Dressy Bessy

...So, I guess I failed to mention that I've been going on some dates lately. The funny part is that the whole point of this blog was to write about all of these experiences in hopes of illuminating some of the differences I am fielding 'before and after' my transition. But... Now that I am actually getting out there and dating, there is this weird guilt that I feel about making any referential points that someone might take personally, even if it's not a complaint. (This is no fun!)

Where do I begin when there is so much to discuss? (This has been part of my radio silence, honestly. When a blog is public, everyone has access to the shit I discuss. Even potentially the people that I hope never stumble upon this little blog of mine might someday find their descriptions on the monitor. How do I proceed?)

I will start with the easy part: my clothes. While preparing for my aforementioned dates, my gaggle of female friends all jumped in to ask me what I was wearing. Generally, this is a common question amongst 'ladies,' with the appropriate responses being: "Oooooh, perfect!" Or, "You know what I like that you should wear?" But with me, it's a little more complicated.

Not only were my friends curious about which 'look' I was going to be displaying, but they were also a tad bit concerned for me. "Um, so I think that soft, broken in, slim fitted salmon colored polo shirt that shows off your newly developed broad shoulders, and your various arm tattoos *might* be one option. I guess I'm just a little nervous that you basically wearing a bold pink polo shirt to show off your muscles might make you seem a little, um... Well – gay."

Riiiiiiiight.

The funniest part was that I had one date on Thursday, and picked out what I thought was the perfect outfit. A vintage (perfectly worn in) Christian Dior navy blue polo shirt, with a thin kelly green stripe, nice dark barely whiskered jeans, my favorite vintage naturally distressed weathered belt, and these great oiled mid toned brown leather side zippered boots with a pointed toe. (I swear it looked less gay than the very description I just penned for you. I promise.) And the polo was a smidge oversized on my frame, which I think added to the straight dude affect, rather than my fitted shirts, that scream 'flamer.' Heh.

But then I had a date for Sunday, and the problem started all over again. With so many of my clothing options apparently being barred by this impromptu gay-proofing fashion brigade, I had to think quickly. Many phone calls were exchanged, followed by a series of self portraits that I took on my cell phone, and quickly emailed to said friends to get their approval before I left for my date. (A dark chocolate brown half zip sweater, with a black t shirt, dark jeans, and dark boots. When I walked in, my date looked me up and down when she thought I wasn't looking. Funny. Was that a good or a bad sign? I nearly peed myself, hoping that my perfectly coiffed hair, and my smart fashion sense wasn't going to back fire on me.)

I kept doubting myself, wondering, "Is this a date, or does she think I'm her new gay best friend?" All the more reason to somehow *prove* that I like women. Huh. How does one do that without coming across as a misogynist, ironically? "You know what I like? Chicks with big..." Ugh, no – I knew enough to side step that disaster. Luckily a few other topics came up over dinner to assert my love of the feminine form (wait, that came out wrong...) You know what I mean.

My date asked me about some of the women I've dated in the past, and I was relieved that she definitively said "women." Siiiiiiigh ~ Phew! I passed. Not only as a straight guy, but apparently one that might have had past experiences dating women. Double phew! I got a little fidgety wondering what exactly to say and fess up about my past life. (Not in the Shirley MacLaine sort of way, but my chronological dating experiences.) I didn't know how to open up that can of worms about my past without everything spilling out. "You know what I like? Chicks with big... Did I mention that I used to be a chick? No? Hmmm. It must have slipped my mind." (I wasn't sure if this woman had read my blog before meeting up with me, so I have no clue what she knows or doesn't know about me. Um, awkward!)

The funniest part to me was that midway through dinner I noticed that the majority of people around us where all queer. Then it dawned on me that the huge queer rights rally in DC that day had ended right before we were meeting up for our date. I stupidly chose a restaurant downtown, in the center of the queer hubbub. Smoove, Will! Nice!

Yes, one of my first "straight" dates with a stranger post transition, and I'm the fucking dumb ass that picks National Coming Out Day to meet up at a restaurant mid queer parade route. WTF? Leave it to me. At least I looked good. Good and straight. Well...