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.
ayon kay Pmack0711 ika-20 ng Setyembre, 2011
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Usually the colder months; i.e. fall or winter, when new relationships start and old relationships turn into engagements. The persons in said relationships are "cuffed", meaning that they no longer seek non-platonic relationships with others.
1) I have lost count of the number of friends getting engaged. Cuffing season has begun.

2) "Are you single?" "Not for long. It's cuffing season."
ayon kay catamountgirl ika-09 ng Nobyembre, 2014
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."
ayon kay men_in_black_1000 ika-17 ng Oktubre, 2010

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