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The three days before and the three days after your female companion, either former or present, is supposed to start her period. It is referred to as worrisome because during this time period, if she does not begin her period, then she is pregnant with your unwanted child and you are now screwed.
Jim: "Jill is suppose to start her period in three days."

Fred: "ahhh. The beginning of the worrisome week!"
by 4pm February 10, 2011
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