Having Sex With My Best Friend Was the Worst Decision Ever

Sleeping with my BFF and roommate was amazing—until it wasn't. So why did I do it all over again with another best friend?

by Jess Thomas; as told to Sirin Kale
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Jan 10 2019, 10:17am

Illustration by Camilla Ru

My First Time is a column and podcast series exploring sexuality, gender, and kink with the wide-eyed curiosity of a virgin. We all know your "first time" is about a lot more than just popping your cherry. From experimenting with kink to just trying something new and wild, everyone experiences thousands of first times in the bedroom—that's how sex stays fun, right?

This week, we're talking to Jess Thomas about their experiences of hooking up with their closest friend. You can catch My First Time on Acast, Google Play, Apple Podcasts, Stitcher, Spotify, or wherever you get your podcasts.

Growing up, I watched all these shows like Friends or Fresh Meat which featured a group of friends who all dated or slept together. So it was always in the back of my mind that maybe one day I’d end up dating someone I was close friends with.

The first time I slept with my best friend, we’d been friends for nearly three years, all the way through high school. He was dating one of my friends at the time, but then they broke up.

The first time we actually had sex together was after a night out. We were both drunk, he was staying at mine because he lived further away, and then it just happened. We'd joked about hooking up before, but one of us would always put the brakes on it. Then we stopped putting the brakes on it, and just did it. At first we both thought it was great: just a bit of fun that we were both enjoying.

Looking back at it now, it was the dumbest decision I ever made! Because after we started sleeping together, we both went to college and made the decision to move in together. It ended up ruining our friendship. Now, we don’t speak any more. But when you’re 19, it feels like a smart move to live with your best friend that you’re also having sex with. I would not recommend doing that to anyone.

We’d both agreed that if either of us developed feelings for the other person, we’d stop sleeping together. Things became more emotionally full-on for me, and I never really spoke frankly about it with him. He met someone else and got into a relationship with her, and our friendship just kind of broke down after that. But because we’d signed a year-long rental contract, there was nothing I could do. I think had we been older, things might have been different, but no-one at the age of 19 is good about talking about their emotions in a very mature way.

The situation got progressively worse. I was depressed all year, we stopped speaking, and eventually I moved out. It was a terrible situation, but I learned a lot from it, even if it was also very scarring.

After that experience, I became evangelical about not sleeping with your friends. Or if people really wanted to do it, I’d say: “This was my experience, if you’re going to do it, at least do it better than me! Don’t do what I did and accidentally fall in love with them, and then have to watch them happily in a relationship with someone else, all whilst living with them.”

The next time I slept with a friend, I was at a music festival with another long-time friend of mine. Before we went to the festival it had crossed my mind that something might happen, but I was convinced he wasn’t interested in me. We were sharing a tent, and there was a moment where we were spooning and then we were kissing. I thought, Wow, this is actually happening. This isn’t a dream.

I definitely was scared going into it, because we had been friends for so long and I was desperate not to lose him as a friend. We actually had a conversation at the festival about what it meant if we were hooking up. I told him it would change the course of my life if we couldn’t be friends any more, and we both agreed that we wouldn’t do it by halves—we had to be all in, or not at all. I explained that after the terrible situation I had been in before, I didn’t want that to happen again, and I wanted to be clear about things this time. Basically, I said: “if we’re doing this, we’re doing this.”

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By that point, we were so emotionally invested in each other’s lives, and sexually attracted to each other, that it was very easy to translate that into a relationship because I already cared so much for him. He felt like someone I could definitely be in a relationship with, and that was comforting to me. So after we hooked up, the rest was history—we fell into a relationship pretty quickly, and we’re still together now.

If you’re thinking about having sex with a close friend, my advice would be: Make sure you aren’t living together! Also, make sure your friendship is very open and communicative. Don’t have sex with someone where you feel like you can’t speak honestly with them, because then the sex will become an unspoken thing between you two, which never ends well.