Date Night

Field Notes In/On Transition

Date Night 

So, the other day, I was feeling particularly pretty, as I am starting to feel a bit more comfortable with doing my makeup. I have got some tips from lady friends, and watched a bunch of videos, as I mentioned in my last post. But there is no teacher like experience... doing the makeup and watching a video are very different. 

On Tuesday, I did myself up I think very nicely, subtle, natural looking, and felt really sexy in my skirt and striped hose. I’ve also found some low heels that are comfortable and cute enough to wear all day at work. Late in my shift an older gentleman (around retirement age, I’m guessing) who I hadn’t seen since well before I started my transition. He was looking at some movies in our staff picks, then came up and rented a documentary on The Beats, and complimented me on my new look, asked me if I would like to go out for dinner, then if I was single, I said yes, to both, without really much thought. 

Getting a compliment from someone obviously attracted to me, made my head swirl a little bit. He was polite, properly gendering me, and not using any sex innuendo, which is usually the kind of compliments many of us Trans ladies (and CIS gendered ladies) receive. He seemed to be genuinely nice. I told him I was busy that night, which I was, playing a game of D&D. I said I could go out on Wednesday, meet me after work at the store.

The most awesome part of the date really was, that he showed up. having given up on internet dating, because of being stood up pretty much every time, I wasn’t expecting him to show. He did. We walked up to the Sushi joint we wanted to hit, but the line-up was huge, and we were both hungry, so we went to a lesser quality (but reasonably priced, and okay taste wise, despite not having any Japanese beer) place down the street. We had a nice conversation over dinner; he said lots of the right things, compliment wise, without seeming to cloying or over eager.

We walked down to my favourite coffee shop and had an after dinner coffee, more chat, then he walked me home. It was a lovely, it was the kind of date I’ve dreamed of having, really, my whole life. He was no George Clooney, mind you, but who is, other than George himself. A nice man, who showed me a nice time. I’m pretty sure we will go out again. That said I’m not looking beyond another date, with him, or anyone. Slow and steady wins the race. It was really awesome to be able to dip my pretty stockinged toes into the world of dating this early in my transition.

Of course, he is someone with a history of “dating Trans,” I don’t expect to be attracting men (or women) who see me as anything other than Trans. Binary living/attraction is of little interest to me.  I’m not expecting to be “stealth” (as in having someone think I am CIS gendered gal,) in terms of attracting folks.  

It is/was a nice milestone for me. It’s beyond what I can really articulate, in terms of feeling like i’m on the right path. I’ve never had anyone ask me out as Josie, at work, nor before as Joe. I never asked anyone else out either, lots of flirting, either way, but only harmless flirting. It’s so amazing to get some attention while coming into my own as Josie. Baby steps? Maybe I’m up to crawling now. Look out when I figure out how to stand up.


  1. Your blogs always make me Smile...:D You smile a lot more too! just an observation


  2. And I am smiling with joy for you. Happy that all went well and crossing all that can be crossed with seriously injuring myself, in hopes that you may experiencce many more nights like this. xoxox love you Barbie


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