Jay Cutler Debuts New Relationship 3 Years After Kristin Cavallari Split

Jay Cutler is dating Samantha Robertson following his 2020 split from ex-wife Kristin Cavallari. The Messenger reported on Sept. 11 that the two had been quietly dating for a while, with the couple making their Instagram debut together last month while posing all cuddled up on a trip to Paris for a friend’s wedding. Then just last week, they posed together after a trip to Montana. 

“Sunsets in Montana never disappoint,” Robertson captioned a photo of her with the former NFL player in front of a sunset. Cutler commented sweetly, “When are we going back?” to which Robertson responded, “I was ready the second we left.” While the two have not publicly commented on their relationship, several of Robertson’s friends referred to the duo as a couple in comments she liked. “Yes best looking couple!! Love u guys….now come home. Thanks ;),” one person wrote, as another commented, “Missing you and very happy for you.” When another person commented, “I love, love,” Cutler replied, “Don’t we all,” adding a heart emoji.

Prior to her romance with Cutler, Robertson was married to Trace Ayala, although it’s unclear when the exes, who share two daughters, ended their marriage. Cutler, meanwhile, was married to Cavallari until the former couple announced in 2020 that they were going their separate ways after 10 years and three kids. “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,” the Laguna Beach alum wrote on 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 divorce was finalized two years later in June 2022, with Cutler celebrating the legal settlement of their relationship 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 would go on to share 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.” Cavallari has been romantically linked with comedian Jeff Dye and singer Chase Rice following her divorce but has not debuted a serious relationship.