Playing The Field! Jay Cutler's Tumultuous Dating History With Famous Women: Photos

It seems Jay Cutler was not just a player on the football field!

The former Chicago Bears quarterback, 39, recently made headlines after reports surfaced that he was allegedly having an affair with a close pal's wife following his split from Kristin Cavallari in 2020.

"Jay went on vacation with his kids and his friend and his wife and their kids," a source dished to In Touch of the supposed tryst. "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."

KRISTIN CAVALLARI SAYS SHE & JAY CUTLER WERE 'CRAZY ABOUT EACH OTHER' BUT SHE 'DIDN'T WANT TO BE IN A TOXIC RELATIONSHIP ANYMORE'

On the other hand, the retired athlete — who shares Camden, 9, Jaxon, 8, and Saylor, 6, with the reality television mogul, 35 — has been known to not shy away from drama in the romance department.

From marrying Cavallari to getting himself wrapped up in a scandalous affair, Cutler has quite the history when it comes to his romantic life.

JANA KRAMER SAYS IT WAS 'HARD' BUMPING INTO EX MIKE CAUSSIN DURING NIGHT OUT WITH JAY CUTLER

Scroll through the photos below to see Jay Cutler's dating history:

Cutler and Cavallari met in 2010 after being set up through mutual pal Giuliana Rancic. The couple got engaged in April 2011 but split for a short period of time after.

After reuniting mere months later, the pair welcomed their first child, Camden, in 2012 and married in 2013. They welcomed son Jaxton in May 2014 and daughter Saylor the following year.

In 2020, the football player and the Very Cavallari star announced they were officially going their separate ways after the dissolution of their marriage was heavily featured on their E! show.

Following Cutler’s divorce, the father-of-three was linked to Southern Charm star Madison LeCroy in early 2021. In a weird turn of events, Cavallari was also spotted spending time with LeCroy’s ex Austin Kroll. However, the alleged relationship between LeCroy and Cutler turned sour after he accused her of speaking poorly about the mother of his children.

The blonde Bravo star shared alleged text messages between herself and Cutler on Instagram that mapped out the end of their romance. "I am disgusted by this whole situation. You reached out to me ... Your intentions may have not been pure but that may be you projecting. I've never said anything about Kristin nor would I. I came into this honestly with good intentions. I want no part of being involved in a payback or drama. But you initiated and pursued," LeCroy's message read.

The last sentence of the lengthy post was cut off by added text that read: "I kept my mouth shut until I get called a liar..."

Following her nasty split from husband Mike Caussin, Cutler briefly dated the country singer in 2021. But according to Kramer, the relationship was not super serious after splitting in October of that year.

“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,” Kramer said of their romance during a December 2021 episode of her "Whine Down" podcast.