Jay Cutler Is Reportedly Engaged One Month After DUI Arrest

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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— is engaged to girlfriend Samantha Robertson, sources claimed to People in a report published on Tuesday, November 19.

The news comes after Robertson was seen wearing what appeared to be an engagement ring at the Yellowstone season 5B premiere on November 7.

Jay Cutler
Former Chicago Bears quarterback Jay Cutler stands on the field prior to the game between the Chicago Bears and the Green Bay Packers at Soldier Field on September 05, 2019 in Chicago, Illinois. In November... Nuccio DiNuzzo/Getty Images

The couple went Instagram official with their relationship in September 2023 with a series of photos from a wedding in Paris, France. Cutler and Robertson cuddled up together in a few pictures amid a carousel of images from the nuptials as well as sightseeing in France.

"Vive la France 🇫🇷Congratulations @chanelhandel @amackenzietemplar. The most beautiful wedding ❤️," Robertson captioned the Instagram post. Less than one week later, the hunting enthusiast followed that up with another post featuring the former NFL player. "Sunsets in Montana never disappoint 🫶🏼," she wrote alongside a photo of the pair posing together in front of a sunset.

The engagement news comes about a month after Cutler was arrested for DUI and gun possession in Tennessee. On October 17, Cutler was charged with four offenses after being stopped while driving in the city of Franklin, Tennessee: DUI, failure to exercise due care to avoid a collision, implied consent, and possession of a handgun while under the influence, as first reported by TMZ.

He was booked into the Williamson County Jail, and released later that same night after posting the $5,000 bond.

For her part, Cavallari briefly mentioned the incident on the October 22 episode of her podcast, Let's Be Honest.

"Really quickly, just before we get into the episode, I wanted to hop on here and just let you guys know that this episode was recorded right before a very public incident happened last week with my ex-husband," she said before beginning the "Breaking Up Sucks" episode.

"Just keep that in mind as you're listening," the Laguna Beach alum continued, noting that she "will not be commenting on what happened." She did, however, say that she does "of course wish Jay nothing but the best and I do hope that he gets the help that he needs." Lastly, she added, "But that's the only thing I will be saying about it publicly."

Cutler was married to Cavallari from June 2013 until April 2020. The couple share three children: Camden, 12, Jaxon, 10, and Saylor, 8.

Robertson was previously married to Trace Ayala, an actor and close friend of Justin Timberlake. The pair share daughters Sophia and River.

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