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What is the most you ever lost in a bet or gamble ?

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hunkalove · 61-69, M
A hundred dollars. Twice.
Madgirl · 26-30, F
@hunkalove what did you gamble ?
hunkalove · 61-69, M
@Madgirl I was in college and had my first ever $100 bill and I told a friend I would give it to him if he could tell me the time on the clock on the back. He instantly told me.

And one year at the beginning of football season I bet an idiot I worked with $100 the Broncos wouldn't go to the Super Bowl. Easy money. I should have bet they wouldn't win the Super Bowl because they did go to the Super Bowl, where they suffered a humiliating defeat.