3 Ugly Signs in Jay Cutler and Kristin Cavallari’s Relationship That Proved They Were Doomed From the Start 

After meeting in 2010 and tying the knot in 2013, former NFL quarterback Jay Cutler and reality TV star Kristin Cavallari tried giving their relationship a try until their marriage ended in a messy divorce process in 2020. Later on, as their divorce was finalized in 2022, a thorough understanding of their relationship revealed that the couple was never meant to be together. 

Doomed from the very beginning with rumors of infidelity on Jay Cutler’s end, resulting in insecurity and coldness from Kristin Cavallari, their marriage dropped early signs of trouble. So let’s take a look at three initial signs in Cutler and Cavallari’s relationship that screamed of potential heartbreak and split 

Into Jay Cutler and Kristin Cavallari’s Messy Divorce 

Former NFL quarterback Jay Cutler and reality TV star Kristin Cavallari popped out on the scene very much in love in September 2010, after Giuliana Rancic introduced the pair. Soon, after eight months since their first meeting, the couple announced their engagement in April 2011, as per US Magazine. 

Jay told me he loved me weeks into our relationship and told me he wanted to marry me after only 2 months. It all happened quickly, but it made sense: He was exactly what I was looking for. I wanted a man, a real man. … Eight months after our meeting came the ring. 

Thereafter, welcoming their first child, a son named Camden in 2012, the couple walked down the aisle in Nashville, Tennessee, on June 7, 2013. Soon after their marriage, the couple had their second boy, Jaxon, in 2014, and then welcomed daughter Saylor in 2015. With three children of their own, they created a happy family for themselves. 

Soon Jay Cutler retired from the NFL in 2017 after 12 seasons, and joined his wife on reality TV, as she made her return with E!’s Very Cavallari, which documented her fashion line, Uncommon James. However, within a few years, things started getting messy for the couple, until they announced their separation in April 2020, after seven years of marriage. 

Soon, by 2022, Jay Cutler and Kristin Cavallari’s divorce was finalized and the former couple went their separate ways. 

The Former Couple’s Brief Break-Up Before Engagement 

Following their divorce, fans took great interest in their relationship to figure out where things went wrong for the happily married couple and parents of three. That’s when Reddit user u/Lantana3012 came up with three early signs of their romance that hinted at their inevitable split. 

The first red flag in their romance was Jay Cutler and Kristin Cavallari’s brief breakup prior to their engagement. Corroborating the report, US Magazine confirmed that the former Hills star and the ex-Chicago Bears quarterback’s engagement and wedding didn’t go off without a hitch. Cavallari had indeed called off their engagement in 2011, briefly. 

At that moment, something wasn’t right. 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. … If I stayed at home, I wouldn’t be happy. And would probably end up resenting Jay for it. 

Implying how Cutler was perhaps willing for Cavallari to become a stay-at-home mother, while she was more interested in creating a career for herself, the reality TV star noted breaking things off for the better. However, despite their differences in opinions, as the couple patched things up and got married, it eventually affected their relationship. 

Jay Cutler’s Lack of Support and Complaints About Kristin Cavallari’s Work-Life Balance 

As mentioned earlier, Jay Cutler and Kristin Cavallari’s unresolved issues about career and parenthood became a huge problem in their relationship. After Cutler retired from the NFL in 2017 and joined Cavallari on her reality TV show, Redditor u/Lantana3012 mentioned how he began complaining about her work-life balance amid her TV show, cookbook, and Uncommon James. 

Kristin Cavallari shared via US Magazine: 

Jay has been great, yes. From the outside, things are so perfect and things are so great. But actually, they’re not. And that sucks. It sucks. That’s the thing, though, with marriage… It’s ups and downs. Jay and I have problem… 

I’ve always been very vocal about that. We have to work at our relationship, so hearing him say that we’re perfect is kind of silly to me. We definitely have issues. 

Much like the Redditor mentioned that Jay Cutler supported Kristin Cavallari onscreen, even the reality TV star seemed to hint at a similar issue. Perhaps his support for Cavallari’s work and brand was all a pretense, given how he always wanted her to stay at home and be a mother and a wife. 

Jay Cutler’s Alleged Infidelity and Denial 

While the couple was already struggling with their marital conflicts, Jay Cutler surprisingly made headlines for his alleged affair with his wife’s former best friend Kelly Henderson. Although the reality TV star addressed the rumors during season 3 of Very Cavallari, she clarified her trust in her husband and claimed to be more upset with how Henderson handled the situation.  

When season 2 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. It wasn’t the actual accusations of them having an affair that made me upset, it was how Kelly went about it. 

Meanwhile, another report of Jay Cutler’s alleged infidelity emerged when a source told In Touch Weekly, that Cutler and his children went on a vacation with his friend and his wife, who was apparently the NFL player’s longtime mistress. So much so that him and his friend’s wife were caught hooking up during the getaway, leading to a confrontation between Cutler and his friend. 

However, despite multiple infidelity rumors, Jay Cutler denied all of them during his appearance on the Sofia With an F podcast. Shifting the blame on Kristin Cavallari, Cutler claimed that he has “never cheated” and perhaps it was Cavallari’s fault that “she fell out of love”. 

Jay Cutler’s DUI Arrest Following Divorce 

Eventually, after repeated issues and alleged infidelity slowly poisoned their trust in each other, Jay Cutler and Kristin Cavallari grew cold and distant, leading to their inevitable split. Following their divorce, the couple sought joint custody, while later on, things changed between the duo, and Kristin Cavallari ended up receiving more custody of her children than Culter. 

Perhaps the decision was for the best, given how the former NFL quarterback was recently arrested for rear-ending a car under the influence of alcohol. According to police reports via TMZ, Culter rear-ended a car at around 5 pm on Thursday and even tried paying off the other driver with $2,000 so they wouldn’t call the police.

However, after the law enforcement officers arrived, they found Jay Cutler staggering around, slurring his speech and smelling of alcohol. Despite the gravity of his situation, the former NFL star turned down the field sobriety tests, leading the cops to arrest him and search his car, where they found a rifle in the backseat and a loaded Glock handgun in the center console. 

Cutler was booked into the Williamson County Jail, where he posed for a scruffy mug shot after he failed to exercise due care, violated implied consent law (denied submitting blood or breath chemical test for alcohol), and was found possessing 2 firearms (one of which was loaded) while under the influence of alcohol. 

Episodes of Very Cavallari are currently available to watch on Peacock.