Jay Cutler’s Dating History Is Star-Studded! From Kristin Cavallari Marriage to Jana Kramer and More

Kristin Cavallari

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, they 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 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. 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.'”

Madison LeCroy

Jay was briefly linked to Southern Charm star Madison LeCroy at the beginning of 2021. They reportedly had a fling after spending some time together at the end of 2020.

Although the relationship was never confirmed, Madison posted “receipts” on her Instagram Story in January 2021 in the form of alleged text messages between herself and the former NFL star. The alleged texts showed the two making plans to meet up and Madison defending herself after Jay accused her of talking badly about Kristin.

Jana Kramer

Jay briefly dated 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.”

An Alleged Affair

In 2022, In Touch exclusively reported that Jay was caught “hooking up with his good friend’s wife” on a family vacation.

“Jay went on vacation with his kids and his friend and his wife and their kids,” a source confirmed. “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.

Kelley Flanagan

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.

Samantha Robertson

Samantha and Jay went Instagram official with their relationship in September 2023. As Life & Style exclusively reported, the two were “close friends for years” before getting together romantically.

Like Jay, Samantha is a parent. She has two children with her ex-husband Juan Trace Ayala. Before the former pro athlete got together with Samantha, their families “hung out and even vacationed together,” according to the source.

“It’s only been a few months,” the insider added in October 2023. “But they’re already pretty serious.”