Many people don't know what to talking a about when dting with a transgender woman or a crossdresser for the first time. You should remember that never talk about your past relationship.
Dating for everyone is a new start, including transgender women and crossdressers. They want to meet new people and start a new relationship. If you keep talking about your past relationship in your first trans dating, I can say that it is your last dating. You can choose some interesting topics to talk about, such as common habits, current affairs, sports and etc..