Who Is Jay Cutler’s Fiancee Samantha Robertson? From ‘Close Friends’ to Lovers

Jay Cutler may have been an NFL star, but he is widely known for his eye-catching dating life. Fans watched his marriage with his ex-wife, Kristin Cavallari, unfold on the E! series Very Cavallari shortly before their divorce in 2020. Jay has since been romantically linked to Jana Kramer and Southern Charm’s Madison LeCroy – but fiancée Samantha Robertson is the one who stole his heart.

The couple has an unconventional love story and they are still going strong.

When Did Jay Cutler Start Dating Fiancée Samantha Robertson?

The CUTS coowner and Samantha went public with their relationship after they went Instagram official in September 2023. She posted a carousel of photos in France with Jay after was her plus-one at a lavish wedding.

Samantha shared another photo with Jay days later when they arrived back home from their international trip. “Sunsets in Montana never disappoint,” she captioned the September 25, 2023, Instagram post. Jay asked when they were going back in the comment section, leading her to reply, “I was ready the second we left.”

After the couple declared their love for each other online, a source exclusively told Life & Style that Jay and Samantha “have been close friends for years.”

Reality Stars, Athletes and More! See Kristin Cavallari’s Dating History

“Their families hung out and even vacationed together,” the insider said of Kristin and Samantha’s ex-husband, Juan Trace Ayala. “It’s only been a few months, but they’re already pretty serious.”

The Gratis Beer founder has yet to add Samantha to his grid, but he confirmed they were still going strong via Instagram Stories on January 19, 2024. The former Miami Dolphins quarterback snapped a picture as he wrote, “Jay [heart] Sam,” in the sand and tagged his lady in the post.

On November 7, 2024, fans noticed that Samantha was wearing quite the sparkler on her left hand at the Yellowstone premiere. Many believed that Jay had officially popped the question and less than two weeks later, People reported that the couple was engaged.

Does Jay Cutler’s Fiancée Samantha Robertson Have Kids?

Samantha and her ex-husband share daughters Sophia and River.

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Who Has Jay Cutler Dated Before?

Jay and Kristin – who share kids Camden, Jaxon and Saylor – tied the knot in 2013. The pair experienced their fair share of ups and downs throughout their relationship and called it quits after seven years of marriage.

Inside Kristin Cavallari and Jay Cutler’ Life With 3 Kids After Split

“From the outside, like, things are so perfect and things are so great. But actually, like, they’re not. And that sucks,” Kristin admitted to her friends during an April 2019 episode of Very Cavallari. “That’s the thing, though, with marriage — it’s ups and downs. Right now, we’re in a low, but in two months we could be up here again. And that’s how we’ve always been, our whole relationship. It is what it is.”

Jay went on a date with Jana Kramer after he was back on the market and they quickly sparked dating rumors. However, the One Tree Hill alum claimed they never had a serious relationship.

“Obviously the whole Jay stuff, that became public because we went out and he was a very public person so obviously that came out, but I never spoke on it because I didn’t know what it was,” Jana explained during a December 2021 episode of her “Whine Down” podcast. “Just because I went on a date with someone doesn’t mean we’re exclusive and he’s my boyfriend. He was never my boyfriend.”