Is It OK To Date Your Ex's Friend?

Can dating your ex's friend cause complications?

By single-ish — Written on Aug 12, 2010

Have you ever made a play for the friend of an ex? I don't advise it. Too bad I didn't take my own advice...

A little background. On my recent trip home to Toronto (I was supposed to go for three weeks; got called back to NYC on a story—more on that later), the friend of an ex caught my eye. Let's call the ex Veronica and her friend Betty. Veronica and I had a tryst a couple years ago, which didn't last all that long. Veronica and Betty are roommates, and when I'm in Toronto we'll often see each other at shows or at parties.

Last weekend, I spent a hung-over day with Betty in the park. We watched dogs and chatted, and when her friends arrived with a picnic, I rested my achy head on her lap. Later in the week, Betty and I were working in a coffee shop (I was writing this blog; she was working on her Ph.D.) with another friend of ours, Reggie. We were both on G-chat so I straight up asked her: "Are you attracted to me."

Her answer: "Totally!"

OK. So game on, right? Wrong. After we'd finished working, we went to a local farmer's market. We bought tomatoes and basil and a bag of peaches, and then walked back to the loft I was renting to have some beers on the roof-deck. Once there, we got to talking, and she told me that she had no intention of hooking up with me because "you made out with my best friend."

I was a little dumbfounded. I have complete respect for the best-friend situation. And I actually value that someone would consider her loyalty over her libido more than any physical satisfaction. That being said, I figured that my past with Veronica was not an issue when I'd so blatantly asked "Are you attracted to me" and her response had been positive.

But Betty wouldn't want to risk complicating a treasured friendship, and I understood that.

We had a few more beers and then walked to the park where our friends were meeting for a birthday party of bocci ball and beer. I was a little frustrated, but ultimately not too discouraged. I told Betty she should ask Veronica if she had any objections to us seeing each other, and if she wouldn't, I would.

But I never got around to it. And I'm not sure if Betty did. We had a great time that night, all of us, and it was probably better that politics never entered into it.

At the end of the day, who really needs hookups when you've got good friends?