is my girlfriend’s CEO hitting on her?

by Alison Green on November 20, 2024

A reader writes:

I previously have asked you a question about whether my girlfriend’s CEO was overstepping (#2 at the link). You very kindly answered my question and I followed your advice and happily let it go as I believed the CEO wasn’t overstepping his professional boundaries. At least not until recently when I read the following interaction between them on a Monday morning at 6 am:

CEO: I’ll see you in the office. At least I have that to look forward to!!!
Girlfriend: See you there!

My mind might be tainted by my previous suspicion, but reading the interaction between them I immediately felt that their level of communication was beyond what I think is “professional corporate level” communication. Or am I completely wrong and see spooks everywhere?

I should mention that I have no access to my girlfriend’s work phone or iPad. Her iPad was on our kitchen counter while she was in the bathroom and the CEO’s text message popped up on the screen, followed by my girlfriend’s immediate answer. The iPad was locked so it wasn’t a matter of me snooping around, just to clarify that!

That is more familiar than I’d recommend to a manager, although it doesn’t necessarily mean anything inappropriate is happening. I can see why it gave you pause, but it’s very far from indicating he’s actually being inappropriate. It could mean he sees their relationship as more friends than boss/employee, but that’s a different thing than what you’re worried about.

And your girlfriend’s reply was as neutral as you can get when responding to a somewhat-too-familiar boss.

I think it would help to hone in on exactly what you’re worried about. Are you concerned that your girlfriend might be cheating or that her manager is just overly familiar (and maybe would like to make a move if given the opportunity)? If it’s the latter, there’s really nothing for you to do here, other than to support your girlfriend (in trusting her own instincts if she starts to feel uncomfortable, and in setting and enforcing boundaries that she is comfortable with) — assuming you trust her. After all, there will always be other people who might hit on her and you can’t wrap her in bubble wrap to prevent that from happening. If you trust her, you have to trust her to navigate that part of life appropriately.

On the other hand, if you’re worried that she’s cheating on you, or would cheat if given the opportunity, that’s an issue independent of whatever is or isn’t happening with her boss. The good news about that would be that you wouldn’t really need to “solve” this if that’s the case; if you don’t trust her, things are broken regardless.

Or is it more of a middle ground, where you’re worried the boss is inappropriate and she’s not going to see it until she’s suddenly in a bad situation? If that’s the case, the right move is to ask her how she feels about their dynamics, and really listen to what she says. Ultimately this is hers to navigate and you have to respect her agency in that, but if you’re worried there’s something she’s not seeing, you can certainly open that conversation and both hear each other out. (But like I said in my original response, you can’t bring it up over and over; you raise it, you listen to each other, and you each figure out what you’re comfortable with from there.)

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{ 217 comments }

{ 217 comments… read them below or add one }

  1. WellRed*

    Time to really assess your feelings and the overall state of the relationship and then have a serious talk with girlfriend. For me, it’s that boss sent the message at 6am! Who does that?

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    1. AvonLady Barksdale*

      Eh, the girlfriend was in the bathroom, presumably getting ready for work, so the 6am doesn’t really bother me that much. Mostly because I’ve been known to check and respond to Slack messages while taking my dog out first thing in the morning.

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      1. WellRed*

        I’m not saying the girlfriend is doing anything wrong, mind you. But I’ve managed to go my whole career without a personal 6am greeting from my boss or any other coworkers.

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        1. Jennifer Strange*

          That’s great for you! Not all jobs are the same as your job, though. The GF didn’t think it was odd and she knows her job better than any of us do.

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        2. Shiara*

          As have I, but my career doesn’t involve being executive assistant to CEOs. Being responsive when the CEO is working at 6 am might be within the expectations.

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        3. Quill*

          If she has to be at work by 7 or 7:30, especially if there’s a longer commute, it comes back around to being more reasonable if it’s important to know the second she got into the office.

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      2. Nonanon*

        Yeah, there are completely innocent reasons for a 6am text; “I’m an early riser but don’t expect you to respond,” “I have an early meeting with client and can’t find xyz, do you know where it is?” “Yes, under filepath>reporttype>clientname”, “U up ;)?”. Text time alone is one of those things that are influenced by a lot of variables, and LW effectively only saw the back half of the message; if the REST of the conversation was flirty/boundary crossing, that’s one thing, but just a 6am text… yellow flag at best.

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    2. Nobby Nobbs*

      I do have a boss who sometimes texts earlier than that. We start early, so if you want to communicate something before your employees head out the door you need to text early. His messages are usually more logistical than conversational, though. (This one might be the tail-end of a logistical exchange, but we don’t have the context to say for sure and neither does OP.)

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    3. Harper the Other One*

      Traffic is increasingly bad where I live so lots of people have been shifting their work hours early – I try to be in the office by 7:30 – and in my experience that means high level managers are checking emails etc. as soon as they’re awake in case meetings need to get changed etc. I’ve definitely gotten early morning (and late night) messages! So to me that’s not a flag at all on its own.

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    4. Jam Today*

      Bosses with no boundaries or possibly who never developed theory of mind where you learn around the age of 3 that other people have other thoughts and behavior that isn’t your own. I’ve had a boss email me at 8pm on a Sunday then yell at me at 9am on Monday for not having responded to them. I’ve had a boss call me at 7:15 on a workday telling me that I need to be in an impromptu client meeting at 7:30 (when I lived 30 minutes away from the office and oh also was still getting dressed for work so wouldn’t even be able to walk out the door til 7:45).

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    5. kicking-k*

      I wouldn’t see that as a red flag – some people are early birds. My previous boss rose early to take a child to before-school swim practice, and often wrote work emails while sitting and waiting, poolside. She had a message in her signature about not expecting an immediate response.

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    6. A*

      My boss often emailed early in the morning. We started work at 7:30 so a 6 a.m. email was pretty typical. He didn’t expect a reply, but since I was getting ready by 6, I usually did reply.

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    7. Can't get the hang of Thursdays*

      I think the OP could be missing context in the message too. There could absolutely be prior messages that say, hey when you get to the office I need you to do x y z, or can you stop on your way in and pick up x from the store for today, that need to be communicated before arrival, and what they’re seeing is the polite end to a legitimate work conversation.

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    1. JB (not in Houston)*

      What part–the boss’s message or the girlfriend’s response? And a red flag for what? Too familiar boss? Cheating girlfriend? Providing more detail would be helpful to the OP (the way Alison’s answer does).

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  3. CeeDoo*

    It sounds like the CEO is testing the waters with her. I’m not an expert, and I am biased. I remember my dad doing that, changing his look and wanting to look more stylish. A few months later, he moved out and moved in with the new coworker he later married. She obviously responded favorably to his advances. None of this shows your girlfriend is reciprocating, and she may err on the side of politeness because she doesn’t want to make waves or lose her job.

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    1. Pastor Petty Labelle*

      That’s the way I read it too. The boss wants more, girlfriend does not. Her neutral response is her trying to keep it professional.

      OP, you can’t stop her boss from being too familiar. You have no control over him and even trying to addres it with him will only harm your girlfriend’s standing at work. What is within your control is how you react to your girlfriend. Right now she needs your support deal with her boss, not your suspicions. Please do not treat her with suspicion. Be open to hearing anything she has to say about her boss. Be supportive if she wants to leave. Do not offer solutions, unless she specifically asks for them.

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      2. Frank Doyle*

        I also agree with all of this. Boss seems like he could be testing the waters/bordering on creeperdom, but the girlfriend is in the best position to judge that, and you have to trust her to handle the situation, and then be supportive however it turns out. Her response to the early message was, as Alison said, the Platonic ideal of a response.

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      3. duinath*

        Yeah, I think LW needs to get right with themselves, figure out whether or not *they* trust their girlfriend, and if they do? Make sure girlfriend knows she can trust them.

        The bottom line for me is girlfriend is acting appropriate and needs to know she can talk to LW about it if boss is not, but I’m not in the relationship and don’t have that bond of trust a relationship needs.

        Figure out how you’re feeling, LW. You can’t decide what to do until you figure that out.

        (To be clear, “what to do” is stay and be supportive or go and move on. Interfering with her business is not on the table.)

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    2. Yellow*

      Agree. I think the CEO is walking a thin line here, seeing what he can get away with. The GF is handling it perfectly. She’s not the problem. He is.
      That said, LW, you’ve seen how she’s responding to him, so you need to trust her now and stay out of this unless she asks for your opinion or help.

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    3. ferrina*

      Yeah, the CEO’s message was very borderline in the kind of way that people do when they want to open the door but also want plausible deniability. My boss adores me, but she doesn’t “look forward” to seeing me at the office every day!

      The girlfriend’s response is non-committal. I don’t know if she’s trying to shut the boss down, or not leave a paper trail, or if she’s even wildly uncomfortable in a way that she can’t communicate.

      None of this helps OP though. The best they can do is 1) figure out if they trust their girlfriend and if so, 2) support the girlfriend in whichever way she wants to handle it.

