'The Hills' star Kristin Cavallari and husband Jay Cutler have been together for 10 years. Here's a timeline of their relationship.

Jeff Schear/Getty ImagesJay Cutler and Kristin Cavallari began dating in 2009.
  • 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, have been dating for nearly 10 years.
  • Cavallari most recently returned to television with Cutler 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.

We first met Kristin 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 most recently returned to television with husband Jay Cutler on the E! series “Very Cavallari.” The parents of three are pretty close now (see how he helped clear her clogged breast milk ducts), but their path was pretty rocky at first.

INSIDER has compiled all the details, including a broken engagement, two weddings, and three babies in four years.

Here’s a look at the relationship between the television personality and her former NFL player hubby.


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

During an interview with web series “A Drink With,” the “Laguna Beach” and “Hills” alum shared that Cutler, who was the then 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.

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.

In her book Cavallari wrote,”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.”


2011: The couple got engaged…

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. 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!”


2011: Then they shockingly split…

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 dumped 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.”


2011: Then they reunited once again.

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.

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 8th.


2013: They finally got hitched.

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

Cavallari confessed 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 new perspective.

“Having a kid made me realise that I wanted the security of a legal union for him. 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 in a civil ceremony and again 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.

“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.”


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 revealed 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.

The proud mum explained, “We picked out this baby girl’s name when I was pregnant with our first. 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 3.5 years later, and we are going to use that name for our little girl!”


2015: Tragedy touches the family.

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

Cavallari went from experiencing the joy of childbirth to suffering great loss with the death of her brother Michael, 30, who had been missing since November 27. His body was eventually found on December 10.

She paid tribute to her older sibling.

“My heart is in a million pieces. 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.”


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. 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.”


2017: Cavallari supports 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 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.”


2018: The couple peeled back the curtains on their life at home.

@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 Jay’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.

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