1 definition by AR-Money

cupping season

The seasons of Fall and Winter, during which vast amounts of people, who are otherwise content with being single, elect to settle down with a significant other. A "couple" is formed, giving rise to the term "cupping".

Sammie: Ashley and Becky just got boyfriends, I thought they were loving the "single life"...
Taylor: Yeah, but it is cupping season, after all

by AR-Money March 14, 2015