I slept with my best friend

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Hi Guys,

A couple of months ago after breaking up with my ex, I slept with my best friend. He was friends with me all throughout high school and through my crappy relationship; he was even friends with my ex. He lives about five hours away from me and the first time I went to see him I didn’t expect to do anything but hang out like we usually did. But after going to a bar, we went back to his house he looked at me and started kissing me and one thing led to another and after three months we still sleep together whenever one of us makes the trip.

Now I’ve started to catch feelings and I think he has too because last time he came up it was just to see me. I can’t tell if it’s just him being the way he is (he’s a very sweet guy) or if he actually likes me. I can’t lose my best friend but I don’t know what to do

Please help,


Dear Lissa,

What exactly do you want?  You say you don’t want to lose your best friend, but you don’t say what it is you want. That might be a good place to start.

Many promising relationships begin with friendships. It’s hard to say if your guy sees you as a friend with benefits, or as someone having long-term relationship potential. However he sees you, it seems that this might be the time to have a heart-to-heart conversation with him, don’t you think? Right now you’re letting the current sweep you away, but you do realize you run the risk of losing him if your new romantic iteration crashes and burns. We’re not saying you should cease and desist, but we are saying you should stop guessing and try talking to him about what’s going on. You need more information so you can proceed with your eyes open.

Relationships require risks Lissa. Nothing ventured, nothing gained. You have to have a little faith when putting yourself out there. Faith in the fact that the person you’re with has your best interests in mind, and will take care of your vulnerable heart. But it doesn’t always work out. In fact, most relationships run their course.

What you need to decide is what’s more important to you: His friendship, or the possibility of a relationship with him? You probably can’t have both.

We hope this helps. If you have more questions, leave them in the comments’ section below. Or any thoughts you might have. (You must be Logged In to do so.)

All the best,


ps. Please let your friends know about us. Thanks!

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