGHT THIS DUDE IS CREEPING ON YOU, and no, he doesn’t see being married as an impediment.

    3. Aurion*

      From experience, oh yes.

      My experience was what taught me to insert figurative steel into my spine, but I hate that this is how so many women learn this lesson.

    4. Anon For This*

      I’m older and have seen a lot of life, but I still look young. It’s interesting to see all the kinds of things people attempt. Now that I have the life experience to know what’s going on. I shut them down and some of them get retalliatory. They don’t like being found out (or called out, although I rarely do that).

    5. No name*

      Yup.

      When I was 24 I said yes to dinner and a drink with the guy I just met, who was 10 years older than me— we were both solo travelers in Latin America, he was nice, it was fine. I said yes to sharing a hotel room with him – two beds, “no funny business”, we were broke, it made sense. I said yes to making out with him after, why not, and I also said “I’m not going to sleep with you.” He said no no of course totally fine haha. And then— I don’t know. I had said no to sex with him once. I didn’t tell him no again. We kept kissing, and he didn’t stop there. I didn’t stop him, but I didn’t say yes either.

      I never know quite how to categorize this incident. For several years I thought of it as “I shouldn’t have had sex with that guy.” Eventually I rephrased it to “he shouldn’t have had sex with me.”

      He knew better. He heard me say no and he pretended it meant “ok but only if you work for it.”

      I was young and alone and depressed, and he knew I was vulnerable. He used that.

      1. Old Admin*

        To me, this is r4pe, and nothing else.
        Just because you weren’t waylaid in an unlit parking lot doesn’t mean it wasn’t r4pe.
        Never doubt that.

      2. Ciscononymous*

        Agree with Old Admin.
        The lack of a no is not a yes. Although in this case there wasn’t even a lack of a no.

  42. Pat Benetardis*

    Back before I was middle-aged (wow I just admitted that!) and became invisible in this way, I used to receive this type of thing a lot. Men would put something out there and if I flat out said no, I’m not interested, he could save face by taking offense, he hadn’t actually hit on me, etc. It’s such a stupid dynamic to have to navigate.

    LW – I have learned some things along the way, one of which is that it is fine to decline an invitation without explaining why. Say no, thank you. Or say that you have other plans. If he asks what they are, you can say its personal without explaining further. Telling someone what you are actually doing opens you up for further dialogue. Sometimes your other plans can be watching tv in bed.

    1. Jules the 3rd*

      Heh – I don’t love the extra 25 lbs, but yeah, I do love the ‘not having to worry about whether they’re going to want sex’ part of middle age.

  43. The Rat-Catcher*

    I think her wording choice at the end is pretty clear, actually. Yes, she brings up the flight, but when he asks her to change it, she says “nah, I’d rather stick to my plans, I’m ready to get home.” Not “I can’t change my flight” or “that would cost money” or any of that, but that she would rather stick to her plans. Plus, she didn’t say that she wanted to go or that the flight was an impetus to hanging out. And I agree with several commenters who said that someone who doesn’t really get social cues would be likely to be more direct, not obtuse.

  44. the flying piglet*

    Long-time lurker here. I’m commenting to respond to the people who objected to the LW’s “signals.” You know, I’m extremely tired of any demonstration of friendliness or decent-human-being-ness being interpreted as an open door for a come-on. Then LW was being nice to her coworker who then took that as an invitation to hit on her. She responded in a way that CLEARLY demonstrates she was not interested in him as more than a coworker and friend. He pressed on anyway.

    To the people here who urged the LW to examine how she acted and to be less “friendly,” and watch her “signals”: you are exacerbating an age-long problem of forcing women to walk a horrible, thin fence-edge. I am constantly trying to curate my actions and appearance in a male-dominated work place so I don’t come off as callous or cold or “too friendly.” If I don’t succeed, I am the one to blame, not the men who wrongly interpret my smiles or friendly colleague-overtures as come-ons.

    The answer to this problem is for all coworkers to be polite and decent colleagues. Interested in dating someone? Ask directly and accept the first NO. The letter-writer clearly said “no” to the first offer hang out one-on-one. It should have ended there.

