re: Ever make an insensitive joke about someone

I used to say "jew me down" a lot when in a negotiation. until I started negotiating with actual Jewish people. I never knew.

I told an off color italian joke to Buddy Amoroso when I was around 12. I had no idea how off color it was until I got older.

Edit for clarity: I didn't know they were Italian nor how proud they were of it.

A dude on our football team in high school had this crazy eye that faced off to the side. We had this one hilarious coach who started calling him "Cockeye." The rest of the team started calling him that, and he took it well. It literally became his nickname that he was cool with. One of my buddies called him Cockeye in front of his mom and she looked at him and said "WTF did he just call you?" He had to explain to his mom that it was cool and just a nickname. One of the more uncomfortable situations I've been in.

I exposed myself to some college cheerleaders. That was insensitive of me.

I once asked a woman if she was pregnant. She wasn't.

Have never asked that question since then.

I used to have a job where I worked alone in a little room. One time I opened the door to carry some things out. When I did, I swung the door a little hard and it hit someone. I just automatically said "sorry, didn't see you." It turned out to be this blind guy that worked there. He seemed alright about it. Later that night we walked into me and said the same thing back to me.

Years ago we were at our daughter's ballet recital (5-6 year olds), there were several groups performing before her group started.  So one of these group performances started with this song about cookies. The first girl that entered the stage was quite chubby, actually very chubby kid in tights... So I blurted out a 'Whoa...' because I could not believe that they would select that song... Evidently, a lot of people heard my astonishment... We quit ballet the next year.

I don’t know if any of these top them but I once got in a fight at school with a kid after I said his dad was doing crack and banging prostitutes. We fight and get in trouble at school, etc. Several years later, my parents send me a picture of the kids dad arrested in a prostitution sting with crack. I guess that is why the kid wanted to fight me so bad because it was true.

I also got McDonalds one time with my buddy and when we got our food, I said man they “jewed” me on my fries. My buddy was Jewish. I just said sorry and looked down.