'The Hills' star Kristin Cavallari and husband Jay Cutler are divorcing after over 10 years together. Here's a timeline of their relationship.

Jeff Schear/Getty ImagesJay Cutler and Kristin Cavallari.
  • Kristin Cavallari, the OG reality star of MTV’s “Laguna Beach: The Real Orange County” and “The Hills,” and husband, Jay Cutler, a former NFL player, are divorcing.
  • Cavallari announced the news on Instagram on April 26, 2020.
  • The pair have been together since 2009 and have three children.
  • They also starred on the E! series “Very Cavallari.”
  • Insider compiled all the details of their relationship, including a broken engagement, two weddings, and three babies in four years.
  • Visit Insider’s homepage for more stories.

Kristin Cavallari and Jay Cutler are getting divorced. The pair announced the news on April 26, 2020.

Fans first met Cavallari as a teen on the trailblazing MTV reality series “Laguna Beach: The Real Orange County” and followed her to its spin-off, “The Hills.” Since then, the OG reality star has launched home goods and jewellery company Uncommon James, written a couple of books, and returned to television with the E! series “Very Cavallari.”

Jay Cutler was an NFL quarterback for the Chicago Bears and Miami Dolphins, before starring with his then-wife on “Very Cavallari.”

The parents of three have been together since 2009. Insider looked back on their relationship, which has included a broken engagement, two weddings, and three babies in four years.


2009: The relationship almost never even got off the ground.

Dan Steinberg/AP Nam Y Huh/APKristin Cavallari said Jay Cutler made the first move in 2009.

During an interview with web series “A Drink With,” the “Laguna Beach” and “Hills” alum shared that Cutler, who was then the quarterback of the Chicago Bears, made the first move but she wasn’t interested in a relationship at the time.

“I got a call from my publicist that Jay wanted to fly me out to Chicago and take me out,” Cavallari recalled. “I didn’t know who he was! I had to Google him. I was in the middle of filming ‘The Hills’ so I was like, ‘I don’t want a boyfriend in Chicago,’ and passed on it.”

Cavallari was also not a fan of his approach. In her book “Balancing in Heels: My Journey to Health, Happiness, and Making It All Work,” she explained why she was initially turned off.

“Plus, to be completely honest, years prior I had had a different Chicago athlete go through my publicist to ask me out, so I was a little weirded out by all these Chicago sports guys wanting to date me.”


2010: Things took a sharp turn the following year.

Katy Winn/AP Nam Y. Huh/APKristin Cavallari’s mum reminded her of Jay Cutler’s previous invitation a year prior.

A year later, Cavallari was in town visiting her mother and got her publicist to hook them up with passes to a Chicago Bears preseason game. She had forgotten about the invitation from Cutler, but her mum was quick to remind her.

Cavallari said that when they finally met, she thought he was “really cute.” And things started moving at breakneck speed from there.

“We hung out two nights later, and that began a swift and intense romance. I flew back to Chicago at least every two weeks,” Cavallari wrote in her book. “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.”


April 2011: The couple got engaged.

Brian Kersey/APCavallari and Cutler got engaged after dating for eight months.

After a whirlwind eight-month relationship, Cavallari and Cutler got engaged over Easter weekend during a Mexican getaway. Sources close to the reality star said she was blindsided by the proposal but very excited. Cavallari also gushed in interviews about her husband to be.

“Jay is a good Midwestern boy,” she told Us Weekly in 2011. “He’s a gentleman. 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!”


Summer 2011: The pair broke up.

Matt Sayles/AP Nam Y. Huh/APKristin Cavallari revealed in her book that the couple split because ‘a few things needed to change.’

A mere three months after their engagement, news came that the two were going their separate ways. Multiple reports claimed that the NFL star had broken up with Cavallari, but she would later refute those claims in her 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,” she wrote.

Among those things was that Cutler “envisioned himself being the sole breadwinner and his wife staying at home.”


Fall 2011: They reunited once again.

Brian Kersey/APIn November of 2011, the couple confirmed that not only were they back on again, they were also engaged.