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      1. MigraineMonth*

        I think the GF’s response was professional, not “non-committal”. It’s the message she would send even if she thought the CEO’s message was too much and she’d decided to tell him he needed dial it ack, because you have that kind of conversation with your boss in person.

        It’s not about not leaving a paper trail, it’s about texting being a terrible medium for conveying the nuances of “your behavior is making me uncomfortable, but you control my livelihood and I need to maintain a close relationship with you in order to do my job.”

        OP, if you trust your girlfriend, the best thing you can do is validate her feelings, trust her instincts and support her choices. Women are socialized to ignore their own discomfort around sexual advances and prioritize the feelings of the men hitting on them; you can counterbalance that by centering *her* feelings about the situation, not *yours*.

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    4. Bitte Meddler*

      I agree with this. In my early career years, I was the assistant to a CEO who was pretty overt about hitting on me. I saw it, the admins who reported to me saw it, the guys in Sales saw it, etc.

      And I handled it like the OP’s girlfriend. I just kept responding professionally. It took a lot of work to school my face so he couldn’t see how annoyed I was.

      CEO: “Hey, Bitte, I had a dream about you last night. We were in the conference room, sitting on top of the conference table and you stretched out and laid your head in my lap.”

      Me: “Haha! Even in your dreams I’m laying down on the job! I’d better step it up.”

      My boyfriend at the time knew about it and would ask almost every day when I got home, “What gross thing did Rick say today?”

      At no point was my boyfriend worried that the CEO hitting on me would have any effect on our relationship.

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    1. Lilo*

      Agreed. Stop seeking outside validation and talk to your girlfriend. Don’t hold her responsible for what other people do.

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      1. ThatGirl*

        Like… either he trusts her or he doesn’t. What matters is how she feels, not how he feels. Maybe her boss is a bit too familiar or flirtatious, but if she is handling it, you gotta trust her.

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        1. Statler von Waldorf*

          Can we not say that one gender’s feelings doesn’t matter? As a man, I’ve been told my feelings don’t matter since I was born, and I think that’s sexist garbage.

          Both side’s feelings matter.

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          1. Fishsticks*

            I don’t think the commenter said ANYTHING about general gender feelings mattering or not. The commenter was pretty clearly stating that in this situation, the girlfriend’s feelings matter because she’s the person our OP is in a relationship with and that relationship hinges on whether or not he trusts her.

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              2. Name*

                They were saying “what matters is how she [the girlfriend] feels, not how he [the girlfriend’s boss] feels” — as in, if her boss had feelings for her, it wouldn’t impact her fidelity to her partner unless she returned those feelings.

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              3. Skelly*

                That’s what the commenter said but I think you’re reading too much into it as coming down to gender. They didn’t say only a woman’s feelings matter and not a man’s. With the context that OP needs to decide if they trust their girlfriend or not, I read it as “What matters how the girlfriend feels about her boss interacting with her, not how the boss feels about the girlfriend.”

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              4. Jennifer Strange*

                Yes, “she” meaning the GF in this case and “he” meaning the LW (the BF) in this case. You can stop grasping at straws here.

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          2. Arrietty*

            No one said men’s feelings don’t matter, they’re talking about this specific couple in these specific circumstances.

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          3. Cicily*

            “Please stop saying a thing that you didn’t come even remotely close to actually saying” is certainly an interesting request.

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          4. Jennifer Strange*

            ThatGirl didn’t say the LW’s feelings don’t matter because they are male, but because their GF is in the better place to know the dynamics of this relationship. Is the genders here were reversed the answer would be the same.

            Side Note: I have a hard time believing anyone has ever told you your feelings don’t matter for being a man. Usually when someone says that it’s because they’ve either been told they don’t understand a certain aspect of what it’s like to be a woman (like health care being taken away or feeling like they can’t even exist without being hit on) or because they’re trying to “prove a point” about feminism.

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            1. American in Ireland*

              I think some wires got crossed here.

              ThatGirl said: “What matters is how she feels, not how he feels.” I interpret that to mean what matters is how the EA feels not how the boss feels.

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            2. Statler von Waldorf*

              I’m skeptical that the answers would be the same. I flat out don’t believe for a second that that the tone of the comments would be the same if the LW was a woman.

              I work in the oilpatch in a remote part of northern Canada, and things are different there in a way that people who have always worked white-collar just don’t get. When I given notice of my layoff last week, my now-ex boss asked me if I was going to cry like a bitch. But go ahead and feel free to dismiss everything I said because you think I’m trying to prove a point about feminism.

              I think it’s best for everyone if I’m done commenting here for today.

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              1. Wayward Sun*

                Okay, but I think it’s projection to assume LW is in a toxic hyper-macho environment like the one you work in.

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          5. Nina*

            I read that less as ‘men’s feelings don’t matter’ and more as ‘the feelings of [person in job] about the job matter more about the feelings of [partner of that person] about the job.’ My (male) partner’s feelings about his job matter more than my (female) feelings about his job, full stop. And vice versa.

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        2. megaboo*

          Right? Maybe this is just my age or something, but if someone is that worried and distrustful of someone either talk to your partner (a sensible approach) or leave them. I would also evaluate myself and say, “Do I do this with every partner?”

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    2. Ask a Manager* Post author

      Eh, he says he listened to the advice last time and happily backed off and now he’s seen this kind of weird text, against a backdrop of already feeling like the guy was A Bit Much. The answer is to talk to his girlfriend and respect her take on it (or if he finds that he doesn’t trust her take, to listen to what that means about the relationship for them both) but I appreciated that he dropped it originally but is now doubting himself because this 6 am text seemed kinda off.

      I’d love to know exactly what he’s worried about (which is why I tried to tackle all the possibilities in my answer) and whether he’s had similar worries in previous relationships or if there’s something about this one situation that feels off to him in a way things normally don’t.

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      1. Lilo*

        It’s that he’s repeatedly coming to you rather than just talking to her that’s the red flag to me. These are also both really innocuous situations.

        And if the CEO I’d being inappropriate that’s really the girlfriend’s thing to handle, not LW’s. He needs to trust her to navigate this situation.

        I’d personally find this really troubling if I found out my significant other was writing to advice columnists about my work without my knowledge.

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        1. Ask a Manager* Post author

          Fair, and I do think there’s a looming question here about why these two aren’t just talking about it. (Although if they have talked about it and he’s unsatisfied with that and so is now looking for an outside authority to back him up that this is weird when she says it’s fine, that would move this more solidly into the You Are The Problem column for me.)

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          1. Lilo*

            I think what I also find troubling is gaming this out. Let’s say you did tell him this was inappropriate, it’s sort of giving him ammunition in a conversation with his girlfriend to do what… she needs to quit her job? Because she’s not the one asking for advice, it becomes problematic. It becomes troubling quickly when you think through the implications.

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              1. Lilo*

                And frankly, it’s a red flag for me when someone wants to disrupt their significant other’s job. You need a really, really good reason for that.

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            2. Harper the Other One*

              Also the vibe I got. IMO this is a personal issue, not a work one, but OP wants to frame it as a work one because he’s either uncomfortable bringing up his personal concerns, or he has and his girlfriend didn’t agree.

              OP, I’d encourage you to consider this: would you feel the same way if a male friend starts texting about, say, “can’t wait to see you at trivia tonight” or whatever? If so then I think you need to acknowledge there is some sort of trust issue going on and investigate the source of that.

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            3. Scarlet2*

              Yeah, I thought the first letter described a totally innocuous interaction with the boss. This new letter, on the other hand, describes a message from the CEO that shows he’s *potentially* trying to cross barriers BUT what really jumps out at me here is that LW keeps appealing to an outsider to arbitrate his relationship instead of just having a conversation with his girlfriend and that raises way more red flags than anything the boss is doing or saying.

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              1. MsM*

                Personally, I have an easier time seeing why OP was uncomfortable from the first letter. This one feels more like grasping at straws.

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          4. Ask a Manager* Post author

            I wish I’d put in my original response that even if we could say for sure that the CEO is hitting on her (which we cannot), the question for the LW is still, “And so?”

            I think it would help him if he can fill in the blanks for himself on “And that would bother me because ____ and I would want ____ to happen as a result.” Does it bother you because you feel threatened by other men being attracted to her? Because it feels disrespectful of YOU? Because you worry for her safety? Because you feel insecure in the relationship and worry she’d be won over by him? Something else? And if you knew he was definitely being flirty, what specifically would you want her to do in response?

            I think those would be clarifying questions! But ultimately it doesn’t matter how the boss feels/acts; it matters how the girlfriend feels about it, and everything else should be stemming from there.

            I do think there’s a version of this situation where the person is not generally suspicious, has been comfortable with girlfriends’ relationships with male colleagues and friends in the past, but something here feels off to him and he’s looking for reasons why he’s feeling that way, and it could turn out in the future that he was right to sense something was up on the girlfriend’s side (not just the boss’s) — I can picture that update. That’s possible. It’s also possible that he’s someone who feels threatened by a girlfriend’s warm (but appropriate) relationships with other men. It’s very, very hard to say what’s really going on from the info we have. What I do know for sure is that they’re not communicating and they need to be (or if they have, the fact that hasn’t solved it is a problem on one end or the other).

