Kristin Cavallari & Jay Cutler’s Relationship Timeline: How They Met

Jay Cutler and Kristin Cavallari arrive at the NASCAR Cup Series Awards, in Nashville, TennNASCAR Auto Racing, Nashville, USA - 05 Dec 2019 — Image Credit: Shutterstock

Fans of The Hills were heartbroken to learn that Kristin Cavallari, 33, and Jay Cutler called it quits after six years of marriage. The couple revealed on their individual Instagram accounts on April 26 that they were getting a divorce, after a decade-long relationship. “With great sadness, after 10 years together we have come to a loving conclusion to get a divorce,” the former Laguna Beach star and mother-of-three wrote. “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.” The pair had a rocky start to their relationship, followed by a broken engagement, two weddings, and three kids within two years. Here’s a full timeline of the relationship between the OG reality star and her former NFL player hubby.

2009: Kristin admitted she initially “passed” on the opportunity to meet the then Chicago Bears player in an interview with the web series A Drink With. “I got a call from my publicist that Jay wanted to fly me out to Chicago and take me out,” she 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.” In her book “Balancing in Heels: My Journey to Health, Happiness, and Making It All Work” she explained why she was turned off by Jay’s approach. “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: When Kristin was given tickets to a Chicago Bears preseason game, totally forgetting about Jay’s request a year earlier, the reality star was introduced to him for the first time. She thought he was “really cute” and their relationship began progressing very quickly. In her book she 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: Talk about a whirlwind year! After just eight months of dating, the pair got engaged over the Easter weekend while on vacation in Mexico. Kristin was reportedly surprised by the proposal, but gushed in interviews about her fiance. “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,” she said at the time. Just three months later, news broke that the couple had called it quits. “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,” Kristin wrote in her book, adding that Jay, “envisioned himself being the sole breadwinner and his wife staying at home.” By October that year, when Kristin was competing on season 13 of Dancing With the Stars, the couple confirmed that not only were they back on again, but 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: Two months into their rekindled romance, the pair shared the exciting news that they were expecting their 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,” they said at the time. Kristin also admitted to People that telling Jay’s “traditional” parents about the pregnancy was nerve-racking but they were supportive. The couple then welcomed their first son Camden Jack on August 8, 2012.

2013: The couple finally tied the knot 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.

2014: Shortly after their two weddings, the pair revealed on Twitter that baby number two was on the way! “Thank you for all the love!! We are so excited for Camden to be a big brother!” Kristin wrote. She then took to Instagram to share the exciting news that her second child Jaxon Wyatt Cutler was born on May 7, 2014.

2015: The couple shared on Mother’s Day that they were “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. Kristin explained her daughter’s unique name. “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 three-and-a-half years later, and we are going to use that name for our little girl!”

2016: After experiencing the joy of giving birth to three children, Kristin had to grapple with the tragic and sudden death of her 30-year-old brother Michael. His autopsy revealed he died as a result of hypothermia.

2017: After suffering multiple injuries, and a tumultuous eight years in Chicago, Jay was cut from his NFL team. “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, who packed up and left Chicago. They relocated to Nashville, however Jay was offered $10 million to play for the Miami Dolphins. Although Kristin was “excited” for her hubby, she had no plans to uproot her family again. “So, I’m a single parent for the next five months,” she told Entertainment Tonight. “It’s a little chaotic, but in the best way.”

2018: In July, E! released Very Cavallari a new reality series chronicling the life of Kristin as she balanced family life with her business ventures. The show had an immediate in-built audience comprised of fans who loved The Hills and Laguna Beach. The show peeled back the curtains on the couple’s life, and viewers have seen the pair do everything, from moving to a Nashville farm, to watching Jay console Kristin on the three-year anniversary of her brother’s death.

2019: Very Cavallari entered its second season, and it was announced in May that a third season was on the way in 2020. The pair also starred in a holiday special titled A Very Merry Cavallari.

2020: Kristin and Jay sadly announced on April 26 that they had called it quits. The each revealed on their individual Instagram accounts that they were getting a divorce after a 10-year romance. “With great sadness, after 10 years together we have come to a loving conclusion to get a divorce,” the former Laguna Beach star captioned the post.. “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.”