This is similar to the “most embarrassing moments” buts its things you did that hurt an innocent bystander’s feelings accidentally.
like asking “how they hanging?” to a guy that was castrated but you didn’t know it.
or “what’s eating you?” to a guy with cancer.
Here is one I will never forget:
a coworker found out I was going to a dr for TMJ (a jaw problem) and she had just had surgery to repair her jaw. I was considering the same surgery. Her face was swollen and out of balance (one side was bigger than the other). well as time went by I kept mentioning how it looked better but still was off. well after a year I mentioned it to someone else who said “no her face was disfigured like that before the surgery”. well I didnt bring that up again! I always wondered how she took my constant questions without saying “look stupid thats just the way my face is”
I was back in my hometown, visiting a friend who is married with two kids, one of whom is a six year-old who was the ring bearer in my wedding. Anyway, his mom is taking him up to bed when he says to me “I’ll see ya next week - we’re going to St. Louis,” which is where I live now, and is also his grandparents’ hometown. I say “Oh, are you coming down to see your Grandpa and Grandma?”
He replies immediately and straight-faced, “Not Grandpa, he died last month. Just Grandma.” And off to bed he went. But I could tell that his mom was about to lose it, and she ended up crashing early too, with muffled sobs coming from the bedroom.
I had been away on business when the Grandfather died and didn’t know a thing about it. I apologized a million times to my friend and his wife that day and the next, and while they were understanding, I just felt terrible.