Kristin Cavallari and Jay Cutler's Ups and Downs Through the Years

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From a broken engagement to three beautiful children! Kristin Cavallari and Jay Cutler’s relationship has been filled with curveballs. Keep scrolling to relive their romance.

August 2010

The Laguna Beach alum and the then-Chicago Bears quarterback began dating in late 2010. Giuliana Rancic revealed to Us Weekly in February 2011 that she set up the pair. “I knew them both for a while and introduced them and they went on a date,” the Giuliana & Bill alum said at the time. “Now they’re dating.”

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April 2011

Eight months later, the couple were engaged. Cutler proposed over Easter weekend, with a source telling Us Cavallari was “so excited and completely blindsided.”

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July 2011

Short-lived bliss. Multiple sources confirmed to Us that the duo broke off their engagement after just three months.

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November 2011

However, Cutler and Cavallari couldn’t make it apart. They were spotted getting close again in the months after their breakup. The Hills alum announced on Twitter that November, “This time it’s official. Jay and I are engaged again :)”

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January 2012

Oh, baby! An insider confirmed to Us that the reality star was expecting her first child with Cutler. “She is really happy,” the source explained. “She is in the early stages, but she can’t wait to be a mom.”

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February 2012

The Very Cavallari stars decided to postpone their nuptials until after their baby’s birth. “I’m not even looking for a wedding dress right now,” she told Celebuzz at the time. “I’m pregnant! I’m not going to go try on wedding dresses.”


August 2012

The twosome’s first child, son Camden, was born on August 8, 2012. “We are thrilled to welcome Camden Jack Cutler into the world,” she wrote on Twitter at the time. “He was born this morning weighing 7lbs 9oz. Everyone is doing great!”

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June 2013

Cavallari and Cutler finally tied the knot on June 7, 2013, at the county clerk’s office in Nashville. “I’m officially Kristin Elizabeth Cutler!!!!!” the designer tweeted. They celebrated one day later with a church ceremony.

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October 2013

The newlyweds confirmed they were expecting baby No. 2 four months after their wedding. “We are so excited for Camden to be a big brother!” she tweeted.

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May 2014

Parents again! Cavallari announced the birth of her second son on Instagram. “Welcome Jaxon Wyatt Cutler,” she wrote at the time. “7lbs 11oz 5/7/14.”

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May 2015

The Uncommon James owner revealed her third pregnancy on her Kristin Cavallari Official app, writing: “We’re at it again! Thrilled to announce baby number 3 is on the way! The cutler crew just keeps on growin’!”

David Banks/Getty Images

September 2015

Cavallari shared her marriage advice in a blog post for Cricket’s Circle. “It’s so important to make time for each other, even if it’s just waiting to eat dinner after the kids go to bed,” she explained. “And even if it’s takeout, light a candle and make an effort to connect. Also, you gotta have sex — men need it, and it’s important for the relationship. It doesn’t have to be all the time, but you have to get it in there sometimes!”

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November 2015

“I’m not ashamed to say that Jay and I consistently go to therapy, because it’s been extremely beneficial for our relationship,” the E! personality told American Baby. She later noted in an interview with SiriusXM’s Wake Up With Taylor that she believed counseling “saved” their relationship.

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November 2015

The couple welcomed their third child, a baby girl, on November 23, 2015. “Saylor James Cutler was born today at 132pm!” the proud mom announced on Instagram.

Andrew Toth/FilmMagic

March 2016

Cavallari shared in her book, Balancing in Heels, why she and Cutler called off their engagement. “At that moment, something wasn’t right,” she wrote. “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.”

Thomas Concordia/WireImage for STYLE360

June 2017

Cavallari also told Us at the time that she and Cutler were “completely done” expanding their family. “I can’t imagine having another one. We got three babies in, like, four years. The baby fever is gone,” she admitted. “We feel like such a complete family. Even if Saylor was a boy I would have been done. But now, especially that we have a girl, we’re good. I don’t want to rock the boat. It feels so perfect and so right that why mess with that?”


June 2018

The True Roots author revealed the secret to her marriage in an exclusive interview with Us. “Jay and I have always had in our favor that we both travel, so we’re able to miss each other, which truly I think is the secret.” She added of finding alone time amid their busy schedules: “It’s hard unfortunately, it is. We have to work on it, like everybody else.”


November 2018

Cavallari admitted to not prioritizing her relationship at times. “It’s hard to balance it all right now. I feel like I’m in a good place with balancing work and kids at least,” she told Us. “I think I could probably put a little more attention on Jay and probably myself as well. But, you know, it’s difficult sometimes.”

Ron Elkman/Sports Imagery/ Getty Images

April 2020

The Very Cavallari star announced via Instagram on April 25, 2020, that she and Cutler have separated. “With great sadness, after 10 years together we have come to a loving conclusion to get a divorce,” Cavallari captioned a photo of the duo. “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.”


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