best friend and ex-boyfriend dating

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I’m not saying it happens often, but at some point in your life, you may find yourself dabbling with the idea of dating your friend’s ex. “Who? Me? Never. I would NEVER!” That’s what you might be thinking. Or, you may be smack dab in the middle of this dilemma and needing to hear this.

It’s not THAT weird to think that you could be into someone that your friend dated, or that he could be into you. Think about it: if you love your friend and he loved your friend, then that probably means you share some common values and interests. It probably means certain personality traits are important to both of you. You have many qualities your friend has. HE has many qualities your friend has. There’s probably some character overlap there.

Hey, maybe you were even there the night they met. If you’d been sitting one seat closer to him or if you hadn’t been there with that first date that didn’t work out, it could have been you two who hit it off and dated. Maybe you even thought he was cute at the time but thought “Meh. Let my friend have him. What are the odds he’d be my soul mate anyways?” But now, here you are, and you two have been exchanging messages.

But stop right there. Really. Stop. Here are very compelling reasons not to date your friend’s ex.

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He’s not your soul mate

Think of all the dudes you’ve been interested in in your life. Okay, now how many of those are you still seeing? Talking to? Married to any? Nah. Didn’t think so. And that’s because 99.9% of the men you’re attracted to in life won’t wind up your soul mate. That’ll probably include him. It’s how the numbers work out. Those are pretty bad odds for such a risk.

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If he will, he’s no good

If he is willing to date his ex’s friend, he’s kinda a bad dude. I don’t care how charming or sweet he seems. I don’t care how well it seems like he understands you. There is something to be said for boundaries. For many good people, the very fact that that’s an ex’s friend should turn off any physical attraction.

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You will lose that friend

You will. She may even pretend at first to be cool with it. Or she may think she is. But the reality will sink in that you were willing to do this to her. She will never trust you the same way again. She will never want to be close to you or share much with you again.

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You’ll lose other friends

Other friends will hear about it and judge the hell out of you. They won’t even care if your friend says it’s fine or you say it’s true love. It just looks real bad. Other friends won’t want you hanging around their men. They’ll think you can’t be trusted.

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What if it doesn’t work out?

Ooooh that’d be real embarrassing. A shame really. You blew up multiple friendships and broke many friends’ trust in you forever all for a dude that it didn’t work out with! So you’re left with nothing, and who is going to console you? Not those friends who don’t like you much right now.

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He may struggle with commitment

If he was able to develop feelings and an attraction for you while he was with your friend, then he likely struggles with commitment. Have you ever heard the saying “Choose your love and love your choice?” It exists because love must be nurtured once it’s found. He probably wasn’t good at that, which is why his eye strayed.

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What if she did that to you?

Imagine if your friend dated your ex. Stop with the excuse making about how this is different. It isn’t. Plain and simple: how would you feel about a friend who dated your ex? Probably not great. You’d probably think that was a sh*tty person.

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Oh, and now she can

By the way, once you date your friend’s ex, she has full jurisdiction to date an ex of yours. Oh yes she does. Where would you get off telling her she couldn’t? You’d have no ground to stand on. So make sure you’re willing to give her the greenlight on that before you date her ex.

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She’ll think this was your plan

She may start to feel that, all along, while she was trying to make that relationship work, you were conspiring against her. When they fought, did you egg him on to leave her? Were you flirting with him the whole time? You can’t really convince her you weren’t if you wind up dating him.

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He was inside your friend

Think about that. When you have sex with this man, you have to know that he was inside your friend. He might be comparing how you are in bed. She knows what you’re experiencing, in detail, in your sex life because that used to be her. And you know what she’s experienced. Yuck.

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They failed for a reason

They did, right? For good reason too. You heard all about it at the end. You know about his flaws. So if those very flaws don’t end the two of you, then your paranoia that the same issues will come up will end you two. You’ll just be waiting for the other shoe to drop.

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You’ll always compare

You’ll always compare how he treats you to how he treated her. Just dinner for your birthday, huh? She got a whole weekend trip.  Taking three months to say I love you? He said it to her in month one! You know too much about his past relationship. How could you not compare?

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You’ll even wind up jealous

You may get jealous because his ex (your friend) will still be in the picture. Hey if she decides to still be your friend (for some reason) then that means his ex girlfriend will be around. It’s not really natural to hang with your boyfriend and his ex. You’ll worry there are still feelings there.

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Explain that to everyone

Try telling anyone at all how you met. Family. Coworkers. Neighbors. Other couples you meet on vacation. It’s shameful. You’ll feel bad telling the story. “Well he was dating my good friend but then…” People will instantly like you both a bit less. It’s hard for them not to judge.

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It’s just wrong

I know that in most cases “It’s just wrong” isn’t the most compelling of arguments, but in this case, it is. The second you open a story—try to tell someone your predicament—you’ll see heads shaking. People feel dirty even participating in the conversation. You know it’s wrong, so have some dignity and tell the dude to stop calling you.