Here is Jay Cutler's dating history over the years

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. While he is still in the midst of this "scandal", I thought it would be interesting to look back at his previous romances.

JANA KRAMER

Jana Rae Kramer is an American country music singer and actress. She is known for her role as Alex Dupre on the television series One Tree Hill. According to USWeekly, the ex NFL quarterback and the actress split after they were first spotted on a date together in September.

Here is one of their pictures:



TOMI LAHREN

While the relationship was never truly confirmed, it was pretty clear that they dated. Tomi went to the University of Nevada, Las Vegas and graduated in 2014 with a BA in broadcast journalism and political science. Although, oddly enough, she doesn't refer to herself as a journalist; she likes to call herself a commentator. She's widely known for her political views, and describes herself as a «constitutional conservative.» She can currently be seen on FOX Nation hosting her own show called First Thoughts, which is a play off of her «final thoughts» segments she'd end with on her previous shows. She's also a part of FOX News as a contributor, and has been there since August 2017.

Here is one of their pictures:


Kristin Cavallari

From a broken engagement to three beautiful children, Kristin Cavallari and Jay Cutler's relationship has had its share of curveballs, culminating in their April 2020 split. They were married for a few years. The relationship was filled with extreme ups and downs.

Here is one of their pictures:


MADISON LECROY

She is a reality TV star. LeCroy made her debut on Southern Charm during season 6, which aired in 2019, after she began a relationship with cast member Austen Kroll. LeCroy made headlines in January 2021 after she sparked romance rumors with Jay Cutler amid his divorce from Kristin Cavallari.

Here is one of their pictures: