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The name stems from Russian Roulette, in that two or more people, usually over MSN or similar online chat, go on UD and hit random page, then link the freakiest shit they can find on the interweb.
Tim: Hey, you wanna play Urban Dictionary Roulette later?
Mike: Sure, but as long as we dont have the Alabama Hotpocket shit again.
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A game where you press the “random” button on urban dictionary over and over with your friend(s), and share your findings with eachother.
Urban Dictionary roulette is a great way to kill a couple hours with the boys.
A game wherein a group of people take turns bringing up "Random Words" on urbandictionary.com. If your random word describes a perverse sex act, you're out. Winner is the last one remaining. Can also be played as a drinking game.
We were playing Urban Dictionary Roulette, and it was down to me and Tom - but then I got "Dirty Sanchez" and it was all over.