Jay Cutler has been with some very pretty women, but Kristin Cavallari’s ex-husband has found love a little too close to home. The former quarterback for the Chicago Bears was caught “hooking up” with a good friend’s wife while their families were on vacation.
Scroll down for a look at his past relationships as well as everything else that we know.
Is Jay Cutler Dating His Friend’s Wife?
It’s not going well. Jay Cutler was caught “hooking up” with the wife of a good friend while they were on a family vacation, and the woman’s husband knows about it, according to multiple sources.
According to a source for In Touch magazine, “Jay went on vacation with his kids as well as his friend and his wife and their kids.” “The husband and Jay have been friends for a long time and also live in the same neighborhood. The children of both families get along well. During the time that they were away, Jay was having sexual relations with his wife.
When the husband “confronted” the couple, he discovered that his wife and Jay’s wife had supposedly been “hooking up for a long time” before the husband found out about it. After that, he contacted Kristin and informed her about the incident; however, the source stated that the founder of Uncommon James “simply wants to separate herself from all of this.”
Kristin, 35, and Jay, with whom she has three children, Camden Jack, Saylor James, and Jaxon Wyatt, will end their 10 years of marriage in April 2020.
In her divorce filing that month, Kristin said that Jay’s “inappropriate marital behavior” made it unsafe and wrong for them to live together anymore. She also said that they had “irreconcilable differences” that led to their breakup.
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Jay Cutler’s Dating History
Kristin, who used to be on The Hills, was Jay’s long-term and most famous girlfriend. In 2010, their friend Giuliana Rancic brought them together. In April 2011, the couple got engaged after a quick courtship. After three months, they broke up all of a sudden, but they got back together in November 2011.
In August 2012, they had their first child, a son named Camden. In June 2013, Jay and Kristin got married in a beautiful ceremony in Tennessee. The couple’s family grew when they had another son, Jaxon, in May 2014 and a daughter, Saylor, in November 2015.
Kristin and Jay broke up in April 2020, after being married for seven years, but they tried to get back together later. “The thing with Jay is that we aren’t getting a divorce because we lost love,” the reality star said on Kaitlyn Bristowe’s “Off The Vine” podcast in October 2021. “That made it really hard because we were crazy about each other.”
“So, I just decided that I didn’t want to be in a bad relationship anymore, so I ended it. But that made it hard, and I sat here and questioned it for a few months,” she said. “But when I went back and dated him for a little while, it made me realize that I was making the right choice.
After that, Madison LeCroy, who is on the show Southern Charm, was said to be dating Jay, but this was never proven. In 2021, the retired athlete went out with country singer Jana Kramer for a short time.
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“Obviously, all the Jay stuff got out because we went out and he was a very public figure, but I never talked about it because I didn’t know what it was,” Jana said on her podcast “Whine Down” in December 2021. “Just because I went on a date with someone doesn’t mean we’re exclusive and he’s my boyfriend,” she said. “We were never dating.”
After the drama with the affair, there were rumors that the former quarterback and Bachelor Nation alum Kelley Flanagan were dating after they were seen having fun together at a Chicago nightclub.
Kristin Cavallari Calls Marriage To Jay Cutler ‘Toxic’ And ‘Unhealthy’
In a new “Call Her Daddy” podcast episode, Cavallari tells people to pay attention to their gut feelings.
The reality star and athlete who used to be together got engaged in 2011. They broke up for a short time, then got back together, had their first child, and got married all within two years.
Cavallari says, “I called off the wedding for the same reason I ended my marriage… If there’s one thing to learn from this, it’s that you can’t ignore warning signs. People are the same. And, you gotta trust your gut.”
Cavallari said on the podcast, “I watch what I say around him because I have three kids with him… My oldest son now googles us.”
But Cavallari did have one thing to say. “It was toxic. I think period, end of story.”