(This might be an oldie, but I got a grin out of it when I remembered it.)
A fellow sitting in a bar noticed that the bartender was staring at him. Each time he'd look away and finally came over, a bit embarrassed.
"I'm sorry sir, let me buy you a drink."
He accepted and accepted the subsequent two apologies and drinks.
"Really sir, surely you know this, you must be the ugliest man I've ever seen and I can't keep from staring at you."
"You think I'm pretty ugly? That ugly? Are you a betting man?"
"Well it depends on what I'm betting on, but I do bet from time to time."
"Do you see that cute little blonde sitting over there with that young man? I've got $50 that says I'll go over there and pick her up."
The bartender accepted immediately, plopping his $50 on the bar next to the customer's who had started to approach the table but wheeled and came back.
"I've got another $50 that says that I'll pat her on the fanny as we walk by you and she'll give you a wink."
The bartender quickly added another $50 and shortly after that the guy walked out with the blonde on his arm and as they went by he patted her on the fanny, she winked at the bartender, and the guy collected the win.
Astonished the bartender went over to the table where she had been sitting to quiz the young man she had been with, he was sitting there with a stunned look on his face.
"My gosh fellow, I'm amazed! What did he do? What did he say?"
"Nothing! Nothing at all! He just stood there; licking his eyebrows..."
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