My most embarrassing analog moment... there are just so many of them.
The funny ones all involve setting my hair on fire. I'm probably too old for it, but I usually have long hair because I'm too lazy to maintain a nice haircut for very long. Every once in a while, I'd end up going into the salon a for a bob or a shag (not the british sort of shag, the seventies hairstyle sort of shag) or something because I'd try to light my cigarette in the wind and burn one side a bit more than the other. In high school, I actually shaved half my head for this reason and called it new wave/punk/alternative.
The most humiliating ones aren't funny to me, but I'll share them in the interest of honesty.
Whenever my kids would walk up to me for a spontaneous hug or a kiss while I was smoking, I'd have to back away in horror so I wouldn't blow smoke on them, and it would hurt their feelings. When my oldest bought me a beautiful, expensive fluffy robe for x-mas, and I accidentally burned a nasty hole in it. When my youngest came home from school crying one day because someone had refused to sit by him on the bus, saying he smelled like cigarettes.
And then there was the last cig I had before finally deciding to get off this crazy train for good- I was on my way to the emergency room, doubled over in so much pain I could barely speak, and had to have one more cigarette before we got there. My face was almost in the ashtray, and I was blacking out, and my middle child held the cig for me so I could have just one more cigarette, because I knew I couldn't smoke in the hospital.
That was embarrassing.