  45. Escapee from Corporate Management*

    LW, having read that Jim has a girlfriend, I am going to triple-down on my recommendation of how you communicate with him. Stop texting, switch to email (so everything is backed-up), take your time to respond, go into business formal mode, and consider copying a co-worker on all messages. After following Allison’s advice about being direct in not wanting to have a relationship with him, keep everything to business communications only.

    Now I will speculate. I may be wrong, but when I hear that a person in their mid-30’s who is in a relationship is sending messages like this to an acquaintance at least 10 years his junior when they are both away from home, my assumption is (1) you are 100% being hit on, and (2) it’s not for the purpose of a long-term business relationship. LW, don’t worry about offending Jim. He needs to be told to back off.

  46. Bobstinacy*

    I love when things I’m annoyed about get posted about in AAM.

    There’s an undercurrent in a lot of the comments here that suggest that the OP lead Jim on or encouraged him by being social and friendly. And I’m just… so tired.

    I long for the day when I can treat men with exactly the same friendly demeanour I have with women without them taking it as flirting. I would especially love if their shoddy read of the situation didn’t leave me having to justify behaving like a normal person like I did something wrong.

    OP, follow the script, be direct, then cut him out unless it’s required for your job. And please don’t feel guilt for what’s happened – I had to deal with this a few days ago when a guy that I’ve hung out with a few times tried to make out with me. I was only ever friendly, and he knew that I’m in a relationship with a woman. None of that stopped him from trying to cast me as the lead actress in the romantic movie he was writing in his head.

    1. LadyKelvin*

      +1
      If I am friendly and social with a gay woman she does not interpret that as me being interested. If I am friendly and social with a straight man, then society blames me for sending mixed signals. How about no.

      1. Broadcastlady*

        This isn’t always true. I was friendly with a gay woman until she decided that I wasn’t really straight(I am, and had certainly never done anything to make her think differently). Hands down the worst ongoing instance of sexual harassment(bordering on stalking) I’ve ever experienced. Literally didn’t stop until I moved to another state. But that is not the only time I have experienced sexual harassment from a lesbian. My husband has two female colleagues who are married to each other and have adopted children. We stopped socializing with them because of constant comments about my breasts and suggesting to my husband they “borrow” me for the night. Those comments were mortifying.

        1. Oranges*

          Yeah, the LGBTQuiltbag has problem people just like any other community (I was told we can’t return Kevin Spacy sadly…). It’s kinda good in a way because it underscores that we are first and foremost human beings with all the normal human variety from saint to evil glassbowl.

          You know what I would like? I would like women to stop being seen as prey. That would be nice.

        2. Bobstinacy*

          I was really debating if it was worthwhile for me to respond but here we go.

          In this thread I was talking about a really specific interaction between men and women based on toxic cultural narratives. Somehow we’re on to stories about lesbians sexually harassing women in response to a comment that pointed out how women aren’t trained to treat each other the same way that men and women.

          I’m just going to throw it out there that I’ve had to do a lot of calibration with things like flirting and friendship because if I hit on the wrong woman the results can be instant, physical, and fatal. The cultural trope of predatory lesbians is alive and well, and it’s dangerous.

    2. Anon For This*

      Exactly. We’ve come a long way in accepting same sex romantic relationships. Why doesn’t that extend to opposite sex platonic friendships as well? If we can date anyone, why can’t we also be friends with anyone? It doesn’t make sense. And why is it that sometimes, when you talk to someone, it’s perceived as a date and sometimes it isn’t? Nothing should be perceived that way unless both people express that kind of interest.

      1. Bobstinacy*

        I think that’s why this particular mindset bothers me; I identify as queer and I’ve dated men, women, enbys, etc. My life would be very lonely if I could only be friendly to the people that give me pantsfeelings.

    4. Katie the Fed*

      Yup yup yup. I was thinking about Charlie Rose talking about how he had thought the women he was harassing shared his feelings. Yeah, no. They’re 1/3rd your age, you old bag. They’re being professional and friendly, not hoping to get boned. You’re the one who assumed their friendliness was interest because of your massive ego.

