I’ll tell mine (it’s more like my 23rd most embarassing moment):
I was dating this woman and I was going to meet her mother for the first time. My girlfriend and her friends had all scared me with stories of how much of a ‘dragon lady’ she was. In short, there was very little chance she would like me and approve of the relationship. Her family is Jewish and wealthy and plugged into the upper levels of Washington DC life and I’m none of those things. The first time I met her was when my girlfriedn and I were going on a trip to the beach for a week, so it added to my anxiety (what with the understood intimacy and all). Y’all should know I’m a goofy guy, and get clumsy when I’m nervous.
I was in the living room waiting for the mom to come in. When she did, I happened to be scratching my cheek and when I went to shake her hand, I did this spastic flailing of my hand, managed to hook my eyeglasses with my thumb, fling them across the room, and hit mom in the face. One of my lenses then promptly popped out and rolled under the sofa.
I got on my knees to get the lens, and while still on my knees trying to fit the lens back in the frame I looked up and mom was still standing, poised with her hand out to shake my hand. She looked at me and asked, “are you alright young man?”
That was probably 7 years ago and I still shudder when I think of it.