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

Meet Jay Cutler’s girlfriend.

The retired NFL star’s romance with Samantha Robertson became official after she uploaded several photos of the couple to her Instagram in September 2023.

“Sunsets in Montana never disappoint,” Robertson captioned her post, with a pic of herself standing with her arm around Cutler as the two posed in front of a colorful sky. In the comments section, Cutler asked, “When are we coming back?” To which Robertson replied, “I was ready as soon as 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 married in June 2013 and have three children together: sons Camden, 12, and Jaxon, 10, and daughter Saylor, 8.

“I hope they find someone, I really hope so,” Cavallari said on Call her dad podcast in August 2022 “I mean, I want him to be happy. My kids benefit from it, you know. So I hope he gets married again. I mean, I really do.”

In October 2024, Cutler was arrested in Franklin, Tenn., after rear-ending another vehicle. He faces charges of DUI and illegal possession of a weapon. Robertson did not comment on the incident.

Here’s what you need to know about Cutler’s girlfriend, Robertson.

Jay Cutler becomes Instagram official with Samantha Robertson 3 years after divorce from Kristin Cavallari

She was previously married

Samantha Robertson.

Samantha Robertson/Instagram

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

In November 2019, Robertson shared a tribute to Ayala on his birthday. “I know you never asked to be the best dad and husband in the world, but you’re absolutely ruining it! 364 more days until we celebrate you again @traceayala ❤️,” Robertson wrote 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 children.

“My three loves! Happy VDay @samanthajrobertson! The journey lasts forever and the fun never stops!!!!” Ayala concluded.

Jay Cutler on co-parenting kids with ex Kristin Cavallari: ‘We did a good job putting them first’

She is the mother of two children

Who is jay cutler's girlfriend? All about Samantha Robertson

Samantha Robertson and her two daughters.

Samantha Robertson/Instagram

Robertson is the mother of two daughters, Sophia and River, whom she shares with Ayala. While most details about her children remain under wraps, Robertson always shares cute photos of her girls on Instagram.

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

“My greatest achievement. I am grateful to you angels every♥single♥day,” she wrote on an Instagram carousel that included photos of Sophia and River.

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She likes to travel

Who is jay cutler's girlfriend? All about Samantha Robertson

Samantha Robertson and Jay Cutler.

Samantha Robertson/Instagram

Before the trip to Paris and Montana that she posted about in September, Roberston had been filling her Instagram feed with travel pictures for years.

In March, Robertson traveled to Colorado and posted several pictures of herself skiing on the slopes for the first time. “First time skiing in the books! A few wipes, lots of layers, totally worth it,” she wrote alongside a carousel of pictures.

In November 2022, the mother of two shared a collection of pictures from her Australian adventure. “Home is where the heart is 🇦🇺 Family is priceless and health is wealth. We miss you all already!” she wrote alongside photos taken on the Gold Coast.

Other locations Robertson tagged her posts from include Costa Rica, Tennessee, South Dakota, NYC, and the Bahamas.

Kristin Cavallari wants Jay Cutler to be ‘happy’ after divorce: ‘I hope he gets married again’

She became Instagram official with Jay Cutler in September 2023

Who is jay cutler's girlfriend? All about Samantha Robertson

Samantha Robertson and Jay Cutler.

Samantha Robertson/Instagram

Robertson confirmed her romance with Cutler on Instagram on Sept. 25 when she captioned her caption with a heart emoji alongside a cozy photo of them together.

In the picture, they posed on a balcony in front of a stunning Montana sunset with Robertson’s hand resting on Cutler’s back as she leaned into his side. “Montana sunsets never disappoint 🫶,” she captioned the snap, tagging Cutler in the post.

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

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