Normally in the fall or winter. a time when people find a boyfriend/girlfriend either before the Christmas, or before valentines day
Guy: "its cuff season! I need a girlfriend!"
Friend: "Go out with your. Neighbor."
Guy: "Yes, she's perfect!"
The two weeks before Valentine's when lonely people find someone so that they aren't lonely on Valentine.
Dude cuff season next week, you better bring your A game.
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Joe: Jessica roll your cuffs!
Jessica: Why Joe?
Joe: Well it's Rolled Cuffs Season!
Jessica: oh..