What is the most inappropriate interaction you have had with a waitress?

I had a job at 15 working as a dishwasher in a crappy bowling alley/restaurant/banquet hall.

One of the waitresses was pretty young compared to the others working there —older than me by a couple of years but not much more. For amusement she often messed with the kitchen help because she was very pretty, very lively, her uniform was tailored more than the other waitresses, and she had a wicked sense of humor (much appreciated when one is working in dirty dishes all evening).

One evening she came into the kitchen, put her buss bin down on the dishwashing counter and asked us if we (me and another guy) could help her clean something. Without looking up I said “yeah, give me a sec.”

I walked around from behind the counter separating us and she blocked the space and showed me where ketchup splashed her blouse on her left breast slightly above the dart.

I don’t recall saying anything other than “uh” but do remember getting a bit faint and her smiling like a cat with a canary. My expression made her laugh. She kept laughing as she took care of it herself, and then my buddy slapped me on the back of my head and said something like “dumbass.”

She got me good. I always kept my guard up with her after that.