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2.
A box of chocolates arranged in random order. They are usually bought on Valentines in a box the shape of a heart. There are several pieces of chocolate that all taste different. When you take one chocolate and eat it, you have no idea which ones are good or nasty so you gamble on which chocolate would be the good one. So before you even touch one of them, its going to be a big surprise. If you pick one thats so nasty that you have to spit it out, you lose.
I just got some gamble chocolate and unfortunately, I bit into the one with toothpaste.
by tatomuck1 April 11, 2009
 
1.
A term that desribes assorted chocolates. One takes a gamble when they take a random piece (a gamble chocolate) from a box of assorted chocolates because the candy could be either delicious or disgusting. The term also serves as an alternative to "assorted chocolates".

Etymology: The term is used in comedian Jim Gaffigan's bit about Valentine's day.
I tried a piece from the box of gamble chocolates I got for Valentine's Day. I don't know why I even bother with these because every one tastes like it was filled with toothpaste.
by improviduto January 29, 2006