Kristin Cavallari and Jay Cutler’s Relationship Timeline

Kristin Cavallari and Jay Cutler were married for nearly seven years.

The exes met in 2010, and Cutler popped the question in 2011. They called their engagement off after three months but quickly reconciled. Cavallari and the former Chicago Bears quarterback went on to welcome their first child in 2012 before tying the knot in 2013. Two more children followed and the family settled down in Nashville.

While it may have seemed like Cavallari and Cutler were the picture-perfect couple, they were privately dealing with marital issues that led to their split in 2020.

“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 Uncommon James founder wrote on Instagram. “This is just the situation of two people growing apart.”

From welcoming three kids together to going their separate ways, here is a complete timeline of Kristin Cavallari and Jay Cutler’s relationship.

2009: Jay Cutler asks Kristin Cavallari out on a date

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In a 2013 A Drink With interview, the Uncommon James founder revealed that the first time Cutler asked her out, she wasn’t interested.

“I got a call from my publicist that Jay wanted to fly me out to Chicago and take me out,” she said. “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.”

2010: Kristin Cavallari and Jay Cutler meet for the first time and begin dating

One year later, the Laguna Beach alum and Cutler finally met while she was visiting Chicago with her mother.

“We ended up going to a pre-season game,” she said on A Drink With. “I had forgotten all about it and my mom said, ‘Didn’t Jay Cutler ask you out?’ 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.”

In her 2016 book, Cavallari said that she and Cutler quickly began dating, with the reality star flying “back to Chicago at least every two weeks.”

“When we were apart, we texted constantly, and he wrote me the sweetest love emails,” she wrote. “He was the strong, manly man I wanted but had a sweet, romantic side as well.”

April 2011: Kristin Cavallari and Jay Cutler get engaged

JB Lacroix/WireImage

After eight months of dating, Cutler proposed to Cavallari while on vacation in Mexico. A source close to the couple confirmed the news to PEOPLE, saying: “He surprised her with a quick trip to Cabo to ask her to marry him.”

“I’m in love and it’s been great,” Cavallari had previously told PEOPLE in January 2011. “Things are really good.”

July 2011: Kristin Cavallari and Jay Cutler split

Three months later, the couple called off their engagement. “She got dumped,” a source told PEOPLE. “She’s absolutely devastated. She can’t believe this is happening.”

The sourced continued, “She was planning her dream wedding, the date was set, the location — everything was set …. She’s in shock that the dream wedding she was planning is going to end this way.”

While at the time it was said that Cutler broke up with Cavallari, she later clarified that this wasn’t the case. “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.

Cavallari also said one of their main issues was that Cutler “envisioned himself being the sole breadwinner and his wife staying at home.”

September 2011: Kristin Cavallari and Jay Cutler begin repairing their relationship

After spending the summer apart, a source told PEOPLE that Cavallari and Cutler were “working it out.”

“They’re not officially back together but they’re definitely talking and figuring things out,” the source said. “Everything happened too fast when they first got together. So this time they’re taking things slow.”

October 2011: Jay Cutler supports Kristin Cavallari at Dancing with the Stars

Brian Babineau/Getty

The following month, Cutler was spotted in the audience during Cavallari’s performance on Dancing with the Stars. PEOPLE reported that the athlete was smiling and clapping as his former fiancée danced with partner Mark Ballas to “Crazy in Love” by Beyoncé.

November 2011: Kristin Cavallari and Jay Cutler get back together

Cavallari and Cutler’s breakup didn’t last long. Four months after the couple split, the reality star shared in November 2011 that they were not only back together, but the engagement was back on.

“This time it’s official,” she wrote on Twitter. “Jay and I are engaged again :)”

January 2012: Kristin Cavallari and Jay Cutler announce they are expecting their first child together

Jeff Schear/Getty

Shortly after reconciling, Cavallari and Cutler revealed 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 couple shared with PEOPLE exclusively.

August 2012: Kristin Cavallari and Jay Cutler welcome their first child

Later that year, the couple announced the birth of their son.

“We are thrilled to welcome Camden Jack Cutler into the world,” Cavallari wrote on Twitter on Aug. 8, 2012. “He was born this morning weighing 7 lbs., 9 oz. Everyone is doing great!”

June 7, 2013: Kristin Cavallari and Jay Cutler get married

Todd Williamson/Getty

On June 7, 2013, Cavallari and Cutler were married in Nashville, where their 10-month-old son Camden was the ring bearer. “Im officially Kristin Elizabeth Cutler!!!!!” Cavallari tweeted after the celebrations along with a photo of their rings.

“The flowers and everything were very simple but it was very warm and cozy,” she later told PEOPLE. “It was all about the lighting and the candles and the atmosphere was just so warm. It was absolutely perfect.”

