A Complete Timeline Of Jay Cutler And Kristin Cavallari's Messy Relationship

Since first appearing on the 2004 MTV show, "Laguna Hills: The Real Orange County," Kristin Cavallari has continued to share bits of her interesting yet mildly chaotic life. From starring in "The Hills," a  "Laguna Hills" spinoff, to starting Uncommon James, a jewelry empire, Cavallari's transformation over the years is one for the books. But beyond her transition into business, we also saw Cavallari become a wife and a mother — all with NFL quarterback Jay Cutler. 

For many years, Cutler and Cavallari were one of Hollywood's favorite reality couples, giving us a glimpse into their love life on E!'s "Very Cavallari." Their relationship, however, was not without its own problems. "I always thought it was interesting when people would refer to us as 'couple goals,'" Cavallari told People in 2020. "I was like, 'If you guys only knew." Between getting engaged, calling off the engagement, getting engaged again, having kids, getting married, and then getting a divorce, there is definitely a lot to unpack with this couple. 

Hollywood is no stranger to matchmaking, and you might just be surprised to hear that some of your favorite celebrity couples were actually introduced by mutual friends. Jay Cutler and Kristin Cavallari just so happen to be one of these couples. In 2011, television personality Giuliana Rancic revealed that she was in fact, the one who first set Cutler and Cavallari up. "I knew them both for a while and introduced them and they went on a date," Rancic revealed at the time to US Weekly. 

However, while telling A Drink With of her earliest days with Cutler, Cavallari left out Rancic's role (rather conveniently, if you ask us) but explained that the NFL star initially reached out to her publicist to set up a date — a gesture she ended up saying no to because, at the time, they were both in different states. "I was in the middle of filming 'The Hills' [in California], so I was like, 'I don't want a boyfriend in Chicago,' and passed on it." 

Things, however, eventually seemed to align for the couple as only a year later, Cavallari found herself in Cutler's city — Chicago. If you are not one to believe in fate, you might as well start now.

A family visit turned into a love story! In 2010, while visiting her mom in Chicago, Kristin Cavallari was reminded of Jay Cutler's advances. "I had forgotten all about it and my mom said, "Didn't Jay Cutler ask you out?" she explained in her interview with A Drink With. This, of course, piqued Cavallari's interest in Cutler — leading her to accept to meet with him. "Long story short, I ended up meeting him, and when he walked in, I was like, 'Oh my goodness!' I thought he was really cute," Cavallari said.

It might have only been their first date, but sparks obviously flew. "We hung out two nights later, and that began a swift and intense romance," the reality star wrote in her 2016 book "Balancing in Heels."  And even though they were still both living in different states, Cavallari and Cutler put in just about enough to make their love thrive. "I flew back to Chicago at least every two weeks," she wrote in the book. "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." Now, who doesn't like a sweet man? Little wonder Cavallari was in love in no time!

Who needs time when you've got love! In April 2011, only eight months into their relationship, Jay Cutler proposed to Kristin Cavallari.  According to People, Cutler popped the big question during a surprise weekend getaway in Cabo San Lucas, with a source telling that outlet that "He surprised her with a quick trip to Cabo to ask her to marry him."  And while the timeline of their romance might have been short, an insider told US Weekly that Cavallari and Cutler were convinced they were meant for each other. "They've only been dating eight months, but by month two, she knew he was The One," the source said. Sadly, sometimes, conviction is just not enough.

In July 2011, multiple outlets reported that the couple had broken up, with US Weekly claiming that the NFL star initiated the split and left Cavallari blindsided. This however, proved to be untrue as the "Laguna Beach" star later admitted to breaking up the relationship. "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," she wrote in her book, "Balancing in Heels."

But in true Hollywood style, where nothing lasts forever, the pair's split was short-lived. By November 2011, not only were they back together, their engagement was also back on. Per E!, this time, Cutler sent the ring via mail, but Cavallari was probably too excited to even care.

2011 was no doubt a very rough year for Kristin Cavallari and Jay Cutler but the new year came with glad tidings. In February 2012, the couple announced that they were expecting their first child together. "We are thrilled to announce we are expecting our first child together," Cutler and Cavallari said in a statement to People. "It's an amazing time in our life and we can't wait to meet the new addition to our growing family."

And even though fans were expecting the couple to also announce a wedding date, Cavallari told Glamholic (via HuffPost) that getting married was not in their immediate plans — but having another baby was. "We're talking about the possibility of having another kid right away and then getting married so we can have 2 kids close in age," the reality star revealed. "We want 4 kids, so we're thinking maybe have one more, then get married, then have two more but we'll see, it all depends on how the first one goes."

