“I have a crush on my casual hookup”

There is this guy right now, and we have this arrangement. I hooked up with him last year during his senior year, but he still comes back to visit my college all the time. And when he does, we always hook up.

He has this habit of not reaching out to me unless he thinks he’s coming back to school. Then he reaches out to me like two weeks out, we chat, and then inevitably hook up when he does come back. I don’t know what the arrangement is, nor if I’m even close enough with him to pry about it, but I’m graduating very soon and moving near him.

I like him, I think, and really would like to try to maybe have something with him. But I have no idea how to even approach the subject without seeming clingy, or if I should even try at all. He insists that he genuinely cares about me, but I feel like he just says this to get sex, because as soon as we hook up, he fades back out for a while, until he thinks he’s going to see me again. I have so many questions and no idea how to ask him about it.

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One thought on ““I have a crush on my casual hookup”

  1. Dennis Hong says:

    If you genuinely like him, then I think you owe it to yourself to at least ask how he feels. And yes, you can definitely do so without seeming clingy. Something like, “So, I really like hooking up with you, and I have to admit that I’m starting to dig you a little. Do you think you’d ever consider something more between us?”

    Something simple and non-confrontational like that. No demands, no ultimatums.

    But here’s the kicker:

    If he says no, or even if he waffles and gives you a vague, non-committal answer, you have to be ready to move on. Because given the way you described the arrangement, I’d say there’s very little chance he’s actually interested in you romantically.

    Because if he were actually into you, he’d want to make an effort to keep in touch.

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