Jay Cutler is reportedly getting married again — two years after his divorce from Kristin Cavallari. The 41-year-old former Chicago Bears quarterback — who was arrested for a DUI in October ...

Olympia following his breakout performance at the Prague Pro. In a recent YouTube video shared on November 20, 2024, Jay Cutler and Milos Sarcev made their case for why this was the best look of ...

Kristin Cavallari is opening up about calling it quits with someone other than Jay Cutler. On Tuesday's episode of her "Let's Be Honest" podcast, the Uncommon James founder opened up about losing ...

Jay Cutler is putting a ring on it — again. The former NFL quarterback is getting engaged to girlfriend Samantha Robertson, People reported on Tuesday night. Cutler and Robertson went public ...

Samantha Robertson/Instagram Congratulations are in order for Jay Cutler and Samantha Robertson! The former Chicago Bears quarterback and mother-of-two are engaged, multiple sources close to the ...

The Very Cavallari star reflected on the demise of her relationship with former pal Kelly Henderson in 2020, revealing how Kelly’s interactions with her then-husband Jay Cutler created friction ...

Former NFL quarterback Jay Cutler throws out a ceremonial first pitch before the game between the Chicago Cubs and the Cleveland Guardians at Wrigley Field. / Matt Marton-Imagn Images Cutler and ...

Jay Cutler is engaged to Samantha Robertson, People reports. Multiple sources close to the couple told the outlet that the former Chicago Bears quarterback took the next step in his relationship ...

“I felt as though one of my best friends at the time, who was on the Very Cavallari show, I don’t think she ever had an affair with my ex-husband [Jay Cutler]. But the viewers of the ...