By October, Cavallari had thrown herself back into work and was a contestant on season 13 of “Dancing With the Stars.” During a sexy samba with pro partner Mark Ballas, set to BeyoncĂ©’s “Crazy in Love,” fans were surprised to see Cutler cheering his ex on in the ballroom.

In November, the couple confirmed that not only were they back on again, they were also engaged. This time the proposal was a bit more unconventional.

“It was so silly,” Cavallari told E! News. “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.”


2012: Cutler and Cavallari welcomed their first child.

Danny Moloshok/APAfter rekindling their romance, the couple announced they were expecting their first child.

Two months after rekindling their romance and engagement, the couple shared some more major developments in their relationship.

In a People magazine exclusive, the pair said, “We are thrilled to announce we are expecting our first child together. It’s an amazing time in our life and we can’t wait to meet the new addition to our growing family.”

Cavallari admitted that telling Cutler’s traditional parents about the pregnancy was nerve-racking but they were supportive. The couple welcomed son Camden Jack on August 8, 2012.


June 2013: They finally got married.

@kristincavallari/InstagramThe couple sealed the deal on June 7, 2013, in a civil ceremony and again on June 8, 2013, at the Woodmont Christian Church in Nashville.

Cavallari later said that she would have been quite content remaining engaged forever and that witnessing her own parents’ divorce had made her a bit reluctant to tie the knot. But the arrival of their son gave her a new perspective, she said.

“Having a kid made me realise that I wanted the security of a legal union for him,” Cavallari told People in 2016. “I wouldn’t want him (or any of our kids, now) to ever interpret our voluntarily not getting married as a sign that Jay and I may not be completely committed to our family.”

They sealed the deal on June 7, 2013, in a civil ceremony and again a day later on June 8 at the Woodmont Christian Church in Nashville in front of 150 family and friends, followed by a reception at the historic Houston Station. Guests dined on Southern food and danced to a five-piece Motown band hand-picked by Cutler, according to The Daily Mail.

“Jay wanted to take the reins on this and spent hours on websites finding the perfect band,” Cavallari shared in her book.


2014: The newlyweds announced another addition to the family.

@kristincavallari/InstagramShortly after their wedding, the couple announced via Twitter that they were expecting baby No. 2.

Shortly after their 2013 nuptials, the newly married couple took to Twitter to announce the impending arrival of baby No. 2.

“Thank you for all the love!! We are so excited for Camden to be a big brother!” Cavallari gushed.

She took to another social media platform to share their new bundle of joy.

“Welcome Jaxon Wyatt Cutler,” she wrote on Instagram next to suede booties. “7l bs 11oz 5/7/14.”


November 2015: They continued to expand the Cutler clan.

@kristincavallari/InstagramCavallari gave birth to Saylor James on November 23, 2015.

Almost a year after the arrival of their second child, the couple shared on Mother’s Day that they were “at it” yet again.

The post made on Cavallari’s app read, “We’re at it again! Thrilled to announce baby number 3 is on the way! The Cutler crew just keeps on growin’!”

Saylor James came into the world on November 23. The unique moniker came from an unlikely place.

Cavallari told the now-defunct blog Cricket Circle in 2015 that they named their daughter after a dog.

“We picked out this baby girl’s name when I was pregnant with our first,” she’s quoted as saying. “I met a woman and her dog and I loved her dog’s name. Funny enough, it was the name she had picked out if she had a girl, but she had boys, so she used it for her dog instead. Here we are three-and-a-half years later, and we are going to use that name for our little girl!”


December 2015: Cavallari’s older brother died.

@kristincavallari/InstagramCavallari paid tribute to her brother, Michael, on Instagram.

Cavallari announced on December 10, 2015, that her brother Michael, 30, had died. He had been missing since November 27. His body was found on December 10.

She paid tribute to her older sibling on social media.

“My heart is in a million pieces,” she wrote. “Mikey, I could always count on you to make me laugh. You had such a good heart and will be forever missed. I’m at a loss for words but I know u are in a better place and finally at peace. I love u so much RIP.”


March 2017: Cutler was let go by the Chicago Bears.

@kristincavallari/InstagramAfter Jay Cutler was cut from the Chicago Bears, Kristin Cavallari made a post about leaving Chicago.

After an injury-plagued season and a tumultuous eight years in the Windy City, Cutler was cut from the team in March.

