Jay Cutler gets engaged to girlfriend Samantha Robertson

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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 with their relationship in September 2023, three years after Cutler and Kristin Cavallari announced that they would be getting a divorce.

Jay Cutler and Samantha Robertson attend Paramount Network’s
“Yellowstone” season 5B NYC premiere on Nov. 7, 2024 in New
York City. Getty Images for Paramount

Robertson, that September, shared a series of photos on Instagram from France that included Cutler, including with a caption that read: “Vive la France” before she shared a photo of the two in Montana.

The former Bears and Broncos quarterback shared his love for Robertson on Instagram in January when he shared a heartfelt photo on a beach with “Sam [heart] Jay” written in sand.

Earlier this month, the happy couple was in New York for the Season 5B premiere of the TV show “Yellowstone,” a few weeks after Cutler was arrested for DUI in Tennessee.

 “I do, of course, wish Jay nothing but the best, and I do hope that he gets the help that he needs, but that’s the only thing I will be saying about it publicly,” Cavallari said shortly after Cutler’s arrest on the “Let’s Be Honest” podcast.

Samantha Robertson with Jay Cutler in France last year. Instagram/samanthajrobertson

Cutler was together with Cavallari for 10 years and married for seven when the two got divorced in 2020.

Two years later, on an appearance on the “Call Her Daddy,” Cavallari said she was “thankful” for her time with Cutler and that he wished him the best in his romantic endeavors.

Jay Cutler and Kristin Cavallari attend the launch event for
“Uncommon James” at Fig & Olive on April 27, 2017 in West
Hollywood, Calif. Getty Images

“I hope that he finds someone, I really do,” Cavallari said then. “I want him happy. My kids benefit from that, you know. So I hope that he gets remarried.”

Cutler and Cavallari shared three children together: sons Camden, 12, and Jaxon, 10, and daughter Saylor, 8.

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