Kristin Cavallari and Ex Jay Cutler's Ups and Downs Through the Years

Kristin Cavallari and Jay Cutler’s relationship had its share of ups and downs before ultimately coming to an end in April 2020. The Uncommon James founder and the former NFL star began their whirlwind romance in 2010, meeting through mutual friend Giuliana Rancic. “Jay is a good Midwestern boy; he’s a gentleman,” Cavallari exclusively told Us Weekly ahead of the couple’s April 2011 engagement. “He opens up car doors and he did the laundry today, which I thought is pretty cool, so he’s a good boy. We’re in love!” Three months after Cutler proposed to Cavallari, the pair split. They reunited in