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Usually asked at the end of a long, boring and drawn out story to give it a more interesting and rewarding ending. Sarcastic in nature. Alternately used in place of "and then I found five dollars" because finding twenty dollars is rewarding enough while still being in the parameters of seeming like you really found something. Saying "and then I found one hundred dollars" sounds too fake and thus brings down the sarcastic tone you're trying to get across to the person because their story was so boring. Finding anything less than twenty dollars isn't really that rewarding.
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