K.Cav and the then-Chicago Bears quarterback first spark romance rumors in 2010 after they meet for the first time following his football game. "They really hit it off," a source tells E! News at the time. "He's crazy about her and she thinks he's cute."
Of the early days of their romance, The Hills star writes in her book, Balancing in Heels, "We hung out two nights later, and that began a swift and intense romance. I flew back to Chicago at least every two weeks. When we were apart, we texted constantly, and he wrote me the sweetest love emails. He was the strong, manly man I wanted but had a sweet, romantic side as well."
After just eight months together, Cutler pops the question. But not long after, Cavallari calls off the engagement and the exes even return their wedding gifts.
"At that moment, something wasn't right," she writes in her 2016 book. "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."
Then in the fall of 2011, Kristin and Jay are back together—and engaged!
"It was so silly," the bride-to-be tells E! News of their reconciliation. "I was in the airport, leaving Chicago. We had just spent however many days together and we were texting and somehow it came up, like, 'Oh, shall we get married?' We're like, 'Yeah, OK.' And then he sent my ring in the mail. So I actually had my ring sitting at home for a couple of weeks before I put it on."
In Aug. 2012, Kristin and Jay welcome their first child together, a baby boy named Camden Jack.
They do! Kristin and Jay officially tie the knot in front of their nearest and dearest in Nashville in June 2013.
It's a boy! In May 2014, Kristin gives birth to Jaxon Wyatt. She tells E! News of her pregnancy experience, "I'm lucky. Both pregnancies have been really easy for me, I've just been really tired. It's just one of those things where I could literally sleep all day everyday but I'm snapping out of it a little bit now that I'm in the second trimester."
More than a year later in Nov. 2015, the proud parents welcome daughter Saylor James.
"Kristin and Jay are so happy!" an insider dishes. "They were surrounded by friends and family. Kristin is so thrilled to welcome her new baby girl to her family. Jaxon and Camden are excited to be older brothers. She is feeling great!"
Kristen speaks candidly about her and Jay's marital struggles, and says therapy "100 percent" saved their relationship.
"Jay and I, our relationship, we are very honest. We don't have a perfect relationship," she tells SiriusXM's Wake Up With Taylor. "We work on it. We're in therapy."
Kristin's brother, Michael Cavallari, is found dead in 2015. As she approaches the one-year anniversary of his passing, the Uncommon James CEO tells E! News exclusively that Jay has been her saving grace throughout the ordeal.
"It's been tough, it's been a roller coaster...I'd be lying if I said it wasn't hard," she says, "I'm going to be with my family on the actual day, which hopefully will help. Talking about it is probably the most important thing so I'm lucky I have a great support system with my immediate family, with Jay and with my parents as well."
Kristin and Jay welcome cameras into their Nashville home on E!'s Very Cavallari. The reality TV series chronicles their ups and downs and no topic in their marriage is off limits.
Kristin experiences a major fallout with her best friend, Kelly Henderson, who is accused of having an affair with Jay.
"When season two was airing, there was a lot of talk on social media about Jay and Kelly having an affair. Not for one second have I ever thought that it was true," she recalls on Very Cavallari. "It wasn't the actual accusations of them having an affair that made me upset, it was how Kelly went about it."
Kristin and Jay take their final vacation together as a couple with their kids. Judging by their Instagram posts, nothing seems amiss during the Bahamas getaway.
On April 26, 2020, the celebs take to Instagram to announce their decision to divorce.
"This is just the situation of two people growing apart. We ask everyone to respect our privacy as we navigate this difficult time within our family," Kristin writes in part.
The former couple shares the same message on Instagram, writing, "The world is full of users. 10 years. Can't break that." However, a source exclusively tells E! News nothing has changed between them. "They are friends and they are single. They will always have each other's back," the insider explains.