Do I tell my friend I'm dating her ex?

RedEye's sex columnist

I've been seeing one of my friend's exes. She was a very close friend years ago, but our relationship has dwindled. They were broken up for two years before we got together, but my friend was totally in love with him when they were dating, he broke her heart, and it took her a very long time to get over him, even when she has had other boyfriends, she was still hung up on him.

I thought it was just going to be a fling, so I didn't think it would be worth it to create a situation and the inevitable drama it would cause. So we kept it on the DL. Now it's been 6 months, and we've become more serious than initially anticipated. He told me the ball was totally in my court as to when to tell her about us, since they didn't maintain a friendship after the breakup. Well, my friend recently got dumped and is sending flirty text messages to my boyfriend/her ex. He messaged her back saying he was seeing someone, she claimed her messaging was all innocent, but now she keeps trying to get him to hang out with her and give her attention. Her persistence is definitely affecting our relationship. Do I tell her? How do I tell her? Do I walk away?

—To tell or not to tell

So, don't rip up my NOW card (that's National Organization for Women) or anything, but I've never been a big believer in the "Girl Code," aka the unspoken rule that friends should never sleep with anyone their friends have slept with. First of all, it's impractical. That rule diminishes your spank bank by at least 30 percent! Second, it's unrealistic. More often than not, we tend to sleep with people in our friend circles. Why? Well, there's a reason that they're our friends. We share mutual interests. We get along. We've already surpassed the awkward small-talk stage of pretending to be interested in their job as an insurance adjuster. It makes sense that sometimes these commonalities translate to the dating realm as well. And that's a reality that far too many of us deny because we're jealous and insecure and needy and possessive of those we've dated or who've seen us naked.

That said, I'm not a total monster. I don't think dating should resemble a Wild West free-for-all where everybody has erections but not feelings. Nor do I think you should throw away friendships willy-nilly, especially not for the sake of some fling putting his willy in your nilly. In other words, casual sex is never worth throwing away an important friendship. But in your case, I'd say it's pretty cut and dry. A considerable amount of time has passed, your friendship with the girl has "dwindled," and the ex in question is someone you're now calling your boyfriend.

You're far past the point where you can try to simply ignore the situation and hope it goes away. And why would you? It has been two-and-a-half years since your friend dated your boyfriend. Unless you want to keep your relationship a secret indefinitely, it's time to air that shit out, and it's better if it comes from you than someone else. It will be awkward, but it will probably get your friend to stop with the flirty advances and help her realize her ex is off-limits now.

How you decide to tell her I'll leave up to you, but be prepared to deal with the fallout. She might not want to talk to you for a while, or possibly ever. She might feel hurt or betrayed. If possible, resist making excuses about the situation or going on the offensive. Stick to simple truths. "I really like him. He makes me happy." Be sympathetic too. She was recently dumped and is trying to cope with that— perhaps not in the healthiest of ways, but getting over a breakup sometimes necessitates less-than-stellar behavior. Good luck!

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