Top Definition
A Jimmy Surprise is when an innocent look into your buddy's room through a fire-escape with unusually good clarity results in the unexpected viewing of your friend masturbating buck-ass naked on his bed to Sportscenter.
I thought my roommate was asleep and I could run in real quick to borrow his stapler, but when I opened the door I was greeted by a Jimmy Surprise.
by Phil Ayshio December 09, 2006

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