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            1. Statler von Waldorf*

              I wish you’d put this in your reply too, because from the comments I’ve read, the community here is not nearly as aware as you are on how hard it is to say what’s really going on from the info we have here. I also can see it playing out in different ways. The comments are pretty much univerally painting his GF as an angel and him as unreasonable, and I haven’t seen many even considering that he could be right other than you.

              I feel sorry for the LW, because he is not getting a fair shake here today. He’s getting told repeatedly that his feelings doesn’t matter and that he’s a walking red flag for even having them.

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              1. Whale I Never*

                LW’s feelings definitely do matter! When it comes to *their relationship with their girlfriend*. If someone feels insecure in a relationship, they 100% deserve to sit down and have an honest conversation with their partner about why, to set personal boundaries, to request (*request*) changes in their partner’s behavior, and to end the relationship if they can’t reach a conclusion for both.

                LW’s feelings don’t matter when it comes to Girlfriend’s relationship with the CEO, because LW isn’t a part of that relationship. LW doesn’t know the CEO and does not have an independent relationship with him, and so any feelings are completely internal, not interpersonal, and theirs to deal with. Many commentors are focusing on that aspect of the letter because the letter came into a WORKPLACE advice blog, which suggests the focus is the working relationship that LW is not part of, as opposed to one of the many RELATIONSHIP advice blogs, which would have focused on the romantic relationship.

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              2. Wayward Sun*

                The red flag to me isn’t that he has feelings, it’s that his feelings seem to be verging on the possessive. I’ve known too many relationships where the guy dictated who the girl could talk to and when to be entirely comfortable with it.

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          5. Rex Libris*

            I suspect one reason they aren’t talking is because the girlfriend finds the “Are you cheating?” dance exhausting. It’s not a productive approach, and probably the energy she’s willing to spend on soothing his insecurity is limited.

            OP, your girlfriend will be way more likely to share problems and come to you for advice (or at least commiseration) if you say basically this: “I trust you, and I know you can handle your own business. Please let me know if you want to talk anything through, or need anything from me.” and then drop it.

            If you don’t feel comfortable doing that, especially the “I trust you” part, the problem is your relationship, not the boss.

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        2. Jellyfish Catcher*

          I’m a woman, worked for decades in a male dominated career.
          If it was one of my trusted long time compatriots, I’d take that comment as nothing more that office banter fun.
          If it was someone I didn’t know well, and texted a valid question at 6 am, it’s early but fine.
          If it was someone that I depended on for consultations, and/or didn’t know well, and I got That Sort of comment. I’d be more vaguely more formal, but pleasant and helpful, just enough difference to get the message across but nothing that could be pinned down.

          This is worse: she’s younger, not as experienced in office behavior, he’s her boss, makes comments about her clothes and appearance and a kinda flirty text – yeah, he knows what he’s doing and knows he shouldn’t be doing it.
          Hopefully, she won’t pay the price.

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      2. JenniferAlys*

        I’m sorry, your advice is usually spot on and was good here, but this is weird behavior on his end. The fact that he is writing into a career advice column instead of checking in with his girlfriend over a message he “happened” to see on her iPad is in itself the red flag.

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        1. Cruciatus*

          And I 100% get what you’re saying, and yet can still…maybe appreciate isn’t the right word, but he’s seeking out advice before reacting. It might be weird that he’s choosing to do it with an advice columnist, but he’s not blowing up and overreacting first, he’s looking for more opinions and Alison helped him before, and maybe thought Alison could help again. Maybe he doesn’t have many people he could ask about this. So I’m torn.

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          1. Name*

            I know we are meant to take LWs at their word, but: On a locked iPad, he would not have been able to see the girlfriend’s response unless he opened the text. Outgoing messages, even sent from another device, do not appear on the lock screen, ever.

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            1. Rotating Username*

              Not to doubt your authority on the subject, but I’ve found that absolute statements are (almost) never correct.

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            3. Peanut Hamper*

              Eh, I have an Android and there is an option to show notifications even on a lock screen. I would imagine an iPad has something similar.

              In point of fact it does. Just google “ipad show notifications on lock screen” and the first result is from Apple support that shows you exactly how to do just that.

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              1. Harper the Other One*

                It will show notifications of incoming messages but I’ve never seen it show my reply, and I’ve never seen a setting that would allow that. I’m not sure why you’d want such a setting because you’re the one who typed the message sent!

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              2. Claire*

                I think the point is that you get notifications of other people’s messages, not your own. The boss’s messages could pop up as notifications on a lock screen, but not the girlfriend’s.

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            4. Cruciatus*

              My boyfriend’s iPad is locked, but I can see text or Facebook notifications as they come in. Only for a second, but I can see them.

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    4. Beth*

      Harshly worded, but I kind of agree. OP, it’s weird that you’ve written into a workplace advice blog twice about a CEO/employee relationship that you’re not even part of. I think you need to find a way to let it go permanently, one way or another.

      Do you trust your girlfriend to not cheat on you? If the answer is yes, then it doesn’t matter who texts what to her. People are going to hit on her–that’s reality, and there’s nothing she can do about it. You need to put your trust into action and figure out how to not worry about it. (The exception: if she tells you that a specific person is going too far and making her uncomfortable, you can worry about that! If she’s being harassed, of course you should take that seriously and support her as she decides how to handle it).

      If you don’t trust her, then there’s nothing anyone here can say that will resolve that. You should talk to your girlfriend about your fear that she’ll cheat on you and see if you can resolve it between yourselves. If you can’t, you should break up. Both of you deserve better than to live with you watching suspiciously for every little sign that she might be connecting with someone else. Either way, it’s something for the two of you to figure out together, not something that the internet can help you with.

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      1. Daisy-dog*

        I disagree. I’m not reading this as OP is afraid girlfriend is going to cheat. I’m reading it that he is afraid she’s going to end up in a situation that she doesn’t want to be in (and doesn’t feel safe in), but doesn’t know how to get out of because it’s her boss. OP is afraid this is a slippery slope and that this 6 a.m. text is the equivalent of a “Good Morning, Beautiful”/flirty text *that could escalate*.

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        1. MsM*

          He can’t be more worried about that than she is, though. At the very least, he can’t tell her what to do about it or jump in to protect her from something that hasn’t happened. He has to trust that she’s prepared to handle herself, and if she does end up in over her head, he has to be prepared to support her and put the blame where it belongs instead of being upset with her for not listening to him and going on high alert from the start.

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        2. Beth*

          That’s still a trust question, though. Does he trust her to know where her own boundaries are? Does he trust her to handle problems that life puts in her path? Does he trust her to ask for help/support when she needs it?

          If he does, then there’s no reason for him to be worrying about this. She’s got it. He just needs to have her back if she asks for support.

          If he doesn’t, we’re back to “you can’t sustain a long term relationship if you don’t trust your partner, you need to either figure out how to build that trust or break up”.

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    5. Dawn*

      Seriously.

      “I wasn’t purposely snooping” no but you definitely didn’t hesitate when the opportunity presented itself, either.

      You don’t trust your girlfriend. Either you don’t trust her not to cheat, or you don’t trust her to be able to handle the creepy men in her life (who, yes, will show up sometimes. It’s a thing that women deal with.) Either learn to trust her, or learn to be single.

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      1. Turquoisecow*

        Yeah, the end advice is the same. Do you trust her? If you do, then drop it again. Maybe her boss is overly familiar, maybe he’s hitting on her, maybe he’s not, but if you trust your girlfriend it doesn’t matter. And if you don’t trust her then break up. Full stop. Because she’s going to interact with other people in the world and sometimes they’ll be overly friendly men. So either you trust her, now and forever, or you don’t. And you can’t be in a long term relationship with someone you don’t trust. If SHE feels uncomfortable enough to quit, she can do that, but you can’t demand it. And she’s not at that point, obviously. So trust her or break up, end of story.

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    6. Pocket Mouse*

      I agree with Alison that the girlfriend’s response is a perfectly fine, neutral way to respond to an overly familiar message, and the LW doesn’t express a concern that she is cheating, or would cheat. LW doesn’t specify what the actual concern with ‘overstepping’ is, if it’s not that she’ll cheat – is it that the girlfriend is or will be negatively impacted? Or, most nefarious, the boss is infringing on the LW’s *property*?

      For me, the LW is at least a yellow flag because either a) the LW isn’t treating his—I forget if it’s specified so yes, I’m making this assumption—girlfriend as a trusted equal about his concerns, or b) the girlfriend doesn’t feel like it would be a good idea to bring up the tricky situation she’s navigating at work with him. My guess is the two are related and it’s both.

      Reply ↓
  5. polly*

    Oof, I’ve had managers text me similar things, particularly when I was early in my career (aka, young and fresh out of college.)

    No, nothing happened, but I definitely was aware the context wasn’t especially PC.

