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, only to reunite in November 2011.
“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.”
The Laguna Beach alum revealed in her book that the pair saw a therapist to rebuild their relationship, which “opened up our eyes to the other person’s perspective and gave us great tools for communication.”
After rekindling their romance, the duo welcomed their first child, Camden, in August 2012. Less than a year later, they tied the knot in June 2013.
The former Chicago Bears quarterback and the Hills alum welcomed their second son, Jaxon, in May 2014 and their daughter, Saylor, less than two years later 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. During a February 2019 episode of Very Cavallari, the Colorado native said their marriage was “in a serious funk” and called out her husband for not being as supportive as she needed.
A few episodes later, Cavallari spoke out about her and Cutler’s relationship status.
“Jay has been great, yes. From the outside, like, things are so perfect and things are so great,” she told friends during an April 2019 episode of the E! series. “But actually, like, they’re not. And that sucks. It sucks. That’s the thing, though, with marriage — it’s ups and downs. Right now we’re in a low, but in two months we could be up here again. And that’s how we’ve always been, our whole relationship. It is what it is.”
A year later, the couple announced their split after spending time together in the Bahamas as a family amid the coronavirus pandemic.
Scroll down to see all of Cavallari and Cutler’s ups and downs over the years.