While Kristin Cavallari’s ex-husband has dated some stunning women, his love interest was a little too close to home.

Jay Cutler has dated some gorgeous women. According to multiple sources exclusively speaking to In Touch, the former Chicago Bears quarterback was previously discovered “hooking up” with a close friend’s wife while on vacation with their families. View his dating profile and learn everything we know by scrolling below.

Alleged Relationship Between Jay Cutler and His Friend’s Wife

According to a source who spoke to In Touch, “Jay went on vacation with his kids and his pal and his wife and their kids.” The husband and Jay live nearby and are close friends. All of their children get along. Jay was having sex with his wife on their journey.

The husband was informed that Jay and his wife had supposedly been “hooking up for a long time” when he “confronted” the couple.

After that, he spoke with Kristin and informed her of the circumstance, but the source claimed that the creator of Uncommon James “simply wants to disassociate herself from all of this.”

All parties were contacted by In Touch, but no response had been received by the time of publication.

Related: Who Is Julie Bowen’s Boyfriend 2022? Is she dating someone?

Who Has Dated Jay Cutler?

The longest and most well-known relationship of Jay’s was with Kristin, a former cast member of The Hills. In 2010, a mutual acquaintance, Giuliana Rancic, introduced the two. After a brief courtship, the pair announced their engagement in April 2011. Three months later, they abruptly broke up before reconciling in November 2011.

kristin cavallari dating history

Son Camden, the couple’s first child, was born in August 2012. In June 2013, Jay and Kristin exchanged vows in a charming Tennessee ceremony. After being married, the couple added another boy, Jaxon, in May 2014, and a daughter, Saylor, in November 2015.

After seven years of marriage, Kristin and Jay announced their separation in April 2020, despite subsequently attempting to patch things up. The reality star said on Kaitlyn Bristowe’s “Off The Vine” podcast in October 2021, “The problem with Jay is, we aren’t getting our divorce because of love lost, which made it extremely tough since we were crazy about each other.”

So I made the decision to end the relationship since I didn’t want to be in a poisonous one any longer. But that’s made it difficult, and for a few months, I sat here and wondered if I was making the right decision.

But after I went back and started dating him again, though, I was able to reinforce my decision, saying, “No, I know that I’m doing the right thing.”

Madison LeCroy, who stars in Southern Charm, was later linked to Jay, however, their relationship was never verified. In 2021, the retired athlete had a brief relationship with Jana Kramer.

During her “Whine Down” podcast in December 2021, Jana said, “Obviously the whole Jay issue, it became public because we went out and he was a pretty famous person so obviously that came out.

jay cutler dating

But I never spoke about it because I didn’t know what it was.” She continued, “Just because we went on a date doesn’t imply we’re exclusive or that he’s my boyfriend. Never was he, my boyfriend, I said.

Following the hoopla surrounding the affair, romance rumours started to circulate about the former quarterback and Bachelor Nation alum Kelley Flanagan when they were spotted having fun together in Chicago’s Tao Nightclub.

Jay Cutler Says Dating Is “difficult” Since Kristin Cavallari’s Divorce:

Former NFL quarterback Jay Cutler also discussed the qualities he is seeking in a lady as he joins the dating scene in his debut podcast episode.

Both Kristin Cavallari and Jay Cutler are still single and available more than a year after they announced their divorce following a decade of marriage. And if you believed that dating was easy for a former professional athlete, Jay has some news for you.

He admitted on his brand-new Uncut With Jay Cutler podcast that “it’s really hard as heck.” “Making friends is difficult. Finding out what people truly want from you, I believe, is probably a problem. With kids, I’m in a different stage of life now. The top priorities have shifted. It’s not just me being entirely self-serving here.”

The previous quarterback for the Chicago Bears continued, “When you return to that world and notice that the entire landscape has altered, there are many other factors that must be taken into account.

There are apps, Twitter, Instagram, and other services; it’s a completely other game. You’re not just going into a pub or restaurant and striking up a conversation with someone. That is no longer a thing.”

With Kristin, Jay has three children: Camden, 9, Jaxon, 7, and Saylor, 5. Peaceful parenting is crucial to both parties, as they have already stated.

The sportsman earlier told E! News about his co-parenting experience, “It’s good.” “Kids are tough, I mean. We’ve done a terrific job of prioritising kids over school and all the other activities.”

During the premiere of his new PodcastOne show, Jay also discussed his ideal next date. His response could astound you.

jay cutler dating

I’m not sure about that, he said. “Sincerely, I don’t know. How I wish I did. Throughout this process, I guess I’ve been attempting to sort things out, but I will. I’m not in any particular hurry right now.”

In addition, Jay has already encountered one issue when socialising in Nashville, his hometown. Every time he spends time with a woman, romance rumours begin to circulate.

Related: Kristin Cavallari’s Dating History: Ex-Boyfriends and More

After spending a chill evening out in September, Jay addressed rumours that he might be dating Fox Nation’s Tomi Lahren. He joked on Instagram while brushing one of the animals on his ranch, “Only lady in my life.” “Internet, be better.” His relationship—or lack thereof—with Madison LeCroy of Southern Charm also garnered media attention.

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