Making money "the hard way" usualy means via anal or rough sex.
"You want to make $14? The hard way?" -- Rodney Dangerfield to Ted Knight's wife, in Caddyshack (1980)
by Publicola June 21, 2006
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How you learn your lessons in life when you never listened to your father.
"That Desmond, he only ever learns the hard way, don't he?"

"He never listened to his father, that's why."
by Colin 100 November 30, 2012
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In Craps making a hard way bet means going for the total of the two dice on doubles. Say you wanted to go for a hard six, the only way to do it is with two threes. It is called the hard way because it is not easy to hit. There are only four hard way combinations: hard 4 (2x2), hard 6 (3x3), hard 8 (4x4), and hard 10 (5x5).
Player bets a "hard way" 4. Roll = 2x2 is a win, anything else, you lose (including 3x1, 1x3).
by Joeseph D Fordaman April 02, 2007
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An impossibility; very hard to achieve. Refers to craps term "the hard way" where two dice must be rolled with matching numbers. EX: 6 the hard way would be 3/3, not 5/1 or 2/4. Therefore, 3 the hard way would be im-fucking-possible.
"Jim's chances of giving mary a cleveland steamer are like 3 the hard way"
by Justin9619 January 18, 2006
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Seven the Hard Way was a Pat Benetar album, and it's a (sort of) reference to the game of craps. "The Hard Way" in craps is rolling doubles - so, Ten the Hard Way is a pair of 5's. (It is twice as hard to get 2 5's as a 4 with a 6). But, you can't roll "Seven the Hard Way" - there's no way to roll doubles and get an odd number!
From the Pat Benetar Fan Club:

"Seven albums in seven years...
Two dice...3½ dots each.
Seven the hard way."
by Firstthingwedo February 23, 2008
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1. A Pat Benatar discography from 1985.
2. Getting seven inches of man meat up a virgin bung.
3. A sexual practice where a woman will do seven guys at once. In the cunt, ass, mouth, one in each hand and one in each ear.
Too bad guys can't do 7 chicks at once. Even if you could use your dick, tounge, both hands and both feet all at the same time you would only have six!
by PeeBee February 21, 2004
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In basketball, a play earning 3 points by scoring a 2 point basket, drawing a foul, and converting on the subsequent free throw. This three points requires more toughness than the three point shot, and so is called "three the hard way."
Dwayne Wade drives to the basket makes the layup and is fouled. He'll shoot a free throw to earn 3 the hard way.
by asdfhj January 20, 2006
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