Quick answer: Cuffing season is the stretch of colder months, roughly from fall through Valentine's Day, when a lot of single people feel a stronger pull to pair up. "Cuffed" is slang for being tied to one person, like a pair of handcuffs. The phrase caught on in the early 2010s. Some winter romances turn into something real. Others are mostly about company on cold nights. What matters most is knowing which one you want.