Strange Things About Kristin Cavallari’s Marriage

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A broken engagement, a proposal by text, and a marriage that’s never stopped making headlines — Kristin Cavallari and Jay Cutler have built their relationship in public.

Kristin Cavallari went from Laguna Beach’s breakout star to a Nashville boutique owner and E! docuseries lead, but the throughline of her adult life has been her marriage to former Chicago Bears quarterback Jay Cutler. The two have been together since 2010, survived a canceled wedding, and reconciled through a proposal that arrived, of all places, over text message. None of it has been conventional, and Cavallari has talked about most of it openly.

  • Cutler pursued Cavallari through his publicist in 2010, and she initially resisted dating him because she didn’t want a boyfriend in Chicago and wasn’t won over by his photos until they met in person.
  • Cavallari called off their engagement in July 2011, just three months after Cutler proposed in Mexico, returning registry gifts to force him to confront serious communication problems — a decision she detailed in her 2016 book, “Balancing in Heels.”
  • After reconciling with the help of couples therapy, Cutler re-proposed by text while Cavallari was at an airport and then mailed her the engagement ring; they married in Nashville on June 7, 2013.

Staged Celebrity Romance Nearly Failed

The relationship didn’t start with a chance meeting or a mutual friend’s setup — Cutler went through his own publicist to get in front of Cavallari in 2010. She wasn’t sold immediately. Cavallari has said she didn’t want to be dating someone based in Chicago while her career and life were elsewhere, and the photos she saw of Cutler beforehand didn’t do much for her either. It took an in-person meeting to change her mind, which set the tone for a courtship that moved fast once it actually got going.

The Engagement That Fell Apart In Three Months

Cutler proposed in Mexico, and by July 2011 — roughly three months later — the wedding was off. Cavallari laid out her reasoning in “Balancing in Heels,” writing that she called off the ceremony and sent back registry gifts specifically to get Cutler’s attention on issues the couple hadn’t been dealing with head-on.

She returned the registry gifts to force Cutler to recognize that serious communication issues needed fixing.

It wasn’t a clean break so much as a deliberate shock to the system. Cavallari’s move worked in the sense that it led somewhere: the couple got into couples therapy, worked through what had derailed them, and reconciled by the end of 2011.

A Proposal By Text And A Ring In The Mail

If the first engagement was made in a scenic Mexico moment, the second one was about as unromantic as it gets. Cutler re-proposed via text message while Cavallari was sitting at an airport, then followed up by mailing her the actual engagement ring. Cavallari has been candid about how far that was from a storybook redo — and it evidently didn’t matter, because the couple married in Nashville on June 7, 2013, and went on to have three kids: Camden, Jaxon, and Saylor.

Life In The Spotlight Neither One Fully Wanted

Cutler has never been comfortable with the paparazzi attention that comes with being married to a reality star, a tension that’s shown up repeatedly throughout their relationship. Cavallari, for her part, has made a habit of clapping back at Cutler’s internet critics — often by poking fun at his appearance herself before anyone else can. Football fans have also directed plenty of social media harassment at Cavallari over the years, adding another layer to a marriage that already gets more outside commentary than most. Anyone following how other celebrity couples handle that kind of scrutiny, like the dynamic explored in Megan Fox’s relationship history, knows the public rarely lets up once it’s invested.

That’s what makes the couple’s next move so counterintuitive: after years of guarding their private life, they opened the door wide open with “Very Cavallari,” the E! docuseries that premiered in July 2018. It’s the same instinct that’s driven other high-profile marriages into the public eye, similar to how Sandra Bullock’s relationship with Bryan Randall has stayed a subject of ongoing interest despite her efforts to keep it low-key.

“Very Cavallari” put Cavallari’s Nashville boutique, Uncommon James, and her marriage back under a camera crew’s watch just months after the docuseries debuted — the same couple who once returned wedding gifts to force a hard conversation now inviting audiences to watch the aftermath play out on E! every week.

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