Do I take the risk?

So there’s this girl who I hooked up with once in middle school, and ever since I’ve found her pretty attractive. Throughout high school we’re nice and friendly to each other, but nothing has happened. I don’t want to start anything serious with her, but before I go to college in the fall, I’m interested in hooking up with her again.

Now, the day of my graduation, we were talking, and she was being very open about her sex life. Like, very happy to talk about it. I’m not so experienced myself, and she made it very clear to me, in a casual way, that she gets plenty from this boy toy of hers. They aren’t together, just fuckbuddies. She then had an epiphany and remembered about when we hooked up in middle school. I had never brought it up since it first happened, and I feel like she was faking not remembering it. I had remembered since it happened. So I feel like, if she’s bringing it up, there could be a reason. Long story short, before I left to walk to the grad ceremony, I felt like she was interested and/or leading me on.

Since then, I’ve messaged her asking if she wants to hang out before we leave for school. The first two times were when I had some drinks in Europe, when she didn’t respond. When I got home, I sent another message saying “Hey, how’ve you been lately? It’s been a while. Oh and I’m sober and in America now, so this isn’t some drunk late night message from Europe”. She responded with “Haha thank you for clarifying :)”. We’ve sent a few more messages back and forth, being friendly and all that. Then I said that, if she would be down, I’d like to hang out with her before we leave for school. She said “Yeah! When do you leave to go to school?” and I asked when she leaves to move in.

Now there hasn’t been a response, but I’ve been thinking, if she doesn’t say anything back, do I take the risk and just explain why I’ve been messaging her. Not in a crude and man-slutty way, but just saying something along the lines of “I’m just going to be completely honest. I’ve found you attractive throughout high school and I want to give what we did in middle school another shot”. Again, with more finesse, but you get the idea. I’m just thinking that, since we will be hundreds of miles away from each other, and it’s my last shot, what could go wrong. She either says yes, no, or doesn’t respond, and none of those events would really upset me. I just want to lay it on the line, and be frank, because I feel like I’m beating around the bush and it’s not getting me anywhere. I don’t think she would use it to embarrass me, because she hasn’t told anyone about us getting with each other before (I would probably hear about it through my four years in high school).

Anyway, what do you all think I should do? Risk it? Stop altogether? Help me out here, because while I’ve gotten with a few girls before, and had a few girlfriends, I want to give this a shot but I don’t have any experience with handling this sort of thing through messaging. If it were in person, I’d probably have hooked up with her already or gotten a hard no and not be worrying about it anymore. Please give me any advice you think is important, thanks!

2 thoughts on “Do I take the risk?

  1. resullins says:

    [Ok, I have a few concerns about this question, as the whole thing reeks of a little immaturity. First, where I’m from, middle school runs from about the ages of 10 to 13. That’s entirely too young to be having sex. And if you did, and you’ve been lusting after this woman from afar for 4 years, I assure you that she knows it.

    It also seems to me that all you want is some sex. And you want it with her, for whatever reason. But the more important thing is that you want sex before you leave her and go off to college. Seriously, don’t do that… don’t use her for sex just because you’re curious. I guarantee you that if she felt the same way, you would know it by now. Which means she doesn’t want the same things you do.

    Move on. You have so many adventure awaiting you out in the real world. You need to grow up, and start thinking of women as more than just something for you to experiment sexually with.

  2. Dennis Hong says:

    [Yeah, I think you’re being kind of a tool about this, but hey, at least you’re being honest with yourself.

    I agree with Res and won’t condone this, but I also get the feeling you’re going to do what you want to do, anyway, and you’re asking for validation rather than permission. So, in that case… good luck. 🙂

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