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“But with my fuck buddies it’s been like, There’s almost a level of titillation to sex stories when it’s somebody who’s not your boyfriend. I wish I knew, so I could bottle it and never be possessive ever again.”For all the benefits of fuck friendery, it’s still possible for this dynamic to screw with your emotions.

“At different points in our relationship,” Casey recalled, “it was hard to respect the line between friendship and flirting when he started dating someone, because I’d known him more intimately than his new partner.

In a few days, I’m going to Cuba on vacation with a guy I’ve been sleeping with for eight years, but whom I've never once called my boyfriend.

We live on different continents, but inevitably, a few times a year, we find each other somewhere in the world, have a few days of romance, and then go our separate ways.

I told Malcolm about my previous relationships, my fantasies, my heartbreak.

Once, he told me this long, complicated story about an affair he had with his cousin, adding, “That’s not something I tell most people.” Probably wise on his part, but I loved that story, as problematic as it may be, because I loved knowing something about him that no one else did.

)One of the most masterful fuck friends I know is my friend Casey, a 26-year-old Ph. candidate in English, who until recently had a FWB for .

And he actually knows me better than a lot of my partners ever did.

So what is it about the friends with benefits dynamic that is more sustainable, and often more transparent, than an actual relationship? They’re like: How can you have sex with the same person, again and again, without falling in love?

This arrangement would generally be called a friend with benefits, or a fuck buddy, or a romantic friendship, or perhaps even a relationship—with “no strings attached.” But let’s be real: There are always strings, aren’t there?

It was while planning this vacation that it hit me: The two longest relationships of my life have both been with men who I was never officially dating.

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