9 People Spill What It Was Like Hooking Up With Their Best Friend

Not everyone’s comfortable talking about their sex life, but knowing what goes on in other people’s bedrooms can help us all feel more inspired, curious, and validated in our own experiences. In HG’s monthly column Sex IRL, we’ll talk to real people about their sexual adventures and get as frank as possible.

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So, have you been thinking about hooking up with your best friend? After a series of shitty break-ups and horrible dating app interactions, shifting your friendship with your BFF to FWB may start to make a lot of sense. They’re your partner in crime, the keeper of your embarrassing secrets, and most importantly, they know what you’re like in a relationship because they’ve been with you through it all. Plus, you already know you like each other and it’s always a good time whenever you hang out.

But putting all of the potential benefits aside, is it possible to really just be hookup buddies with your friend and still somehow preserve what you have? Well, it depends on your situation and what you’re looking to gain. A 2020 study shows that while it’s easier to transition back to friendship after intimacy, it’s admittedly more difficult to obtain a romantic relationship if that’s your endgame. Another study notes similar findings with some people reporting that after it ended, they felt lonelier, less connected to their friend, and potentially deceived if the friendship wasn’t prioritized. It could be a seemingly perfect situation in theory, but only with some effort. Putting it into practice can be a different story if intentions aren’t clear and radical honesty isn’t consistently honored every step of the way.

In honor of National Friendship Day on August 1st, I spoke with nine people who shared their true feelings about what they were hoping to get out of the hookup and what it was like transitioning the friendship to something physical. They revealed what it was like initiating intimacy for the first time, if sex changed their connection, and where they stand with their best friend today.

The friendship and bond were all over in just one night.
“I had been in love with my best friend since the day we stepped into college. We even started our entrepreneurship journeys together. But I could never gather the courage to tell him because I couldn’t afford to lose him as my best friend. He was even dating someone else. I always had a minor crush on him and as our friendship grew, my crush changed into genuine feelings. They continued to grow no matter how hard I tried to suppress them.

“There was this one day where we were just chilling on his balcony with drinks and soothing music. And in the next moment, I found myself kissing him. Both of us were equally involved in the kiss. He didn’t push me away and that’s what made it the most amazing moment of my life. The world ceased to exist in those few moments and it was just me and him. I seriously thought we had something between us but he ghosted me the very next morning. We never talked after that. He wouldn’t answer my texts, calls, and acted like he couldn’t hear me when I went to his place to talk to him. I gave up trying and whenever we saw each other in college, it would be really awkward between us. The friendship and bond were all over in just one night.

“When I look back now, I feel I misinterpreted his behavior. The way he used to care for me, compliment me, make plans to hang out with me, all drew me towards him. For him, I think he just wanted to find some comfort in a pool of unknown faces. None of his friends were in the same college as him, and I was familiar. That may have pushed him to talk to me. Maybe he didn’t see me as a potential partner but he didn’t want to say it to my face because I know he cared for me. But even if he didn’t feel the same way for me, we could’ve at least gone back to being friends. Personally, I feel there’s been a weird awkwardness among us since that day and it fills me with regret every time I think about it. I still miss the friendship and would’ve been happier if he was still my best friend but I need to accept life as it comes, not the other way around. I’m in a relationship now and it’s going well.”

— Sara, 28, Texas, US

But when we finally went for it and had sex, the chemistry didn’t really click.
“I was always physically attracted to him but as I got to know him better, I was also attracted to his chaotic energy. He’s a wild card. We got along really well and had easy conversations. It was one of those things where we had been thinking about it for a while and if I’m being completely honest, I think we were just bored during the pandemic and started flirting over text. I don’t think either of us ever thought we would be more than friends and we were only interested in a casual relationship. Luckily, we were both on the same page and didn’t need to have ‘The Big Talk.’ We broached the topic in texts and then met up for a casual drink that led to a hookup. But when we finally went for it and had sex, the chemistry didn’t really click. Sometimes there are people where you so want it to be great, but your pheromones just aren’t that compatible.

having sex with best friend
“It was awkward seeing him for the first time after the hookup but soon, we were back to our normal relationship. The physical relationship naturally fizzled out with no hurt feelings and then he started seeing someone else. Our hookup isn’t a secret and we both feel pretty neutral about it now, [although] when I would hang out with just the two of them, I did kind of get a weird vibe from her. My friend and I do bring it up sometimes around each other but mostly as a joke. We’re both happy the way we are. Also, it’s not completely off the table that we wouldn’t hook up again. We just play it by ear.

“A lot of the drama that comes with hooking up with a friend is a lack of communication. Ideally, this would be something you talk about beforehand, but a lot of times it doesn’t work out like that! It definitely helped that we both understood that the situation was casual from the beginning so it wasn’t very hard. Why stress out trying to guess what the other person wants or assuming they feel weird when you can just ask them where they’re at?”