    Reply ↓
    1. NotBatman*

      Yep. Reminds me of the guy who used to do shit like “Oh, I love your pants” [leans over and rubs my knee]. I have no idea if that was prelude to further creepiness, since 6 months into our working relationship we had a major falling out about him trying to get me to change a work process that I’d already okayed with my manager. But in retrospect, I can say that the vibe was way off.

      Reply ↓
      1. ampersand*

        Yes! I think that’s what’s bugging me here. Like nothing too weird has happened, but something about it feels off. I agree with you; it does sound like he’s testing the waters. At best that’s annoying.

        Reply ↓
  6. Lilo*

    To be blunt LW, you’ve now written two letters to Alison about your girlfriend’s CEO about issues that are eh, but don’t explicitly cross lines.

    Stop emailing Alison and just talk to your girlfriend. Stop asking strangers for opinions on your relationship. We don’t know the context, other stuff going on, how your girlfriend handles things, etc. Maybe in larger context this is a red flag. Maybe it’s not. But you really can’t be micromanaging those interactions like that, she can’t control what her boss says to her.

    Reply ↓
    1. Not on board*

      Even if the boss has a big crush on her, and is hitting on her, it doesn’t mean the boyfriend has anything to worry about.
      1. girlfriend could be oblivious to the romantic/sexual overtures
      2. girlfriend could just have it handled
      3. so far, it doesn’t look like boss has crossed the line
      4. if you think your girlfriend is going to cheat on you with her boss, then it’s likely she might cheat on you with someone who’s not her boss – just break up already.

      Reply ↓
      1. Richard Hershberger*

        Even the boss in fact having a crush on and/or lusting after her is an open question. Stipulating that the language is flirty, recreational flirtation with no intend from either side to do anything more is a real thing. Whether it is appropriate to the workplace, much less from the boss, is a separate and legit issue.

        Reply ↓
      2. londonedit*

        I agree – I find it vaguely insulting or at least icky that the assumption from the OP seems to be that his girlfriend will just jump into bed with the CEO based on a few messages, and the assumption that she doesn’t already have this handled. Reading that exchange I can well imagine her rolling her eyes and thinking ‘FFS Dave’ before sending her ‘Yes, see you there!’ reply. It’s so non-committal. Her boss may well be a creep, but she may well also be dealing with it herself, as a grown adult woman.

        Reply ↓
        1. Nina*

          Do you trust your girlfriend not to cheat on you?
          Do you trust your girlfriend to know when to say ‘okay stop please boss’?
          Do you trust your girlfriend to decide what job she does?

          because if the answer to any of those is ‘no’ then the relationship between LW and his girlfriend is in trouble, regardless of what the girlfriend’s relationship with her boss is like.

          Reply ↓
    3. Whale I Never*

      Yeah, I assumed from the opening that this would be an obvious escalation from the first letter in a way that would justify a second letter, but it seems like more of the same–and Alison’s response is a slightly longer and more in-depth version of the same advice.

      From my reading, it’s very easy to assign both innocent and malicious intentions to LW and to Girlfriend’s Boss, which means there’s not much to be gained by continuously asking strangers on the internet to litigate. Every commenter is going to see things from their own filter! Nothing is objectively, egregiously wrong, and LW is far better off having an honest conversation with their girlfriend, and a personal soul-searching moment.

      Reply ↓
    4. ferrina*

      In defense of the LW, the CEO is carefully making overtures without crossing the line. Just because a line isn’t crossed doesn’t mean the behavior was good.

      And if LW doesn’t have an outside support system with good judgement to help them navigate this, AAM is a good place to come. I’m someone who grew up in a toxic family of origin, and all of my reference points from childhood are bad ones. I had no reference point of what a healthy romantic or work relationship looked like. I was not lucky enough to find another support system (my romantic partner isolated me from friends, and my family’s advice is usually incredibly bad). The other part of that is that you don’t trust your own judgement. Human brains tend to favor what is familiar, and if familiar things are all toxic, your brain will guide you back into toxic situations. For a long time I couldn’t know whether my brain was saying “this is a good relationship” because it was actually good, or because it felt familiar to me like the toxic relationships I had witnessed day in and day out as a child. I used to believe that communication solved all things, but then I got mixed up with a partner that lied all the time, and I had too much empathy for his excuses and improbable explanations. Having an outside gut-check is a good thing, and a necessary thing. But you need an outside gut-check you can trust.

      Reply ↓
      1. MsM*

        Okay, but he clearly doesn’t trust the gut check he’s getting here, because the lack of absolute affirmation in the posted response or consensus in the comments should tell him that he’s not going to get the unequivocal “yes, this is dodgy” response he seems to be looking for. Which means he needs to examine why he’s so certain it’s dodgy and decide what he wants to do about it that’s actually in his power to control.

        Reply ↓
      2. Whale I Never*

        Even saying “the CEO *is* carefully making overtures” is really definitive, though, and I don’t think anyone here can say for sure that’s what he’s doing.

        1) CEO could be very deliberately trying to suss out girlfriend’s interest in a romantic relationship
        2) CEO could have romantic feelings for girlfriend, but he knows they’re inappropriate and thinks he’s being platonic, because being affectionate towards people we like isn’t always deliberate
        3) the above, except the CEO doesn’t even recognize his feelings are romantic
        4) CEO could have no romantic feelings whatsoever, and is saying those things because he is naturally a bubbly person, or because he comes from a family/past workplaces that were effusive like that and he thinks its normal, or because he got little sleep last night and was feeling a little loopier than usual, or because he used to be very stiff and formal with employees and is overcompensating based on feedback he received.

        I think that’s what most commenters are getting at in these responses. There are dozens of different explanations for why the CEO may be behaving this way, and LW is never going to know for sure because they don’t have a relationship with the CEO, let alone a deep relationship where they would really dig into the personal motivations that could be influencing his behavior.

        Reply ↓
  7. Dido*

    it’s 100% obvious that at least the CEO has a crush on your girlfriend, whether she reciprocates it or not is the question

    Reply ↓
    1. Seashell*

      Or maybe he’s a rather enthusiastic gay guy with zero romantic or sexual interest in a woman?

      I wouldn’t say 100%.

      Reply ↓
    2. Not on board*

      Even if the CEO does have a crush on her, it really doesn’t matter as long as he doesn’t make her uncomfortable.
      If he doesn’t trust the girlfriend not to reciprocate, or to not cheat, then he should break up with her. After all, there are probably plenty of people who hit on her regularly, and nothing comes of it.

      Reply ↓
    3. MsM*

      I can imagine multiple bosses of mine sending a similar message. All of them are/were married straight women. I feel comfortable saying there are other explanations.

      Reply ↓
    4. biobotb*

      Maybe. But at least, if there’s a crush and she reciprocates it, her response would have been very different. Instead it was quite generic.

      Reply ↓
    5. Lynn*

      I wonder about that too

      I am dealing with the same issue where I work at as well

      I get the sense that one of the assistant managers has a crush on me going by his behavior when I am around him

      He is single

      I am married

      He has met my husband

      I keep everything above board when dealing with him

      The OP’s girlfriend needs to do the same, which I am hoping she is doing

      My husband and I had a conversation about the assistant manager’s behavior, which is the best thing we can do

      The OP and his girlfriend need to do the same thing as well

      Reply ↓
      1. Coffee Protein Drink*

        I would bet that he wants to approach the conversation with “See, a professional person says I’m right,” as ammunition.

        Reply ↓
    8. anonymous anteater*

      Just based on the information we have here, I just don’t see things pointing to an inappropriate relationship. A highly effective EA will usually work very closely with an executive, and make her or his life considerably easier. It can be a high stress work environment, and having colleagues that you genuinely enjoy working with makes it all better. My workplace is pretty strong on expressing appreciation to all staff including supporting staff, and viewing everyone as a person first. So all those comments, including those from the previous letter, would not be inappropriate here.
      They could, with other dodgy context, just not based on what the letter writer has told us.

      Reply ↓
    9. Rex Libris*

      No, it’s 100% certain that he comes across overly-familiar. We have no way of knowing if he just generally acts a little too flirty, or thinks he’s just being friendly, or whatever. In the world of lascivious text messages though, that one’s pretty G rated, if it is one.

      And if there is a problem, it’s still the girlfriend’s to handle.

      Reply ↓
    1. Charlotte Lucas*

      I could totally see a similar exchange between our director and her EA. (They are both straight women, but have a strong working relationship.)

      Reply ↓
      1. Bawls Targaryen*

        I am a woman working for a straight woman, and I’ve gotten messages like this from her before. I’ve also worked for men who have written me messages like this and weren’t hitting on me. It’s of course possible…but based on the evidence we have, I don’t think it’s likely.

        Reply ↓
  9. Angstrom*

    The most innocent explanation is that the CEO had a miserable day lined up on his calendar, and was happy to start the day by meeting a friendly colleague before diving into the shark tank. I’ve looked at my calendar and had similar thoughts.

    Reply ↓
    1. CL*

      This was exactly my thinking. I would probably send the same text to my platonic work friend (or receive it from her) if I knew a rough day was coming.

