What I wish I knew before dating my best friend

Jake (name changed to protect the heartbroken) was one of my first friends in college—a tall, charming boy-down-the-hall, with a floppy haircut and a definite eye-twinkle. We had a love-like relationship that volleyed, and I’m not really sure who took the first swing. I do remember Halloween, a quick kiss, and the ever painful I’m-just-not-that-into-you rejection. Cue a relationship rapidly switching sides—always together, but never together. We went to dinners, held hands, and watched movies. It was an uncomfortable security, which we both knew would inevitably change. Dating your best friend is a major risk, but holds the promise of amazing rewards. These are some of the things I wish I knew before I took that leap:

It can be the greatest relationship you’ve ever experienced.

Easy flowing conversation? Of course. Inside jokes? Built in. Endless fun times to be had? Always. Dating your best friend is like pressing the fast-forward button on all of the getting-to-know-you awkwardness of the first handful of dates. You know each other better than anyone—this includes the good and the bad—and have already decided that you accept each other, as is.

You tell your best friend everything, including relationship drama. This changes when your best friend is your partner.

Timing was never our strong suit. I had a boyfriend, then he had a girlfriend. But for a brief semester, both single and realizing what we had been looking for all along was right in front of us, we made it official. And it was great for a while. But when an ex I had not quite let go of admitted he hadn’t let go of me, I was thrown into an emotional panic. Jake, the person I would normally discuss this confusing situation with, was now invested in our situation. Maybe I was naïve; maybe I was taking advantage, clinging to a familiar presence who always felt like home. Not wanting to hurt him, I kept my conflict inside until it imploded into a hazy mess.

You have to be prepared to lose a friend.

Even though our romantic relationship mutually fizzled, our friendship dynamic never truly recovered. Our hangouts grew more infrequent, but picked up like they had never left off. We continued on with our individual dating lives, but always wound up back in the murky in-between. We graduated, moved away to different cities, and desperately tried to keep our friendship afloat. I called him when I got my job; I called him when my boyfriend broke up with me and moved out of town; I called him when I hated my job. He would update me on graduate school, how happy he was to be back in his hometown, and his government job that he was enjoying. Then, I went to visit him.

When I arrived, after months of planning this long-weekend trip, I knew something was up. There was a new girl in the picture, and she did not care for me. Maybe she knew the backstory, maybe she felt the tension. I honestly don’t know. What I do know is that a day into my visit, I was treated like a burden. Plans were cancelled, and I was pawned off on a mutual friend who lived a few blocks away. The last time I ever saw Jake was when he put me into a cab for the night out we had planned—alone.

I thought it was just a fight. But I didn’t see him again before I left the city. When I got back to Florida, I sent an apology text, expecting things would be fine. No response. I called; no response. Emails, texts, calls—I am a little embarrassed to admit how long it took me to understand, he wasn’t ever going to respond.

Breaking up sucks. But losing your boyfriend and your best friend is a whole different level of heartache.

Then one day, two years later, he spoke. A few weeks after my engagement, flush with celebrations and congratulatory Facebook posts, he wished me a happy birthday. And I immediately called him. To my surprise he answered, and listened as I called him out on being a terrible friend, on ignoring me, on treating be like a bad breakup. “But Glenna,” he said, “it was a breakup.” And I realized it was, just like any other. Although I continue to miss him (and probably always will), he wasn’t a horrible person. I had to accept the fact that I had rolled the dice, and lost my best friend.


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