Why You Shouldn’t Date Your Friends

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Why You Shouldn't Date Your Friends


I have a bad habit of dating my friends. I blame my refusal to date online and my moderate social anxiety for this pattern in my love life. I just can’t help myself.

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Dating a friend, whether it was a chummy co-worker or a cute classmate with whom I already shared inside jokes and flirty glances, was just so much easier than trying to strike up intimacy, let alone a decent conversation, with a perfect stranger.

I was already in my zone with these guys. I felt comfortable enough to be myself while also maintaining some mystery, which made things easy yet still exciting.

One too many glasses of wine after work or class and next thing we knew, lips had been touched, boundaries had been crossed, and our relationship would never be the same again.

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You might think that’s a touch dramatic, but here’s the thing: Intimacy changes everything. It’s not just bumping uglies that transforms your friendship from frivolous to fragile, it’s also the late-night sharing of secrets, the daily texting, the inside jokes, and not to mention the feels you ultimately can’t help but catch.

Will* and I had been friends for a decade when a long weekend in New York turned into a romantic rendezvous, which suddenly spawned a four-month relationship. It swept us up in a whirlwind of emotions and intensity, including a honeymoon-like trip to Paris and London.

Talking to Will had been easier when we were just friends. We could easily banter about pop culture and politics, but once we were “more than” friends, our conversations became heavy and loaded with subtext. There were so many unanswered questions between us, including the big one: “What exactly are we doing together?”

On paper, we were a pretty darn good match. In reality, we were more of a jigsaw puzzle with a missing piece. Will’s “know-it-all” attitude that had been easy to shrug off as a friend became increasingly annoying, as well as condescending, as a girlfriend.

The sex was just okay. And the jokes we had made about his unwillingness to commit when we were just friends soon became my reality, and thus nnot so funny anymore.

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Despite my gut telling me differently, I held onto our relationship for far longer than I should have. Looking back, my grip on our relationship was really my way of trying to hold onto the amazing friendship we once had.

After all, Will had been my go-to guy whenever I needed help; like when I was moving from Toronto to New York, he was there. When I got into a car accident, he was there. But as his girlfriend, when I needed him in a different way, he wasn’t there.

I witnessed the cracks and shadows that I hadn’t been privy to when we were “just friends,” resulting in me discovering a side of him that changed everything for me. I could never go back. And when we finally broke up, my heartache was a double whammy. Not only did our short-lived romance end, but so did our 10-year friendship.

Not soon after, I became involved with another friend of mine. He was familiar. He made me laugh. It was my M.O. I was comfortable with him, which made me comfortable to reveal different parts of myself (including a NSFW pic).

But, like Will, as soon as we crossed the line that defined friendship versus romantic entanglement, everything changed. We were different around each other. Things got awk, fast. Our easy vulnerability as friends suddenly became more strained. Intimacy had made us strangers. When we finally parted ways, we bid adieu to our friendship, too.

Though the sappy Pinterest memes and The Bachelor franchise might have you believe that dating your best friend is the ultimate happy ending, your best friend isn’t always your best shot at a soul mate. We can form friendships with our romantic partners, but those relationships don’t necessarily have to start off as a friendship.

Turning a friendship into a romantic relationship is, of course, possible. But it’s tricky. Communication and connection are especially vital, because if you break up, you risk losing your friendship. Looking back, I would have preferred remaining friends with the guys I had dated. Crossing that Friend Zone line wasn’t worth the loss in the end.

*Names have been changed.

Brianne Hogan
Brianne Hogan

Brianne Hogan is a freelance writer in Toronto who loves coffee, cats and astrology. Her byline's been featured on HelloGiggles, Elle Canada, Flare, Thrillist, among others. Keep up with her on Twitter, Facebook or her blog.