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Here’s How Jay Cutler Remembers His Proposal to Kristin Cavallari

jay cutler kristin cavallari "The One Where Jay Goes Cray" --- Pictured: (l-r) Kristin Cavallari, Jay Cutler -- (Photo by: Jake Giles Netter/E! Entertainment/NBCU Photo Bank/NBCUniversal via Getty Images)

A recent trip abroad reminded Jay Cutler of his proposal to Kristin Cavallari from close to a decade ago. While his wife was out shopping for a diamond, Cutler caught up with two friends and recalled the events leading up to his engagement in 2011. “I did it,” he said in a teaser for E!’s Very Cavallari. “It’s just nerve-racking… [Like,] get this ring out of my face.”

While Cutler didn’t cry himself during the gesture, he admittedly did gray out during parts of the proposal. “She shed some tears,” the former Chicago Bears quarterback remarked, while recollecting that the most challenging portion of the process actually involved other members of the family.

“Asking permission [from] Kristin’s dad?” he continued. “That’s rough. Just the buildup. I don’t remember that either.”

The couple first connected in 2009 when Cutler reached out to Cavallari’s team with interest in the MTV Laguna Beach star. “I got a call from my publicist that Jay wanted to fly me out to Chicago and take me out,” Cavallari recalled on A Drink With. “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.”

Eventually, Cavallari met Cutler for the first time in person at a Chicago Bears game. It was fireworks for the two, who dated eight months before Cutler proposed. All seemed to work out when the pair initially got engaged in Cabo San Lucas in 2011. However, their wedding planning process was atypical.

A few months later, they broke it off. “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,” Cavallari previously expressed in her book, Balancing in Heels. One of the biggest issues for the pair was a disjointed perception of working roles in the household, where Cutler had “envisioned himself being the sole breadwinner and his wife staying at home.”

They reconciled a few months later and Cutler proposed—via text—a second time. “It was so silly,” the Hills alum 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, okay.’ 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.”

They are now happily married and parents of three. Recently, the couple enjoyed their second honeymoon and together, they are now starring on their E! show.

About the Author

Esther Lee
Esther Lee
Esther is the Senior News Editor at The Knot. A self-proclaimed pop culture enthusiast, she appreciates a good celebrity interview just as much as she adores Nancy Meyers movies. You can find her kicking off her mornings with barre and a green juice, traveling and exploring new cultures, and rapidly scrolling her feed for the latest and greatest news. Follow her on Instagram and Twitter at @theestherlee.