The one that got my husband happened when he was 36.
He took out-of-town clients to the country/western bar they requested. They all asked girls to dance (hubby was raised in West Texas and is quite good at Western Swing, etc., loves to dance.) As he was walking one girl back to her seat before he rejoined his clients, he casually asked her age. She told him she was 18.
He freaked out. He told me later, "What was I thinking?! I was TWICE her age! I bet she was wondering why some old man was asking her to dance! How embarrassing!!! I will NEVER do that again!"
(Did I assure him that 36 wasn't old?

What do you think?)