Thank you everyone for the comments! It did go very well on Saturday, in fact we probably only talked about it a few minutes since it really didn't come as a surprise to her (we talked longer about "Star Trek," having not previously known of each other's love of the franchise).
The more interesting part of the conversation to me ended up being about dating. I haven't dated anyone in quite awhile, but feel more motivated and more confident to pursue that area of my life now that I'm starting to be more honest with myself about who I am. Since I was trying to be something else, obviously the people I tried to date weren't really right for me - hopefully now I can do a better job of it
Eve, I agree with your prediction about my wardrobe - the only things I've purchased recently are women's clothing, the only thing that currently keeps me from scrapping everything else is money. But I'll be replacing everything over time!