A Look Back on Kristin Cavallari and Jay Cutler's Relationship in Photos
From long-distance love to one big happy family, the couple has endured plenty of ups and downs over the years
LOVE AT FIRST SIGHT
Cutler made the first move back when Cavallari was still filming The Hills, but things didn't quite go to plan for him right away. "I got a call from my publicist that Jay wanted to fly me out to Chicago and take me out. 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," she revealed in an A Drink With … interview. A year later, however, she found herself in Chicago, and met up with Cutler and it was instant chemistry. "When he walked in I was like, 'Oh my goodness!'"
A WHIRLWIND ROMANCE
The couple began dating long distance in the fall of 2010, and by April 2011, he popped the question. "I'm in love and it's been great," she told PEOPLE in January 2011. "Things are really good." Cavallari opened up about the their "swift and intense" romance in her 2016 book, Balancing in Heels, saying, "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. Jay told me he loved me weeks into our relationship and told me he wanted to marry me after only two months. It all happened quickly, but it made sense: He was exactly what I was looking for."
NOT A FAIRY TALE ENDING
Their fairy tale romance hit a rough patch in July 2011, when the pair called off their engagement after 10 months together. However, despite their shocking split, the couple managed to put their differences aside and in November of the same year, they announced on Twitter that they had reconciled. "This time it's official," Cavallari wrote. "Jay and I are engaged again :)."
AND BABY MAKES THREE
The roller coaster wasn't done yet! Just a few months after getting engaged again, the couple announced 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," the told PEOPLE. Camden Jack Cutler was born on August 8, 2012.
HAPPILY EVER AFTER
The following summer, Cutler and Cavallari tied the knot in a romantic ceremony in Nashville, Tennessee, with son Camden serving as a ring bearer. "The flowers and everything were very simple but it was very warm and cozy," Cavallari told PEOPLE in June 2013. "It was all about the lighting and the candles and the atmosphere was just so warm. It was absolutely perfect."
A GROWING FAMILY
Camden became a big brother for the first time in May 2014, when the couple welcomed their second son, Jaxon. A year later, the boys were joined by their baby sister, Saylor James, who was born on November 23, 2015. "She's going to steal Jay's heart, which will in turn melt mine!" Cavallari told American Baby in 2015. "I'm excited for the boys to grow up with a sister. I think it will help them to better understand and respect women." In that interview, she also revealed that she and Cutler had been going to couples therapy, and credited it with keeping their marriage strong. "I'm not ashamed to say that Jay and I consistently go to therapy," she said. "It's been extremely beneficial for our relationship."
A HEARTBREAKING TRAGEDY
Sadly, the couple's happy mood was darkened when Cavallari's older brother, Michael, was found dead in December 2015, two weeks after he had been reported missing. "My heart is in a million pieces," she wrote in a touching tribute on Instagram. "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." Cavallari credited her family, especially baby Saylor, with helping her through her tragic loss. "My little angel, Saylor. She has been my light throughout this whole thing and has given me so much strength," she wrote on Instagram. "Thank you baby girl for coming when u did."
STRONGER THAN EVER
In January 2017, after three years of marriage, Cutler and Cavallari seemed happier than ever while celebrating her 30th birthday. "He threw the most amazing surprise party and made me feel so special and loved," Cavallari gushed about her husband on Instagram, "and I will forever be grateful for this man, my family, and all my amazing friends. I am the luckiest girl in the world to have such incredible people in my life."
GOODBYE, WINDY CITY
In March 2017, Cutler was cut from the Chicago Bears after eight seasons, and after he spent most of the 2016-2017 season battling injuries. With her husband now a free agent — meaning any NFL team could potentially sign him — the family had to say goodbye to Chicago, their home for the last five years. "I'm really gonna miss this place," Cavallari wrote in an emotional post on Instagram. "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 mom who has become my best friend, I've made some amazing girlfriends, and I've really enjoyed being back here."
In 2017, the couple returned to Cutler's old stomping grounds in Nashville, Tennessee. Cutler played for Vanderbilt University's football team and the pair married in the southern city.
In July 2018, Cavallari returned to reality TV with Very Cavallari, which gave viewers a look into her life as a wife, mom and businesswoman. Cutler made appearances that made for great TV, too.
On April 26, 2020, Cavallari announced she and Cutler are divorcing. "With great sadness, after 10 years together we have come to a loving conclusion to get a divorce. 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," the mom of three wrote on Instagram.
"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," Cavallari said.