Was 4 or 5 years old in kindergarden, had some song and dance thing where we all stood in a circle, several people got to dress up and act out their roles. Did not know the difference between a prince and princess so I kept insisting that I wanted to be the princess(it was the last role left and I never got picked for anything), instead of the teachers informing me that's a role meant for girls they handed me the dress and I got in it realising I had fucked up. Spent the whole time crying while everyone was singing or laughing at me. I learned the difference between the two after that, fun times.
There have been 16 items by MichaelTheCrow (Search limited from 20-August 18)