Kristin Cavallari and Jay Cutler are two people whose decade-long relationship might have been doomed from the start—but they certainly can’t get called for lack of trying.
You might know NFL quarterback Jay Cutler from his days with the storied Chicago Bears franchise. And you’ll remember his estranged wife Kristin Cavallari from old binge-worthy Laguna Beach episodes, where she had her own fair share of relationship ups and downs. Does the name Stephen Colletti ring a bell?
The rollercoaster continued for Kristin as she and Jay got together, broke up, got back together, got married, got divorced, and had some kids along the way (mostly in that order), all over the span of ten years.
We provide the lowdown on this infamous pair, who they are, how they met, and why they just couldn’t keep their love out of the news.
Introducing the Players: Kristin Cavallari and Jay Cutler
Before internet users were Googling “Kristin Cavallari divorce,” they were likely Googling something along the lines of “Kristin Cavallari Laguna Beach” or “Kristin Cavallari and Lauren Conrad.”
This is where she got her start, as a teenager on an MTV reality tv show that documented her and several members of her friend group. As a high school junior, Cavallari was already showing a lot of promise for entertaining, adopting a bad-girl personality. She eventually went on to star in MTV’s The Hills.
Finally, Cavallari started her own reality show, Very Cavallari, which often featured her NFL star husband. It ran from 2018 to 2020, but Cavallari wanted to stop the show during her divorce to protect the privacy and integrity of their family.
She’s quite popular on social media as well, with well over 4-million people following her on Instagram.
Jay Cutler is a former NFL player who played for the Denver Broncos, Miami Dolphins, and Chicago Bears.
He was a good player—throwing 227 touchdowns in his career—but a polarizing one, too. One thing that overshadowed his talent was a tendency toward turnovers.
He initially retired from football to be a sports commentator but never ended up doing so. One reason is that he came out of retirement to play for the Dolphins. Still, after that final stint, he never went on to commentate—yet!
How Did These Two Lovebirds Meet?
Kristin Cavallari and Jay Cutler have a long history, having met in 2009.
According to Kristin, Jay made the first move, and not in a way that appeased her. Jay went through her publicist, asking if Kristin would come to Chicago for a date. Kristin was doing The Hills at the time and apparently had no idea who Jay even was, so declined.
A year later, Kristin went to a Chicago Bears game with her mother where she saw Jay Cutler—in person this time. Kristin remembers thinking he was really cute, and days later the two had their first date, really hitting it off and marking the beginning of a whirlwind relationship.
Kristin Cavallari And Jay Cutler Have Their Ups and Downs
Of course, the honeymoon phase can’t last forever. Over the course of the next ten years, the celebrity pair rode quite the relationship rollercoaster, always keeping curious fans on their toes.
Their timeline, starting in 2009 and ending in 2020, had several blips on its radar, both good and not-so-good. These are some of the notable ones:
- 2009: The two meet; Kristin denies Jay’s first attempt to date her
- 2010: The pair begin dating
- April 2011: The two get engaged for the first time
- July 2011: The engagement gets called off
- November 2011: The two reunite and begin dating again
- August 2012: Kristin and Jay have their first child, a boy, Camden
- June 2013: The couple get married
- May 2014: The couple have a child, their second boy, Jaxon
- November 2015: The couple have their third child, a girl, Saylor
- 2017: Jay retires from the NFL
- April 2020: Even a Bahamas vacation can’t keep this family together; the two announce their split
After ten years together and three kids within three years, the pair called it quits, citing irreconcilable differences.
According to Kristin, it was one of the hardest things she’s ever done, and it’s easy to see why. With a history like that, it’s safe to say their lives were very tangled.
In a post on Instagram, Kristin released the following statement about their split:
“With great sadness, after 10 years together we have come to a loving conclusion to get a divorce. We have nothing but love and respect for one another and are deeply grateful for the years shared, memories made, and the children we are so proud of. 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.”
Where Are They Now?
Unfortunately, the divorce didn’t go as amicably as we hoped.
Jay Cutler is currently fighting for half of Kristin’s brand, Uncommon James. The company, created by Cavallari during their marriage, offers home goods, jewelry, beauty, and child’s clothing. Because of Cutler’s demands, the divorce is taking a bit longer than anticipated.
Kristin seems to be doing okay post-divorce, staying busy managing her company and even getting photographed with another man, her alleged comedian boyfriend.
The two did agree on one thing, at least: joint custody. The three kids go back and forth on a weekly basis, becoming a top priority for each parent in those short-but-sweet seven days.
They’re still navigating the waters of divorce and family, go-parenting during crazy times and under stressful circumstances. It appears that initial, more petty arguments have subsided in favor of a peaceful situation.
Let’s hope this is one trend that has staying power!
All’s Fair in Love, War, and Celeb-Reality
Kristin Cavallari and Jay Cutler tried their darndest to make their relationship work—so let’s all give them a round of applause. Pat yourself on the back, you two!
Still, it wasn’t meant to be. Google searches change—from “Jay Cutler wife” to “Jay Cutler divorce.” People change. Partnerships change.
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