The One Time It Might Be OK To Date An Ex’s Friend


Remember the scene in The Player’s Club where Diamond comes home to find her boyfriend in bed with her cousin and flips out? Yeah, devastating. Well, I watched the entire rest of the film, rape scene and all, and couldn’t get over how evil it was that her cousin and boyfriend betrayed her. And though Diamond came to a resolution with her cousin at the end, I could never have come to forgive her.

Having sex, or making out, or even heavily flirting with a friend/family member’s significant other has always been unforgivable to me. It’s a betrayal on multiple counts. A two-for-one special of disloyalty, deception and selfishness.

And in my experience, there are few times that this offense occurs where it’s not a subliminal attack on the victim, whether the angry lover pursues the friend out of spite (this has happened to me recently) or the friend seduces the lover out of envy (this has also happened to me recently).

But…sometimes when an event you dread occurring finally happens to you, you realize it’s not as bad as you anticipated. Stay with me.

In high school, I fell in love with a guy. Mentally, I’ve never been more stimulated by someone of the opposite sex. Charm, intelligence, wit, charisma, humor, depth, wisdom, hustler’s ambition, he had at all. I liked everything about him: the way he walked, how all his friends followed him, the passion he exuded about his art, the (rightful) arrogance he showed about his smarts (he was a genius at math, and made sure everyone knew it).

I especially liked the way that he liked me. I delighted in being the apple of his eye. There’s a spark and constant flow of creative energy I have that I think he enjoyed. And no one could match him in a debate like I could. He respected that. When he looked at me, his eyes would just sparkle and I’d feel special.

Maybe that was the problem.

Because there was nothing special about his affection. He was young, charming and attractive. And there were plenty of women at our school who noticed and were happy to entertain him, whether through a one-night stand or a “fuck buddy” arrangement or more.

We were friends first, which would be a great thing had it not given me a front row seat to all the women that casually came in and out of his life. As much as he seemed to like me, he loved easy women that much more. And relationship just didn’t seem to be in his vocabulary.

Feeling strongly for him and occasionally dating but not committing, was an ordeal. I was a wreck and constantly confiding in my girlfriends to make sense of my mixed feelings, especially The Friend, who was my closest confidant at the time.

When he opened up to The Friend about me, in the cafeteria or by the lockers, she’d report what he’d said later and I’d hang on to every word. And thank God she was there when I broke down after news hit the school rumor circuit that he had a girlfriend (which to no one’s surprise, only lasted two weeks).

He and I stayed friends, but eventually I moved on to a guy who wanted a serious relationship, and eventually, we all moved on to separate colleges. Life happened, and we fell out of touch.

Fast-forward to four years later. We’re at a mutual friend’s birthday party and though we haven’t seen each other in what seems like forever, our chemistry is still the same, like it’s been bottled up all these years.

We’re having small talk. He works at a law firm out of D.C. I ended up in PR, living in The Bronx. After five minutes of high school reunion talk about who got married, who got into the music business and became an overnight success and who came out of the closet, The Friend comes up.

“Do you still talk to The Friend?” he asks.

“Not really, no real reason,” I lie. “Well, actually, we had a falling out. But our lives went in different directions anyway.”

“Well, I used to talk to her,” he says.

He doesn’t mean what I think he does. “Talk about what?” I respond.

Talk to her. We dated for awhile.”

Suddenly, I had to concentrate on breathing. “When?”

“Like two years after we graduated…” He went on for awhile about their relationship, how they started going out, what they used to do together, but I barely heard a word. Erratically, I blurt out: “Did you have sex with her?”

“Yeah, I did.”

I grimaced. I had been trying to hide my emotions, but I couldn’t anymore. Wasn’t that, like, incestuous? I told myself to be calm. “Why’d you break up?”

“It’s a long story…but basically, she’s crazy. She was too attached to me and one night, we got into an argument after sex and she kicked me out of the house naked and threw all my clothes out of the window because I wouldn’t tell her I loved her,” he pauses. “Are you okay?”

By this point, the details of their relationship (nakedness? love?) were too much for me to handle and my face had completely betrayed me. I was floored.

“I didn’t realize you guys were that close,” is all he says. “I’m sorry.”

In the cab ride home, my emotions vacillate between anger and pain. But the more I think about it, the more I wonder if technically I have a right to be upset (of course, theoretically, you can’t help how you feel and the fact that I cared about him, and her, would naturally make me feel hurt).

But he and I weren’t together.

It was years after we were involved that he slept with The Friend. And by then, she wasn’t even my friend anymore.

And as he emphatically brought up during our conversation, I never gave him the goods anyway.

Just because he dated me at one point, and we still were fond of each other, does that mean that everyone I was close with at the time is off limits to him? That doesn’t really make sense, what if my ex-high school BFF could be his soul mate?

Would the unspoken rule of “not dating an ex’s friend” prevent them from exploring a worthwhile romance? They’d be stupid to let what he and I had in high school get in the way of something special. Even if it hurt me in the process.

Which leads me to the question…when is it okay to date an ex’s friend?

Though society would have you believe dating an ex’s friend is a cardinal sin, there are exceptions to every rule. What circumstances would make it forgivable? Discuss.

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