Oct. 30, 2013: Kristin Cavallari and Jay Cutler announce they are expecting their second child

Just a few months after getting married, the couple shared that they had another baby on the way.

“Thank you for all the love!! We are so excited for Camden to be a big brother!” Cavallari wrote on Twitter.

She later revealed that they were expecting a baby boy. “We decided to announce that we’re having another boy!!” the reality star shared on Instagram. “We couldn’t be more excited!”

May 7, 2014: Kristin Cavallari and Jay Cutler welcome their second child

Cavallari announced the birth of her second son by sharing an Instagram photo of her hospital bracelet perched on top of a baby hat and booties. “Welcome Jaxon Wyatt Cutler 7 lbs., 11 oz. 5/7/14,” she wrote in the caption.

May 10, 2015: Kristin Cavallari and Jay Cutler announce they’re expecting their third child

Jason LaVeris/Getty

On Mother’s Day in 2015, Cavallari announced that she and Cutler were expecting their third child.

“We’re at it again! Thrilled to announce baby number 3 is on the way!” she shared in a post on the Kristin Cavallari Official app. “The Cutler crew just keeps on growin’!”

In July, Cavallari revealed that she was having a daughter. “The boys are so excited for a little sister!!!!!! 🎀” she said on Instagram, sharing a black-and-white photo of herself holding a pair of pink baby sneakers as she and Cutler embrace.

Nov. 23, 2015: Kristin Cavallari and Jay Cutler welcome their third child

“Saylor James Cutler was born today at 1:32 p.m.,” Cavallari announced via Instagram on Nov. 23, 2015.

The star previously told PEOPLE that she and Cutler had picked out the name Saylor when she was pregnant with their first child. “I met a woman and her dog, and I loved her dog’s name,” she said. “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.”

June 8, 2016: Kristin Cavallari and Jay Cutler celebrate their three-year wedding anniversary

Kristin Cavallari Instagram

In celebration of three years of marriage, Cavallari shared a photo of herself and Cutler on Instagram. “Happy anniversary to my man! I truly love him more and more everyday and there’s no one else I would rather be on this wild ride with #Sober #JayDoingHisBestBlueSteel,” she wrote in the caption.

Cavallari also shared a scenic photo from the couple’s honeymoon in Italy. “Jay took this picture on our honeymoon 3 years ago when we were up in a hot air balloon,” she wrote. “We went over Tuscany early in the morning and it was one of the most beautiful and memorable things I’ve ever done.”

March 20, 2017: Kristin Cavallari and Jay Cutler announce they are leaving Chicago

Following Cutler’s departure from the Chicago Bears and his retirement from football, Cavallari shared that the couple and their children were planning to leave the city.

“So we’re moving from Chicago soon and I gotta say, I’m really gonna miss this place,” she wrote on Instagram. “Not only we’re all 3 of my babies born here, it’s where it all began with jay … thanks for all the good times, Chicago. This will always be a special place for us.”

A few days later, a source confirmed to PEOPLE that the couple was planning a move to Nashville.

“It’s where Jay went to college and he’s got lots of friends there,” the source said. “Nashville has a special place in her heart as it’s where she got married.”

March 2017: Kristin Cavallari and Jay Cutler vacation in Mexico

While vacationing in Tulum, Cavallari shared several Instagram photos of the couple’s romantic getaway — including one that caused a bit of controversy.

​​”‘Good times, no tan lines. Let the sea set you free,'” Cavallari captioned a now-deleted photo of a nude Cutler looking out over the ocean.

Later, in an interview with Access Hollywood, Cavallari said that she and Cutler “were just being silly,” while also clarifying that she had her husband’s OK to post the picture.

“I mean, Jay was feelin’ it, so I just decided to post a picture,” she said. “I did ask him if I could. I want to clear that up.”

August 2017: Kristin Cavallari celebrates Jay Cutler’s return to the NFL

Kristin Cavallari Instagram

Three months after he announced his retirement, Cutler made his official return to the NFL — signing a one-year, $10 million contract with the Miami Dolphins.

Cavallari congratulated her husband on Instagram and captioned a photo of the couple, “And he’s off … but this time as a dolphin 🐬 so excited for my man on this next journey #MiamiDolphins.”

January 2018: Kristin Cavallari and Jay Cutler say farewell to Florida

Following the end of Cutler’s one-year contract with the Miami Dolphins, Cavallari shared that the family would be leaving Florida.

“The end of another chapter,” she captioned a photo of the couple kissing on the beach. “Feeling very grateful for the past few months.”

“Thank you @miamidolphins for taking such great care of me and my family,” she continued. “Back home and this time we took Jay with us 💛.”

July 2018: Kristin Cavallari says she and Jay Cutler are done having children

In July 2018, Cavallari told PEOPLE Now that she and Cutler were not planning on having more kids and that her family felt complete. “I love having three kids,” she said. “I especially love having two boys and a girl — we feel like a very complete family. We’re good, we’re done.”

“My daughter is 2½ and I don’t have to lug around a diaper bag anymore and all the crap,” she continued. “We’re finally at a really good place where we can just pick up and go.”

January 2020: Kristin Cavallari addresses rumors that Jay Cutler cheated

On the season 3 premiere of her E! reality show, Very Cavallari, the star revealed that she and her best friend Kelly Henderson had a falling out over a rumor that Henderson and Cutler were having an affair.

“When season 2 was airing, there was a lot of talk on social media about Jay and Kelly having an affair,” Cavallari said in a confessional during the episode. “Not for one second have I ever thought that it was true. It wasn’t the actual accusations of them having an affair that made me upset, it was how Kelly went about it.”

March 2020: Kristin Cavallari says Jay Cutler has been her “constant” in hard times

Kristin Cavallari and Jay Cutler.
Timothy Hiatt/Getty

In a season 3 episode of Very Cavallari, the star reflected on her relationship with Cutler.

“It’s been a bit of a rocky year,” she told Cutler as they sat down to dinner. “I feel like the older you get, the more you realize who is supposed to be in your life. You figure out who your real friends are — friends come and go. It’s nice that I have you as my constant. You’re my common denominator.”

April 26, 2020: Kristin Cavallari and Jay Cutler announce they are divorcing

After a decade together, Cavallari and Cutler shared that they were ending their marriage in April 2020.

“With great sadness, after 10 years together we have come to a loving conclusion to get a divorce,” Cavallari wrote on Instagram alongside a photo of the pair walking together with their backs turned to the camera.

“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,” she continued. “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.”

In the divorce filing obtained by PEOPLE, Cavallari cited both “irreconcilable differences” and “inappropriate marital conduct” as grounds for the split, whereas Cutler only cited “irreconcilable differences.” Cavallari also petitioned for full custody of their three children, seeking to be designated “the primary residential custodian” of their kids, with “reasonable periods of parenting time” for Cutler.

May 2020: Kristin Cavallari and Jay Cutler reach joint custody agreement

Amid their divorce proceedings, Cavallari and Cutler agreed to be named “joint primary residential parents,” each spending 182.5 days with the kids a year and dividing up the holidays, according to documents obtained by PEOPLE.

The documents also stated that Cutler agreed to release funds that allow Cavallari to purchase her own home after closing on their property in Nashville.

June 22, 2020: Kristin Cavallari and Jay Cutler celebrate Father’s Day together

Kristin Cavallari Instagram

Shortly after filing for divorce, Cavallari shared a Father’s Day tribute to Cutler on Instagram.

“Happy (late) Father’s Day to Jay,” she captioned a photo of her three children watching the former NFL player from the sidelines. “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.”

Sept. 23, 2020: Kristin Cavallari opens up about her divorce from Jay Cutler

In an exclusive interview with PEOPLE, Cavallari shared that she and Cutler had been struggling privately for years.

“I always thought it was interesting when people would refer to us as ‘couple goals,'” she said. “I was like, ‘If you guys only knew.’ ”

The star couldn’t point to one specific issue within their marriage; rather, she chalked it up to growing apart.

“I met Jay when I was 23. I was a baby,” she explained. “Jay and I had so much love for each other, but we grew up.” She added, “When you work at something for so many years and nothing’s changing, I think you have to just make a decision. We all want to be happy.”

Jan. 22, 2021: Kristin Cavallari and Jay Cutler reunite on Instagram

In matching Instagram posts that have since been deleted, Cavallari and Cutler shared a photo of themselves smirking at the camera.

“The world is full of users. 10 years. Can’t break that,” both captions read.

Aug. 25, 2021: Jay Cutler discusses dating again

On the first episode of his podcast Uncut with Jay Cutler, the former NFL quarterback spoke about getting back into the dating scene following his divorce from Cavallari. He admitted that a lot has changed since he was last single and said he is in “no rush” to start dating again.

“There are a lot of other aspects that have to be taken into consideration whenever you get back out into that world and the whole landscape has changed,” he explained. “There are apps, there’s Twitter, there’s Instagram, it’s a whole different ball game. You’re not just walking into a restaurant or bar and talking to somebody. That doesn’t exist anymore.”

He added, “I’m at a different phase of my life now with kids. Priorities have just changed. It isn’t just a purely selfish play by my part.”

October 2021: Kristin Cavallari calls her divorce “probably the best decision I’ve ever made”

During an appearance on Kaitlyn Bristowe’s podcast Off The Vine, Cavallari opened up about her divorce and called it “the brightest and saddest” time of her life. She also revealed that after the split, she and Cutler went on a few dates to try to work it out again. However, Cavallari broke it off and is confident she made the right decision.

