What was the worst "why the f*** did I say that" moment?

Ugh so I was walking down the street in Vegas with like $3,000 cash on me, all in hundreds m, after a good poker session and it's 3:00 in the morning. A white homeless guy comes up to me and asks me for change and I say no, smallest bill I had was between $20 and $100. He then starts to scream at me and I walk away. About half a block later, an African American hotel employee cuts me off in the middle of the sidewalk. He doesn't say anything, he just steps in front of me. I try to kind of put on a juke move to go by him but he cuts me off and informs me the sidewalk is closed. He had no uniform to indicate he worked for the hotel so I had assumed he was also a homeless guy asking for money and I was a little rattled.

After the juke move I pulled, I didn't want him to think I thought he was a mugger or something so I said "oh sorry I thought you were asking for money". Which I then realized doesn't make me look any less racist. I tried to explain the context and why I was a little rattled but I think the damage was done.

Thinking back on that makes me cringe so hard.

/r/AskReddit Thread