One of the funniest signs for me was when trying to design a VR game with a friend. For some background, it was a first person game where you can play pool remotely with others. With more of an emphasis on the social aspect than the game of pool. Didn't end up getting past the design phase though (yay ADHD).

At some point in our conversation, I brought up player character model - whether you should even have one, what is should look like, etc. I mentioned being able to select or change gender of this model, but he seemed a bit confused by that, and told me it would feel a bit wrong or uncomfortable in VR to look down at yourself and see a different gender. This confused the shit out of me, so I responded something like, "Really? I'd actually prefer looking down and seeing myself as a woman."

It would be another few years before my egg finally cracked.

The funniest sign for me was not realizing why I was so uncomfortable with the changing room for gym class, to the point that I'd run there so I could change before anybody else showed up. Probably got more exercise in that sprint than the rest of the class. XD

„Hey, do you think I could dress up to the point of fooling people into thinking I'm a woman? That would be so funny, I'd love that!“

I had this self insert character in the comics I made (when I was a kid) who was originally supposed to be a girl but progressively kept getting more and more masculine. Soon the character just straight out looked and acted like a dude, but I was like "This character is just masculine in very single sense of the word but is FEEEEEEMALE." Then I found out that trans people were a thing and

"...Oh. It all makes sense now."

Being physically incapable of choosing/making a male character in video games

I really wanted to buy a womens rain coat because people might think im a girl. Because id really like to be seen as a girl by strangers. This was long before I realized, too

Wanting blockers was probably pretty ducking obvious