Who Is Jay Cutler's New Girlfriend, Samantha Robertson?

In an era when football stars and their girlfriends are making headlines, Jay Cutler has just entered the scene with his new boo, Samantha Robertson. Cutler was formerly married to reality star Kristin Cavallari for seven years before the two divorced in 2020. Following their split, Cavallari shared on the "Call Her Daddy" podcast that she hopes her ex will find love again, even though their relationship was "toxic." The "Laguna Beach" star stated, "I hope that he finds someone, I really do. I want him happy. My kids benefit from that, you know. So I hope that he gets remarried" (via Us Weekly).

It seems that Cutler has indeed found someone and his relationship with Robertson looks like it's going strong. They first went Instagram official on September 20 when Robertson shared a carousel of pics of the two celebrating a friend's wedding in France. A source close to the couple revealed to The Messenger that they "have been dating for a while" and had "met through mutual friends in Nashville." The insider also revealed that Cutler and Robertson's children have already met. While Robertson isn't as high-profile as Cavallari, here's everything to know about the former NFL player's new girlfriend.

Like Jay Cutler, Samantha Robertson was once married and shares two daughters, Sophia and River, with her ex Trace Ayala, who is close friends with Justin Timberlake. According to TV Guide Time, Robertson and Ayala started their relationship in 2010 and got married three years later. It's unclear when their marriage ended but it seems they were together as recently as January 2022. The two enjoyed a trip to the Bahamas with their daughters and a group of friends with their children as well. "Back on island time! Holding onto these memories extra tight," Robertson wrote on Instagram. In 2019, she gave Ayala a birthday shoutout and gushed, "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."

Robertson often takes her daughters on trips with her and in March they had a visit in New York City. "Spring break in the city," she wrote while sharing many pictures of their adventure. The family also took a trip to Wyoming in 2021, including Ayala. "To the moon and back," Robertson captioned. It's clear she dotes on her daughters and just like their mom, they have an adventurous side.

Jay Cutler better be able to keep up with Samantha Robertson's adventurous streak! She not only loves to travel, but she's also not afraid to hunt her own food. In April 2018, she shared a photo of her wearing camouflage clothing while holding a massive turkey and stated, "Some people go to the store to get their turkey, I go outside to get mine." In 2020, Robertson explored the oceans of the Bahamas while snorkeling. "Took a plane, a car and a boat to come hang out with the cast from finding Nemo. Grateful for this beautiful place and friends surrounding me," she wrote.

Robertson's kids are also daredevils and she shared a video of one of her daughters on a mini ATV barreling around their home. "Watch out, we've got a speed demon over here!" she captioned. They're also skilled at riding horses and spend family time enjoying the equestrian life together. When she's not hunting or diving underwater, Robertson's other skills lie in interior design and she once helped a famous History Channel star decorate his guest house.

Samantha Roberston runs in famous circles. Not only is she connected to Justin Timberlake through her ex-husband, but she is also a close friend of "American Pickers" star Mike Wolfe. The treasure finder embarked on a project to renovate and design vacation rentals and he asked Robertson, along with designer Trinity Shay, to help him with his Tennesee home. "[Two Lanes Guesthouse] is finally coming together! And will be opening in about a month. This @airbnb is in a 1857 building downtown #columbiatn filled some of my favorite picks..Perfect place to chill for the weary traveler," Robertson reposted on Instagram.

As for how Roberston became involved in the project, Wolfe told Antique Archaeology, "The three of us live in a little village called Leiper's Fork, Tennessee. In a small town like ours, you quickly get to know your neighbors. I was always a huge fan of their aesthetic and ability to see the beauty in distressed, and sometimes discarded artifacts." He praised Robertson's "free-spirited approach to design" and acknowledged her tastes that come from being well-traveled.

Robertson and Cutler not only visited Paris and Montana together, but they celebrated his cover for Haute Living magazine in Naples, Florida. They were captured getting cozy in front of cameras and the two are obviously not afraid of displaying their newfound love for each other.