update: is it OK to vacation with a friend from work?

by Alison Green on December 17, 2024

It’s “where are you now?” month at Ask a Manager, and all December I’m running updates from people who had their letters here answered in the past.

There will be more posts than usual this week, so keep checking back throughout the day.

Remember the letter-writer asking if it was OK to vacation with a friend from work (#3 at the link)? Here’s the update.

Thanks so much for your advice on going on vacation with my work friend (as well as all the comments!). I’ve got a quick update for everyone.

I did decide to go on vacation with my coworker Brad, and nothing untoward happened while on the trip. No lines were crossed, we finished the trip cordial but slightly less chatty. I assumed that was because we ran out of things to talk about after a few days by the pool, but it’s clear that wasn’t the case.

It’s been 3 months or so since the trip, and things have been a bit frosty between us. Occasionally I’d texted Brad to grab dinner or something after work, but I always got turned down. All conversations and messages were clipped/rude, including conversations about work topics.

After being in my new department for 6 months now, I’ve picked up some red flags about Brad that I missed before (or chose to ignore due to our friendship). He is consistently rude/uncooperative/unhelpful with the whole department, to the point of people being nervous to talk to him.

I’ve stopped messaging/talking to Brad unless I have a work request, and even then I’m wary of approaching him. Occasionally I’ll get a late night text asking to meet him at the neighborhood bar after he’s had a few drinks, but then he’ll go back to avoiding me the next day.

All things considered, I’m still glad I went on the trip with Brad, it was a nice vacation and it opened my eyes to how he is. I don’t think this strained our work relationship, from what I can tell he now treats me like he treats everyone else on the team (minus the drunk texts!).

Thanks again for all the feedback from everyone in the comment section (and Alison of course!)

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{ 63 comments }

{ 63 comments… read them below }

  1. caro*

    My money’s on this: Brad had a crush on you, assumed something would happen on the trip but was too nervous to make a move, was disappointed when nothing happened and is feeling rejected, hence the frosty behavior with late night drunk texts. Tell me I’m wrong!

    1. amy*

      I was thinking along the same lines. Hopefully he’s not the type to think the LW ‘owed’ him ‘something’ in return.

      1. 1-800-BrownCow*

        Ugh, I used to work with one of those guys. He asked a friend (not from work) to go with him on a cruise because he didn’t want to go alone. He even paid for them to be upgraded to a nicer room (she paid the base price for her part of the cruise). When he got back from that cruise, he was going around work complaining to multiple women about how his friend refused to “put out” on the cruise, even though he was nice enough to invite her and pay for their upgrade. I guess they stopped speaking halfway through the cruise because he kept pushing and she kept saying no. This guy had the audacity to be shocked that every woman he complained to basically told him they sided with his friend and that she didn’t “owe” him “something” in return.

        Oh, and this guy was in his 60s and never married, only dated, because “marriage means compromising and no one is ever happy compromising”.

    4. a. thrope*

      +1

      Absolutely what I’m reading as well. Especially with drunken texts asking to meet up at a neighborhood bar even after becoming Mr Freezemeister! I try not to read the minds of strangers on the internet but I’m getting major “no head?” vibes from this guy.

    9. 2 and a Possible*

      I too can be oblivious, only to notice the frostiness devolve into “no contact” before it even occurs to me that unrequited affection is the cause.

    16. Thegreatprevaricator*

      This, very much this. I’ve been the oblivious ‘friend’ / letter writer. I am now able to recognise the signs, and also not in the life stage where it might be a thing that happens. I would encourage a bit of cynicism tbh.

      1. OP*

        Hey All! OP here.
        In hindsight, I totally agree with this. There was some talk around the office about how nice he was to me when I first started, and how abnormal that was (aka he’s a jerk to everyone but me). Might have been a red flag!

        1. Hannah Lee*

          Oh boy! That’s a ‘thing’ too.

          Men who sidle up to the latest new woman in the office, befriend her to try to get … whatever it is that they think they are entitled to. And then go frosty when their Master Plan fails horribly.

          They don’t bother with cultivating, maintaining relationships people already there, because they’ve already covered that ground and burned those bridges or the women already there have heard or seen that the guy’s a manipulative jerk not acting in good faith, so he’s not able to strike up the ‘friendship’ in the first place.

  2. HiddenT*

    Oof. Sounds like maybe Brad was hoping something would happen during the trip that didn’t. Sad to say (because of what it says about the reality of living as a woman in modern society) that I’m glad him being a jerk was the only fallout.

