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1.
During the Fall and Winter months people who would normally rather be single or promiscuous find themselves along with the rest of the world desiring to be "Cuffed" or tied down by a serious relationship. The cold weather and prolonged indoor activity causes singles to become lonely and desperate to be cuffed.
Brittany: Why is everyone trying to holla this week like outta no where?

Tiara: You know cuffing season is in full effect right?

Brittany: Oh yeah you right. I know I wont be sleeping alone this weekend.
de Pmack0711 20 septembre 2011
 
2.
the time of year in which more people are "talking" and start going out.
Karen: "Well, homecoming is underway"

Ellie: "Of course, Jake is my date"

Karen: "Ooh, are you guys talking?"

Ellie: "No"

Ellie: "Why do you ask?"

Karen: "Well, homecoming is usually cuffing season".

Ellie: "Oh."
de men_in_black_1000 17 octobre 2010