      Reply ↓
      1. Sola Lingua Bona Lingua Mortua Est*

        That’s where my mind went, too, but then the EA being a silver-lining pushed things back into the questionable territory for me.

        Reply ↓
    2. Damn it, Hardison!*

      Apparently I wouldn’t know if a coworker was hitting on me because that text exchange seemed very normal to me.

      Reply ↓
      1. amoeba*

        Huh. I mean, maybe it’s the different fields, but I’d find it very, very clearly flirty if a coworker or boss sent me that message, unless we were really, really good friends at work. Like, besties.
        So, dark orange flag for me at least (on his side! Nothing here to suggest see reciprocates at all.)

        Reply ↓
        1. Charlotte Lucas*

          Where I work it would depend on the person, but I work at a health agency, and this kind of message wouldn’t be out of place.

          Reply ↓
          1. Charlotte Lucas*

            But my guess is that most people don’t go to work and spend a lot of time talking about social -emotional development, accessibility, and inclusivity, etc.

            Reply ↓
    3. Anandatic*

      I don’t think the CEO would say this to a male colleague he was friendly with, and that alone makes this a gendered and flirty comment in my books. I don’t think you can mean this in a platonic way.

      Reply ↓
      2. Angstrom*

        Sure you can. He could say that to Bob thinking “Oh good! At least I get to spend a few minutes talking to Bob about the Cubs game last night before that #@!& meeting with BlobCorp”.

        Reply ↓
        1. learnedthehardway*

          Similarly, I can see one of my clients telling me “At least I will see you there” at an industry event we are both going to, that neither of us wants to attend. In fact, I think one of us said exactly that!!

          Definitely ZERO romantic intentions on either side.

          Reply ↓
        2. ferrina*

          That makes sense for a colleague that you don’t see all the time. But generally an EA will see their boss repeatedly throughout the day (not always; different companies/individuals operate differently. But that’s true of the companies I’ve been at). I don’t tell someone “At least I get to see you!” in a platonic way if I already see them every day.

          Reply ↓
      4. Redaktorin*

        I think toxic masculinity has men scared to say a lot of things to other men that are, frankly, super normal.

        I’d say something like this to men, women, or my coworker’s cute dog. It’s just nice to see a work bestie on a day when you’re expecting to struggle. Or any other day.

        Reply ↓
  10. Apex Mountain*

    Without knowing anything about their other communications or their overall relationship, I don’t think any of us can say whether or not this is meaningful. This is one message out of hundreds or thousands.

    Still, you must be feeling insecure or suspicious about something, though it’s hard to see what, since this and the prior letter both seem pretty mild

    Reply ↓
  11. bamcheeks*

    trust! your! girlfriend! Or don’t, and break up with her! But this weird detective thing you have going on is gross!

    Reply ↓
    2. ferrina*

      Adding on to this- if you can’t trust your girlfriend, you don’t need proof to break up.

      You don’t have to have justified mistrust in order to break up with someone. You don’t need proof. It’s okay to say “This relationship is making me stressed and unhappy. I don’t know why, but I know that I can’t continue like this and need to end the relationship.”
      There are so, so many reasons to end a relationship, and being unhappy (for whatever reason) is one of the best. Maybe you aren’t ready for a relationship right now- if so, that’s a great reason to break up! Maybe there are other subtle things that make the two of you incompatible- if so, it’s okay to break up! Maybe your unconscious is picking up on other red flags that you can’t quite put your finger on- if so, you may look back on this in a few years and be glad you broke up!

      I’ve stayed in relationships way too long because I thought I needed a “good enough” reason to break up. Just being unhappy is the best reason that there is. Some people will claim “but that’s not fair to the other person!” No, it’s not fair to either of you to continue a relationship where one of you is unhappy. That seeps out.

      Reply ↓
  12. londonedit*

    I would say that you don’t have all the context here. There’s absolutely no chance of my boss hitting on me for several reasons, but this is within the scope of the sort of messages that have occasionally been sent between me and my boss. We have a very collaborative relationship and my boss will often send me the odd rant about something annoying that’s happened in their general life – I can absolutely imagine getting a message from my boss in the context of them having recently been complaining about their broken boiler/the roadworks keeping them awake for the last three nights/etc saying something like ‘See you in the office – at least I have that to look forward to!!!’, as in, ‘It’ll be a million times better than sitting here listening to the road being dug up’ or whatever. And I agree with Alison that your girlfriend’s response was as non-committal as it could possibly have been.

    I totally agree that this is not a problem of whether or not your girlfriend’s CEO is hitting on her or not – if he is, that’s for her to sort out, and it’s your role to support her in doing that. But if you think your girlfriend is going to have an affair with her boss, that’s something you need to look at – why do you think that? What makes you not trust her? Why would you assume that she’d drop everything and have an affair just based on a few messages? Is it a lack of self-confidence, or a lack of trust in your relationship?

    I’d also caution against looking at your girlfriend’s messages, even if the iPad is ‘just there’.

    Reply ↓
  13. lyonite*

    I agree that’s a borderline way to talk to an employee, and I second everything Allison says above about being ready to support your girlfriend if she feels like she’s uncomfortable. However. . . you do seem very focused on their interactions, however “accidental” you insist it is that you saw this exchange. Do you find this happening a lot, that you see suspicious things in her interactions with men? Are you frequently “happening” to see her communications? Ultimately, you either trust your partner or you don’t, and trying to control who they talk to, and how, won’t be good for either of you.

    Reply ↓
    1. Anandatic*

      I think you hit the nail on the head here. I agree that the CEO’s comment was borderline, but the girlfriend hasn’t done anything that raises red flags. I think she works for a CEO who wants an overly familiar working relationship, and it’s up to your girlfriend whether she’s okay with that. Either you trust your partner, or don’t and break up. But she hasn’t done anything wrong here.

      Reply ↓
  14. Freddy*

    I might be in the minority here, but I can see why OP is concerned. I’m a woman and have never had a male coworker or manager interact with me in this way. And if it did happen I’d be on high alert.

    Reply ↓
    1. ThatGirl*

      I mean sure he can be concerned but as I noted above, either he trusts his gf or he doesn’t – what matters is how SHE feels about it.

      Reply ↓
    2. Dr. Rebecca*

      You being on high alert would be appropriate, because you’d be the one in the (hypothetical) situation. Someone being on high alert *for* you without even asking you if you minded, like the OP hasn’t asked his girlfriend? That’s…kinda weird, actually.

      Reply ↓
      2. Freddy*

        I don’t think it’s weird at all. I’ve had boyfriends (and now my husband) tell me when they thought some dude was hitting on me. And I’m trying to directly address OPs question. (As for what to do about it I’m with Alison)

        Reply ↓
        1. Beth*

          It’s one thing to notice someone’s hitting on your partner. That’s fine.

          It’s also fine to ask your partner, “Hey, I got the vibe that X is hitting on you. How do you feel about that? Is there anything I can do to support you as you handle it?”

          It’s another thing to write into an online blog repeatedly, without any mention of talking to your partner, looking for–what? Backup from the internet, so when you talk to your partner you can add the weight of “And all these people think this is off too, it doesn’t matter if you agree, you have to admit I’m right”? Permission to get mad at your partner’s boss and potentially mess up her work situation? Permission to stalk your partner’s communications for proof of infidelity? I can’t imagine what good OP gets from coming here instead of just talking to their partner. That’s what makes this weird.

          Reply ↓
      3. ferrina*

        Nah, not weird. Have you been out with friends and not liked the way some guy was treating a female friend? You ‘happen’ to need something from the car at the same time as her so she’s not alone. You keep an eye on whether he’s standing too close, because you can read her body language and she’s not signaling any interest and you’re wondering whether to interupt.

        I’m not saying OP should insert themself AT ALL. But it’s not weird for OP to want to keep an eye on things. And OP should DEFINITELY be talking to the girlfriend. Not to say “this guy is creepy”, but to say “hey, how do you feel about your boss?” and giving her a safe space to process if she needs to. The boss clearly has power over the girlfriend’s livelihood, and she may or may not think that over-familiarity is an acceptable behavior (myself and so many other women have been socialized to assume “oh, he’s just awkward, it’s not his fault.”).

        I don’t know the girlfriend or the nuances of the situation. It may just be a normal situation with a extremely familiar boss who isn’t good at optics (getting a massage certificate for a direct report, as happened in OP’s first letter, is just weird). It may be that the boss is a bit inappropriate, but the girlfriend has it handled. Or it may be that she doesn’t feel comfortable and feel trapped, but is doing the best she can. Or maybe she’s a willing participant. And I don’t know OP- maybe they are overly suspicious in other scenarios, maybe they are usually chill but fixate on the boss dynamic, maybe they are picking up on something. There are so many iterations of what could be happening with so few details. But glancing at an SO’s messages occasionally (if we take OP at their word) isn’t a terrible crime (though if OP has a history of getting suspicious, it’s not a healthy habit for them).

