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 November 2011. The former reality star explained that seeing a therapist ultimately helped them reconcile. "At that moment, something wasn't right," Cavallari wrote in her 2016 book, Balancing in Heels. "A few things needed to change, and I knew the only way Jay would see how serious I was, was if I ended the relationship." They expanded their family with their son Camden in August 2012. Less than one year later, Cavallari and Cutler got married in June 2013. Their second son, Jaxon, was born in May 2014, with daughter Saylor joining the family in November 2015. The couple hit another rocky patch while trying to navigate their new roles of Cutler being retired - he left the NFL in 2017 - and Cavallari launching her lifestyle company, Uncommon James. Their divorce was finalized in 2022, two years after they announced their split. Keep scrolling to look back at Cavallari and Cutler's ups and downs over the years: