Who Is Jay Cutler’s Girlfriend? All About Samantha Robertson

Meet Jay Cutler's girlfriend.

The retired NFL star's romance with Samantha Robertson was made official after she uploaded a few photos of the couple on her Instagram in September 2023.

"Sunsets in Montana never disappoint," Robertson captioned her post, featuring a scenic picture of herself standing with her arm around Cutler as the two posed in front of the colorful sky. In the comment section, Cutler asked: "When are we going back?" To which Robertson replied, "I was ready the second we left."

Cutler's new romance began three years after he and Kristin Cavallari announced they were ending their marriage in April 2020. The former couple tied the knot in June 2013 and share three children together: sons Camden, 12, and Jaxon, 10, and daughter Saylor, 8.

"I hope that he finds someone, I really do," Cavallari said on the Call Her Daddy podcast in August 2022. "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 was arrested in Franklin, Tenn., after rear-ending another vehicle. He faces charges of a DUI and illegal possession of a gun. Robertson has not commented on the incident.

Here's what to know about Cutler's girlfriend, Robertson.

She was previously married

Robertson was previously married to Trace Ayala, an actor and close friend of Justin Timberlake. While few details are known about their relationship timeline, the two have posted about each other on their respective Instagram platforms.

In November 2019, Robertson shared a tribute to Ayala for his birthday. “I know you never asked to be the worlds best dad and husband but you’re absolutely crushing it! 364 more days until we get to celebrate you again @traceayala ❤️,” wrote Robertson at the time. 

In February 2022, Ayala shared a tribute to Robertson on Valentine's Day. "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 began his caption alongside a photo of Robertson and their kids.

"My three loves! Happy VDay @samanthajrobertson! The road goes on forever and the party never ends!!!!" Ayala concluded.

She’s the mother of two children

Robertson is the mother of two daughters, Sophia and River, whom she shares with Ayala. While most details about her kids are kept private, Robertson is always sharing sweet photos of her girls on Instagram.

In March, the mom of two posted about her girls' trip that she took with her kids when they traveled to New York City for spring break. In January 2022, she shared fun-filled photos of her kids during their trip to the Bahamas.

"My greatest achievement. Grateful for you angels every♥single♥day," she captioned an Instagram carousel that included photos of both Sophia and River.

She likes to travel

Prior to the Paris and Montana trips she posted about in September, Roberston had been filling her Instagram feed with travel pics for years.

In March, Robertson traveled to Colorado and uploaded a few images of herself skiing on the slopes for the first time. "First time skiing in the books! A few wipeouts, sooo many layers, totally worth it," she captioned the carousel of pics.

In November 2022, the mom of two shared a collection of pics from her Australian adventure. "Home is where the heart is 🇦🇺 Family is priceless and health is wealth. Missing you all already!" she wrote alongside photos taken on the Gold Coast.

Other locations from which Robertson has tagged her posts include Costa Rica, Tennessee, South Dakota, N.Y.C. and the Bahamas.

She went Instagram official with Jay Cutler in September 2023

On Sept. 25, Robertson confirmed her romance with Cutler on Instagram when she concluded her caption with a heart emoji alongside their cozy photo together.

In the pic, they posed on a balcony in front of a stunning sunset in Montana with Robertson's arm resting on Cutler's back as she leaned into him.

“Sunsets in Montana never disappoint 🫶,” she captioned the shot, tagging Cutler in the post. 

“When are we going back?” wrote the athlete in the comments section.