— Jenna, 29, Chicago, Illinois

We ended up having sex that day and all the days to come.
“At the time, I just had a baby and I was living with my boyfriend/the baby’s father. My best friend invited me to her birthday trip to Cancun. Prior to that trip, we never had any sexual relations, nor had there been any hidden crushes. But on day one of the trip, we got really drunk and something about the moment caused us to become sexually attracted to each other. I know we had been drinking a lot but we had been drunk a million times together before! Nothing ever happened then. We ended up having sex that day and all the days to come. We did it once on the beach, too, which was fabulous.

“When we came back from vacation, it was awkward. Things weren’t the same for three months. One time, she even tried to make a pass on me. I pretended I didn’t notice and we kept it moving. Fast forward two years later, we’re completely back to normal. No awkwardness. She even comes over and hangs out with my family and everything.”

— Anonymous, 25, New Mexico, US

The sex is very good, the best head I’ve ever had!
“I’m in something casual with a friend right now. We’ve been close for years and I was always attracted to him. We discovered we liked each other but never dated since he moved away and I was in a relationship. But we recently both came out of a long-term relationship and we’ve been supportive of each other. [Being physical] happened naturally between us. We are career-driven, good friends, and have other areas of focus, so it’s nice and easy. There’s nothing awkward and it’s not complicated since we know the rules.

“The sex is very good, the best head I’ve ever had! He’s affectionate and not selfish, which has been nice for a change. He’s also super confident, which I find massively attractive. As it’s a friends-with-benefit situation, I just make sure he’s not hooking up with anyone else and if he plans to, he will tell me. We spoke about what our ambitions are and we are completely on the same page about what we want. We have a good understanding of each other. I think it’s important that there’s good communication otherwise it gets very messy.”

— Amy, 27, Chester, England

I wanted him to be my boyfriend but he didn’t know what he wanted.
“Our families have known each other forever. I think I always considered him off-limits, almost like a brother, until one day I looked at him and something inside of me switched. I saw how attractive and charming he was. The timing didn’t work out for a few years and I kept my feelings for him in my back pocket until we were single at the same time. I confessed my crush to him when I was drunk and while he was surprised, he admitted he had thought about us getting together, too. For a few months, it worked out pretty great. The sex was awesome and the ease we had with each other naturally transitioned to the bedroom.

“But I caught feelings for him and he wanted to keep it casual because he was still getting over his ex. I started to get upset and play games with him because he wasn’t returning his feelings for me the way that I wanted. I stopped being his friend and started being this needy, insecure girl. I wanted him to be my boyfriend but he didn’t know what he wanted. It reached a point where it got pretty toxic and he ended things to take some space from dating. He’s now seeing this girl that he’s pretty serious about. She didn’t want us to stay in contact since I was pining over him. I wish that we never hooked up, or maybe, I wish that we had talked about what we wanted. I think I wrongly assumed he would know what I was feeling because we were so close. That’s my biggest regret. I miss my best friend. Our families miss hanging out, too. I hope we can get back to a somewhat normal place in the future but I want to respect his new relationship.”

— Susanne, 32, Los Angeles, CA

We parted ways amicably and we’re proud of ourselves for having done so.
“Her first impression of me was as a brainy goofball. I thought she was intelligent with a great sense of humor. We’ve known each other since middle school and we did everything together. We loved to laugh a lot, she always knew how to make any situation seem comical.

“I guess a surface-level attraction developed when we got to high school, but I never really acted on it since we had relationships at the time. But once those ran their course, we were drawn to each other mainly because of the familiarity. During my college years, we got together. And that’s exactly how hooking up was: familiar. It felt like home: comfortable, easygoing, something (in this case someone) you’d always run towards at the end of the day. The first time having sex, there wasn’t any awkwardness and there wasn’t much lust the first time around either. It was very much like how you’d picture it happening in romantic comedies between friends-turned-lovers but with a lot of laughs and giggles. We ended up going separate ways after she got a job in the Far East after graduation.

“We decided not to pursue the long-distance engagement because of the headaches, and because we might end up resenting each other. We parted ways amicably and we’re proud of ourselves for having done so. I’m married now and [my wife] is aware of that part of my life. She’s been really understanding about that dynamic. My best friend and I treated it as an ‘interesting’ phase of our relationship but we try not to delve into it too much as a sign of respect to our current spouses. We are very much content with being friends. Especially after it ended, we realized that we were definitely better off with a strictly platonic relationship. It’s difficult to have a mature conversation but it’s the ultimate test of emotional maturity. To save it from turning ugly, I’d say the most important tip would be to think about what’s best for both of you, not just for your individual selves.”

