Reading another thread on here about coming out to a new girlfriend, I realized that I'm holding the other end of that stick... I'm generally out, so when I meet someone interesting at a party, they know I am a man in a dress, but when and how do I reveal the man himself? Our general experience is that people who know only one aspect of me are not likely to recognize the other, if we made a lunch date they'd walk right past, and we'd be having the big reveal in public front of the maitre d'.
Happened last week, my wife and I wanted to see more of a couple we had just met, so I texted them a thank you follow up note with a selfie en drab. Seemed to work OK. How do others manage this?