Ask Wendy

Can I Date My Friend’s Ex?

Reprinted from April 21, 2017
Hey Wendy,

I’m on an online dating site, and I recently connected with a good-looking guy with a great profile who looked familiar to me. I messaged him to tell him he looked familiar, thinking maybe we went to college together or something. He messaged me back, we couldn’t figure out how we knew each other, but we kept chatting and we get along well. Then it dawns on me, he is the ex-husband of an old friend of mine. This friend and I used to be close to years ago. But I haven’t spoken to her in about 7 years. We are Facebook friends, but don’t even communicate on there. Back when they were married, I didn’t know him, I’d never even met him or heard anything about him.

He wants to get together for dinner or drinks and see if we connect in person. I am very interested in getting to know him better but not sure what to do. She recently moved out of state to live with her boyfriend of about a year.

Do I go or not go? Do I tell her first or wait and see if he and I like each other?

Danna L - Queens, NY

Hey Danna,

Let me get this straight: You want to know if it’s okay to go out with a guy who used to know someone you used to know, but neither of you are in contact with her anymore? A friend whom you no longer talk to, who lives out of state with her boyfriend. You’re afraid to go because she might find out and be what, mad? Um, no—GO, girl!

It’s dinner, not your engagement party. You don’t need to tell your now-distant Facebook acquaintance you have a dinner date with her ex. If this date turns into more, you send her a PM on Facebook that says something along the lines of, “Hey friend! Long time no talk. Funny thing…I met a great guy online and we’re dating now—I think we’re a pretty good match for each other. Want to know the slightly awkward part? It’s Tim, your ex-husband. Thanks for making him a better person, you’re a good woman. Just wanted to let you know so that there’s no surprises!”

That is all you owe her.

Good luck!

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