        Reply ↓
    3. Beth*

      I can see why OP’s GIRLFRIEND might be concerned. If it was her writing in, expressing concerns that her CEO is hitting on her and asking for advice on how to handle that given that she’s not interested but there’s an obvious power dynamic, I think there’d be room for a lot of really good advice.

      But that’s not what’s going on here. This isn’t OP’s problem unless 1) his girlfriend tells him she’s uncomfortable with it and asks for his support in dealing with it (which hasn’t happened) or 2) he thinks his girlfriend will cheat on him given the chance (which is about him not trusting his girlfriend–the work setting is honestly kind of irrelevant, it’d be the same problem if it was a guy on her softball team or a neighbor or whatever).

      Reply ↓
    4. Pyjamas*

      If I were this uneasy, I’d go ahead and look at the text exchanges .. because my partner has my iPhone password and I have his. We don’t generally read each other’s text threads but neither of us would be bothered if the other did. If gf finds this an invasion of privacy—they’re living together so really seem more like domestic partners—that’s a bigger red flag than the boss.

      But my guess is emotional affair. And that OP hasn’t brought it up bc he knows he’s more into her than she is into him

      Reply ↓
      1. Bridget*

        Wow this is INCREDIBLY off-base for so many reasons. My partner has my iPhone password for logistical reasons but if I found out he’d read any of my texts without asking, I would be FURIOUS – either he trusts me or he doesn’t!
        Just because it’s a boundary you have doesn’t mean every couple has the same boundary; it sounds like they don’t have permission to go through each others texts to telling OP to just go read all of her texts is WILD – if he did this, I’d tell HER to break up with HIM.
        And there is ZERO EVIDENCE in either letter that there’s ANYTHING indicating an emotional affair! What an outrageous thing to say.
        Honestly, it sounds like YOU have trust issues and you’re imputing them onto OP’s relationship. Don’t do this.

        Reply ↓
  15. happybat*

    In the 1930s, the right of men to read their wives’ letters was a question (see for example Dorothy Sayer’s ‘Busman’s Honeymoon’). It seems that in the 2020s, the right of access to social media and texts is similarly at issue.

    I don’t think you should read anything into your girlfriend wishing to keep her texts and social media to herself. They are, after all, hers. She is likewise entitled to manage her work and personal relationships as she sees fit.

    If you can no longer give this woman your trust, leave. Whether your mistrust is well-founded is really beside the point.

    Reply ↓
    1. MsM*

      I don’t think OP in particular should read anything into his girlfriend guarding her privacy, when he seems determined to dissect every message and jump to the worst possible conclusion.

      Reply ↓
    2. Hlao-roo*

      I read all the information about how the letter-writer happened to see the messages in a “I want to show that I wasn’t snooping and it was happenstance” sort of way, not in a “I don’t like that my girlfriend locks her iPad” sort of way.

      I read a fair amount of advice columns and there’s a lot of “I wasn’t snooping, I borrowed my partner’s phone/computer and just ~happened~ to scroll through five years of email/text history until I found something that upset me” in other letters. I would say that scenario is snooping. Seeing messages pop up on a phone/tablet that was left lying around is more of a “it just happened” scenario.

      Reply ↓
  16. Seashell*

    I really don’t see this exchange as a big deal, but my opinion might vary based on the person’s personality. Some people lean towards being over the top, so extra enthusiasm would mean even less coming from them.

    I think the only person whose opinion matters on whether or not it’s appropriate is your girlfriend. Assuming she’s a functional adult, she can tell if CEO is a creep or not.

    Reply ↓
  17. Margaret Cavendish*

    I think probably both – it is a little more familiar than most professional relationships, AND you may also be overthinking due to your past experience.

    The advice is the same, though. See if you can figure out what’s bugging you most, and then talk to your girlfriend! It might be good to do these things with the help of a trained counsellor, if you can – do either of you have access to an EAP? Not because anything is necessarily wrong or needs fixing, but you’re both likely to have big feelings about this, and it might be easier if you have a neutral third party to guide you through the process.

    Reply ↓
  18. Not on board*

    The 6am-ness and the “At least I have that to look forward to” seem a little overly familiar from a boss to an employee. Your girlfriend’s response seems very neutral so it doesn’t appear that she’s being overly familiar with her boss.

    If you trust your girlfriend not to cheat, then that’s it. If you think she might cheat, then break up. If her boss IS hitting on her, or just has a crush on her, it doesn’t matter. As long as he doesn’t cross the line, make your girlfriend uncomfortable, it just doesn’t matter. And if he does, then that’s on her to navigate and she would need your support without the “I told you so” aspect of it.

    Reply ↓
    1. NobodyHasTimeForThis*

      My boss will regularly tell all of us that we are our favorite part of their job. It is not sexual, it is that we make her very stressful job manageable and often fun.

      Reply ↓
      1. Not on board*

        My assessment is based on the message without additional context, like the personalities and their specific work norms. But saying the only good part of coming to the office is seeing your employee – which is what is implied here is a little overly familiar. I didn’t say it crossed a line – just that it gives the sense of a having a crush.

        Reply ↓
  19. Feelings Can Be So Inconvenient*

    LW you need to talk to your girlfriend. I’d first have an honest conversation with yourself about why this bothers you so much because it reads more like you don’t trust your girlfriend to know how to handle this. That could be justified or not, but it’s not a great foundation for a relationship. Time to have a good sit down conversation when both of you have space for that.

    Reply ↓
  20. Awlbiste*

    If I got that message from my boss it would give me the ick. I think it’s too personal. But that’s just me and my own boundaries and how I feel. There are other people right here in the comments that it wouldn’t bother at all. Just ask your girlfriend how she feels, that’s literally the only way to find out.

    Reply ↓
    2. Charlotte Lucas*

      If it came from my direct boss, I would be surprised and grossed out, but I dislike my boss on a personal as well as professional level (many do!), and it would be weird and unexpected. On the other hand, with bosses in the past, if I knew my boss might be having some tough meetings or something that day and I might not think twice.

      I think industry also makes a difference. I’m not a touchy-feely person, but many in my industry are, so YMMV.

      Reply ↓
  21. Claire*

    I have no idea what the dynamic is with your girlfriend and her boss. But I can say that if a male colleague texted that to me, it would give me pause. It would definitely cross my mind that they were trying to flirt. I can’t picture any of my male colleagues over my 20-year career sending me that message, tbh.

    Reply ↓
  22. xylocopa*

    With this and the earlier examples you gave, I get why you feel like there’s something off about the CEO’s communications. In your girlfriend’s place I–personally–might be uncomfortable with the tone and the massage gift card, etc. I don’t think you’re wildly off base to find this odd.

    But like Alison said, it still comes down to the same thing: listen to your girlfriend and either trust her or figure out what it means for your relationship that you don’t trust her.

    Reply ↓
  23. Diomedea Exulans*

    It’s clearly very weird if a manager is sending such a message. It’s okay between colleagues/work friends, but a bit questionable coming from a manager, that too at 6 am.

    Reply ↓
  24. Juicebox Hero*

    The fact that she left the iPad in the open where you’d be able to easily see it plus any messages that happened to pop up makes it seem that she both trusts you and doesn’t think anything her boss is doing is outrageous. EAs and their executives seem to have a different and more chummy relationship than the average boss/employee. He could also just be a jokey kind of guy, a dork who doesn’t realize how remarks like that can land, or a workaholic who doesn’t have many friends so he tries to buddy up to his employees. She seems to have mastered the art of letting him know he’s heard without encouraging him.

    The fact that his behavior still bothers you means it’s time for a heart to heart with your girlfriend, and I really think you’d benefit from some kind of therapy to help yourself understand where it’s coming from.

    Reply ↓
    1. Bawls Targaryen*

      “EAs and their executives seem to have a different and more chummy relationship than the average boss/employee”

      Yup. A lot of non-assistants chiming in here saying this is weird? It really, really isn’t.

      Reply ↓
  25. HugeTractsofLand*

    My first thought is that he’s reaching out because he (or they) have a crappy day lined up and he knows she’ll sympathize or is also going to have to deal with it. Could be a stupid training scheduled for all morning or a meeting with someone they agree sucks, or maybe something they both had to prep for or talked about prepping for. These two people work together, so they’re going to have communications that you aren’t in on and that’s ok! I wonder if it bothers you because you don’t have a similar rapport with your gf, or you feel generally that work gets all her attention and the CEO is just a personification of that.

    You say your girlfriend was already up in the bathroom, so the 6am of this message isn’t a red flag if they work at a job that gets them both up early. I agree that it’s a tiny red flag from the boss *in the larger context*, but your gf didn’t escalate and a quick convo with her should put things to rest.

    Reply ↓
  26. Unkempt Flatware*

    I don’t think the interactions between boss and gf are the issue here. Clearly, there is some lack of trust or confidence and self-esteem. Maybe even some lack of mutual respect? I don’t know but I do know that what seems to be isn’t at all.

