My scariest moment was when I came out fully to my wife.
I told her, we talked and talked and cried and cried. Then she was going to a function for her company. It was employees only so I told her I was going to dress fully for her and I would be there when she got home. I was shaking so bad I could barely do my makeup or get dressed. I was ready an hour before she got home and couldn't sit still.
Then the door opened and she saw me for the first time.
The next scariest was my first outing to a mall. It was much easier being among hundreds than it was just being with my wife that first time.