Hmm, I've done a lot of silly things during my transition and I'm sure there will be plenty more silliness as time goes on.
One thing that happens to me a lot is taking more time to decide what I'm gonna wear to go shopping than the time it actually takes to finish the shopping trip, then regretting that I wore high heels. Or making sure that I'm passable and looking good when I'm taking out the trash because I might meet a neighbor during that minute I'm outside my apartment.
At one time I apologized to a woman for almost bumping into her but then it turned out that I was a little lost, turned the wrong way at the top of the stairs in a hotel and I almost bumped into a wall, covered with a big mirror and I didn't recognize myself in the mirror. I felt quite silly after that but I was also happy that I passed in my own eyes