Who Is Samantha Roberston? What Know About Jay Cutler’s Girlfriend After Kristin Cavallari Divorce

Who Is Samantha Roberston What Know About Jay Cutler Girlfriend After Kristin Cavallari Divorce
Jay Cutler and Samantha RoberstonCourtesy of Samantha Roberston/Instagram

Jay Cutler has officially entered his boyfriend era with Samantha Robertson.

The former NFL star hard-launched his relationship via social media in September 2023, years after his divorce from Kristin Cavallari. Cutler and Cavallari were together for 10 years before announcing their split in 2020. They share three kids.

While neither Cutler nor Robertson have publicly confirmed their relationship status thus far, Robertson shared several Instagram photos of the duo looking pretty loved up.

“Vive la France 🇫🇷Congratulations @chanelhandel @amackenzietemplar,” Robertson wrote alongside a pic with her arm wrapped around Cutler at a September 2023 wedding. “The most beautiful wedding ❤️.”

Patrick Mahomes and Tom Brady have more NFL fans than they can count, but their kids are the only cheering squad they really need. Mahomes and wife Brittany Matthews were empty nesters when he won his first Super Bowl with the Kansas City Chiefs in February 2020. However, when Mahomes took home his second championship […]

Days later, Robertson dropped another photo of herself and Cutler.

“Sunsets in Montana never disappoint 🫶🏼” she captioned the snap. Cutler commented, “When are we going back?”

When another commenter wrote “I love, love,” Cutler responded, “Don’t we all ❤️.”

The Messenger was first to report in early September 2023 Roberston and Cutler were a couple, with a source revealing that they had been “dating for a while.” The insider added that “their kids have also met.”

Who Is Samantha Roberston What Know About Jay Cutler Girlfriend After Kristin Cavallari Divorce 2
Jay Cutler and Samantha RoberstonCourtesy of Samantha Roberston/Instagram

Keep reading for everything to know about Cutler’s new girlfriend:

1. Robertston Is a Divorcee

She was previously married to Trace Ayala. While it’s unclear when they split, Robertson was last featured on Ayala’s Instagram in February 2022.

“The road goes on forever and the party never ends!!!!” he wrote, when celebrating Valentine’s day.

Robertson, for her part, last featured Ayala on her Instagram in November 2019.

“I know you never asked to be the worlds best dad and husband but you’re absolutely crushing it!” she wrote at the time.

2. Robertson Has 2 Daughters

Throughout their time together, Robertson and her ex-husband welcomed two daughters, Sophia and River, who make frequent appearances on her Instagram.

Who Is Samantha Roberston What Know About Jay Cutler Girlfriend After Kristin Cavallari Divorce 3
Chanel Handel, Samantha Roberston, and Jay Cutler.Courtesy of Samantha Roberston/Instagram

3. Robertson Has a Surprising Connection to Justin Timberlake

Her ex-husband, Ayalaa, is the “Creative Director to Mr. Timberlake,” per his X (formerly Twitter) bio.

Alaya and Timberlake’s parents were friends from high school and welcomed their sons within three months of each other. “They did, and still do, everything together,” a GQ article read of the pair, and even launched the William Rast brand together.

From a broken engagement to three beautiful children, Kristin Cavallari and Jay Cutler’s relationship has had its share of curveballs, culminating in their April 2020 split. The Uncommon James founder and the former NFL star began their whirlwind romance in 2010, meeting through mutual friend Giuliana Rancic. “Jay is a good Midwestern boy; he’s a […]

Robertson, for her part, showed support for Timberlake by reposting one of his Instagram videos in January 2018.

Who Is Samantha Roberston What Know About Jay Cutler Girlfriend After Kristin Cavallari Divorce 4
Jay Cutler and Kristin Cavallari on April 27, 2017 in West Hollywood, California.Jason LaVeris/Getty Images

4. Robertson Has Other Famous Friends

Other than her connection to Timberlake, it appears that Robertson has a bond with some other celebrities. Rita Ora, for one, follows Robertson on Instagram. Robertson also shared photos from a January 2022 vacation featuring former NASCAR driver Clint Bowyer and his family.

5. Australia Is Robertson’s ‘Home’

“Home is where the heart is 🇦🇺 Family is priceless and health is wealth,” Robertson captioned an Instagram post from November 2022. “Missing you all already!”

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