I think that's a huge problem with a lot of transpersons is that they either go through a second adolescence or really had the breaks put on growing up and when they wake up they are pretty far behind their peers so it would help to come up with a strategy to try to bridge that gap. You'll be up against - and dating is competition - with guys who, regardless of how 'male' anyone looks, are going to come across as much more mature (and chicks dig mature, guys' not so much) and stable and secure. They have been out on their own for a decade or so, have a household, if not a house, and lots of experience. It takes a few mis-steps along the way to get it right, I went through three GFs before I learned a very basic rule about gifts like: Don't buy her anything that plugs in. Really, she doesn't think that a waffle iron is a set up for hot Valentines Day sex. Also you don't have that old boys network to run all that info through. I would have given out five or six more waffle irons had a buddy not set me straight on that. So you should try to find one/create one somehow. After all, few things in the world are as complex as a relationship with a straight women. And the older the person is, the more the security deal weighs heavy on their mind. Living an artsy-fartsy boho life of milk crate furniture, Ramen noodles and jug wine is pretty romantic at 19, at 29, not so much. I think the older people get, the less the trans thing might matter, but the more the rest of that other stuff, security, maturity and independence do.
Point is, lot more to all of this than a couple of shots of T.