Jay Cutler Is Engaged in Wake of DUI Arrest

Two years after finalizing his divorce from Kristin Cavallari, Jay Cutler has found new love. The former Chicago Bears quarterback, who was arrested for a DUI in October, is reportedly engaged to Samantha Robertson after more than one year of dating.

Neither Cutler, 41, nor Robertson, 33, who have been linked since September 2023, have commented on the reported step in their relationship at this time. However, as the couple stepped out for the Yellowstone Season 5B premiere together on Thursday, Nov. 7, Robertson was seen wearing a diamond ring on that finger. Sources close to the pair later confirmed their engagement to PEOPLE in a report published on Nov. 19, but details about how the proposal went down weren’t provided, and it’s unclear when exactly Cutler popped the question. Reps for Cutler did not immediately respond to PEOPLE‘s request for comment.

Cutler and Robertson sparked romance following their respective previous relationships. Robertson was previously married to actor Trace Ayala, whom she shares daughters Sophia and River with. Cutler, meanwhile, was married to Cavallari from 2013 until 2020. They finalized their divorce in 2022. The pair, who starred alongside one another on Very Cavallari, share sons Camden, 12, Jaxon, 10, and daughter Saylor, 8.

Three years after his split from Cavallari, Cutler went public with his relationship with Robertson when they went Instagram official in September 2023. At the time, Robertson shared several photos of them in front of a dreamy subset in Montana, writing, “Sunsets in Montana never disappoint.

The couple’s reported engagement comes amid a troubling time for Cutler, who in October was charged with DUI, illegally possessing a weapon while intoxicated, implied consent, and failure to exercise due care to avoid a collision. The former NFL quarterback was arrested in Franklin, Tennessee on the night of Oct. 17 after he allegedly rear-ended another vehicle and attempted to flee the scene of the “minor traffic collision,” a police affidavit said. Cutler reportedly had “bloodshot” eyes, was “thick-tongued, slurred and mumbled” when he spoke, and “had an overwhelming odor of an alcoholic beverage emitting from his person,” the responding officer noted. A search of his vehicle led to the discovery of a rifle and a loaded handgun.

All four charges Cutler is facing are misdemeanors or civil offenses, according to Tennessee law. The football star was booked into the Williamson County Jail and released later that same night after posting a $5,000 bond.

While Cutler hasn’t publicly addressed his arrest, Cavallari briefly mentioned the incident at the top of the Oct. 22 episode of her Let’s Be Honest podcast when she said, “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.” Cavallari said that she would “not be commenting on what happened,” but added that she wished Cutler “nothing but the best and I do hope that he gets the help that he needs.”