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To set one up for failure or embarassment either intentionally or unintentionally
I set my dude up for the wooskie when I gave him the shaken up can of beer when he was wearing his nice wife beater.

My best friend set me up for the wooskie when he set me up on a date with a woman with three inch long nails knowing I liked my prostate massaged.
by CD's Nutz August 17, 2009
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