Is It Ever Okay To Date Your Friend’s Ex?

It’s always wrong to date your friend’s ex, right? Despite what girl code might say, it’s not always so black and white. There are no hard and fast rules when it comes to getting involved with a friend’s ex-boyfriend, especially since every person and every situation is different. While you shouldn’t go out of your way to fall for the guy, sometimes you can’t help who you fall for. So, what’s a girl to do?

When it’s okay to date your friend’s ex

  1. It’s an old ex she no longer cares about. If it’s been a few years and your bestie has definitely moved on, give it a go. She’s obviously over him. You were a good friend and kept your feelings to yourself for long enough. This is especially true if they dated as teenagers or only dated casually for a couple of weeks.
  2. It was a mutual breakup with no hard feelings. Breakups aren’t always bad. Sometimes both parties agree it’s not working out. If there aren’t any hard feelings, she’s probably not going to mind. Just make sure she’s not still interested in him first.
  3. They’re still friends. This is the ideal situation. The breakup went well and they’re still friends. They’re both happy dating other people and there’s no jealousy. Go ahead and ask him out. It’s okay.
  4. You ask and she’s fine with it. Still not sure if it’s okay? Just ask her. She might get pissed at first, but she’ll get over it. As long as you respect her wishes, you won’t lose her as a friend and you’ll know for sure whether to date the ex or not.
  5. She’s moved on and is in a happy relationship. Is your best friend in a happy, committed relationship? Know what that means? You’ve got the green light to date him if you want to. She’s over it and happy. If she’s really your best friend, she’ll just want you to be happy too.
  6. You love him more than her. Think carefully about how you feel. Do you really love him more than you do her? If you date him, you could lose her friendship forever. But sometimes, the heart wants what it wants (sorry for getting Selena Gomez stuck in your head). You shouldn’t date your friend’s ex just because it’s something to do. There needs to be something deeper there.
  7. It was never serious. Did the relationship only last a few weeks? Was it ever official? Was it more of a fling? If it was never anything serious and it didn’t end badly, she’s probably not going to care. It didn’t mean anything to her. She’ll likely just give you her blessing.

When it’s not okay

  1. It was a messy breakup. Anytime it’s a messy breakup, you shouldn’t date your best friend’s ex. The odds of her getting upset having him around are high. It’s just not worth putting her through all that. At the very least, wait a while so she can move on before you try to date your friend’s ex.
  2. She’s not over him yet. Be respectful and give her time to get over him. Seeing the two of you together will just hurt her. Do you really want to do that to your best friend? It’s never a good idea to date the ex if she’s still got feelings for him. “If your friend isn’t over it and is still actively requiring your support, it’s not very ethical to go in,” says Brandy Engler, Ph.D., author of “The Women on My Couch.”
  3. She gets upset when you mention him. Try bringing up his name and see how she reacts. Does she explode or start crying? Does she seem agitated? The wound’s still wide open. Dating him is like pouring salt in the wound. Give her a break. Don’t torture her by bringing around the guy that still makes her heart ache.
  4. He cheated on her. I don’t care how much you think you like this guy, DON’T DATE HIM. If he cheated on her, he’ll cheat on you. It’s not just disrespectful to your best friend, but you’re disrespecting yourself. Cheaters are never worth losing a friend over. Besides, it’ll be over the moment you catch him with someone else. He’ll never be yours, so don’t ruin a friendship over it.
  5. You ask and she flips out. When you asked her if it’d be okay, did she flip out? Do I really need to spell it out for you? Listen to her. She’s not okay with it. Forget about him.
  6. You love her more than him. Is your friendship more important than some guy? Are you really sure he’s the one? If you love your best friend far more than her ex, do the right thing and find another guy. A crush passes, but a best friend is forever. If you do decide to date your friend’s ex, you may need to say goodbye to her. “If your friend isn’t OK with it, they’ll cycle through feelings of yearning, resentment toward you and their ex, and jealousy,” says relationship expert Chantal Heide says. “It will erode your friendship and affect your relationship with your love interest.
  7. They just broke up. You’ve probably had a thing for the guy while he was with your best friend. You might be able to date him, but not right now. Never, under any circumstances, try to date the ex right after they broke up. Even if it was a mutual breakup. Give it a little time. Otherwise, she’s always going to wonder if you’re secretly trying to steal her boyfriends.
  8. They tend to break up and get back together a lot. If they have a history of being on again, off again, you’re better off steering clear than trying to date your friend’s ex. “You should first determine if your friend and their ex have broken up or if they’re on a break. Because if they have a history of breaking up and getting back together, you could be ruining a future for them,” advises Richard Tatomir, certified counselor and founder of Relationship Experts Vancouver.


Crystal Crowder is a freelance writer and blogger. She's a tech geek at heart, but loves telling it like it is when it comes to love, beauty and style. She's enjoys writing music, poetry and fiction and curling up with a great book. You can find her on Twitter @ccrowderwrites or check out her other writing on Medium.