I've read all the comments up to #69. The only other possibility and it may be a long shot is he was an off duty police officer approaching you to see if you were going to solicit him for sex....prostitution bust.
I'm actually going with making you feel comfortable out and about as either a cross dresser or a transwoman. It may very well be he has a brother, cousin or close friend you is a cross dresser or a transwoman who feels awkward or insecure when out and about. Or, even a sister who is a transman. I don't think a totally straight guy would show such an interest with his buddies so close. If you were so close to be within ear shot of their conversation, and, did not hear joking or condescending words espoused, I think he was just being friendly. Maybe I'm being a little judgmental, but, I think you're going to run into more refined people at a wine bar than the local neighborhood beer hall.
I think most men and women looking to "hook up" make it really obvious real quick.
