“Should I Have Dinner With My Ex’s New Girlfriend?”

I dated Mike for a brief period of time and we broke up over a year ago. We’ve remained friends, as we have lots in common, and he is a genuinely good person. We have not hooked up after the breakup — and won’t ever! The friendship is truly platonic. I only see him a few times a month, and always in public places (ie. lunch at a restaurant). We used to see each other more often, but since we have started dating new people, that’s naturally decreased. He is in a relationship with a girl named Megan, who, from what he tells me, has a very controlling and confrontational personality. I am also in a new relationship, and very happy. Recently, Megan has requested to meet me, so I have given a few suggestions for a meet-up that might limit awkwardness — I feel like it’s going to be an interview on her part, to make sure I’m not into her boyfriend — but she has shot them down, and is insisting on dinner and drinks. I completely understand that she must be curious about me, and doesn’t like the idea that her boyfriend is friends with an ex, but I am completely dreading meeting her (mostly due to the negative way she’s been portrayed by Mike)! But if I don’t agree to meet her, Mike won’t be “allowed” to contact me at all anymore. So, do you think I should I meet her — The Friendly Ex

If you want to remain in Mike’s life, you need to suck it up, meet her and be nice. You may be pleasantly surprised to find that she’s nowhere near as bad as Mike portrays her. Maybe she’s even cool. Regardless, if we can learn anything from this morning’s letter, it’s that if you want to remain friendly with an ex, it’s much easier to do so if the new girlfriend/partner accepts you. Going out to dinner with Mike and Megan is the first step toward acceptance, but luckily, it’s actually much less about you passing an interview as it is about simply letting Megan publicly mark her territory.

Of course, there will be an interview portion of the evening and doing well on it pretty much depends on one thing and one thing only — whether or not you threaten Megan. You’ll have a better shot at achieving this if you agree to meet her on her terms, bring along your new guy so it’s a double date, and refrain from looking too sexy. Once you’ve got those bases covered, the next best thing you can do is let her have the mic. People love talking about themselves, so ask her lots of questions and give her a chance to show-off and shine. If you make her the star of the show, not only is the spotlight off you and your friendship with Mike, it gives Megan a chance to toot her own horn and remind her boyfriend what a catch she is — basically, the female equivalent of marking her territory.

Yes, it’s annoying … and maybe even a little degrading. But it’s the price you have to pay if you want to remain friends with an ex whose new girlfriend is controlling and insecure. You already expect your friendship to change to an extent — like, don’t count on seeing him “a few times a month” for much longer; try “once a month” if you’re lucky — but hopefully if you can convince Megan you aren’t a threat to her relationship, you can keep your buddy. … And if they ever get married, you can attend the wedding without feeling like your attendance is the bride’s worst nightmare.

*If you have a relationship/dating question I can help answer, send me your letters at wendy@dearwendy.com.


  1. I’m a bit concerned that Mike is saying negative things about Megan, the current GF, behind her back. What is he saying about the letter writer to the current GF? It sounds kind of passive-aggressive to me.

    1. amandalee says:

      I agree Pinky! If I found out my boyfriend was saying negative things about me to an ex/now friend he kept in contact with, I’d probably be a little angry.

      I also feel for the girl that wrote the letter, but at the same time, her tone seems kind of off putting. The first part of her letter was fine, but when I got to the he won’t be “allowed” to talk to me part, she just seem a little too sarcastic for my taste. If keeping Mike as a friend is so important, I don’t get why the meeting has to be on your terms. Maybe you’re making it more awkward by limiting when and where you meet up.

      1. elisabeth says:

        Re: making it awkward by limiting when and where the meet happens – from the LW’s initial remarks, it seemed as if her friend’s SO is the one who is limiting the conditions of the meetup by wanting exclusively dinner and drinks and shooting down the LW’s several suggestions.

    2. I agree; it’s very disrespectful to complain about one’s SO to an ex! That says something about Mike’s character, or at least his maturity level.

  2. The LW never mentioned a dinner with all three of them. Seemed like it would just be the two of them.. Yikes!
    Oh how I would dread that.
    But maybe you two can become friends?

    1. I know that sounds a little scary. Just the two of them. It might have been less intimidating to do a double date. But, it seems like if she wants to keep the friendship she needs to play nice with the new girlfriend. And if the boyfriend wants her to meet hig gf so bad it must mean he thinks she’s going to be around for awhile.

  3. sobriquet says:

    If he’s already complaining about his new girlfriend, the relationship probably won’t last very long. Especially since he’s complaining about major aspects of her personality. Yikes.

    Take Wendy’s advice and make nice. If you end up hating her, take comfort in knowing that she probably won’t be around very long.

  4. As silly and as lame as Megan sounds, Wendy is right. If you want to be able to remain friends with her since apparently he is going to need her permission to hang around you, then go do dinner and drinks. Though to be honest, if he’s already commenting that she’s controlling, the relationship may not last too long.