  4. Kate*

    I imagine there will be a lot of consensus around this, but Brad was hoping for something to happen and is now nursing his wounds. And sounds like a bit of a baby, given his inability to make an open and honest play for LW and his behavior to other coworkers. Brad needs to watch fewer romantic comedies!

    1. Caramel & Cheddar*

      Brad needs to watch more romantic comedies, because at least in those someone admits their feelings and says something about it so that the other person can admit they too have been harbouring secret feelings this whole time!

      I do think, if this is indeed what happened, it’s a good example of the kind of entitlement people sometimes feel towards their crushes. He’s feeling rejected, but he didn’t even give LW the opportunity to reject him! All LW did was go on a trip with their friend, and a trip with a friend is what everyone involved got.

        1. Caramel & Cheddar*

          Absolutely, but sadly for Brad you don’t get to feel aggrieved that other people aren’t mind readers.

      2. amoeba*

        To be fair, I think dumping their feelings on OP would have been much more inappropriate. If he actually now treats her like he treats everybody else, well… that’s actually what he should be doing! Doesn’t change the fact that he’s kind of a jerk to everybody, but I guess that’s a separate problem.

        I don’t love the drunk texts, but generally, he didn’t behave that badly in my view? Like, he didn’t try to force anything on OP, and when it turned out his interest wasn’t reciprocated, he took a bit more distance and now treats her the same as everybody else. Could be worse.

        (Although yeah, it’s pretty disappointing when you think you have a genuine friend and then later find out, nope, it was romantic interest and they don’t actually want to be friends with you.)

        1. learnedthehardway*

          Given that Brad seems to be generally a jerk to everyone, I think the OP should choose their friends more carefully.

          Someone who is nice to you but not nice to everyone else is NOT a nice person.

          Having learned this one the hard way, myself, I can say that observing how people treat others and applying that to my choices of friends has saved me a whole lot of headaches.

  5. Ann O'Nemity*

    I think Caro’s explanation above makes a lot of sense—Brad might have been hoping for something romantic to happen and is feeling frosty because it didn’t.

    Another possibility is that the intense togetherness of a vacation was simply too much for your new friendship. I once took a trip with a work friend, and unfortunately, it ended up straining our friendship. There wasn’t any big blow-up, but we seemed to get a bit tired of each other during the trip. Afterward, we were less social and never quite recaptured the spark of our early connection and camaraderie. Without the trip, I think we would have eventually realized that we didn’t have as much in common outside of work but the vacation hastened that conclusion.

    1. Sloanicota*

      Yeah, I realize everyone’s gonna go for the other conclusion, but it is also possible to get sick of each other on a trip / annoyed by the other person’s little foibles after traveling together.

    2. a clockwork lemon*

      This was my thought more than some sort of weird unrequited love situation, especially since OP says Brad is treating her exactly the same as everyone else in the office (and that the general consensus in the workplace is that Brad is kind of a dick!)

      Stronger and longer friendships than “friendly remote colleagues hanging out a few times after one of them moves to the same office” have been torn asunder by traveling with someone, often for no real reason other than arbitrary vibes.

      1. Ellis Bell*

        I mean the fact that he’s a dick to anyone who doesn’t serve his aims kind of supports the jilted lover theory imo, and I’m always suspicious of late night drunken texts, especially if the person apparently decided we had nothing in common!

    3. Myrin*

      Yeah, I was wondering if it was my asexuality which made me not immediately jump to the “rejected romance” theory – which I think makes a lot of sense! I can totally see it! – but I think it’s actually more an experience I had in my early twenties, where I was very close to a group of young women with similar interests for more than two years, and when we finally spent a week on vacation together, we realised that we… apparently didn’t actually like each other very much. Or rather, that we’re all very different regarding things which wouldn’t necessarily come up at the level of closeness we’d had before but which certainly became apparent during a week of always-togetherness. I lost contact with three fifth of these women basically immediately after and with the two others it slowly tapered out over the course of the following years.

    4. allathian*

      I guess either explanation could work for me. The drunk texts make me think that the unrequited crush is the more likely explanation in this case.

      That said, I love my friends dearly, but I wouldn’t really want to travel with any of them. In my case it’s mainly a difference in energy levels. I don’t do weekend getaways with friends anymore, simply because as much as I love my friends, I can’t tolerate anyone’s company for more than about 8 hours straight except for my immediate family, and with them my limit’s about 3 days.

        1. OP*

          OP:
          I was also worried about this going into the trip! I’ve had the same problem where I’ve gone on vacation with a friend and gotten very tired of spending time with them, I think this may have been a factor also.

