Recently, I reconnected with an old friend online whom I haven’t seen in probably six years. He divorced two years ago and is the father of an adorable 7-year-old. Anyway, we met up for cocktails, one thing led to another, and we ended up having mind-blowing sex for the entire night until the sun came up. I completely did not expect it, but I don’t regret it either. Now comes the issues: we saw each other three times last week, went out one of those times for drinks and to hear music, but the rest of the time we hang out it’s only sex. I think I even made the GIGANTIC mistake of saying to him on one of our outings that he makes a perfect “friend with benefits.” Our sex can be very hot and intense, but also very romantic (we shower and he washed my hair, he kisses my forehead, he plays with my hair, etc.) and it is making me fall for him. Problem is, I’m terrified to have the “what are we?” conversation with him because I don’t want to lose him as: a) my sex buddy or b) my friend.
I have no idea what he wants out of our relationship, but I’m leaning towards just sex. He says things like “I’m not looking to remarry, but I don’t want to just hook up with someone and waste my time;” but I feel like he only hooks up with me, so am I a waste of his time? I feel like I deserve more but that I cheated myself out of it by sleeping with him so early on and making comments about being friends with benefits. Oh, we also text every day throughout the day and at night, so whatever it is I have going on with him it’s making it where I have no interest in pursuing anyone else because I’m wrapped up in him and wondering if we have a future together. I honestly don’t think he wants that, but I need an unbiased ear to give me the hard truth. — More than a Friend
You’re 36, not 16, and if you want to know if a guy “likes” you, the best way to find out isn’t by analyzing his behavior and the things he says — or worse, polling random people on the internet, which is kind of what you’re doing here — but having a real grownup conversation with him. I know you dread the “what are we?” talk, but what’s worse: the risk of rejection — because, come on, that’s what you’re really afraid of here, or the risk of losing this guy to someone who makes her intention much clearer than you have? If all you wanted was a “friend with benefits,” I doubt that as a sexually adventurous woman, you’d have much trouble finding that with someone else. So stop kidding yourself that you’re afraid you’ll lose that by opening up about how you really feel. What you truly want here is a relationship — an honest, open, adult relationship. And you aren’t going to get that by acting like a timid teenager who’s afraid to get her feelings hurt.
You wanna know where you stand with this guy? Sit him down and say, “You know how I said I thought you made a great “friend with benefits”? Well, I think I said that as a way to protect myself in case that was all you were interested in being. I wanted you to know I was open to that and OK with it. But as we spend more time together, I’m realizing that my feelings for you are developing into something a little deeper, and I’m wondering if yours are too.” Yes, you’ll be putting yourself on the line by asking this. You will risk having your ego and your feelings hurt. But if you don’t find out now where you stand, and you continue sleeping with this man you’ve got feelings for, and you continue analyzing his behavior, looking for signs that he has feelings for you, all the while shutting out any other potential mate because you’re solely focused on this one man, then he isn’t the only person you’ll be screwing in the long run. You run the risk of being deeply hurt if/when this FWB thing runs its course and he moves on to a woman who has made herself open — and yes, vulnerable — to him in more ways than one. If you don’t want to lose this man, you have to open up. And if you can’t do that, then you aren’t ready to be in a mature relationship, end of story.