One of the first things a guy needs to work out is at what level of transitioning does someone you date need to be at. Personally my first date was with a girl who had no surgery. It was a real shock as I had no idea until we got back to her place. Like many guys I tried to have an open mind and after a while it didn't seem so strange. There are some guys out there who won't date someone without breasts for example, so it is best to be sure what you will be comfortable with before making any arrangements.
Transwomen are often quite insecure as they have had to deal with a lot of personal issues within themselves and from the outside world. So taking extra care to consider their feelings will be appreciated. The best compliment you can give them is to treat them like a real woman. Be proud when in public, even if the situation makes you nervous at first.
When it comes to finding someone to meet you will probably have just two options if you live in Europe of the USA. Firstly you can go to a bar in a gay friendly area where transwomen hang out. I have found this to be a bad option as many will not actually be 'full time' and these places are often rather seedy. The second option is to look online. There isn't a large selection of transgender dating sites but that isn't such a bad thing. It is easier to pick a site and then get going. TS Dating Guide reviews the different options available.
If you are nervous at first don't force things, she will probably understand if you want to take things slow or meet in private initially. The most important tip when starting a relationship is to be as honest as possible. It sets the tone and both parties will feel more at ease. My long term relationship was started on an almost 'buddy' vibe. We were both not trying too hard to impress one another and it felt like there were no secrets. In the long run this has proven to be a great foundation.