  48. Anon anon anon*

    He’s pressuring her to hang out with him. He’s being manipulative. What usually works best with manipulative text messages is not to respond. When you respond, you give them something to work with. When you ignore them, you could be busy or your phone could be turned off, any number of things. They have no way of knowing. Then, if they continue to act weird, you can say, “This is too much. Let’s keep things professional,” and loop in someone else if necessary. But take screenshots of those texts and back them up. This could fizzle, but it’s best to be prepared in case he turns out to be more of a creep and you have to report the whole thing.

  49. Spek*

    I think, based upon the diverse interpretations here – some say he is being creepy, and others say she has interacted with him socially and he is understandably responding to those cues – that his behavior is in a bit of a gray area. I would hold off on solution #3 until she is more direct with him. From his point of view, looking at her invites and responses so far, if out of the blue I had someone from HR contact me about “harassment” or “inappropriate conduct”, I would be plenty pissed. I’m not victim blaming, but based on her actions so far, I think he deserves a straightforward “no” before escalating this.

      1. Viva*

        Thirding. A clear ‘not interested, please stop’ is needed first. Only if that clear stated boundary is violated should HR be notified.

  50. Indie*

    So a man person is hitting on you, but is so subtle there’s no clear opportunity for you to say no. Being subtly unresponsive is not working. The minute you go out on a limb you know he will scoff at your vain presumption. Here are a few options:

    The ‘I don’t get it’.

    He may not have the balls to ask you out, but visualise each awkward overture as a softball being lobbed in your direction. Have great fun with the scenario in which you watch the ball closely, not moving your arms at all, and when it hits the floor you look curiously at vague-man and ask him what he just did. Here’s what this looks like:

    Softball question: “Do you want to go do *date disguised as networking/platonic thing*?”
    Fallball response: “Just the two of us? *makes face* Why would we do that without the gang? *waits curiously for response*.

    Softball question: Sends a too intimate but still vague message like “I reaally like spending time with you” (true story).
    Fallball response: *crickets* (if queried claim how your ALL your CLOSE friends know you don’t use/check the medium he chose ). Or “Dude, you mistakenly sent me this message meant for your date about an at home hangout!” if he persists it’s for you, reply *I don’t get it. What are we talking about?* or *Huh?*

    Just constantly respond to anything he says with “Huh?” and “Wut?” Or “Why?”

    Softball question: “You should totally spend more time at my favourite hangout/taking part in my favourite hobby/this bar I want to try/sport I want to watch.” (They dont care what you’d like)
    Fallball response ‘Nah I’m not interested’ but repeated to the point of absurdity. (if he looks/acts stunned or rejected look plausibly confused, as you’re only rejecting his plan of comic books not him personally right?).

    Softball question: “Hey let me tell you all about my day/bad relationship/intimate matters because I’ve decided to completely ignore your hints that we’re not that close”
    Fallball response “Hey let me stop you there. You don’t want a work person/acquaintance knowing this much stuff about you. We’re not close enough and youll regret it” or “You should probably should talk this out with your girlfriend/close friends because I don’t know you well enough to help*

    THE GLOVES ARE OFF

    1) Let me be clear I’m not interested in hanging out one on one.
    2) *surprised tone* Why are you telling me what to do? (These guys always use the word ‘should’ or command sentences)
    3) I’m not free to talk much. *waits for him to go*
    4) Do you really think that’s an appropriate thing to say to someone you hardly know?
    5) *raises eyebrows* *allows silence to swallow the universe*.
    6) Go straight to *block* collect 200 do not pass go.
    7) Oh yeah, my new number? I’m just keeping my number for close friends and family these days. Y’know, people who have my schedule, know my interests etc.
    8) Wait? What!? Almost sounds like a date! If I didn’t know any better! *peals of laughter * *walks away chuckling*
    9) I love having an acquaintance who is like my little brother. I always wanted one.
    10) *makes a sharply interruptive tangent* You know what I hate? Those guys who ask you out without asking you out so you can’t say no. Do you know any guys who: *list all of his sins*

  51. Velvet Goldberg*

    Wow, this was a hot topic. It was actually really enlightening to read the back and forth. Given that commenters had such diverse and different reactions, it seems pretty obvious to me that regardless of this guy’s morality (I would not be happy if I was his gf), the fact that folks disagreed about his intentions or attentions, kind of proves there’s no one right answer. Perception is a sticky wicket. Good luck OP!!

