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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{ 44 comments }

{ 44 comments… read them below or add one }

  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!

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    1. amy*

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

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    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.

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    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.

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    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.

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  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.

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  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!

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    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.

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        1. Caramel & Cheddar*

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

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  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.

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    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.

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    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.

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  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.)

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    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.”

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      2. Slippers*

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

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  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?

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      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.

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    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.

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  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

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    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.

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    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.

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  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

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  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.

    Reply ↓

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