Wager jokes

I bet my friend $5 that he would die drowning.

A depressing but satisfying victory.

Why did Al Qaeda lose $100 on a bet?

They bet $100 that they wouldn't crash when they went through the Twin Towers.

Ukraine (🇺🇦) vs Russia (🇷🇺), place your bets!

I bet Steven Hawking $100 if he could catch me.

As soon as he said yes, I climbed up the stairs.

Women are like blackjack. I’m trying for 21, but I always hit on 14.

I saw a fortune teller the other day. She told me I would come into some money.

Last night, I fucked a chick named Penny. What are the odds?

Two deer walk out of a gay bar. One of them turns to the other and says, "I can't believe I blew forty bucks in there."

I bet a disabled kid on a wheelchair that if he could catch me, I'd give him 1000 dollars. He said deal, and I went upstairs.