The Adventures of the Boi Wonder: Shy, Single and Trans
May we present, for your reading pleasure, the third installment of Levi’s new series: “The Adventures of the Boi Wonder”

Photo by Bogotron
âYou wonât talk, wonât look, wonât think of me
Iâm the epitome of public enemy
Why you wanna go and do me like that?
Come down on the street and dance with meâ
—Weezer âEl Scorchoâ
Okay, this may not exactly be the most appealing thing to admit, but Iâve been terminally single for over a year and a half, as well as really quite romantically and sexually inexperienced. I have changed a lot since that brief relationship (which also happened to be my first), and figured out much about myself and people, some of it good, some of it plunging me further towards total misanthropy. But close to year ago, I realized it would be nice to try to hopefully find someone I could date/get into a relationship with.
But Iâm quite hesitant to âget into the game.”
There is the initial issue of my semi-well-known and pretty apparent social awkwardness, but what makes me the most nervous is figuring out how to approach the issue of me being a rather non-âpassingâ transguy. Â As if I needed another potentially hindering factor to make my love life (well, complete lack of one) harder.
I am quite shy when I first meet people, am terrible at approaching people in person, and tend not to put myself out there. Large groups make me really nervous, and I donât drink or party (but I do like smallish concerts, intimate gatherings, and TNG events that catch my eye). I am not opposed to internet dating, but I find all the waiting and rejections very frustrating and, honestly, depressing. Not to mention trying to reconcile the fact that you can only select âManâ or âWomanâ as your gender and seek out only âMenâ or âWomen.â  And letâs not even get into the fact that those sites arenât cheap.
Yes, I have heard of trans and trans-friendly dating sites, but I am slightly wary. I have heard the rumblings and rumors of trans-fetishists (sometimes referred to unkindly as âtrannychasersâ) frequenting them, and while I have no problem with people interested in that, I want personality and mutual interests foremost in a relationship. Not sex. Even thinking about how I might deal with a real sexual situation sets off all my various neuroses and my Woody Allen tendencies kick into high gear. Right now, Iâm not even completely sure how to react to the idea of someone thinking I am cute.
Another problem plaguing me about the dating situation: Is there a specific timeline to telling a romantic interest/person you are dating that you are trans? When you meet them? On the first date? On the third? Right before sleeping with them? And what if they freak out? What if they donât really know how to get over that fact?
I shall willingly admit to you all that I grow increasingly obsessed with the concept of âpassingâ and being able to âpassâ. When it comes down to it, in my extremely inexperienced, but highly observant opinion, if you do âpassâ well there is a MUCH higher likelihood that you will be approached as your non-birth-assigned gender – the optimal goal and victory (to me, at least).
If you donât pass, well⌠it can suck, to say the least. Not to mention it can be confusing and dangerous when it comes to things such as restrooms. To me, there is little more disheartening than someone really attractive coming up and saying, âI saw you standing over here and thought to myself, âThatâs a really, really fine GIRL.” Cue instant self-esteem deflation. I know I donât âpassâ as male very well; at my best I come off like someoneâs middle school kid brother (complete with ADHD tendencies!). Thatâs not exactly sexy.
In truth, thinking about everything that could come up while trying to date just gives me very little hope and one of my stress-induced headaches. Yet I still fixate on it, because beneath all my pessimism there is still a person who wants to be loved and desired.
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You complain about dating sites only offering “men” and “women” options, but then relegate people who might be into trans folks as “fetishists” and “only about sex”. Bit of a double standard? While certainly there are people who fetishise trans people, you do yourself and other trans people a disservice by assuming that the only reason someone might be attracted specifically to trans folks (just like some people are attracted to cis men, or to cis women) is because they fetishise us. Obviously, you are free to date or not date such individuals as you choose, but you might want to consider more carefully before painting them all with the same brush.
Also, while passing can be very important to your self-confidence, it makes the question of when to out yourself that much more critical. To me, the prospect of having someone express interest and then reject me when they find out I’m trans is just as, if not more, invalidating than not passing in the first place. I’ve frequently considered getting a shirt or something identifying me as trans, so I can avoid wasting everyone’s time.
Actually, I don’t consider everyone who is interested in transfolks to be fetishists. I recognize that there is a very distinct difference; hell, I haven’t ruled out trans and trans-friendly dating sites, I really just want to make sure that the site focuses on my particular wants…Same as any other dating site.
I apologize if it came off in an offensive manner.
I wasn’t offended, but thank you for clarifying. A lot of trans people do seem to think all “chasers” (for want of a better, commonly known term) are by definition fetishists, as if trans bodies cannot be attractive for what they are, as opposed to always comparing them to cis bodies.
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