look up any word, like ratchet:
 
1.
Pulling your ball-sac over your dick so you look like you have a vagina. After viewing this in the mirror you begin to cry.
Riley just played the crying game.
by Tribe11 April 13, 2011
 
2.
(n.) Sick ass movie about an IRA man feeling guilty for a British soldier he allowed to die and comforting his girlfriend. However, when Fergus and Dill are getting it on...watch the movie.
Mayor Quimby: The chick in the crying game is really a man


Crowd: boo!


Mayor Quimby: I mean...man, was that a good movie

Crowd: yay!
by Gumba Gumba May 25, 2004
 
3.
To beat off and cry while doing it.
Damn...all porn is blocked in the middle east. When I find a site that goes thru all I can do is watch the 10 second preview and play the crying game.
by Cock Jamison April 22, 2011
 
4.
When you go on a management retreat and your CEO breaks down crying like a little girl because when he was a young man, his blue-collar parents wouldn't let him spend their hard-earned cash to major in music and be an opera singer.
"Can you believe the crying game we just had to sit through?"

or

"I wonder if this is going to be another episode of "the crying game" because his parents don't love him."
by TomT February 01, 2006