You Need Help: Is It Okay to Date My Ex’s Friend?


My ex and I broke up four months ago. We’re on good terms but not in touch because space is important. I have feelings for a mutual friend and feel like it really might be mutual. Should I say something? Or is this super off limits?


Hurting others is one of my greatest fears. I avoided casual dating for years with the hope that I could avoid causing pain. If I promised nothing, I could never disappoint; if I took nothing, nothing would be required in return. I was drawn to people who felt unattainable, because they wanted less from me, and I thought I could always count on leaving the situation as the hurt party. But people surprise you and I ended up hurting people I never thought I could hurt. I’ve started to accept that’s just part of dating. No matter how cautious we try to be, we are going to hurt people. The question then becomes: when is it worth it?

I don’t really believe in strict morality when it comes to dating. If everyone involved is a consenting adult, then all the other issues feel circumstantial. I’m not going to sit here and tell you that dating your ex’s friend four months after your break up is “super off limits,” because it’s not. But I will ask: is it worth it?

How strong are your feelings for your mutual friend? What kind of relationship are you looking for with them? Could you find that with somebody else? Do you want to?

I understand the temptation to be told either yes this is okay or no this is bad but it’s just not that kind of situation. I’ve dated people when I knew it was going to hurt someone else’s feelings but I decided it was worth it to me. I’ve even had casual hook ups I knew were going to hurt someone else’s feelings but I decided it was worth it to me. Would I date my ex’s friend four months after we broke up? Probably not? But I don’t know! Depends on how strong my feelings were! So if it’s worth it to you? Go for it.

But I would push you to question why this is happening — especially if it’s a pattern. I think sometimes we create chaos in our lives, drama in our lives, hurt in others’ lives, for no reason at all. It’s really just coming from a place of boredom and destruction. You totally might have feelings for this mutual friend. This mutual friend might be someone who could bring you so much fulfillment and joy as a romantic partner. This moment of hurting your ex could be an unfortunate blip in an experience that overall means so much more. Or you could just be lonely and horny and about to hurt someone you care about for no reason except that chaos feels satisfying.

I’m not saying that the seriousness of your eventual relationship should be the determining factor. A one night stand can hold meaning in its own way. I just want you to really think about what you’re about to do. If whatever this thing you’re feeling could be satisfied with someone else then maybe you should do that instead. But maybe it can’t! Or maybe you don’t want it to! That’s okay. That doesn’t make you a bad person and it doesn’t even make this action a bad action. It’s just a choice you’re making that will have the repercussions it has and if you’re okay with that then I’m okay with that.

I don’t believe in war, but I sort of do think all’s fair in love.

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Drew Burnett Gregory

Drew is a Brooklyn-based writer, filmmaker, and theatremaker. She is a Senior Editor at Autostraddle with a focus in film and television, sex and dating, and politics. Her writing can also be found at Bright Wall/Dark Room, Cosmopolitan UK, Refinery29, Into, them, and Knock LA. She was a 2022 Outfest Screenwriting Lab Notable Writer and a 2023 Lambda Literary Screenwriting Fellow. She is currently working on a million film and TV projects mostly about queer trans women. Find her on Twitter and Instagram.

Drew Burnett has written 521 articles for us.


  1. As someone who has previously made a dating choice that I knew would hurt someone I care deeply about but that I knew was the right choice for me, reading this felt so affirming.

    I especially appreciate your acknowledgement that the seriousness of the eventual relationship and/or the specific person you’re planning to date don’t have to be the determining factors in the decision, because sometimes there’s a lot of other really important stuff going on!

    I feel like I’m still wrestling with the simultaneous truths that sometimes a choice causes different hurts than we expect; and that sometimes the things we try to do to minimize hurt are the best we can do in that moment, but the aftermath shows us how we could do better; and that sometimes a choice was right for us even though it hurt someone. It’s all very messy.

    But in any case, this advice question and response are helping me continue to process through it, so thank you!

  2. I spent many years mostly always erring on the side of trying to never hurt anyone’s feelings, and those years were spent mostly full of loneliness and regret. Also none of the people involved in any of those scenarios are an important part of my life anymore.

    I would imagine your ex might be hurt regardless of who you started dating after them. Does that mean you shouldn’t date anyone again? Of course not. I don’t see this as any different. They might feel hurt, but if they’re worth keeping in your life, they should also understand that your happiness is important. Their hurt is their own emotion to manage in this situation, not yours. Life is too short and too difficult to give up potential happiness for the sake of someone else’s (likely temporary) discomfort.

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