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Is It OK To Date Your Ex's Friend?

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one man with two women lying down
Can dating your ex's friend cause complications?

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.

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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.

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