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Who is Jay Cutler dating? Former NFL quarterback finds love again three years after his divorce from Kristin Cavallari

Jay Cutler is dating Samantha Robertson, who was previously married to Trace Ayala, the best friend of actor and Grammy-winner Justin Timberlake
PUBLISHED OCT 6, 2023
Kristin Cavallari's ex-husband Jay Cutler went Instagram official with girlfriend Samantha Robertson (Instagram/@samanthajrobertson and Getty Images)
Kristin Cavallari's ex-husband Jay Cutler went Instagram official with girlfriend Samantha Robertson (Instagram/@samanthajrobertson and Getty Images)

LOS ANGELES, CALIFORNIA: Three years after his split with ‘Laguna Beach’ alum Kristin Cavallari, former NFL quarterback Jay Cutler has found love again in his new girlfriend Samantha Robertson. 

The couple went Instagram official on September 20, 2023, as The Messenger reported them enjoying a scenic vacation in France to attend a wedding.

Robertson, who was looking resplendent in a green slip dress, shared a slew of photos of the couple with the caption, “Vive la France 🇫🇷Congratulations @chanelhandel @amackenzietemplar. The most beautiful wedding ❤️.”

Robertson’s father David Robertson also seemed to have given his blessing to the couple as he commented, “Great photo of you and Jay. Congrats to Chanel, the wedding looks fantastic, love to all. Love Dad ❤️.”


 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by Samantha Robertson (@samanthajrobertson)


 

In a more recent post, dated September 25, Robertson wrote, “Sunsets in Montana never disappoint 🫶🏼,” while sharing a picture of the couple in front of a picturesque golden sunset.

Cutler and his rumored lady love engaged in a short social media banter under the post as Cutler asked, “When are we going back?” to which Robertson replied, “I was ready the second we left.”

While the couple has not yet officially made a statement about their romance, their friends and fans have started gushing over their camaraderie.

One of the social media users exclaimed, “IG official 👀 so happy for you gf! You deserve all the happiness in the world. 😘.”


 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by Samantha Robertson (@samanthajrobertson)


 

Who is Samantha Robertson?

Robertson was previously married to Trace Ayala, the best friend of actor and 10-time Grammy-winning musician Justin Timberlake. Ayala is also the business partner of Timberlake and they co-founded their apparel line called William Rast.


 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by Samantha Robertson (@samanthajrobertson)


 

While it is exactly not known when Robertson and Ayala split, Page Six reported that the duo were together during Valentine’s Day of 2022.

Robertson is a mother of two as she has two daughters with Ayala -- Sophia, 11, and River, nine.


 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by Samantha Robertson (@samanthajrobertson)


 

An insider told The Messenger, "Jay and Samantha have been dating for a while," before adding, "They met through mutual friends in Nashville."

The insider continued, "Jay recently flew with Samantha to Paris. Their kids have also met.”

Dating status of Kristin Cavallari

Cutler and the ‘Uncommon James’ founder got married in 2013 after three years of dating.

The pair, who have three children together -- sons Camden, 11, and Jaxon, nine, and a daughter Saylor, seven, -- got divorced in 2020.

NASHVILLE, TENNESSEE - DECEMBER 05: Jay Cutler and Kristin Cavallari attend the Monster Energy NASCA
Jay Cutler and Kristin Cavallari got divorced in 2020 (Getty Images)

Their divorce battle settled in June 2022, with the couple getting 50-50 custody of their children.

Like Cutler, Cavallari has also been back in the dating space.

MTV star Kristin Cavallari with ex Jay Cutler and their kids (Instagram/@kristincavallari)
MTV star Kristin Cavallari with ex Jay Cutler and their children (Instagram/@kristincavallari)

She shared on the 'Jennifer Hudson Show' on April 19, 2023, that she has been dating actively, as per E! News.

However, she added, "I just have taken a stance that until I'm in a serious, committed relationship there's nothing to really report," before adding, "I'm having fun. I do have good dating stories."

She also revealed that casual dating is new to her and said, "This is the first time in my life that I've really dated," before adding, "I've always had boyfriends, I got married very young so I am just enjoying it."

When asked about her dating status, the actress replied, "I'm an active dater, … and it's been fun."

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