  52. sfigato*

    There are already a million replies, but I wanted to say this:

    OP, he is hitting on you, it’s not your fault, he’s being being inappropriate. Follow AM’s advice, but I’d also recommend telling HR or your boss, especially if they are a woman. Maybe he is totally well intentioned and not a bad guy at all and just thinks he found his soulmate, or maybe he does this to all the cute 20-somethings and someone needs to have A Talk with him about it. Hell, even if he’s well intentioned, someone should tell him how creeptastic he is being.

    I’m a forty-something dude who was socially awkward and bad at hitting on women when I was single, and I belonged to a professional association in my 30s and many of the members/staff were women in their 20s. He’s trying to hit on you, and he’s veering off of Flirtatious Road onto Creepy Lane and getting really near Harassment Blvd.
    Ok, so you haven’t totally nuked him or told him flat out “NYET.” But you also haven’t given him grounds to expect a late night booty call to work out well or for you to change flights to hang out with him. Like, i wouldn’t ask my close friends to change flights to hang out, much less a casual work friend. He’s hitting on someone – it’s up to him to read signals and give you an out, which he is doing a bad job at. Sure, you could have changed how you worded your texts, and you could have been more blunt and direct, but all that is putting the blame on you rather than on him for being crappy at reading signals. You being nice to someone isn’t telling them you are into them or leading them on.

    1. Chickaletta*

      Yep, he’s hitting on OP, but in a very sloppy way (especially for someone who’s in his 30’s by now, I’ve seen teenagers more suave than this character). I’d address it head on and tell him you’re not interested. His response will tell you everything.

  53. ArtsNerd*

    I want to put an anecdote in the mix for those who think being blunt early would have nipped it all in the bud.

    I was once asked to attend a sporting event and bring a [nonspecified] female friend by a coworker above me in the org chart, who got my cell phone number under the pretext of putting together a contact list for emergencies. He was engaged. This was long enough ago that he actually called me on the phone to talk with his voice (I know! I’m ancient) and I… well, I kind of flew into a rage at him.

    His response included the phrase, as verbatim as I can remember: “It’s not like we’re going to rape you.” Other things happened, and it ended with me quitting a job I really loved otherwise, and took me off a career path that I’m only just now coming back to.

    It’s the one story (of many I could have picked from) I told my father today – before seeing this – to try to explain why the sexual assault news onslaught is so draining for me and other women.

    I picked it for its ordinariness.

    I’m feeling so angry and so validated by so many of the comments in here. And so full of regret. OP, I hope you ALWAYS trust your instincts on these things. Never feel guilty about doing so. Please keep us updated.

  54. Agent Diane*

    LW – I’m actually coming back to this in the morning because of Alison’s step 3. If steps 1 and 2 don’t work, and you remain reluctant to take step 3, have a chat with any other 20something women you work with. Don’t say “Is Jim creeping on me?”, but ask “what do you think of Jim?”.

    Because I wouldn’t be at all surprised if he’s been making those same plausible deniability passes at other women in your org. “Hmmm, Jane didn’t want to come over for ‘couch’ time, I wonder if Jill is in town and more willing?”.

    And it’s not a problem if Jill is more willing. That’s Jill’s call. But she might not be. Or she might be not wanting to say anything for the sake of her career too. Or she may have gone along with it, thinking she needed to. So asking around may give you extra confidence that Jim is stepping over the lines.

    To be clear: you are not responsible for anything he may be doing. At all. But if he doesn’t back off after step 2, you shouldn’t back off from step 3. His actions will have put him there, not yours.

  55. HRVP*

    OP — I also work for an association so I totally understand the member-dynamics you’re talking about. I’ve seen some members get a little bit of an attitude along the lines of “I pay a lot of dues; these people work for ME” Not often, but a few toolbags can have a strong feeling of positional power over Association employees. Therefore I STRONGLY recommend that you loop in your employer NOW. If this guy is highly thought of within your organization, he may start using opportunities to disparage you if he responds poorly to rejection (and, based on your letter, he’s not good at respecting boundaries). If you are already on the record with your employer, any future attempts he may make to undercut you will have some context and will help you protect yourself.