On August 8, 2012, the couple, Camden Jack Cutler was born. Cavallari shared the exciting news with fans on Twitter, writing:  "We are thrilled to welcome Camden Jack Cutler into the world. He was born this morning weighing 7lbs 9oz. Everyone is doing great!"

Kristin Cavallari and Jay Cutler might have wanted two kids before walking down the aisle but life seemingly had other plans for them. In June 2013, nearly one year after their son was born, the couple decided it was time to make things official. Per Daily Mail, Cavallari and Cutler obtained a marriage license on June 7, before having an intimate church ceremony a few days later. "I'm officially Kristin Elizabeth Cutler!!!!!" Cavallari announced on Twitter.

Even though the ceremony was nothing like the typical celebrity weddings we've seen in Hollywood over the years, it was everything Cavallari wanted. "The flowers and everything were very simple but it was very warm and cozy," she told People. "It was all about the lighting and the candles and the atmosphere was just so warm." The reality star also revealed to the outlet how unreal it felt to be married. "We were both just like, 'I can't believe we did it!' " Cavallari said. "Especially Jay, because he's never worn a ring before. It's going to take some getting used to."

When you've been together for years, share a baby, and are absolutely in love, we guess making things official seems like the next big step — or so it seemed for these two.

Getting married might have been surreal for Kristin Cavallari and Jay Cutler, but parenting was something they clearly enjoyed as they were soon ready to expand the family. "We want to have a second sooner rather than later," Cavallari told E! in September 2013. "We're working on it!" And boy, were they working!

In November 2013, the reality star confirmed that she  and Cutler were expecting her second child. "Thank you for all the love!! We are so excited for Camden to be a big brother!," she wrote on Twitter. Their couple's son Jaxon Wyatt Cutler arrived on May, 7, 2014, as revealed by Cavallari on her Instagram.

Of course, this was not the end road for the NFL star and his wife as their lovely family soon increased by one. In May 2015, the "Laguna Beach" star announced that she was pregnant with their third child. "We're at it again! Thrilled to announce baby number 3 is on the way!," she revealed (via ABC News). "The Cutler crew just keeps growin'!" Saylor James Cutler, their third child and only daughter arrived on November 23, 2015.

According to Sportskeeda, Jay Cutler started his NFL career in 2006 when he was drafted by the Denver Broncos. Three years later, he received an offer from the Chicago Bears, a team he played with for nine seasons. But Cutler wasn't just playing, there was something that kept him on the team — his impeccable skills. "I played 11 years. He's the best quarterback when it comes to accuracy, power, knowledge of the game. The best quarterback, hands down, that I played with," Devin Hester, one of Cutler's former teammates once told B/R Gridiron. However, despite his undeniable talent, Cutler's relationship with the team was not the smoothest, leading to his eventual release in March 2017, per ESPN. 

Kristin Cavallari and Cutler then decided it was time to move to leave the Windy City. "So we're moving from Chicago soon and I gotta say, I'm really gonna miss this place," Cavallari wrote in an Instagram post. "Thanks for all the good times, Chicago. This will always be a special place for us." 

Truly, Cutler and his family eventually moved to Nashville, but only a few months after, they went through another major change. In August 2017, Miami Dolphins struck a one year contract worth $10 million with Cutler, as reported by USA Today. This meant one thing — they had to relocate to Miami, yet Cavallari decided it was best to stay back in Nashville with the kids.

What is better than having an exciting life? Having an exciting life on TV! In April 2018, E! announced that "Very Cavallari," a new docu-series, was set to be released on the network in the summer of that year. Season 1 episode one of the show premiered on July 8, 2018, introducing us to Cavallari's life as a mother, a wife and an entrepreneur. But while the show was largely centered around Cavallari, Jay Cutler also made several appearances, eventually drawing in fans with his charm and wit.

Speaking to Page Six in March 2019, Cavallari could not help but gush about her husband whom she described as the breakout star of the show. "I think we both really like hearing that Jay is the breakout star!," Cavallari quipped. "I think for both of us it's been really nice to have people finally get to see his real personality and get to see how funny is because I mean that's why I love him. Because he's so funny."

By the end of its first season, it had become obvious that "Very Cavallari" was a success. Cutler went from being just an NFL star to being a modern day reality star. Sadly, fame comes at a price, and he and Cavallari soon realized that.

Rocky marriages are no news in the celebrity kingdom — we hear about it every other day. So when rumors started swirling that Kristin Cavallari and Jay Cutler were facing problems in their relationships, it was not so much of a surprise. Per People, Cavallari revealed in Season 3 of "Very Cavallari" that she had fallen out with her then-best friend Kelly Henderson.