    In the mean time, when you go to dinner, if she does question you about the extent of your relationship with him, do not lie. If she finds out that you lied to her, it will only make things worse. I’m not saying you should answer all her incredibly personal questions (stick to your boundaries) but don’t intentionally mislead her. Also, be sure you mention your boyfriend and how happy you are with him, but mention it casually. Do it so she is aware, but don’t throw it out there too much otherwise you may look suspicious.

    1. *remain friends with him

  5. ArtsyGirly says:

    Agree Agree and Agree with Wendy and the readers. Go out and make nice. Allow her to control the meeting because you have already gotten it from Mike that her personality will demand it. The big thing is that you don’t have to be a part of her life so if she is a B*tch to you it doesn’t matter because you don’t have to date her. I know it sucks possibly having to scale back your friendship, but if she is so manipulative and controlling it might let him know how much his relationship negatively affects other parts of his life. If you totally hate her, pray that the relationship will die a natural death quickly.

  6. Remember the social protocols: if she invites you to dinner and drinks, it does mean it is “dutch” so let her pick up the check. It sounds as though Megan is dealing with the LW thru the BF, which is pretty stupid and immature. That’s a red flag right there IMHO. People, by and large, do not go out and have “dinner and drinks” with exes. It is soooo lame. I would recommend that if the friendship with the ex BF is that important, simply tell him (since Megan refuses to call evidently) that “time is pretty valuable but maybe a quick drink would be ok”. If he presses for the dinner drill, then you just have to stand firm with “that’s all I have time for”. Just because LW is a “friend” of the BF doesn’t mean she has to feel subordinate to the forces at work here. As to LW’s new BF tagging along, I disagree as that is bad form. You are putting some new guy in a situation he doesn’t need to be dealing with on your own. Sounds like the old BF deserves Megan and I predit that relationship won’t last that long anyway.

  7. Great advice Wendy.

    Hmm this is definitely a unique situation. As someone else suggested, it is concerning that your ex is saying bad things about his current girlfriend to you but she does seem extremely forward by demanding dinner and drinks with you.

    Whatever you decide to do I just wanted to mention that she’ll probably be more comfortable with you as time goes on and she gets more comfortable with her own relationship. When I started dating my boyfriend, I felt really threatened by his ex; they dated for several years and continued to “see each other” for another couple years after breaking up. Plus I had met her a few times through mutual friends before I started dating my boyfriend and she’s gorgeous and mysterious. It was to the point where I would feel really defensive if he or his friends told stories that involved her. But as time went on, I became more and more comfortable with my relationship and, now, his past doesn’t matter any more. I recently hung out with her (his ex) and mutual friends and I discovered we have a lot in common and could probably actually be really good friends. It’s still a little bit awkward that we’ve both seriously dated the same guy, but you know what, I really enjoyed hanging out with her. That being said, I wouldn’t have been ready to be friendly with her when I first started dating my boyfriend; I just needed some time.

    Just food for thought…

  8. My first thought would be to look at and evaluate your conduct around this chick – are you positive that you’ve done nothing to feed her misgivings? To be fair, she does sound insecure in their relationship.
    I would also ask why you’re not interested in getting to know her, since you’d like to continue seeing him as a buddy – after all, if you’d never had a romantic relationship with him, you’d accept his lady friends as part of that friendship (I hope). If he was a platonic friend, wouldn’t you want to get to know her, simply as a part of your social circle?
    I say go for the drinks/dinner and let her explain her motivation for wanting to see you, it’d be a good way to assess the situation and see what is really happening. Good luck!

  9. fallonthecity says:

    Just try to forget all the bad stuff he’s told you and just meet her. Smile, introduce yourself, and just be genuine. Try to make her comfortable (but don’t let her make you uncomfortable). It’s just a couple hours, and it’ll probably make your life (and your buddy’s life) easier.

    Good luck!

  10. I would have to judge, how important is Mike’s friendship to me. Sounds like to me she needs to get her in check. Mike and his new fling has some trust issues they need to work out.

    If Mike’s complaining about her, it does not sound like he is going to be around for long. I would not start something or give her the “control” the new girlfriend seems use to getting. I would not be catering to her insecurities. We meet as a group or we don’t meet.

  11. belongsomewhere says:

    I think Wendy is right that the best thing to do is let the new GF be the star. I would even do some self-deprecating and say some very flattering things to this girl. Here’s what I would say:
    “Mike and I really just weren’t compatible as a couple. We knew it just wasn’t going to work, but we had so much in common. It really makes more sense that we’re platonic friends. It sounds like the two of you are much more compatible. Mike has said great things about you [even if this isn’t true, I’d say it to make her feel good about herself and secure in the relationship], and I hope that my being friends with Mike doesn’t bother you because I think you and I could also really get along.”
    If she asks about what it was like dating him, why you broke up, give very short, unsentimental answers. Say you always had a good time with him, but that it was a short relationship and you just didn’t make sense as a couple. Don’t let the conversation venture into anything that’s too personal–don’t let her compare her relationship to Mike to your relationship with Mike.

  12. The way he is talking about his SO to LW makes me wonder how he talks about LW to SO. Either playing weird games or maybe isn’t as over the LW as she thinks. Maybe he foments jealousy and drama..

Leave a Reply

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