’36 Years Old and Just Had My First One Night Stand’: Jay Cutler’s Sobering up, While Ex-Wife and Mother Of Three, Kristin Cavallari Embraces Single Life

Former Chicago Bears quarterback Jay Cutler’s post football life hit some rough roads as he’s battled alcoholism and a failing marriage and probably some other challenges that NFL players deal with once they leave the gridiron for good. He and his ex-wife, reality television star Kristin Cavallari, divorced in 2022 after nearly a decade of marriage and three children together. After the split, Cavallari has not shied away from trying to find a spark again within the pro sports world. 

RELATED: Jay Cutler’s Ex-Wife Calls Their Marriage “Toxic, Period, End Of Story,” And He Responds

Jay Cutler’s Ex-Wife Kristin Cavallari Is Back Strong On Dating Scene

While Cutler has laid low since serving a four-day jail sentence in Franklin, Tennessee in September stemming from his October 2024 DUI arrest, his ex-wife is experiencing life as a single woman. Cavallari has been very active in pursuing new love interests, continuing her TV career and she’s also staying in the sports realm to find new dating partners. She’s not shy about having moved on. 

Back in April, Cavallari, 38, revealed she had a brief relationship with a former NHL player. Recent reports say she recently shared one date with Utah Jazz head coach Will Hardy some months ago, but ultimately there was no sustainable love connection between the Laguna Beach star and the 37-year-old rising coach.

“It was one date and that was it,” a source told  Us Weekly. “She never saw him again.”

Cavaliari’s glowing words about Hardy on  a previous episode of her podcast, suggests it could be something more, 

“He is represented by CAA. So am I. Our two agents made it happen,” she said. “He flew to Nashville, took me to dinner, such a great guy.”

“I know after the first date if I’m going to like someone or not,” Cavallari added. “I was trying to make it work, and I kept talking to him, and I was going to see him again and everything in me was telling me not to. When I’m out of alignment for what is meant for me, everything in my body screams at me. He is such a good guy. I enjoyed talking to him. … It just wasn’t right.”

Back In October, she began admitting to having one night stands, referencing one particular one in Spain that she had. 

“Im 36 years old and  just had the first one night stand of my entire.  life. It was in Miami I met a guy who just moved her from Spain. Had the best night of my life. It was so romantic and sweet. I was like I’m in love with this man and he’s in love with me. Then I came home and I said, “what am I doing? I have three kids. My life is stable and normal.” 

Fans React To Jay Cutler’s Wife Saying She Had First One Night Stand Of Her Life 

“Jay Cutler”s biggest win in his life was not on the football field. It was divorcing this crazy ass b**,” one fan said under the video. 

“First one night stand…that week,” quipped another fan. 

“Bro she’s been taking random D since Laguna Beach drama days ..,” recalled a third fan in response to Cavallari’s video. 

“Would be a great night, insane decision to marry her though,” one commenter posted on X. 

“She could definitely drive man to drink and smoke,” another fan captioned along with a graphic of Cutler smoking a cigarette while in uniform. 

Why Did Former NFL Star Jay Cutler and Reality Star Kristin Cavallari Divorce? 

Jay and Kristin announced their divorce in April 2020 in a joint statement on social media.

“With great sadness, after 10 years together we have come to a loving conclusion to get a divorce,” the two said.

However, Cavallari went on a podcast to air Cutler out and further explain why she had to separate from the former Chicago Bears quarterback.

“Basically, I called off the engagement [for] the same reason I got a divorce, and so I guess if there’s any takeaway from that is you can’t ignore red flags,” Cavallari said on an episode earlier this month of the “Call Your Daddy” podcast. “People don’t change, and you’ve got to trust your gut.”

Cavallari Says Marriage To Former NFL QB Jay Cutler Was ‘Toxic’

Cavallari has said that there wasn’t one thing that led her to file for divorce from the former NFL star. However, she said she was “really unhappy” with her “unhealthy relationship” with him and thought about her children; she didn’t want her children to believe that the energy in her marriage “was normal.”

“It was just time,” Cavallari continued. “Nothing major happened. At the end, it was just time. It’s the scariest thing. It’s always the saddest thing. I mean, it’s so many emotions, but it can also be the best thing. I’m very careful about what I say,” Cavallari said, adding that Camden even Googles his parents. “It was toxic, period, end of story. That’s all I need to say.”

Cutler Responded to Cavallari’s Accusations Of Toxicity In Marriage

Cutler heard the noise and responded that he doesn’t like his marriage playing out in public over social media. 

“I’ve kind of steered clear of all of that,” Cutler said to Sofia Franklin on her podcast, “Sofia with an F.”

The once-happy couple were married from 2013 to 2020, and they have three children: sons Camden, 12, and Jaxon, 11, and daughter Saylor, 9. The two mutually agree that their children are the main priority.

“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,” Cutler continued. “If that’s the way she feels, but I also don’t understand,” he continued.

Cutler described his ex-wife as a clout chaser and says he celebrated when the divorce went through.

“When the settlement came through, I threw a party,” a laughing Cutler said during a conversation with Clay Travis on the latest episode of his “Uncut with Jay Cutler” podcast. “I don’t recommend divorce for anybody, let me go ahead and say that,” Cutler said. “It’s true and funny and it is what it is. It is a happy ending,” Cutler said. “Kristin got what she wanted. I won on the other side of it, so it is what it is. Everybody wins.”

What’s Good With Jay Cutler? 

Despite the blame throwing, it’s clear that it was time for the couple to separate. Cutler also has to take control of his life once and for all. Cutler, who played for the Denver Broncos, Chicago Bears and Miami Dolphins during a 12-year NFL career between 2006-17, was originally charged with driving under the influence, reckless driving that caused a crash, violating implied consent laws, and possessing a firearm while intoxicated.

Police found a loaded gun in his vehicle during the traffic stop. In addition to the public humiliation, the 2008 Pro Bowler also had his license suspended for one year, was smacked with a $350 fine and was assigned one year of unsupervised probation and mandatory DUI safety classes. When Cutler pleaded guilty to the DUI charge and the brief jail stint, prosecutors dropped the firearms charges.

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