Dating a friend is a bad idea

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  5. Dating Your Friend's Ex.
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The Dating Nerd is a shadowy figure whose whereabouts and identifying details remain unknown. What we do know is that he is really, really good at dating.

Do Listen to Your Gut.

He's been on more dates than you can shake a lengthy bar tab at, and he's here to help the average guy step his dating game up a notch — or several. I'm in a pickle. Over the last couple of weeks, I've been hanging out with a close friend's ex-girlfriend, platonically, after we ran into each other at Starbucks.

We have a real connection. I can't stop thinking about her.

I'm kind of obsessed. And I think she wants to take it to the next level, too. The problem is, my friend had a deep relationship with this girl, and I think he's still kind of in love with her.

5 Crucial Dos and Don’ts for Dating Your Friend

So what do I do here? Can I get away with dating my friend's ex? Will he be able to handle this? This is a tough one, because dating a friend's ex is one of the most essential dating taboos.

You are here

Which is that people never really get over significant romantic relationships. I don't mean that you can never be happy again after breaking up with someone.

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Of course you can. But it's largely a matter of compartmentalizing. You get a new and even prettier girlfriend, or hang out with your friends more, or get into jiu jitsu or knitting. You get a new life so you don't spend all your time sitting around and crying about your old one like the baby you are. Sure, people will talk about their old relationships and say that they're "over it" or that it "wasn't meant to be," or pepper you with other related nonsense phrases, but what they mean is they're not thinking about it right now. All of those old wounds stick around, just waiting to be re-opened.

You're always going to feel weird when you see your ex, at least a little bit. If you're still friends with your ex , it wasn't that serious, or it's still serious.

Can You Date Someone After Being Friends First? - AskMen

And, if you date your friends' ex, you're telling your friend that your romantic feelings are more important than their happiness. Because they're going to see you holding hands with their ex, and remember how nice that felt, and if you think they won't envision you having sex together, you're being naive. Of course, that's going to hurt. Inherently, it's a selfish thing.


You're saying, "screw you and your silly emotions, I've got to get laid. Does this mean you should never, ever date a friend's ex? It means that it's a bad idea, but that's not the same as "never do it. It's possible that you've got an uncommon romance on your hands. Maybe this is your future wife, or muse, or whatever it is that you're looking for.

If this is the case, you'd be missing out on years of potential passion if you passed up on this girl for the sake of sparing your friends' feelings.

Like I said, this is a tough one. Is it worth damaging the friendship over. Would your friend do this to you. Quite simply, some friends are better friends than others. There are probably other friends of yours who are fiercely loyal, who will always stand up for you, and who would never do anything that might hurt you or your friendship. Friends like that can be hard to come by.

Dating a Friend’s Ex: Your Play by Play

And if the ex you like belongs to one of those friends, you might want to reconsider. Consider testing the waters. Before you do anything, think about talking to your friend about your situation and seeing what his or her reaction is. Their reaction might be way better or way worse than you expect. The shadier you act about it, the worse it is. View the discussion thread. Sex isn't always easy to talk about.