  56. Willow Sunstar*

    My previous co-worker hit on me for months. I did have to go to the boss at one point, because he was standing up for minutes at a time and looking down at me over the desk partition “wall” without saying anything. Asking him directly to stop because I felt uncomfortable got the response “How dare you ask me to stop?” What made it worse was that he was half my age, and from another country (though English speaking.)

    Ignoring his weird random work IMs got the response “please don’t ignore me, I can’t stand being ignored.” I can’t tell you how many times I literally copied & pasted the “your attention on me is unwanted, please leave me alone” line, and he would be doing the same thing a couple of days later.

    Management repeatedly would do nothing except talk to him because he would act like he had either a possible disability mentally and/or illness and was a minority. So they had to get their tax break. It took me faking having a boyfriend and ordering roses for myself, and “accidentally” leaving a card on my desk with a random male friend’s name, and suddenly developing an interest in heart-shaped jewelry, to get him to stop.

    It was certainly on the list of reasons why I left that job.

    Even at my new job, he sent me e-mails still of questions on things he should have known after having been there for 3 years, and he had asked them before, and were documented well. Forwarded them all to his new boss and said he should be asking others since I was now in a new position with tight deadlines.

    Him asking me all the inane questions, I strongly suspect now, was his way of trying to get me to speak to him because he knew I otherwise would not.

    So glad I am not in that job anymore.

        1. WillowSunstar*

          I have no evidence other than the one time I went to my old boss about him, so at this point, it would be my word against his. I also don’t think they would believe me or do anything, because he did act like he might have something mental out of the ordinary going on some days. So that’s now more than one protected class.

          Once, I asked the IT dept. if they could bring back old IMs used on the work system, and they said no. So I do regret not screen-shotting them. It’s the kind of thing where if he had said it once, you wouldn’t think anything of it, but over time and all of it taken together, it really sends up a lot of red flags.

          I’ve moved to a new position in a totally different building, and no longer am required to interact with him for my current job.

  57. Willow Sunstar*

    Oh btw, I am a normal-looking overweight middle-aged woman, do NOT ever show anything at work, and the only thing I did was be nice to him because niceness is forced in the company. If you are not nice to your co-workers, you get written up, unless of course, you are in management. They can treat people however they want.

  58. NoTurnover*

    I know this is late and there are a ton of comments, but I haven’t seen anyone else bring up the fact that he’s a member of her association.

    OP, he’s being kinda inappropriate and that is not your fault, and you should feel zero guilt in shutting it down and carrying on with your life.

    And also, when I worked at an association, most of us avoided hanging out with members socially at the conferences. It was just too easy to blur the lines of work and personal when you’re going out for a bunch of drinks or exploring the city with a member, and then next year you have to reject their book proposal or they’re suggesting some really terrible idea for a major fundraiser. You never wanted someone to feel like they had been personally hurt by you because of the relationship you had outside of work, and as staff there was a little bit of a power differential (you often have influence over some of the things they want to do professionally, and they often have a lot of influence as the “customer”). So while we would be friendly with members, talking about hobbies and families and such, we kept any socializing to pretty limited contexts, like 5 of us staff are there and we’re having dinner in the hotel restaurant. I think that was a pretty good way of handling things if you can going forward.

  59. kckckc*

    How about let’s stop mincing words and make it easier on everybody:

    Person 1: I think you are cool and I’d like to go on a date with you.

    Person 2: Yes, I’d like that too. / No thank you.

    The days of hinting around or throwing soft passes need to be over. Grow a pair and be clear on your intentions. That goes for pursuer and target.

    1. kckckc*

      FWIW I should have taken my own advice when I was in my 20s. Now I’m in my 40s and married (but don’t wear a ring) so I just drop my husband into to conversation when I see things going sideways.