    Reply ↓
  27. The Minotaur*

    As can be seen from the comments, some people find this totally innocuous (that’s where I land) and other people think it’s flirty. No one cab know but the CEO. Maybe not even the girlfriend. If I thought my boss was flirting with me, I’d tell my husband, because I trust him and know he’d help if I needed it and would laugh with me if I found it amusing. If I found out my husband had written twice to an advice columnist about this, I’d find it incredibly off putting and a red flag for jealousy. Talk to the girlfriend, interrogate your own jealousy, talk to your friends or a therapist, and think about why you don’t seem to trust the GF. If you cannot trust her no matter what she says and does, break up. I wonder what Captain Awkward would say about these letters—it reminds me if some past posts of hers.

    Reply ↓
  28. Nonanon*

    To use terms from another venue, soft NAH:
    1. LW provided no evidence to be concerned about girlfriend cheating, just boss being inappropriate; I would be worried if I (female) thought my partner’s (male) boss was being inappropriate, it’s not abnormal to be worried about your loved ones.
    2. LW did not state this or the previous instance was brought this up with girlfriend, a better first step than writing an internet advice column. That being said, it is a hard conversation to have and it’s possible that they just wanted advice first.
    3. Some bosses are simply more friendly than others, with no ulterior motives. Friendliness can still result in weird boundaries (like the massage gift cards from the first instance; I say this as someone who gets massages for medical issues, my boss knows this, and I would still be a little skeeved if they gave me a gift card, so take it as salty as you want), but not all “it’ll be great to see you” messages are sketchy in nature. It isn’t clear if LW has ever met the boss; we effectively don’t know what their general personality is like.

    Reply ↓
  29. Expert Paper Pusher*

    Context is going to be extremely helpful here, and the best way to get that is open communication with your girlfriend. I’ve had a boss with no sense of personal boundaries who sent me texts like the one you saw– not because she was hitting on me, but because she was going through some big problems at home (including caregiving for a dying family member) and was barely holding it together. The only way to know what’s going on is to talk to your girlfriend and trust her.

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  30. Keymaster of Gozer (she/her)*

    Eh, wouldn’t bother me. I’ve got on very well with a boss before and had joking/friendly interactions. Also, what people say on email/text can be way more casual than in person.

    Here’s the real issue here though: you’re not communicating with your girlfriend. I doubt she’d be impressed if she found out you’d written in twice to a columnist about her work life. You either trust her to handle her own boundaries or you don’t.

    Women deal with men hitting on us or harrassing us a LOT more often than you realise. We’ve generally got our own mechanisms for dealing with it if it does happen.

    Her work, her job, her boss, her business.

    Reply ↓
  32. Tobias Funke*

    A lot of women who respond to this, myself included, are going to be coming at this from the perspective of someone who has been pressured to quit a job because of a partner’s jealousy and it is likely to be a large theme in the responses you receive. I did end up quitting and it stole three years of my life. I am still financially recovering and it’s been ten years since I quit.

    If I’m the woman in this situation, I am rolling my eyes and shuddering and replying neutrally like your partner did. I can live with an overly friendly text from a boss. I’m up at 6 anyway. What I cannot live with (ever again) is constant surveillance and suspicion supposedly due to the actions of another person whom I cannot control but are really about insecurity and control.

    It concerns me you are snooping and writing mental fanfiction about what you find. Do you see why it concerns many commenters when you go back to an advice column instead of talking to your girlfriend? It can bring up a lot of adjacent questions. Are you printing this out and saying everyone agrees with you? Are you leaning on her to leave her job? Do you ever show up at her job unexpectedly? What if she does leave her job and she works for a man again? Do you lean on her to not work and to let you take care of her for awhile? What about if she goes to get groceries and the cashier is friendly? Does she only do pickup orders now? What if the guy loading up the car says it’s great to see her? Is it delivery time then? Do you track her location “for safety”? Does she know you do it? Are there cameras or tracking devices on her car she did not put there?

    I realize this all sounds hyperbolic. And that’s why I encourage you to think about this shit right now before you “just see” one more text. You can turn this around. Maybe not in this relationship, but you can turn this around. A partner acting this way is far more harmful than a boss with happy pants.

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    1. Lilo*

      This absolutely hits the nail on the head of my concerns. I feel like this person is trying to get ammunition to be used against the girlfriend and this makes me incredibly uncomfortable.

      Reply ↓
      1. JenniferAlys*

        Yes, all of this. OP is being controlling and gross. Newsflash. Men hit on women all the time and women just handle it, without cheating on their partners. Even if he is hitting on her, what next? Either way this is not his problem to solve.

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    2. kicking-k*

      This seems well said. I don’t think we’re in the disaster zone here but the letter writer needs to take a dispassionate look at their own reactions, and then have a sensible, non-accusatory conversation with the girlfriend.

      Reply ↓
    4. bamcheeks*

      I completely agree with all of this.

      I’d also add that IF you have been doing the Heavy Boyfriend stuff, and your girlfriend has been laughing and telling you there’s nothing going on here, but then something about the relationship with her boss changes and she starts to feel that it is a bit off — you’ve just raised the stakes on her telling you and coming to you for support. Because now it’s, “great, and if I tell Steve about this, he’s going to be all, “I told you so!”” So maybe she ends up trying to deal with a gross boss by herself, or concealing the fact that she’s dealing with a gross boss, or denying to herself that there’s something ooky going on because YOU’VE made it weird.

      trust. your. girlfriend.

      Reply ↓
      1. kicking-k*

        Yes, absolutely. “Make yourself a safe person to come to,” is an important principle in any relationship though I hear it more with parents and children.

        Reply ↓
      2. MsM*

        100%. It’s hard enough to deal with someone who seemed like a decent person revealing themselves as a creep without having to face that you misjudged them badly. It’s even harder when the person who warned you insists on making the situation about them (including blaming you for not seeing it) and/or dictating to you how they think you should handle it instead of just going “I’m sorry; how can I help?”

        Reply ↓
    6. Ever and anon*

      A warning bell in this story for me is the idea that OP saw their girlfriend’s *reply* “just pop up” on her locked iPad. That’s not how iPad notifications work — you don’t get notifications about your *own* messages, even if they were sent from a different device. You’d have to be logged in to different accounts on each device and have both of those accounts participating in the same text/chat thread, which is highly unusual (especially for two work devices, which OP said these are). Fully expect OP might claim that’s what happened rather than admit that they were snooping. But this gives me pause and I agree that the OP needs to take a hard look at their own patterns of behavior and motivations.

      Reply ↓
    7. Anonanonanon*

      I agree. I think OP’s behavior is more worrying than the boss’s. I was getting strong “I’m looking for an excuse to make her quit her job so she’ll be more dependent” vibes, and that type of situation will never end well for the GF.

      If OP doesn’t trust his GF, he should break up with her. If he does, he should let this go and trust that a) she can handle this and b) if she needs his opinion or assistance, she’ll ask for it. “Accidentally” reading her texts, obsessing over what could be innocent messages, and writing in multiple times to seek validation of his suspicions instead of just talking to her is n not the behavior of someone who is acting in good faith.

      Reply ↓
  33. Annastasia Von Beaverhausen*

    My boss (also the CEO) says things like this to me, and occasionally at 6 AM depending on what the plan for the day is.

    He also lives with his boyfriend, sooo.

    OP, you need to talk to your girl friend and not a bunch of randos on the internet (Alison excepted).

    Reply ↓
  34. ijustworkhere*

    My thinking remains the same. Your girlfriend does not need you to protect her from her boss. The issue isn’t her boss –the issue is the trust, or apparent lack thereof, in your relationship.

    Reply ↓
  35. Charlotte Lucas*

    I am low-key fascinated by the number of people who are fixated on the fact that the message came at 6 am. I work a hybrid schedule, and it is very common for people to sign in early to check messages, schedules, etc. I just assumed that Boss saw a busy, potentially frustrating day ahead, and wanted some commiseration.

    Reply ↓
    2. cosmicgorilla*

      I work with people that prefer to get started no later than 6 AM.

      I also work with people across different time zones, so it’s entirely possible for me to send a message that’s 9AM for me but 6AM for the recipient (not expecting a response.)

      Reply ↓
  36. I should really pick a name*

    If he IS hitting on her, what does the LW plan to do about it?
    That detail is missing from both this letter and the previous one.

    Reply ↓
    1. dulcinea47*

      “make” her quit, I’m guessing. (that is written with a massive eye roll. This guy needs to let his gf handle her own business. Any sign of unwarranted jealousy is a huge red flag to me.)

      Reply ↓
  37. CatsOnAKeyboard*

    Heck, this could have been his response to her message of something like “I’m going to swing by the bakery to grab a box of bagels before the 7:30 team meeting, I might be a few minutes late” or anything else regarding the plans for the day … the looking forward to might not even be about seeing her but a previous thing.

    But even if it was about seeing her, that’s 100% the sort of exchange I’ve had with my current boss when we’re in the midst of some crunchy projects and the only thing keeping us going is the ability to mutually snark about the issues. This feels like searching for a problem.

