The romance between Jay Cutler and Samantha Robertson became public when she shared several photos of them on her Instagram in September 2023.
In her post, which showcased a picturesque sunset in Montana, Robertson wrote, “Sunsets in Montana never disappoint,” while the couple posed together. Cutler commented, “When are we going back?” to which Robertson enthusiastically replied, “I was ready the second we left.”
Cavallari expressed her hopes for Cutler’s happiness during an interview in August 2022
Cutler’s relationship with Robertson began approximately three years after his marriage to Kristin Cavallari ended in April 2020. The couple married in June 2013 and have three children together: sons Camden, aged 12, and Jaxon, aged 10, as well as 8-year-old daughter Saylor.
In August 2022, Cavallari expressed her hopes for Cutler’s happiness during an appearance on the Call Her Daddy podcast. She stated, “I hope that he finds someone, I really do. I mean, I want him happy. My kids benefit from that, you know. So I hope that he gets remarried. I mean, I really do.”
In October 2024, Cutler faced legal issues after being arrested in Franklin, Tennessee, for rear-ending another vehicle. He is charged with DUI and illegal possession of a firearm, but Robertson has not publicly commented on the situation.
Robertson’s background includes a previous marriage to Trace Ayala, an actor who is a close friend of Justin Timberlake. Although specific details about their relationship timeline are scarce, they have shared tributes to one another on social media.
For instance, in November 2019, Robertson celebrated Ayala’s birthday with a heartfelt post, stating, “I know you never asked to be the world’s best dad and husband but you’re absolutely crushing it! 364 more days until we get to celebrate you again @traceayala ❤️.”
On Valentine’s Day 2022, Ayala reciprocated with a tribute to Robertson, declaring, “When I said ‘I could never love anything as much as I love you!’ you quickly proved me wrong when you gave me these two!” He included a photo of Robertson and their children, emphasizing their strong family bond.
As a mother of two daughters, Sophia and River, Robertson often shares heartwarming moments with her girls on Instagram. While she maintains a level of privacy regarding their lives, she frequently posts photos that highlight their adventures together.
For example, she shared memories from a recent trip to New York City for spring break and a fun-filled family vacation in the Bahamas in January 2022. In one post, she expressed her gratitude, writing, “My greatest achievement. Grateful for you angels every♥single♥day,” alongside a carousel of photos featuring Sophia and River.
Traveling is a passion for Robertson, who has been documenting her adventures on Instagram for several years. Most recently, she posted about her skiing trip in Colorado, describing it as her first experience on the slopes, sharing her excitement despite a few wipeouts.
In November 2022, she reflected on her trip to Australia, posting a collection of pictures and expressing how much she missed her family, writing, “Home is where the heart is 🇦🇺 Family is priceless and health is wealth. Missing you all already!” Other locations she has tagged in her posts include Costa Rica, Tennessee, South Dakota, New York City, and the Bahamas.
On September 25, 2023, Robertson made her relationship with Cutler Instagram official, concluding her post with a heart emoji next to a cozy photo of the couple together.
In the snapshot, they stood on a balcony against the backdrop of a breathtaking sunset in Montana, with Robertson leaning into Cutler while resting her arm on his back.
She captioned it, “Sunsets in Montana never disappoint 🫶,” tagging Cutler in the image, to which he responded in the comments, asking, “When are we going back?”
