Kristin Cavallari, Jay Cutler's Ups and Downs Through the Years (2024)

From a broken engagement to three beautiful children, Kristin Cavallari and Jay Cutler’s relationship has had its share of curveballs, culminating in their April 2020 split.The Uncommon James founder and the former NFL star began their whirlwind romance in 2010, meeting through mutual friend Giuliana Rancic.“Jay is a good Midwestern boy; he's a gentleman," Cavallari exclusively told Us Weekly ahead of the couple’s April 2011 engagement. "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!"Three months after Cutler proposed to Cavallari, the pair split, only to reunite in November 2011."At that moment, something wasn't right," Cavallari wrote in her 2016 book, Balancing in Heels. "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."The Laguna Beach alum revealed in her book that the pair saw a therapist to rebuild their relationship, which “opened up our eyes to the other person’s perspective and gave us great tools for communication.”After rekindling their romance, the duo welcomed their first child, Camden, in August 2012. Less than a year later, they tied the knot in June 2013.[sendtonews type="float" key="k29qfMD8SD-3112647-14453"]The former Chicago Bears quarterback and the Hills alum welcomed their second son, Jaxon, in May 2014 and their daughter, Saylor, less than two years later in November 2015.The couple hit another rocky patch while trying to navigate their new roles of Cutler being retired — he left the NFL in 2017 — and Cavallari launching her lifestyle company. During a February 2019 episode of Very Cavallari, the Colorado native said their marriage was “in a serious funk” and called out her husband for not being as supportive as she needed.A few episodes later, Cavallari spoke out about her and Cutler’s relationship status.“Jay has been great, yes. From the outside, like, things are so perfect and things are so great,” she told friends during an April 2019 episode of the E! series. “But actually, like, they’re not. And that sucks. It sucks. That’s the thing, though, with marriage — it’s ups and downs. Right now we’re in a low, but in two months we could be up here again. And that’s how we’ve always been, our whole relationship. It is what it is.”A year later, the couple announced their split after spending time together in the Bahamas as a family amid the coronavirus pandemic.Scroll down to see all of Cavallari and Cutler’s ups and downs over the years:

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.”

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

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

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 :)”

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.”

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.”

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!”

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.

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.

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.”

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’!”

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!”

“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.

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.

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.”

“I know that Jay and I have to make a conscious effort. You have to put in work for a relationship,” she told Us exclusively of the pair’s struggles. “You can’t just get complacent and lazy. You have to still value and appreciate the other person. I think that when you don’t that’s probably when you start to get in trouble. And, I mean, we have our issues. Our relationship isn’t perfect. But we love each other and we work on it and we make a conscious choice to work on the relationship and I think that that’s what you just have to do.”

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?”

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.”

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.”

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."

After arguing over custody and property in their first round of divorce docs, Cavallari and Cutler came to an agreement in May 2020. In addition to splitting their time 50/50 with their three kids, Cavallari was granted permission to buy the new home she wanted after her funds were temporarily frozen. While things between the former couple appeared better on paper, a source told Us at the time that things were still tense between them.

Amid their divorce battle, Cavallari paid tribute to Cutler in a belated Father’s Day post. “Saved the best for last….happy (late) Father’s Day to Jay,” she wrote, sharing a throwback pic of their children sitting on the sidelines of a football field. “We had a beautiful day together yesterday at my new house. Modern family? Co-parenting? Whatever you want to call it, we are navigating it the best way we know how.”

The entrepreneur shared what she’s been focusing on amid her divorce battle with Cutler. “This is the first time in a very long time that I feel like I can take a breath. I’m enjoying things slowed down and having more time to focus on what really matters in life,” she exclusively told Us. “I want to take this extra time I have right now to better myself and be the best mom I can be and continue to grow Uncommon James.”

Cavallari added, “I’m not thinking about what I want to be doing next year or the year after that. I’ve driven myself crazy with that mentality the past few years. Right now, I just want to be present and enjoy this journey.”

Cavallari admitted that the decision to call it quits “didn’t happen overnight” for her. “We tried really, really hard for years and years. It was the hardest decision I’ve ever made,” she told People. “I still care so much about him and talk to him almost every day.”

The reality star said the choice “wore on” her daily, adding: “A year ago, I felt like I was drowning. I’m proud for making this decision. … I feel like my whole world is opening up now because of it, and I’m just feeling the best I’ve felt in a really long time.”

The former quarterback showed his estranged wife some love in October 2020 in support of her new cookbook release. “I got mine for free but it is worth the price,” Cutler wrote alongside a photo of the True Comfort book via Instagram. “Well done @kristincavallari.”

The designer and the former athlete reunited in October 2020 to celebrate Halloween with their three kids. Cavallari dressed as a unicorn and Cutler wore a striped black-and-white jumpsuit.

Six months after announcing their split, Cavallari told Us that she planned to spend Thanksgiving with her estranged husband and their three little ones. “I’m actually gonna be spending it just with my kids and Jay Cutler as a family. So, I’m looking forward to that,” she told Us ahead of the holiday. “Jay and I were discussing the menu together yesterday, and he’ll be on meat duty. I think he’s gonna fry a turkey and smoke a lamb leg, and then I’m gonna do everything else.”

When Turkey Day rolled around, however, Cutler celebrated with friends Carrie Underwood and Mike Fisher. “We had it all. And when I say we, I mean @carrieunderwood and @mfisher1212,” Cutler wrote alongside a video of their Thanksgiving spread via Instagram. “I watched a large turkey cook in a vat of oil. Carrie and Mike had enough for 20 people. Hope everyone had a great Turkey day.”

Cavallari, for her part, did a tipsy social media Q&A on the holiday, joking about “accepting applications” for a new man. The same weekend, Cutler posted a video on Instagram with his estranged wife’s former employee Shannon Ford, who was famously fired from Very Cavallari after one season.

Usconfirmed in May 2021 that Cutler is fighting for half of his estranged wife's lifestyle brand, Uncommon James, because she launched it while they were married. Meanwhile, according to TMZ, she does not agree since it was funded by her own money.

“For me, it’s just about putting the kids first,” Cavallari exclusively told Us of her and Cutler’s plans for the holiday season. “The kids are the only thing that matters and what’s best for them. That’s how I look at it. You’ve just got to make the most of it. … Luckily, we are able to spend it together, and I’m really grateful for that.”

An insider exclusively told Us that Cutler was still harboring lingering feelings for his estranged wife as they awaited the finalization of their divorce. "Jay is still very much hung up on Kristin," the source said. "He still has a lot of love for her and wishes things weren't as they are. ... They are coparenting well — he just wishes they were still together."

Cavallari called her marriage "toxic" during a candid interview on the "Call Her Daddy" podcast, acknowledging that briefly splitting before their wedding day should have been a warning sign. "I called off the engagement [for] the same reason I got a divorce — same reasons, I should say," she revealed. "I guess if there's any takeaway from that, it's that you can't ignore red flags, people don't change, and you gotta trust your gut."

However, she noted that she wished Cutler all the best. "I hope that he finds someone, I really do," the reality star said. "I want him happy. My kids benefit from that, you know. So I hope that he gets remarried."