A gentlemen shot is referred to a shot in beer pong where you are standing with your hip faced toward the cups and the ball is thrown behind the back. If the shot is made (highly rare) the team must drink two cups instead of one. You must say gentlemen shot before you shoot.
"Last night we were playing beer pong and I made a gentlemen shot and we won the game!"
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Any indoor or outdoor activity that exhibits an extreme amount of rules and etiquettes which at first seem to be counterintuitive but in reality, the only way it can be.
Golf is often considered a gentlemen's game - you've gotta have all these irons, drivers, and hybrids with all these accessories and your grass has to be so and so... all to see who can hit a ball into the hole first.
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A woman's vagina/private area.
Uh-oh, crazy Britney Spears showed her "gentlemen greeter" again when she was getting out of her car at Starbucks.
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Basically its a classy way of saying you're getting a booty call.
Oh no you can't come over, I have a gentlemen caller coming by later
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An whiskey thats cheap, but tastes good as hell.
I had five shots of Kentucky Gentlemen last night and was set for a while.
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Joesph: Guess where this guy had to get the word "Mini" tattooed to win a free Mini Cooper from this German radio station?
Henry: The Plums, chest,....?
Joesph: No, his Gentlemen's Sausage. Not the first word you'd want down there.
Henry: I'd put Gigantic down there in really small letters so you'd think it's to scale
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