1. Traditionally done by Hassidic Jewish people. A special sheet is worn between the man and woman so that no bodily contact except for sex occurs. 2. When you put a blanket over a girl so you don't have to look at her during sex usually because she is ugly.
Yeah I'd fuck your girlfriend, but I'd have to window box her first.
by B.I. Josephs August 14, 2006
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That sexy open space between a hot girl's legs where her legs don't quite touch eachother in the crotch area. Usually seen when wearing a bikini. Originally derived from George Carlin's stand-up comedy when referring to marijuana.
I was surfing on the internet while my bro was watching tv when he said, "Whoa, toledo window box!" which caused me to quickly turn around to see a fine piece of ass.
by trouty42 August 26, 2009
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An expression used to state the feeling of sadness and indifference that one feels at the end of the night while window shopping at a brothel, bordello, or whore house for a prostitute or hooker.
- "After Mike couldn't get that bombshell blonde in the sack, he left the bar for the red light district and found himself deep in the window box blues."

- "I stayed out until 5 in the morning when the window box blues over took me."
by 3s&7s August 13, 2011
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