Jay Cutler Debuts New Relationship With Samantha Robertson After Kristin Cavallari Divorce

Jay Cutler Seemingly Debuts New Relationship With Samantha Robertson After Kristin Cavallari Divorce
Jay Cutler and Samantha Robertson Courtesy of Samantha Robertson/Instagram

Jay Cutler has seemingly entered his first public relationship since his divorce from Kristin Cavallari.

Samantha Robertson hard-launched their romance via Instagram last month.

“Sunsets in Montana never disappoint 🫶🏼,” Robertson captioned a snap of herself and Cutler, 40, posing together in front of a sunset. Cutler left a sweet comment on the post, writing, “When are we going back?”

Earlier that month, Robertson posted several snaps from the pair’s trip to Paris for a friend’s wedding. “Vive la France 🇫🇷Congratulations @chanelhandel @amackenzietemplar. The most beautiful wedding ❤️,” she wrote alongside pics from the event, at which she sported a sage green slip dress and Cutler donned a tan suit, white dress shirt and a black tie.

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Though the pair have yet to publicly comment on their relationship status, several of Robertson's friends referred to them as a couple in the September 20 wedding post. “Yes❤️ best looking couple!! Love u guys….now come home. Thanks ;),” one person wrote in a comment “liked” by Robertson. Another comment approved by Robertson reads, “Beautiful couple see you both sometime Downunder ! Sam you're glowing !😊♥️😘🌺.”

When a third person wrote, “I love, love,” Cutler replied, “Don’t we all ❤️.”

Shortly before the social media pics, the Messenger reported on September 11 that the two had been quietly dating for a while. Robertson was previously married to Trace Ayala, a friend of Justin Timberlake. It is unknown when the exes, who share two daughters, called it quits. Us Weekly has reached out to Cutler’s team for comment.

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The former NFL star was previously married to Cavallari, 36. The pair announced in 2020 that they were parting ways after 10 years together. “We have nothing but love and respect for one another and are deeply grateful for the years shared, memories made, and the children we are so proud of,” Cavallari wrote via Instagram at the time. “This is just the situation of two people growing apart. We ask everyone to respect our privacy as we navigate this difficult time within our family.”

The former couple tied the knot in June 2013 after nearly three years of dating. Cavallari gave birth to the duo’s first child together, son Camden, one year before their nuptials, and they went on to welcome son Jaxon and daughter Saylor in 2014 and 2015, respectively. They now share 50/50 custody for their three kids.

Jay Cutler Seemingly Debuts New Relationship With Samantha Robertson After Kristin Cavallari Divorce
Jay Cutler and ex-wife Kristin Cavallari. Jason Kempin/Getty Images

It took more than two years for the former spouses to finalize their divorce as they argued over funds and ownership of her lifestyle brand, Uncommon James.

Their divorce was ultimately settled in June 2022, after which Cutler celebrated by throwing a party. “I don’t recommend divorce for anybody. I’m just gonna go ahead and say that, but, um, it worked out,” he shared on an episode of his “Uncut With Jay Cutler” podcast at the time. “It worked out for Kristin. It worked out for me, so it is what it is.”

Just like Cutler, Cavallari is also moving on in her love life. “I’m dating,” she exclusively revealed in her Us cover story interview last month. “I’ve gone through phases of going on a million first dates, and I’ve gone through phases where I’m not dating at all. At the moment, it’s not my priority, but I’m open to it.”