Former NFL quarterback Jay Cutler is giving marriage another go.
According to People, Jay is engaged to Samantha Robertson. The mother of two– who debuted her relationship with the former Very Cavallari star on Instagram in September 2023– attended an event with Jay in New York City earlier this month where she was photographed wearing a diamond engagement ring.
As fans of ‘Very Cavallari’ know, Jay was previously married to the show’s namesake, Kristin Cavallari, from 2013 to 2020; however, the couple’s divorce wasn’t finalized until 2022.
Jay and Kristin share sons Camden, 12, Jaxon, 10, and 8-year-old daughter Saylor. Meanwhile, Samantha shares two daughters with her ex-husband, actor Trace Ayala.
While Kristin has yet to comment on her ex-husband’s engagement, she revealed on a 2022 episode of the Call Her Daddy podcast that she hoped Jay would eventually remarry.
“I hope that he finds someone, I really do,” Kristin told host Alex Cooper. “I mean, I want him to be happy. My kids benefit from that, you know? So I hope that he gets remarried. I mean, I really do.”
(Kristin was recently in a relationship with TikTok star Mark Estes, though she announced in September that she and the 24-year-old had split after seven months together.)
The news of Jay’s engagement comes just a month after the 41-year-old was arrested and charged with DUI and possession of a handgun following a collision in Franklin, Tennessee. Police reportedly responded to a call around 5 p.m. on October 17 regarding a white truck that allegedly rear-ended another car and then attempted to pay the other driver $2,000 to not contact police. Upon arriving at the scene, cops claimed to have found Jay staggering around, slurring his words and smelling of alcohol.
During a search of Jay’s vehicle, police discovered a rifle in the backseat, as well as a loaded Glock handgun in the center console. He was arrested for DUI, Possession of a Handgun While Under the Influence, Failure to Exercise Due Care and Violation of Implied Consent Law, and was booked into the Williamson County Jail. He went on to be released that night after posting $5,000 bond.
Jay’s court date is set for January 2025.
Following the news of Jay’s arrest last month, Kristin briefly addressed the incident on an episode of her Let’s Be Honest podcast.
“I do, of course, wish Jay the best and hope he gets the help he needs,” she said. “But that is the only thing I will be saying about it publicly.”
Kristin also made a point to tell listeners at the beginning of the podcast that the episode– on which she discussed breakups, including her and Jay’s divorce– had been recorded prior to the “very public incident” involving her ex-husband.
“ … So just keep that in mind as you’re listening,” she said. “I will not be commenting on what happened.”
(Photos: Instagram; E!)
6 Responses
IDK if he has an actual drinking problem, but cutler has ALWAYS looked to me like he just woke up from a 3-day bender. scruffy, unkempt, like he smells of cigarettes and stale booze.
Good for him for taking his time and not just jumping into another relationship!
I don’t follow them much but seeing what I have, over the years- He’s a mess. He looks terrible- unhealthy, really. I’m an alcoholic but in recovery now for over three years and honestly, he sort of looks like he’s an alcoholic. If you are an alcoholic in recovery, you know what I mean but he looks like we do when we are deep into our drinking. Can’t really explain it. This engagement is probably just a welcome distraction and way to avoid the fact that he likely needs to do some work on himself.
I think every sober day is a day worthy of celebration! Well done!
He’s also diabetic, which boggles the mind how he also has an alcohol problem.
Unfortunately, it doesn’t discriminate. I come from a long line of alcoholics sadly. Both grandpa’s died from drinking related issues- one being my paternal grandfather was a diabetic and not only drank after being diagnosed but also ate very unhealthy. I can’t imagine what a diabetics body feels like while also drinking, let alone being an actual alcoholic. He’s got money (I think, still) so he likely counteracts the sugar from the alcohol with insulin. I know insulin and diabetic medication has increased over the years dramatically, but he likely doesn’t worry about it if he’s got the funds to get it.