AITA for being frustrated that my 25-year friend let his 3-week fling derail our long-planned trip?

So I (37F) flew to Japan this week for a trip I’ve been planning forever. A big part of it was finally meeting this friend (39M) I’ve known for 25 years. We were close on and off (sometimes more-than-friends, sometimes just friendship) but we had never met in person until now.

We’d been talking for MONTHS about how excited we were to finally meet. He agreed to go on a multi-day road trip with me, and he even renewed his international driver’s permit literally for this trip. This was all set up way before I left.

Then, right after I walked through airport security at my departure airport, he just casually calls me with: “btw I went on a date this week and now she thinks she’s my girlfriend.”

It felt like… really??? NOW you bring that up?
Then he tells me this woman he’s known for like 3 weeks wants to join us on the whole 4-day road trip. And he was kinda pushing the idea?? Saying she’d “help translate,” “help drive,” handle logistics, whatever. He even offered to pay her way.

I said I wasn’t comfortable with that. I barely know HIM in person yet, let alone a random woman who suddenly thinks she’s his girlfriend. I said it politely. He dropped it.

But after that… he got super weird. Overly polite, conflict-avoidant, vague about literally every plan except the one day I’m visiting his school. He still helps me with directions but he won’t actually answer if he wants to spend time together besides that. It’s like he shut down emotionally.

So I just asked him straight: “Do you actually want to hang out while I’m here, or should we just stick to Thursday?”

And his response was vague AGAIN.

Honestly it feels like he handed all his decision-making to this woman he’s known for 3 weeks… even though he told me for MONTHS how excited he was to finally meet in person. If he had just said “hey things changed,” I would’ve respected that. But instead I’m stuck pretending everything is normal while he treats me like the optional extra on a trip I arranged and paid for after flying internationally.

So… AITA for being upset and feeling blindsided?

14 thoughts on “AITA for being frustrated that my 25-year friend let his 3-week fling derail our long-planned trip?”
  1. NAH He doesn’t want to date you. He wants to date this girl. It’s disappointing for you but do your own thing. Let him go.

    1. Yeah and that’s fine. He doesn’t owe me romance. But canceling plans last minute like this and not even hanging out just as friends?

      1. I mean you said in another comment that her coming on the trip would ruin it because there were implied more-than-friends plans.

        Anyone in a relationship should cancel a romantic getaway with another woman. That’s just basic human decency. I’m sorry you got left holding the bag, but would you want your new boyfriend going on a trip like this?

  2. NTA, and your so-called friend is being incredibly rude. His girlfriend will be there after you leave, he can do whatever he wants then. If he’s genuinely so spineless that he’s already knuckling under to her every whim then I don’t see your friendship continuing, sadly. It seems as if his gf is already threatened by you.

    I hope you manage to enjoy your trip anyway.

  3. NTA Although I’m unsure why you’re blaming this girl he’s dating, this is a friend issue regardless of whether his reason is that now he’s got a gf he no longer needs you as a dating option, whether he doesn’t want to go days without being laid or whether he’s just straight up too infatuated at the moment. The reason is somewhat irrelevant, he’s ultimately ditching you at a moment’s notice and showing you how much he values you in reality.

  4. At this point I feel you have two choices: 1) let her come, 2) do the trip by yourself

    Honestly it’s only 4 days. I’d personally choose option 1 and be prepared to bail on them if it’s no fun

    \> We were close on and off (sometimes more-than-friends, sometimes just friendship) but we had never met in person until now.

    INFO: How can you be more than friends if you never met in person ?

    1. Info: We were young and stupid lol.

      I’m leaning towards just doing the trip myself versus feeling like a third wheel.

      1. I would ditch him (and her!).
        Tbh I suspect he was keen as thought there was a chance of the more than friends scenario arising during this visit. But now has this new date who he wants to bang and is more of a sure thing. This is very speculative but my point is you’re not going to enjoy her tagging along or his company after this abrupt change.

  5. Q – Has he been equally invested in this trip? Not just “Oh, I’m so excited to see you.” But actually “I’ve made XYZ plans, I’ve booked XYZ tickets, Ive made reservations for XYZ”? 

  6. I mean… is he really your friend? I’d be pissed if I put so much money, energy and effort into a trip to see someone (and I don’t even mean in a romantic, flirty type of way) just for them to drop a bomb like this. Tbh, this would be the end of my friendship with this person.

    Maybe there’s two situations:

    1 – He’s getting cold feet and doesn’t want to be alone with you for some reason,
    2 – He really likes this girl and wants her to come along.

    Either way, I’d go on the trip on my own. Let him have his “girlfriend” of one date.

  7. NTA but instead of framing it in your mind as “handing all his decision-making over to this woman,” you can try to more generously think of it as he doesn’t want to make his new gf feel insecure/jealous of you and he is protecting his new relationship. sucks for how he’s treating you, but i can understand him wanting to make sure his new gf doesn’t feel threatened by you (i think most new SOs would feel jealous of/threatened by a long-term maybe-more-than-friends doing this kind of visit, honestly. it is not that kind of unreasonable/irrational jealousy.)

    he wouldn’t be AH if it weren’t for the fact that he basically bait and switched you after you spent a lot of time and money to visit him. not nice.

  8. NAH.

    If he’s at a point in life where he’s taking relationships more seriously, it’s not surprising that someone talking about a serious relationship with him doesn’t want him to go on a vacation with his “more than friends” buddy.

    He absolutely needs to communicate better. And you have every right to feel hurt and disappointed. But I do think this is your wakeup call. Either be friends, so that future partners aren’t threatened and you can both have other relationships, or try being together. Because anyone y’all date in the future is probably going to see issues with this “sometimes we’re platonic, sometimes we’re not. But we’re going on vacation together, hope that’s cool babe.”

    3 weeks is short, but honestly my husband and I dealt with the same thing a month in. We were both at an age where we were dating to find a spouse and start a family. He was going on a vacation with a girl he used to sleep with, it was all planned, and he told me. I told him that I can’t control him, but I don’t see myself marrying someone who goes on trips with exes. I won’t be happy, and I don’t want to spend a few years trying to see if I can stomach the unhappiness, so let’s just call it off now. He decided instead to cancel the trip, and later ended the friendship with the ex as well (she justifiably resented me a lot after that, and made a lot of really mean digs at me and our relationship).

    Male-female friendships can get complicated when there’s sexual and romantic history, especially with a new partner involved. If this friendship is going to survive, y’all need to clearly decide what you are and what boundaries you have.

  9. NTA this may be a controversial take but you are not friends. You can’t be real friends with someone you never met in real life. You’re a pen pal. You don’t really know him. He responds when convenient. He is prioritizing spending time with his girlfriend over taking a road trip with his pen pal. Sucks but he’s not interested in meeting without his girlfriend present. He passed up the opportunity to meet you. It’s time to close the door
    on this friendship.

Leave a Reply

Your email address will not be published. Required fields are marked *