The situation that always got me was getting carded for alcohol or to get into clubs/bars. Let's face it, folks, I'm middle aged and kinda look it. There is no planet on which I'm 20, not even Mars (I'd be like 24 there

). I never bought that whole "well, you look kinda young" thing for one second. We all know that you wanted to see if I was really more like a "Jack" than a Jill.
What I did before I made my name and gender legal was this- I put an expired license in front of the then-current one where I was 23 in the picture, clean-shaven with long hair and quite frankly looked female. Then I took a fortune cookie fortune that obscured the name and gender marker, leaving the DOB visible. If I was ever asked to take it out, I refused, claiming I already proved my age and that my name and address were irrelevant and none of their damned business. It worked every time.
Another awkward moment was when I tried to use my debit card at a wine shop that I've frequented for years. My bank reissued the card with my new name but kept the numbers the same. We ran the card, but it was red-flagged as fraudulent because the name didn't match the numbers that were on file. I gave them my ID, shrugged my shoulders and told them that I've never had this issue before.
"I'm sorry, Ma'am. I'm going to have to hold on to this while my supervisor checks out this situation."
"I don't get it. There's certainly no fraud going here."
"The thing is that we happen to have a regular customer who happens to have your same numbers and street address. This is way fishy"
"You mean Gregory <lastname>?
"Do you know him?"
"That was me before I transitioned to female."
The look on his face was priceless. I don't think he'd ever encountered a transsexual before.