I’m having post-hookup doubts

A couple of days ago, I finally slept with this guy after knowing him for quite some time. We'd flirted and talked in the past, but before we started talking this time around, we hadn't been in contact in almost a year.

It was a great night. After it was over, we cuddled and talked and made out. I want to continue seeing him, in a purely friends-with-benefits way, but I'm worried I'll still end up very hurt. He's very notorious for being selfish and insensitive. I know that he cheated on his last girlfriend with multiple other women.

Though I feel comfortable with him (we've known each other for a while; he wasn't a complete stranger), I'm fearful that given his past, he's just playing me. Am I overthinking it or should I genuinely be concerned? I started doubting him when he said nice things to me when we were together. Do I call things off completely before we get more involved? Or is it possible that he's changed since the last time I knew him?

– Concerned


Before you spend too much time worrying about whether you can trust him, think about whether you can trust yourself. You say you want this guy as a friend with benefits, but you're asking questions that suggest you're looking for more. What does the best-case scenario look like in your head? Are you expecting a commitment? Exclusivity?

My guess is that there's too much drama here – too many insecurities and question marks – to make the relationship worth your while. You can't even take a compliment from this person without second-guessing his motives. That doesn't sound like much fun.

But if you want a real answer, talk to him about what happened. Ask him what he's looking for, and think about whether you can believe him. If you doubt every word, he's no friend, and the benefits aren't good enough.

- Meredith

Readers? Should she pursue this casual relationship if she doubts him this much?