Online Dating and Me

[This post is a follow up to last week's Missed Connections. It is also the one year anniversary of this self deprecating piece of trash. Enjoy them, if you'd like, before reading this garbage. Or just read this one; I don't know how much time you have before your boss comes back.]


I am seldomly a practicing homosexual. The past decade, I'd say I've tuned my skills 1.25 times a year. It's hard to tell if I'm genuinely disinterested in most guys, lazy, or just content with my current lifestyle; either way, my love life has always lacked total mutual attraction.

As far back as my elementary school years, I can remember that none of the girls I pretended to date were especially into me. They appreciated the attention, but they usually dismissed me as the silly smart kid. It wasn't until high school when I met my first girlfriend that I would become the one giving less than 100% to the relationship. Don't get me wrong; I took her on dates and made up for all the time our separate schools would take away from us. But I was never fully into her. Besides her being a little unbalanced emotionally at the time, I think we all know why it didn't work out between us. Before my junior year was over, I broke up with the girl who messaged me via MySpace.

Two year laters, MySpace would strike again, as a stranger messaged me from what I can recall as the first time. The attention he gave me was very welcome, and before the summer was over I had my first boyfriend. On our second date, I invited him over my mom's house to practice. It was during this session that he revealed that he loved me. I was 19, so I lied and said the same back. A week after, I returned to college and realized he was much more into me than I was into him. Not wanting to string him along, I broke it off with him by revealing how untruthful I had been. It wasn't a clean break, from what I remember, but eventually I turned into enough of a jerk to ward him off.

Since those two relationships, no one else has been interested or crafty enough to trap me into a relationship. Sure, there have been dates and hookups sprinkled between now and then, but nothing that stuck. The closest someone came was a guy from Montreal.

How did I end up talking to a fellow from Montreal, you might ask. Well, the internet is again a wonderful thing, and homosexuals have several apps and websites to choose from. I don't feel like disclosing what kind of website it was, but it wasn't a fetish website. (It was basically a fetish website.) He gave me enough praise and attention to reel me back in after he would start to creep me out and/or become more invested in me than I was him. He kept saying I should move to Montreal to be with him, but I never seriously entertained the thought. I did eventually, however, see him when I traveled to Canada with a group of friends last year. We spent two nice nights together. If I lived in the providence of the French, there's a chance we might have actually started dating. But I knew myself well enough to know long distance wouldn't work. So once again, I activated my jerk factor until he left me alone. (He's currently reaching out to me again. What can I say, attention is ok.)

Hopefully you've noticed the trend, because it took me until last year to figure it out. My pattern seems to be to crush on guys that I don't think I can obtain (straight, in a relationship, out of my league), so I wait for someone to come to me. The problem then becomes that I'm generally uninterested in those attempting to court me. I haven't fully determined why this Venn Diagram doesn't intersect yet, but something tells me I'm a self-saboteur.

Part of me has always thought I'm not ready for a relationship, be it either financially or emotionally. Even though I developed a fairly positive value in my worth, it's still hard for me to see it as a product others would purchase from my merch store. So what is it about me that refuses to sell when someone wants in?

There are most recent tales I can recount from the past few months, but for the sake of time, let's return to my adventure with Puma from last week.

Puma messaged me a couple days after I sent him a message asking how he liked Baltimore in Conservation. His response lacked next to no awkwardness. This must have communicated to my subconscious that he was ready for all of my anxiety, so I revealed how "nervous" I was to the point of sounding like an idiot. We traded messages for about half an hour before things died down because I felt I had sabotaged myself enough. The validation of him responding back to me was enough. Since that interaction last week, I've thought of him on and off, but nothing that warrants me reaching out to him again.

I really wish I could unlock whatever last block that's keeping me from a successful dating career. A psychiatrist would help, but who has money for that? And I always mean to discuss this pattern with friends, but I usually forget about myself as I listen to their weekly recaps. My good friends (and associates), I beg for your help on this one. I don't want to write another piece about how single-but-fine-but not-really I am this time next year. Help me break the cycle. Or just start having kids, so I can distract myself with becoming more of a gay uncle.

Word.