— Jack, 50, San Francisco, California

having sex with best friend
We ended up in a romantic relationship for nine months, then a weird one-off thing.
“We were in the same swim club together and had been best friends for a year before we hooked up. He would have parties at his house and we would always share a bed whenever I would spend the night there. Usually, nothing ever happened and we never even touched each other when we were in bed. But one night, we were at a friend’s house for a pool party and they put us in the same room together because that was the nature of our friendship. We decided to snuggle and we just turned over and started kissing. It was really exciting for both of us to cross the threshold. It wasn’t really spoken about but it wasn’t awkward at all, we giggled about it and felt very comfortable since we were so close.

“There wasn’t an overwhelming amount of sexual tension but more of a curiosity. There’s this heteronormativity that exists when a guy and a girl are best friends with each other like that. Everyone kind of wonders, which makes you wonder. It wasn’t a secret relationship by any means, we ended up in a romantic relationship for nine months, then a weird one-off thing. We broke up because I didn’t want a committed relationship and he did. It led to a lot of issues with jealousy because he agreed to an open relationship even though he didn’t want it.

“I wouldn’t want to get back with him because we want different things in life but we were able to remain friends because we have a high amount of respect for each other. It’s a slippery slope of potentially ruining the friendship but being friends and communicating well made all the difference with our connection. We keep in touch and he has a girlfriend now. We all talk about meeting up and getting drinks whenever I’m back in the states. It’s been four years and still, he’s my favorite ex that I’ve had. I’m a huge advocate for hooking up with your friends if you think there’s some potential there. Although it wasn’t perfect, I think that was the relationship I had the most fun in. I wouldn’t take it back at all.”

— Mary-Frances, 25, Guatemala City, Guatemala

We tried to shrug it off but we ended up having a huge falling out when she hooked up with another colleague.
“My best friend and I ended up abroad together to teach English in Ukraine and to just generally have a good time. I could tell she was attractive and very bright in college but I was seeing someone at the time so we were firm friends. We decided to get together after she told me that she’d been going through a mega dry spell. I wanted to hook up with her because I was curious to explore whatever sexual chemistry we had and cross the bridge between BFF and a casual, sexual encounter. We planned it so it wasn’t a surprise but there was awkward chemistry, at least initially. It felt totally familiar and yet unfamiliar. Though honestly from that point on, it was all clothes off.

“At first, we decided to keep it a secret because we didn’t want anyone else to think our friendship had changed and it was fun that it was secretive. It was very chilled out but, of course, the information leaked eventually and people expected us to end up together at the end of each night. We tried to shrug it off but we ended up having a huge falling out when she hooked up with another colleague. It didn’t work out. I believe we were on the same page about the hookup and I don’t think it caused major complications, although, the reaction of those around us forced a change in our dynamic and we grew distant. We never discussed it again because we didn’t feel like we had to or wanted to. It was swept under the rug because there was a shared desire to not let this change our friendship or romantic outlooks. We are civil friends now and somewhat in touch, but not best friends anymore.”

— Dylan, 28, London, England

Everyone was rooting for us to date and they were super excited when they found out.
“We met in our first year of college and lived on the same floor together. I liked him right away, which surprised me. I never felt drawn to someone so aggressively, but I was immediately attracted to his fun personality. I felt like there was something about him that was unexpected and wonderful. I didn’t tell him that I had feelings for him though because we were in the same group of friends and I was afraid that it would mess up our strong friendship. A lot of situations could go south really quickly if it’s one-sided and the other person doesn’t feel the same way.

“I ended up living with him when we got an apartment off-campus with our other friends. It was tough living together for those few years while I was secretly harboring feelings for him but there were small moments that made me think he could like me, too. We would cuddle while watching movies or sit very closely on the couch where our legs would touch. Still, things went unsaid. At that point, we didn’t really communicate how we were feeling as we increasingly became more physical. One day, we went on a walk and were going out of the elevator when he suddenly grabbed me and we started making out. Kissing felt weird at first but once we quickly realized that we were both on the same page about our feelings, being physical felt very effortless. Whenever it felt overwhelming, we would just laugh about it like, I can’t believe this is happening!

“It didn’t feel strange at all to be naked together for the first time, it was extremely natural and fun. I think because we were friends first, sex became another fun activity where we could joke around about it in a low-stakes way. There’s no pressure and it’s truly such a lovely time connecting with him physically. We kept our friends in the dark about our relationship for a few months while we were figuring things out. But I was lucky that we were in a pretty unique situation. Everyone was rooting for us to date and they were super excited when they found out. I was always worried about ruining our friendship because I knew how much I loved him but to my relief, everything worked out. We are still together and ridiculously happy.”

— Amber, 29, New York, NY