when I was dating I would let the girl know on the second date that I was a cross dresser. If it was a deal breaker, it was far better to let them know early on. It would be disastrous to wait for a couple of years or after we get married. I need my SO to know who I am and accept me as much as I accept them. My SO and I have been together for over three years now. She loves spending time with my Amy side. She will buy me clothes and encourages me in ways that I never thought anyone would. She has even said that if I decide to transition one day, that she would still love me all the same. It really does help to be honest up front. You don't have to hide, and its far less embarrassing than letting her find out on her own or years down the road.