The Athlete Lifestyle logo

NFL alum Jay Cutler reportedly engaged 2 years after Kristin Cavallari divorce

Sophie Hessekiel

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.
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
In this story:

Retired Chicago Bears quarterback Jay Cutler is reportedly tying the knot! People has reported that sources close to the 41-year-old athlete, who officially divorced from The Hills star Kristin Cavallari in 2022, have confirmed his engagement to aspiring actress and influencer Samantha Robertson.

Cutler and Robertson have been dating for at least a year. The couple “hard launched” on Instagram in September 2023, when Robertson shared a picture of them in front of a sunset. “Sunsets in Montana never disappoint,” Robertson wrote in the caption.

Cutler and Robertson each have kids from their previous marriages. Cutler and Cavallari share Camden, 12, Jaxon, 10, and Saylor, 8. Robertson, who was previously married to actor Trace Ayala, shares two daughters, Sophie and River, with him.

Cutler shared a photo on his Instagram from the season 5B premiere of Yellowstone, which he attended with Robertson, on November 7. Many followers noted that Robertson was sporting an engagement ring.

This happy announcement was likely a welcome change for Cutler, who was arrested in October for driving under the influence of alcohol and illegal possession of a firearm.

Cutler and his team have not yet publicly confirmed the engagement.

— Enjoy free dish of rich and fabulous players with The Athlete Lifestyle on SI —

Super fans: Russell Wilson’s wife Ciara stuns with GloRilla after Steelers win

Terrible… not: Livvy Dunne’s perfect Steelers fit outshines bf Paul Skenes at game

Oopsie: Britney Mahomes’ penalty-worthy playground fail with her kids

Hook ‘em: Loreal Sarkisian rocks leather and lace ‘game plan’ fit for Longhorns

Disappearing act: ESPN’s Molly Qerim’s fit goes missing in UFC 309 busy backdrop

Published
Sophie Hessekiel
SOPHIE HESSEKIEL

Home/Relationships