Hooking Up: The Ex Files

Only the worst kind of girl would ever date a friend's ex-boyfriend. To violate the bonds of friendship for some guy? Please. That would never be me. At least I thought it would never be me ... that is, until The Poet asked me out. He was boyishly handsome and good with a clever phrase. The problem was, he used to hook up (opens in new tab) with my good friend.

It's not like their relationship — which, mind you, had wound down a full two years earlier — was going anywhere; it never even got legitimized by Facebook. And my friend didn't shed a single tear when the fling finally, inevitably, dissolved. She wouldn't care; I was sure of it. Still, I did what any good friend would do: I asked for her permission.

She looked a little taken aback, then said simply, "Yeah, sure." So I brushed off the slightly tense vibe and went on my date. We had pizza and sat outside on the steps of his apartment building. I joked that his next poem should be about me, and he made up a few corny, iambic lines about how much he liked me. As he walked me home, I slipped my hand into his sweatshirt pocket and linked my fingers with his. Feeling giddy the next day, I was dying to divulge all the gritty details to my friend, but she didn't ask, so I didn't tell.

I wasn't callous about it; if my phone vibrated with a text from him when she was around, I'd ignore it. And we mostly hung out at his place to avoid any awkwardness if she came knocking at mine.

Then one night, my friend and I went to a house party. The minute he walked in, I sensed her tensing up. And I took such pains not to appear an intimate of either that I found myself standing alone somewhere between the beer pong and the blaring speakers.

That's when I finally took a step back. Had I been unfair in asking her whether I could date her former fling? Did she have any choice but to say yes? Say no, and she would've risked exposing exactly what "hooking up" aims to hide: emotional attachment.

We all throw the term around with such studied bravado these days — as if these encounters don't mean a thing. As if we don't leave a sizeable piece of ourselves behind every time we exit someone's bed. Thinking back to my friend's discomfort and her valiant effort to suppress it when I sought her approval, I realized what I'd probably known deep down all along: that she'd actually had an investment in the guy.

What she didn't have — being a modern woman and all — was the nerve to say so. I knew then that The Poet wasn't worth the risk of losing her, almost certainly a better bet for relationship longevity. In letting him go, I won back my friend — making it by far my best breakup yet.