I feel an extreme anxiety about relationships. And this is an understatement. Every time I meet a cute girl and I hit it off with her, a whole stream of questions plagues my mind: Does she like me? Or does she just like talking to people? Is she expecting me to do something? Is she a lesbian? (For a mainly heterosexual guy who hangs out in the queer community a lot, the last question is important—perhaps the most important.) And then I end up not doing anything because I’m too nervous, and before I know it, once more I have permanently landed myself in the dreaded friend zone.

For me, my insecurity lies in the fact that I simply haven’t lived the male social experience for that long. While the boys learned how to talk to girls and the girls learned how to talk to boys, I just stood there from the outside looking in, watching it all play out in front of me. But I was never allowed to try it out myself, never allowed to enter this sexual discourse between boys and girls. So I simply never learned. It wasn’t until two years ago that I figured stuff out and entered this whole dating scene. But having a bio-guy’s usual 20 years of experience against my two means that there’s a lot of catching up to do.

There’s this whole idea that I have to initiate, that I have to take charge, that I have to be the one asking for dates. As much as I would like to do those things, this isn’t something I inherently learned as a kid. I never grew up as a boy, so I never learned how to act around girls as a guy. I knew how to act around girls as me, but sometimes I feel that acting like me isn’t going to get me a date. Being a man is still something that I’ve been getting used to. From years of watching, I would know right away if one person was hitting on someone else. But I’m completely oblivious when a girl hits on me, something that causes my friends moments of both embarrassment and amusement.

But at the same time, I don’t want to go off and experiment and see for myself. I don’t want to make a girl regret what she did the night before because I decided to fool around a bit. I’ve had female friends who have told me about how they felt like guys took advantage of them at parties while they were drunk. And I don’t want to be “that guy.” I would hate myself if I did that to someone.

There’s also this extreme anxiety about not being “manly” enough. As I wrote about before, I’m not exactly the most masculine guy, and I sometimes get labeled as gay because of it. In fact, there are some lesbians in the queer community that are more masculine than I am. I like being myself and bending the gender norms ever so slightly. However, I don’t think that’s going to get me a girl. Not to mention that I never think a girl would want someone like me. I know it’s kind of stupid, but there’s a thought in the back of my mind that I’m defective because I can’t give anyone kids or anything, and they would have to put up with the possible crap they’d get for having a boyfriend who’s trans, especially from family members. And I don’t want to do that to a girl who probably just wants a normal life with a normal boyfriend. I understand that what I’m feeling is also common with other guys, who feel awkward and inadequate. Mine is just a different anxiety, and one I hope resonates with a lot of other guys.

What is my view on relationships then? I guess you could say that I’m horribly old-fashioned—f I’m the sort of guy who likes asking a girl out, going on a couple dates, taking it at her pace. I don’t plan on having sex with a girl until I am in a committed relationship with her. I feel like that’s the right thing to do. But part of me wonders if I should let go of this whole idealistic paradigm, especially in the context of this hook-up-focused college environment and the fact that I’m not as experienced as even some of my freshmen—but I wouldn’t have it any other way. I’m hoping one day it will pay off. Maybe it will, maybe it won’t. I guess we’ll see.

Give Cristopher some dating advice so he stops failing at life. E-mail him at [email protected].