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You Asked: I Want More From My One Night Stand

Dear Sugar,

I was in a serious relationship for six years and I am now single. Up until last week, I hadn't had sex in eight months! On Saturday night, I met up with a guy I used to have feelings for. I invited him over and we had sex. There wasn't much flirting, kissing, or any kind of lustful passion. We did it and then hung out for an hour afterwards. I thought that would be the end of that, but he called me the next day and came over. We just hung out that time, but the following day he texted me and we started flirting. It's clear to me that he's looking for a hookup and that he's used to this lifestyle. He's incredibly sexy and I could see him getting girls easily. I know I was wrong for sleeping with him so quickly, but I like him now. Is there anyway to change the direction of our relationship at this point? He obviously sees me as a sex buddy, but I want more. We've been hooking up almost every day now.

— Hooked Up Hilary

To see DearSugar's answer,


Dear Hooked Up Hilary,

It sounds to me like you and your one night stand have become friends with benefits, at least in his mind. I can't say whether or not you guys can have a more serious relationship — that's up to the two of you — but of course it's possible to try. In order to do so, you're going to have to tell him that you have feelings for him and put an end to the booty calls. But keep in mind that because of how your relationship has been established, your friend may not share your feelings or desire to embark on something more committed. If that's the case then I think it's in your best interest to avoid continuing the friends-with-benefits deal you have going on because it's likely that your feelings will grow, but unlikely that a relationship will blossom. The sex might be nice, but not at the sacrifice of your emotional well-being.


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