    Reply ↓
  38. dulcinea47*

    The real problem here is the jealousy about something the gf is not causing or doing and the fact that she’s not trusted to handle it herself.

    Reply ↓
  39. Lemons*

    Agree with what most folks are saying, yes, the CEO is out of line, but your GF rebuffed it in the most professional way possible. “Yep, see you there” is not how someone who’s cheating or tempted to cheat would respond. She’d say “same” or send a heart emoji or reciprocate/acknowledge in ANY way, which she didn’t. Most women have to professionally shut down a man at work at least once in their lives, that’s what your example shows.

    This is a you problem! You don’t trust your GF. Maybe send this one over to Captain Awkward, because this is a relationship problem.

    Reply ↓
  40. Almost Empty Nester*

    I would absolutely receive a text like this from my manager (and have) and I know without a doubt that he’s not sending them with hopes of our relationship moving past manager/employee. My sight line for this goes as follows: boss is having a crappy week, for whatever reason, maybe found out something he was hoping to have happen in another part of his life isn’t going to happen, and sends that text to his trusted employee. She provides a very neutral response. I see nothing out of the ordinary and if my husband asked me about it, I’d probably laugh. Then again, I travel regularly with 20 + men in my team along with maybe 3 women, and any of them hitting on me or any of the other women would be laughable (for the record, we’re all around the same age). I treasure the friendship of all of them, including my manager. Sometimes work is just work, and the adults involved realize that.

    Reply ↓
  41. Jennifer Strange*

    I bet that if the CEO was a woman the LW wouldn’t be twisting himself into knots to overanalyze every little thing, even though some women are romantically/sexually interested in other women (and some men aren’t romantically/sexually interested in other women). That’s not to ignore the gender dynamics that do exist, especially in employer/employee relationships, but if a woman saying this to the GF wouldn’t raise one’s heckles, it’s a good indicator that the issue is more with the LW than with the GF.

    To be clear, if the GF were the one feeling uneasy about this the advice would be different (it’s her relationship, after all). And I could easily see a woman feeling uncomfortable about this sort of interaction from another woman, especially one who was her boss! But ultimately the GF knows the dynamics of her and CEO’s relationship better than the LW, and if he trusts her all he can do is let her handle it.

    Reply ↓
  42. Why winter?*

    Please don’t do or say anything that would make your girlfriend afraid to tell you if the CEO’s behavior becomes harassment. She would need your support – not your suspicion.

    Reply ↓
  43. blupuck*

    I used to be an EA.
    There is nothing to see here. An EA exists to make the boss look good. That’s the job.
    Your girlfriend seems to be very good at her job, so much so that the boss is thankful she is there and looks forward to her presence. He’s a bit casual about it, but as an EA, I would not think twice about that comment. I’m his right hand. Of course he’s glad I am there.
    I’m also guessing by the 6 am text that they have a rough day ahead. All the more reason why he is looking forward to her being there.

    Talk to your girlfriend, listen to what she has to say and trust her! or don’t and break up.
    This is a you problem.

    Reply ↓
    1. PegS*

      Yeah, I have close friends who are/were EAs, and it can be a very differently relationship than most manager/employee relationships, so this wasn’t necessarily something that looked that odd to me. However, I do agree that the LW needs to talk to his girlfriend. This isn’t about the boss; this is about whether he trusts her or not.

      Reply ↓
  44. i babysit adults in the sky*

    I can’t speak to how notifications from other apps — such as Slack or Teams, etc — show up on a locked iPad screen, but if they were just texting her reply would *not* have popped up as a notification. He would have had to be in app… aka snooping.

    Reply ↓
  45. HonorBox*

    I think that the boss is being overly familiar. This gives me vibes of the person (forgetting some of the details) who told a coworker that they were the highlight of their day.

    That said, I think this is a yellow flag. The response from the girlfriend is about as neutral as it gets. She acknowledged, but didn’t reciprocate any sort of emotion. She seems to be approaching this activity from her boss appropriately. Maybe it creeps her out. Maybe it doesn’t. But unless and until she says something, or there’s a more specific instance that the LW can point to, I wouldn’t bring it up. If, for instance, the boss is leering at the girlfriend at a holiday party, maybe you bring it up just by asking her if she’s ever uncomfortable. But otherwise, I think you need to leave it alone. She’s giving no indication that she’s doing anything untoward, so trust that she’s doing nothing untoward. But support her in the future if she ever is uncomfortable.

    Reply ↓
  46. Csethiro Ceredin*

    The 6am thing doesn’t strike me as too odd – I have a direct report who will text me then to tell me something she has heard from her team or if she is running late or whatever.

    The boss sounds a little flirty to me, though whether he is flirting With Intent or just casually I can’t say. However OP’s girlfriend replied totally neutrally and just how I would if I thought someone was coming on a bit strong, but not worryingly so.

    As Alison says it really comes down to whether OP is afraid the boss with try something, or whether he is afraid his girlfriend may not be faithful.

    Reply ↓
  47. oooooooooh*

    FWIW, this guy jumps awfully quickly to “I’m being cheated on” with very little reason to do so (that he’s provided here). Might be time for him to examine why he believes that’s the case so often, and to have a real conversation with himself about whether he’s truly happy and confident in his relationship, because this reaction kinda indicates otherwise.

    Reply ↓
  48. NobodyHasTimeForThis*

    This has nothing to do with her boss. Or really her for that matter.

    You are feeling insecure. Work on yourself and your relationship. That’s it. Quit trying to figure out how to convince your girlfriend that she should be feeling a different way than she is.

    There is nothing less appealing than a jealous/controlling partner.

    Reply ↓
  49. CzechMate*

    Yeah, I’d say this isn’t a big deal. If this is a small company with an owner/CEO, it’s more likely they’ll be sending messages at weird hours, particularly if an event is coming up. The CEO *is* being pretty familiar, but that’s not too weird at a smaller company. Plus, there are too many unknowns here. How do we know the CEO even likes women? How does the CEO treat other employees? Did the CEO know OP’s girlfriend before? Has OP’s girlfriend ever done something that made OP trust their judgement?

    OP, I might recommend talking to a therapist about this to unpack some of this. To me, this reads as more of a question about trust with your partner, and so meeting with a professional who can help you unpack that is probably the best approach.

    Reply ↓
  50. North Bay Teky*

    It could be something as simple as the boss is really grateful for the level of competence she brings to the office and saves his tush on the regular. He’s a little too familiar, but he might be having a bad day already.

    Reply ↓
  51. Peanut Hamper*

    1) Stop writing to advice columnists and talk to your girlfriend.

    2) Either break up or get some couple’s counseling to work through these trust issues.

    3) Get some personal therapy to work through your insecurity issues.

    Note that therapy isn’t necessarily forever, but just long enough to get the information you need to lead a happier, healthier life.

    Reply ↓
  52. Jeneral*

    I would personally feel very awkward getting this message from anyone at work no matter what time. I think it does hint at overly personal, inappropriate interest, and no one needs that from their boss. Even if a coworker meant it platonically, it would be very clingy. I met my best friend at work, we were very close, and it’d be really weird to get a message like that from her.

    If your girlfriend were my friend, I would ask her about all this, because if her boss is trying to start something romantic, it’s her career that’s more likely to suffer, not his. She may not realize that.

    Reply ↓
  53. How is this a question?*

    Geez dude…

    I work in a very friendly field and this wouldn’t be an issue at all. I would frame it as “I’m looking at my day and it looks pretty crappy but at least you are there to suffer with me”

    Reply ↓
  54. Bitte Meddler*

    It seems like the message OP saw from the CEO was the continuation of a text conversation about work.

    CEO: “Do you know where the file on the XYZ issue is? I have an 8:00 AM meeting with the client and it’s going to be a bad one.”

    GF: “It’s password protected in the G: drive. I’ll be there at 7:00 AM and send it to you.”

    CEO: “I’ll see you in the office. At least I have that to look forward to!!!”

    Girlfriend: “See you there!”

    Reply ↓
  55. Sleeplesskj*

    The only red flags I see here are on the OP’s part. If you don’t feel like you can trust your girlfriend, you should leave. Or get couples club to see what’s really prompting you to worry. You’d drive me crazy with all of that suspicion.

    Reply ↓
  56. Jodi*

    This is coming across as way too controlling and invested in the girlfriend’s job relationship. As the OP has taken the time to write twice about it , I can only assume he makes more of an issue on a regular basis with his gf . Does he expect her to quit and go work for a “ non-threatening” boss?

    Reply ↓
  57. FG*

    Dude, stop policing your girlfriend, or “protecting” her, or whatever bee you have in your bonnet. Handling him – and any job consequences – is her business, not yours. If you are generally supportive and have a relationship that’s communicative, then she’ll let you know if there’s something to worry about. If not, then that’s the issue, not the boss. So put away the caveman club and chill the f out.

    Reply ↓
  58. TheLoaf*

    Your girlfriend isn’t a toy to be fought over. She is a whole person who deserves to have agency over her life. You are treating her like a possession. Stop.

    Reply ↓

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