Is he really that great, or will I find something out that will make him just all the other guys? If he is that great, will he be interested in little old me? Am I misreading his kindness, and projecting that he is romantically inclined, or does he just wanna be friends?Thoughts we all have at some point. But for me and my 'situation,' I am finally now realizing how much I stumble, even without leaving the starting gate.
Another friend of mine decided that she was going to take matters into her own hands, and actively try to set me up on some blind dates. If you haven't guessed by now, I am a bit wobbly in my shyness upon first meeting, so this seemed like a strike against me already. I went along with the game plan, and did pretty well when surrounded with others in our social circles. I was able to put my listening skills to their test, and asked pretty good questions to prove that I am interested and attentive. But then, the unthinkable happened: I was left to my own devices... The social circles parted ways, and days went by as I churned out dozens of ideas of how to make a reproach for future 'hang outs,' but none seemed to be ideal. Swirling around in the multitude of options I started to find clarity. Not for which date to suggest, but just how much the game has changed for me.
Before I transitioned, I was clearly a female. When meeting a new woman I was interested in, it started off as just being friends, and it was simple. There were no implications that I'd have any other intentions. And as we'd get closer, sometimes feelings would be developing on both sides, seeming confusing for these straight women that never had feelings for a member of their own sex. But even as much as that might have seemed like a set back, often times, they felt close enough to me to put their histories aside, and follow their hearts to be with me. Sometimes for months, sometimes for years – just like any other romantic line up.
I was flattered that these women trusted me enough to immerse themselves in new amorous terrain by dating me. We went from there, talking it out, and being candid about issues as they surfaced. It was at times challenging, as all relationships can hit those bumps in the road, regardless of gender roles.
These relationships were built on a foundation of friendship first, and foremost. I was the trusted confidante, and adoring partner. It was comforting, and seemed to be working fine, as I hadn't spent much time single since I first started dating women when I was 15. Friends of mine joked that I should write a dating guide book for straight men, since I typically had better 'success rates' for dating hott, desirable, feisty straight women than my straight male counterparts. It was like I somehow asserted myself as an alpha-male, even though I was a female wooing these ladies...
So, it goes without saying that when I decided to transition, and look more like a guy, I assumed it would only increase my chances of dating the straight women I had been encountering. Uh-no!
Now that I am seen as a man, the foundation of friendship that formerly started all of my romantic inclinations now appears to be off the table from the get go. When a man talks to a woman, there is an implied, implicit assertion that he is sexually, and (hopefully) romantically interested in this woman. It is an act of pursuit, where the woman then either accepts his advances, if she mutually fancies him, too, or shoots him down out of disinterest in his approach or his appearance. It's a much shorter window of appeal. This new guy either has a chance to try to prove himself, or he's out from the start.
It's SO different.
Before I transitioned, I would have been friends with women for months, and really getting to know them before anything turned more all lovey-dovey. Now, I feel like I have three minutes to not seem like a douche bag, or I'm kicked out of the running. Awesome!
Despite enough people telling me that they think I've turned into a pretty cute guy, that alone doesn't secure my place as a contender. (Sadly, as I've learned the hard way! wah wah wah...) Instead, I need to rock the party the moment I step into a room. Being on the shy end of the spectrum, having enough bravado to woo a complete stranger is still a bit off-putting to me. And I'm not cute enough to have that trump whatever social deficiencies I might have.
It is incriminating to talk to a woman and have her assume that I am hitting on her, even if I'm not. Or if I want to be, but haven't polished off my one liners yet, I'm screwed. And because I am nervous, and don't give off that cocky air of confidence all the time, I think I mistakenly project a meek, timid image that seems disinterested, or even gay. It also doesn't help that I look a lot younger than my age of 34, so women my age don't take me as seriously. Looking young, coupled with the lack of manly bravado has definitely thrown a wrench in my dating statistics. It's so frustrating.
So, if you are one of those women that I awkwardly tried to ask out – now you know why I was so bumbling. And if you have any advice, feel free to send it my way, care of:
"Will-work for dating advice" (scrawled in Sharpie on my cardboard placard, as I weave through cars stopped at red lights near urban centers)
–––> "Sister can you spare a dime, or tell me how the man of your life won your heart???"
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