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I Want to Pursue My Best Friend's Ex Girlfriend 

Dear Athena,

My best friend just broke up with his girlfriend of a few months. They had this on-and-off thing for a while. He and I have been friends for more than 10 years, and we're really close, but I am so into this woman. We've both known her for a long time, and he's been into her for a while, but I am in love with her. I know I like her more than he does, but he's still single and talks about her sometimes, like he's not over it. I want to be with her, but I'm afraid he'll hate me — like, it's not cool to go for her. What should I do?

Sincerely,

Perplexed About P.

Dear Perplexed,

Life is short; take a chance. 'Fess up and tell your friend that you've been pining for his ex and you can't take it anymore. Hopefully, he'll be big enough to cheer you on.

He might have stuffed his feelings for her in the dresser of his memories, but my fingers are crossed that he can stifle his shit so you, his buddy, can chase your dream girl. I've been in your situation, and it's not easy. You feel like you're standing on a fine line between your happiness and that of your best pal. But if he's a confident, mature person and a true friend, he'll back off and understand.

And if he's not, what's the worst that can happen? It may be hard for your friend to let go of that relationship. He may not be emotionally ready for her to move on with any new partner. But that's not under his control, and if he's really broken up with the woman, he simply can't hold on anymore. And, in theory, that means you have a shot.

I say "in theory" because: Do you have reason to believe this woman wants you? Or even would be open to her ex's best friend pursuing her? Your letter doesn't seem to consider her feelings.

Worst-case scenario for you here? Your friend is angry with you for wanting his ex, and she rejects you.

But you'll survive, and so will he. If your friendship is as tight as you suggest, he'll forget this awkward moment in time and stand by you regardless of her response to you.

If you're not willing to risk it, you could certainly stay mum and hope that your feelings for this woman eventually fizzle. But I don't recommend that. You will kick yourself for not testing the waters with your love interest, and you might even grow bitter toward your bud. That's the stuff country songs are made of. Don't be that kind of song.

I wish I could tell you what will happen. I know the prospect of being rejected — by either of these people — is scary, but you have to put yourself out there or you'll never know. And not knowing is a lot worse than the "Sorry, but no thanks" you could get from her. But I can say with utter confidence that, should that happen, there will be other ladies, other loves and better days ahead.

Yours,

Athena

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