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Is it ever okay to date your best friend’s ex?

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It’s always wrong to date your best friend’s ex, right? Despite what girl code might say, it’s not always so black and white.


I’m not saying go ahead and jump your friend’s ex right now. It all comes down to how your friend feels about it.

If it’s going to hurt her, is it really worth it? Remember, it’s a tricky situation and if you don’t do your homework, you could lose your best friend.

Pay close attention to when it is and isn’t okay to date her ex.

When it’s okay:

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.

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).

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.

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.

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. When 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.

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.

There you have it. Clear guidelines on when to bother with a best friend’s ex. Use your best judgment and hopefully you’ll get the friend and the guy.

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