Now Reading
The Pros and Cons of Hooking Up With Your Best Friend

The Pros and Cons of Hooking Up With Your Best Friend

You’ve been friends for years and the thought has come across your mind of taking things a bit further. He’s cute, funny and what’s the worst that could happen? Well, a lot actually. Here are the pros and cons of hooking up with your best friend (with a first hand perspective of the pros!).

The Pros

There’s already a level of comfort.

When I hooked up with my best friend Hayden*, I never thought in a million years that I’d ever try it. Then one day, we flirted and one thing led to another… It was empowering for me to go for something that I wanted and leave satisfied. Honestly it wasn’t perfect or anything like the movies, but it was special in its imperfections. We were both nervous, which was expected, considering that we hadn’t felt this way before, and excited all the same. It was oddly comfortable even though we’d never touched each other this way before. The longer we were together, the more I felt a connection between us strengthen. We had quiet moments being in each other’s arms, listening to the rain and that was the closest I had ever felt with him.

They know your (romantic) history.

It had been months since my last breakup and I refused to be defined by my ex. Hayden knew all about my messy breakup – making it easier for him to understand the type of comfort I was seeking in someone else. He knew I wanted a casual hookup and was so incredibly understanding and (thankfully) up for the notion.


There’s mutual respect.

Looking back on my experience, I say if you want give hooking up with your best friend (someone who you know who loves and respects you) a go, you should do it. I do caution you to approach it at the right angle. If you think that it’ll fill a void that an ex or insecurities have made in you, maybe reconsider. Once you begin hooking up with your best friend, it’s probably going to change your relationship, no matter how the situation plays out. Just remember, hooking up won’t magically take away your pain. Make sure you and your partner are on the same page the whole way.

The Cons

The possibility that it could cost your friendship.

There’s always that chance that the change of intimacy in your relationship makes things go sour. Whether one of you ends up not feeling it, he turns out to be the person you never thought he was, or there’s just no sexual connection – a botched hookup could result in a lost friendship.

See Also


You get attached and he doesn’t. Or vice versa.

Talk about awkward. If you begin hooking up with your best friend and then all of a sudden decide you’re just simply not into it…what do you do? Especially if he begins to get attached – now you’re going to have to turn him down, probably making a big blow to his ego and creating tension for the future of your friendship.

It’s plain out awful.

Again: AWKWARD. Hopefully if you decide to start hooking up with your best friend and it ends up being downright awful and not what you expected, you can both just laugh it off. If you were good enough friends to begin with, chances are you probably can. But if not, expect to say “bye bye” to your friendship…and probably never speak again.
*Names have been changed.
Featured image source: