Who Has Jay Cutler Dated? Everything to Know About His Love Life Before ‘Hooking Up’ With Good Friend’s Wife

While Jay Cutler has dated some beautiful women, Kristin Cavallari‘s ex-husband found a love interest a little too close to home. The former Chicago Bears quarterback was previously caught “hooking up” with a good friend’s wife while on a getaway with their families, multiple sources exclusively tell In Touch. Scroll down for everything we know and a look at his dating history.

Jay Cutler’s Alleged Affair With His Friend’s Wife

“Jay went on vacation with his kids and his friend and his wife and their kids,” a source tells In Touch. “The husband and Jay are good friends and also neighbors. Their kids are all friends. While they were on the trip, Jay was hooking up with his wife.”

When the husband “confronted” the pair, he came to learn that Jay and his wife had allegedly been “hooking up for a long time.” He then reached out to Kristin and told her about the situation, but the source said the Uncommon James founder “just wants to distance herself from all of this.”

In Touch reached out to all parties but did not hear back by the time of publication.

Who Has Jay Cutler Dated?

Jay’s longest and most high-profile relationship was with the former The Hills star Kristin. The pair were introduced in 2010 by mutual friend Giuliana Rancic. After a whirlwind romance, the couple got engaged in April 2011. Three months later the two abruptly split, only to get back together in November 2011.

The couple welcomed their first child, son Camden, in August 2012. Jay and Kristin became husband and wife in a romantic Tennessee wedding in June 2013. The newlyweds then expanded their family with the addition of another son, Jaxon, in May 2014 and daughter Saylor in November 2015.

Kristin and Jay announced their split in April 2020 after seven years of marriage, although they later made attempts to rekindle things. “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,” the reality star explained during Kaitlyn Bristowe‘s “Off The Vine” podcast in October 2021.

“And so, I just decided I didn’t want to be in a toxic relationship anymore and I had to break it off. But that’s made it hard and made me sit here and question it for a few months,” she continued, adding, “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.'”

Jay went on to be linked to Southern Charm star Madison LeCroy, though the romance was never confirmed. The retired athlete briefly dated country singer Jana Kramer in 2021.

“Obviously the whole Jay stuff, that became public because we went out and he was a very public person so obviously that came out, but I never spoke on it because I didn’t know what it was,” Jana explained during her “Whine Down” podcast in December 2021. “Just because I went on a date with someone doesn’t mean we’re exclusive and he’s my boyfriend,” she added. “He was never my boyfriend.”

Following the affair drama, romance rumors began swirling about the retired quarterback and Bachelor Nation alum Kelley Flanagan after they were photographed partying together at Tao Nightclub in Chicago.