“The thing with Jay is, we aren’t getting our divorce because of love lost, which made it really challenging because we were crazy about each other,” she explained. “And so I just decided I didn’t want to be in a toxic relationship anymore and I had to break it off.

She continued, “But that’s made it hard and made me sit here and question it for a few months. But then going back and dating him a little bit made me reaffirm it like, ‘No, I know that I’m doing the right decision.’ ”

June 29, 2022: Kristin Cavallari talks life post-divorce

While appearing on The School of Greatness podcast, the mom of three discussed what life has been like since her split from Cutler and her newfound happiness.

“The scariest thing that I’ve ever done is get a divorce,” she told host Lewis Howes. “But it’s been the best thing that I’ve ever done and that has really jump-started my journey on self-love and figuring out who I am now.”

Cavallari added that she is in a “a really peaceful place. I feel the best I’ve ever felt in my whole life. I’m the happiest I’ve ever been. I’m no longer afraid of getting hurt.”

The Hills alum also feels hopeful about finding love again in the future. “I’m actually excited to see who I can be in a new relationship because I feel like I’ve done so much work the last few years,” she said. “I’m in no rush to be in a new relationship, but when I am, it will excite me to see how different I can be.”

August 2022: Kristin Cavallari says she hopes Jay Cutler gets remarried

In August 2022, Cavallari appeared on an episode of the Call Her Daddy podcast and admitted it took her “a few years to actually pull the trigger” and end her marriage with Cutler.

“It was toxic. I think period, end of story. That’s all I kind of need to say,” she shared, before adding that she still chooses her words carefully when talking about Cutler.

“Because I have three kids with him, I’m very careful about what I say. If you and I didn’t have microphones in front of us, I’d f—ing tell you but you know, that’s their dad and my oldest Googles us now, and I just want to be very careful,” she explained. “My mom never said anything bad about my dad growing up and I really respected that, and I want to be that kind of mom.”

August 2022: Jay Cutler responds to Kristin Cavallari’s claim their marriage was “toxic”

After Cavallari called her marriage to Cutler “toxic,” the former athlete went on the podcast Sofia with an F and called his ex-wife’s claims “comical.”

“If she wants to say stuff, she can say stuff. I’m not going to go down that road about her. I mean, she’s still the mother of my kids.”

“But I also don’t understand,” he later added. “It’s two and a half years (since the marriage ended). Why are we having these conversations?”

January 17, 2023: Kristin Cavallari says she doesn’t want to date another athlete

Cavallari opened up about dating athletes during an episode of her Dear Media podcast, Back to the Beach. “Here’s my deal. I dated a hockey player. For me, now in my life where I’m at, it’s more about schedules,” The Hills alum explained. “So baseball, they’re gone all the time. Basketball, they’re gone all the time. Football’s reasonable. Hockey, they’re gone a lot, but it’s doable.”

“To be honest — I don’t want to say anything I’m going to end up regretting — but I don’t think I want to date another athlete,” she added. “I’ve done that. I want to leave that in the past.”

April 19, 2023: Kristin Cavallari opens up about her dating life after her divorce from Jay Cutler

Cavallari spoke about her post-divorce dating life during an appearance on The Jennifer Hudson Show. The reality star explained that while she is dating again, she doesn’t want to discuss her romantic life in-depth yet.

“I just have taken a stance that until I’m in a serious, committed relationship, there’s nothing to really report,” Cavallari told Jennifer Hudson.

Still, it seems Cavallari is enjoying the single life. “This is the first time in my life I’ve really dated,” she explained. “I’ve always had boyfriends, I got married very young, so I am just enjoying it.”

June 21, 2023: Kristin Cavallari opens up about why dating isn’t a priority

Alberto Rodriguez/Variety via Getty Images

During an interview with E! News, Cavallari said that dating is “not important to me right now,” noting that she’s a mom “first and foremost.”

However, when she does date, the reality star said that she prefers to make connections in person rather than on dating apps or online. “Anyone can be great on paper, and you gotta have that chemistry,” she said. “I want to meet someone organically.”

September 20, 2023: Jay Cutler and girlfriend Samantha Robertson make relationship Instagram official

Jay Cutler and Samantha Robertson.

Samantha Robertson Instagram

The pair made their relationship Instagram official when Robertson posted photos from a trip to France with Cutler. A few days later, she shared a cozy image of the couple in Montana.

February 27, 2024: Kristin Cavallari and boyfriend Mark Estes debut their relationship

Kristin Cavallari/ Instagram

Cavallari debuted her relationship with Mark Estes, 24, on Instagram. “He makes me happy,” she captioned a selfie of the couple from their romantic getaway in Cabo, Mexico.

According to a source, the reality star and former college football player have been “dating longer than people think.”

The insider added: “They’re really happy together. He’s been so great to her and is just a really nice guy. He’s not your typical 24 year old. She’s having a great time and is living her best life with him.”

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