“We are grateful to Jay for all he did as a Bear,” Bears chairman George McCaskey said in a statement. “We wish Jay, Kristin, and their three kids all the best.”

This meant major changes for the family as well: They would be leaving Chicago. Cavallari said goodbye to the city in an Instagram post.

“So we’re moving from Chicago soon and I gotta say, I’m really gonna miss this place,” she wrote. “Not only we’re all 3 of my babies born here, it’s where it all began with jay, it brought me closer to my mum who has become my best friend, I’ve made some amazing girlfriends, and I’ve really enjoyed being back here (a lot of people don’t know I lived here when I was younger).”

She added, “Thanks for all the good times, Chicago. This will always be a special place for us.”


August 2017: Cavallari supported Cutler’s move to the Miami Dolphins.

@kristincavallari/InstagramAs Jay Cutler moved on to play for the Miami Dolphins, Kristin Cavallari expressed her excitement.

A few months after the family moved back to Nashville, where Cutler attended Vanderbilt University, he got an offer he couldn’t refuse – to play for the Miami Dolphins on a one year deal worth $US10 million. The mum of three said she was “excited” for her man but reluctant to uproot her kids.

“So, I’m a single parent for the next five months,” Cavallari told “Entertainment Tonight.” “It’s a little chaotic, but in the best way.”


July 2018: The couple launched their reality TV show, “Very Cavallari.”

@kristincavallari/InstagramCavallari’s new E! show, ‘Very Cavallari,’ gave fans a look at her and Cutler’s family life.

On July 8, E! premiered “Very Cavallari,” a new reality series chronicling the life of Cavallari as she balanced family life with her business ventures.

The show also gave fans a glimpse into the typically low-key Cutler’s true personality. Throughout his playing career, he gained a reputation for being a bit surly, but has since emerged as the breakout star of the show.

Over the past two seasons, we’ve watched the couple move to a Nashville farm, looked on as Cavallari shared with friends how Cutler’s oral skills have improved thanks to a GQ article, and watched him comfort her on the three-year anniversary of her brother’s death.


January 2020: “Very Cavallari” addresses cheating rumours.

caption
Kristin Cavallari.

On the season three premiere of “Very Cavallari,” the show addressed cheating rumours between Cutler and Cavallari’s best friend, Kelly Henderson.

Henderson, who was a full-time cast member on the show in seasons one and two, did not come back for season three. Cavallari said on the show it was because of the way she handled these rumours.

“I kept trying to reach out to her and talk to her about it and tell her how I was feeling, and instead of her just owning her side of it and being like, ‘I’m sorry. Oh my god, that was never my intention,’ or whatever, she kept giving me pushback and would get really defensive,” Cavallari said on the show. Eventually, she said Henderson “just stopped responding.”

Both Henderson and Cutler denied an affair.


March 2020: Cutler and Cavallari were stuck in the Bahamas with their kids during the coronavirus pandemic.

caption
Cavallari with her son Camden while on vacation in the Bahamas.

During the coronavirus pandemic, Cutler and Cavallari were stuck on an “empty island” in the Bahamas during March and early April.

They were travelling along with the family of Cavallari’s friend and hairstylist Justin Anderson, who said on his social media that the group “couldn’t leave here if we tried.”

By April 7, all parties had returned home after facing backlash for vacationing during the pandemic.


April 26, 2020: Cavallari announces that she and Cutler are divorcing on Instagram.

caption
Kristin Cavallari and Jay Cutler.

Cavallari shared the announcement about her in an Instagram post, saying: “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.”


April 27, 2020: Us Weekly reports Cavallari cited “inappropriate marital conduct” and “irreconcilable differences.”

caption
Kristin Cavallari and Jay Cutler.

The reality star reportedly cited “inappropriate marital conduct” and “irreconcilable differences” as reasons behind her divorce from Cutler, according to court documents seen by Us Weekly.

Cutler, the outlet reported, initiated the proceedings on April 21 and asked for joint custody. Cavallari filed three days later on April 24, according to an earlier Us Weekly report.

On April 27 when Us Weekly’s report came out, Cavallari removed “wife” from her Instagram bio.

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