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CONFESSIONS: Here’s What Happened When I Slept With My Best Friend

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Neither of us intended for it to happen.

Katie had been my best friend since childhood. It was a friendship first orchestrated by our parents. We ran around in our diapers and watched Barney, or whatever it is you do when you’re a very small human. We attended each other’s birthday parties and continued having playdates, even when we learned about cooties.

I don’t remember a time in my life when Katie wasn’t part of it.

There’s this thing that happens when you’re a heterosexual guy and one of your closest friends is a girl: you think about fucking her.

I know that sounds gross. Sometimes we men are gross. It doesn’t mean you ever act on it. It also doesn’t mean you aren’t capable of a genuine friendship. But yes, it’s something that you think about at least once. It’ll cross your mind.

The first time I looked at Katie differently was during puberty. I could blame the hormones, but Katie’s also just an obscenely beautiful person. And not just physically. Katie is kind and sweet and everything that equates to perfect Girl Next Door.

But she was my best friend and any inappropriate thoughts I had I learned to control. That’s just what you do when you have a super hot friend. You train yourself to not focus on the hotness.

I was sort of the Gordo to her Lizzie McGuire.

Yeah, I thought she was cute, but most importantly, she was my friend. We survived high school together. Instead of attending our prom, we held our own very 90s movie inspired Anti-Prom Prom. She wore all black and I wore my converse. We ate popcorn and watched shitty movies all night. It was perfect. I couldn’t have imagined a better night.

When it was time for college, we landed at schools in different time zones. I was accepted to NYU and she went to The University of Texas at Austin. It was the first time we’d been apart for that length of time. We promised to stay in touch and Facetime and text. But college happens and we got sucked into our new lives.

The contact became less frequent. We weren’t talking on the phone anymore. It was a ‘like’ here or there. Someone would send a text about something crazy that happened, but the conversation would quickly fizzle out.

During our sophomore year, we were both home for winter vacation. The previous year she’d gone away with her family and spent the summer break in a study abroad program. We’d barely seen each other since leaving for college. But we were both home for a month at the same time so she texted me about catching up. I picked her up from the airport and was pleasantly surprised at how quickly we fell back into a familiar pattern. It was like no time had passed. She was still the same Katie that had been my best friend my whole life.

One night, whatever was left of our group of high school friends congregated in our stoner friend Paul’s garage. His parents were always pretty lax about what we did and unless something was on fire didn’t even check in. Katie made everyone screwdrivers and we spent the night reminiscing and being obnoxious.

By 3 am, people were starting to fall asleep or call Ubers to go home. Despite being bartender for the night, Katie wasn’t drinking. Her mom was a recovering alcoholic so Katie preferred to stay sober. I was a shade under tipsy. Wouldn’t have driven but definitely wasn’t drunk. Katie offered to drive me home.

During the drive, she told me about a guy she met in one of her classes. They’d apparently hooked up a few times and she liked him, but wasn’t really sure what he felt. I gave her my standard advice (“Guys are terrible, don’t trust them”) and she laughed.

“Why can’t they all be like you?”

I don’t know if it was all the time away from each other or the fact that I’d been awake for nearly 24 hours, but I couldn’t stop imagining what it would be like to kiss her. She has these heart shaped lips that always form such a perfect pout. I wondered if they were soft. I could kiss her gently. I could slam her against the wall, if that’s what she wanted.

A mile or so from my house, Katie suddenly veered left. To get to my house, you go right. I asked if she forgot where she was going.

She shot me back this smile I hadn’t seen from her before. Never intended for me, that is. If I didn’t know any better, I would have thought she was flirting with me. And turns out, she was.

She pulled over on a street that dead ends. There weren’t any streetlights and I assumed everyone in the nearby houses were sleeping, so it was practically total darkness. We were both silent.

I wanted to kiss her and had she been anyone else, I would have made my move instantly. But this was Katie. The girl I had sleepovers with when I was nine and brought me soup and the homework I missed when I was out of school for a month with mono. This was Katie.

I awkwardly fumbled and started talking Netflix’s TV model and how eventually cable will be a thing of the past because apparently that was worthy of mentioning?? But Katie stepped in. She kissed me. And I kissed her back. It went from there.

I’ll spare you the details because hooking up in a car is never as sexy as it’s advertised to be. But there was something undeniable about it: Katie and I had something. Whatever our relationship had been, well, it was different now.

I could tell you about what happened after. I could tell you about the nervous giggling and the week of pretending nothing happened. I could tell you about going back to college and missing her. I could tell you about the phone call at midnight. I could tell you about deciding we were going to visit each other. I could tell you about flying to see her in Texas. I could tell you about the confessions and the kissing and the sex in places that weren’t cars. But that would take far too long. And you’re not interested in hearing years worth of stories.

But what I will tell you? Katie and I effectively ruined our platonic friendship that night.

Because we’re getting married this summer.

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