    5. Not the one*

      This was a thought I also had. Years ago, I had a back and forth relationship with someone. We met in college, it never got serious, we went our separate ways, saw each other at a wedding, chatted long distance for a while – all seemed great. He came to town to visit family and we went on an actual date for the first time. That was pretty much the end of it all. I think we realized that the flirting and anticipation was fun but in reality, we were not compatible. Sometimes when any relationship – platonic or not – gets a microscope, you realize it just isn’t what you thought.

  6. Carol the happy*

    But, but, but- weren’t you blown away by the magnificent house, the warm sultry breezes, and the raw maleness of his- maleness? Didn’t you gaze longingly at him, wishing those strong arms would just sweep you off your feet and hold you close for a magical, passionate moment before you melted with passionate passion?
    No?
    Join the club of Unfeeling Women who don’t have real emotion because they’re frigid and harsh.

    Sheesh. (So sorry about the Harlequinade, but maybe in his conceited brain, women can’t have male friends; men are just lovers who haven’t been swooned over. Yet.)

    1. Ellis Bell*

      I said in the original comments that the visiting his family home idea made me wince, not because it’s a bad idea at all, or something that OP should have been suspicious of, but because I’ve met Brad before and this is how it always goes. It’s always a silent mental calculation of “I just haven’t created the right romantic vibe yet” or “I haven’t put enough friendship tokens into the love vending machine yet”. Nothing directly said, or even indirectly said, that would scare away the mark/daydream. I remember OP coming into the comments to reassure us, saying that she’s talked with Brad to ensure same-pageness and platonic feelings, and felt very cynical when I found myself thinking “yes, but they all say that.”

      2. Slippers*

        “I haven’t put enough friendship tokens into the love vending machine yet” made me want to die. THE ACCURACY

  7. Yvette*

    I agree with what pretty much everyone else is saying, but at least He didn’t try anything and maybe he’s being a little frosty because he might be a little embarrassed?

      1. foofoo*

        He only does when drunk though, which definitely pushes this all back to “dude was expecting something more”. He lets his guard down when he’s in his cups.

    2. Education Mike*

      I don’t get what he’d be embarrassed about? Not trying something and subsequently not being rejected?

      Not to say you’re wrong, clearly whatever is going on w this dude is not logic based.

  8. Dido*

    Brad obviously didn’t see their friendship as “strictly platonic” like the LW wrote in her original letter. She sounds like she was really naive about this

    1. Ellis Bell*

      It’s not really naive to take someone at their word after a couple of years of knowing them, when their actions have been what you expect the whole time. Do you know what true naiveté looks like? Thinking that telling a woman you only have platonic feelings for her is going to lead to some big romantic moment a week later.

    2. Education Mike*

      We don’t even have any idea if this is what happened. I have gotten very sick of/annoyed at people on vacation. He’s a difficult person in general, he could have decided any number of slights or annoyances meant the friendship was over.

  10. ChattyDelle*

    I trust you are not responding to the drink late night texts to “meet for drinks”, or just responding “no”? Brad definitely thought something “spontaneous” would happen & still thinks you’ll fall into his arms one of these nights. I recommend you stay away, he is Not Safe

    1. Poison I.V. drip*

      C’mon, I don’t see anything about his behavior to indicate he’s not safe. He never made a move on her and turned down subsequent chances to get together. The swings between chilly when sober and cheery when drunk mean he’d be a lousy boyfriend, but not safe? We don’t have the evidence to make that conclusion.

      1. Elspeth McGillicuddy*

        In fact, I would say he’s definitely safe! Because if he wanted to harm OP, he had plenty of opportunity. Does that make him a good person? No, it’s the bare minimum. But it’s not fair to assume he’s below that line either.

  11. Blinded By the Gaslight*

    I re-read the original post, and yeah, Brad definitely thought he had all the ingredients to Love Potion #9 with that Florida get-away. Men, save yourselves the trouble and just say the magic words, “I really enjoy spending time with you. Would you like to go on a date?” Amazingly, the woman will either say, “Yes, that sounds great” (lucky you, now you have real plans!) or some version of “No,” in which case, still, lucky you! Now you can redirect your energy to someone else instead of manipulating everyone into a phony vacation.

  12. OP*

    Thank you all for your comments! I’m glad you all reinforced my thoughts after the trip, glad Brad is treating my like everyone else (barring the drunk texts).
    These late night texts have fizzled out recently, but I always chuckle a little bit whenever I see them.

    1. Hannah Lee*

      I wonder if you can do something on your phone to silence the after hours texts from Brad.

      Like you still want to know if he’s sending them, but you don’t need your phone dinging at you at all hours when you’re asleep or in the middle of a Netflix binge watch.

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