The reason? There were rumors that Cutler had an affair with Henderson. It was, however, not the rumors itself that tripped Cavallari off — it was apparently how Henderson handled the situation. "When season two was airing, there was a lot of talk on social media about Jay and Kelly having an affair," Cavallari said in a January 2020 episode of "Very Cavallari" (via E!). "It wasn't the actual accusations of them having an affair that made me upset, it was how Kelly went about it." 

Despite these rumors, neither Cavallari nor Cutler came out to admit whether or not the affair happened. Henderson however seemingly had a lot to say in this regard. In an October 2020 appearance on the "Domenick Nati Show," the celebrity stylist alluded that Cavallari only fueled their rift to get more ratings on "Very Cavallari." "I got a text from her a week before filming started that she was upset with me," Henderson explained. "Unfortunately, I think it played into they needed a story line for a show."

Everything that has a beginning has an end — or so they say. In April 2020, 10 years after they first started dating and seven years after tying the knot, Jay Cutler filed for divorce from Kristin Cavallari, citing irreconcilable differences, per E!. The NFL star also cited April 21 — the same day he filed for divorce — as their official separation date. Cavallari soon fire back with a filing of her own, citing marital misconduct and irreconcilable differences, according to ET.

A few days later, Cavallari and Cutler confirmed their split in a joint statement released on Instagram. "With great sadness, after 10 years together we have come to a loving conclusion to get a divorce," they statement began. "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."

A source echoed similar thoughts to US Weekly, noting that, "There's nothing scandalous or suspect about their split." Going by this, it appeared the decision to split was mutual and there was no bad blood between the estranged couple — or so we thought.

According to People, Jay Cutler declared himself as a stay-at-home parent and the primary caretaker of his and Kristin Cavallari's kids in his divorce filing. To this effect, Cutler asked for joint custody — seemingly opting for a drama-free divorce process. Cavallari however had other plans. Negating claims that there was no bad blood between the estranged, ET reported that Kristin Cavallari asked for primary custody of the kids — a move that left Jay Cutler reeling. "Kristin filing for primary physical custody upset Jay," a source told the outlet. "He loves his children more than anything and thinks the couple should be reasonable and split custody."

Per People, the "Laguna Hills" star denied Cutler's claims of being the primary caretaker of their kids, adding that she was the "primary residential parent" for many years. She further requested that the NFL star be made to cover the children's medical expenses. A few days later, E! reported that Cavallari had filed yet another petition, this time accusing Cutler of denying her the funds to buy a new home. According to her, this was the NFL player's way of punishing her for not agreeing to his custody terms.

After weeks of going back and forth, Cutler and Cavallari reached a temporary custody agreement in May 2020 when they agreed to split time with the kids. According to Page Six, Cavallari was also granted access to the funds required to buy her new home.  

As with most celebrity divorces, Kristin Cavallari and Jay Cutler's split opened up a can of worms. Amid their divorce proceedings, a source revealed to Page Six that the pair's marriage might have come to an end because Cavallari was tired of watching the NFL star laze around the house. "She was growing increasingly impatient with him.  He was supposed to take this big job at Fox Sports and have a life after football that would get him up off the couch and do something," the insider revealed. "Instead, he backed out — this is [three] years ago — and joined the [Miami] Dolphins. That didn't pan out well, and he was left with no TV gig until she got the show for them." US Weekly, however, refuted these claims, with a source once again noting that the couple simply stopped loving one another.

Cavallari also implied this in an interview with People where she revealed that her marriage to Cutler had just stopped working. "We definitely kept a lot of stuff private," she said. "We tried really, really hard for years and years. It was the hardest decision I've ever made." The "Laguna Hills" star further admitted to still caring about Cutler, adding that because of their three kids, he would be in her life forever. 

In October 2020, TMZ reported that Kristin Cavallari had been caught locking lips with comedian Jeff Dye. Though Cavallari nor Dye confirmed if there was a romance brewing between them, an eyewitness confirmed to E! that the pair looked very much like they were together. "I saw Kristin yesterday afternoon. She was very smiley and giggly and walked right past me and my friends," the eyewitness explained. "She was definitely super flirty and giggly with him as they were walking."

Cutler was not very pleased to see Cavallari with another man amid their divorce, because, according to what a source told US Weekly, feelings towards Cavallari lingered. And perhaps to stir up some drama, the NFL player seemingly launched his own revenge move. According to Cosmopolitan, Cutler was spotted hanging out with Shannon Ford, a former cast member of "Very Cavallari," whom Cavallari fired from the show in Season 2. Whether or not this was a deliberate move, there is no denying that it did seem very shady at the time.

These days, Kristin Cavallari is seemingly single — having since split from Dye. And Cutler? US Weekly reports he is still has feelings for the reality star. "Jay is still very much hung up on Kristin," a source told the outlet. "He still has a lot of love for her and wishes things weren't as they are." Oh well, if only wishes were horses!