    2. WillowSunstar*

      They don’t always take a blatant no for an answer. I blame part of this on Hollywood. There are a lot of movies where the girl keeps saying no but the guy is persistent to the point of being creepy, and gets her in the end. So a lot of younger men especially have unrealistic expectations, and sometimes think women are just playing hard to get.

  60. bopper*

    If you don’t want to have a relationship with someone, don’t have a relationship.

    He took your inviting him to join you as interest.

    Stop doing that. Don’t reply or use any of the tactics mentioned by AAM.

    At the next meeting, just don’t respond. Pretend you didn’t get it.

  61. S*

    Something similar happened to me, and I gave him the benefit of the doubt that he was a decent guy all the way to the end. These comments are really ringing true for me, i.e. plausible deniability, fear of rejection, ‘hang’, incessant asking, etc. We did go out for a drink ONE time — I decided it wasn’t worth the complication at work, and he was too flaky to make concrete plans anyway: “When are we hanging out?”. Months later, we reinitiated contact on a personal level, and I did not think more of it than flirting and a lot of suggestive texts on his part. I got bored/tired of this and after awhile, it got really annoying. He’d come by my desk when he didn’t work in the same building (actually a river away). He called my coworker’s line when I didn’t respond to a text one time (I was sick, in bed at home). He asked within earshot of our coworkers what I was “up to” after a social event at work, at which point it was past 10pm.

    Towards the end, I would straight up ignore his comments and texts asking me to grab lunch. Once he called me on the office line which I have to pick up because our teams work together, and he proceeded to ask about lunch again. It was a purely social call; not even a pretend question about work. I realized after reading about Trump’s interaction with Comey and how it paralleled predatory behaviors by men harassing women that I was essentially cornered into giving an affirmative. I couldn’t say no at the office, and I felt bad about saying no over other forms of communication as I tried to maintain a positive working relationship between our teams. I demurred and said I was just really busy during my last days at work.

    I thought nothing more of this guy. Generally thought he was a Nice Guy, really socially awkward at times, too honest potentially in a wear-your-heart-on-your-sleeves way, was skating by on looks more than actual charm in his dating life, definitely was trying his luck with multiple women (not at work).

    Upon leaving the organization we worked at, I have since found out that he has been targeting people in the same general ethnic category as me. Others have noticed his predilection towards this group. All the other women he repeatedly asks out around the organization seem to be in lower positions than myself or him. (I thought it was worth mentioning this as I don’t think of my interactions with him has the same kind of power dynamic he has with the others.) He seems to also casually mention his close relationship with the head of HR often — I cannot confirm its veracity but I can only imagine how that sounds to others who hears it. He was on/off dating a coworker in his own team which is against policy. Even knowing just bits and pieces of information now about all the other on-goings of this man, I am so disgusted about how he must behave 100% of the time.

    All of this just to say I wholeheartedly agree with Alison:
    “In fact, your employer has a legal obligation to keep you and other employees from being sexually harassed by members, and you’d be doing them a favor by letting them know what’s happening.”

    Also I think all the sexual harassment allegations in the news now really goes to show how there’s a tiny marginal chance that yes, the OP’s coworker could potentially have made a real misstep which was harmless and just accidentally creepy. But if he doesn’t learn from this now, there is also a big chance that he can be a Weinstein or an O’Reilly who constantly excuse their behaviors as “boys being boys.” I’m sure both were harassing women as strapping young lads and got away with it back then because of the times and also because some women were more receptive to it (when the men were better looking, younger, less arrogant, less leering, more charming, whatever it is). After all, they both had wives. I think it might be a good learning experience for this coworker to realize that he crossed professional boundaries. If he wanted to pursue a relationship, he should have been more straightforward and take the first veiled rejections by OP as a no. If he needed to get some, he should look outside of his workplace. There’s really no room for error when your career is on the line, and as someone in his 30s, he should really know better than to try to make booty calls to a coworker when they are not Officially Dating.

    1. S*

      Just realized he’s a member — that it’s a professional thing only on her part. I still think in his 30s, he should be more aware of his standing and the power he has if he was a decent person.

      My guess is that this probably isn’t the first time HR has heard of something similar by this person.

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