My friend is really excited about a new boyfriend, and last night we went out to drinks so I could meet him. Turns out I already know him…because we used to sleep together occasionally a couple years ago. It was always a drunken booty-call kind of a thing, and it ended after he told me that he needed to “work on things with his girlfriend.” Apparently, he’d had one the whole time. I don’t really want to mention my sexual history with my friend’s new guy, because I think it would make things awkward, especially when she’s so into him. But I feel like she should know he’s a cheater. Do I say something, or just bite my tongue?

-The Other Woman

I understand why you’d rather not speak up, but even without the cheating factor (which is a HUGE factor), I’d tell you to.

Why? Because certain information, when withheld, might seem like something you’re trying to hide, rather than something you see as irrelevant. Your claim that you’re over him will have much more weight if you’re up front about it than it would if (when) your friend finds out on her own that you and her guy have a past.

You don’t have to go into lurid detail about when you called each other and exactly how good he was in bed, but do tell your friend that it’s “such a small world” and that you and the guy had a fling a while back, one that never went anywhere and that you’ve long since moved past.

…and then you have to say more.

Tell her you know how happy she is, and that you don’t want to hurt her, but you’re afraid she might be more hurt in the future if she doesn’t know that this guy has a history of straying. Tell her you know because you’re one of the people he strayed with.

She might have a shoot-the-messenger reaction for some period of time–cut her some slack if that happens. Who wouldn’t need time to process “my bestie hooked up with my apparently-cheaty-pants new man?”

Just make sure you reiterate that you’re only telling her because you care, and because you don’t want her to get hurt. Then say that if she decides to stay with him, you’ll never say anything about it again (and follow through on that promise).

Once you put the information out there, you’ve done your duty. If she prefers love la-la land to a hard truth, that’s her (likely future) problem.


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