Who Is Jay Cutler’s Fiancée Samantha Robertson? All We Know About Their Relationship Timeline

As a lifestyle expert, I must say that Jay Cutler’s love life has been quite intriguing to follow! His relationship with Samantha Robertson is a perfect example of how friendships can blossom into romantic relationships.


Jay Cutler is not an ordinary NFL player; he’s one who has garnered a significant and dedicated fanbase. His marriage to former reality TV star Kristin Cavallari was chronicled on E!’s Very Cavallari. Unfortunately, they split in 2020. Since then, the Chicago Bears’ record-holder has been associated with numerous individuals. However, it’s Samantha Robertson who captured his affection in the end.

Back in the vibrant autumn of 2023, I couldn’t help but share the thrilling news that my beloved idol, Jay Cutler, and the radiant Samantha, had taken their relationship to the next level. You see, it was on Instagram where they proudly declared their bond, a move that sent ripples of joy through my fangirling heart. It all started when Robertson gracefully unveiled a series of enchanting photographs, capturing moments of pure bliss as we both reveled in the enchanting French countryside with the NFL star himself.

The pictures were from a lavish wedding where Samantha was Cutler’s plus one.

A few days following our overseas adventure, I shared another snapshot alongside Jay Cutler upon our return home. Accompanying the image was a caption that read, “The sunsets in Montana never fall short of breathtaking.

On September 25, 2023, as per an Instagram post, the CUTS co-owner inquired about Samantha’s next travel plans. In response, Samantha expressed her readiness to depart immediately, should the opportunity have arisen earlier.

According to a source, it was revealed that Cutler and Robertson had been good friends for many years before their romantic involvement, as mentioned in Life & Style magazine.

“It’s only been a few months, but they’re already pretty serious,” the source added.

Despite the fact that the Gratis Beer founder isn’t very active in sharing details about his personal life on social media, he did express his fondness for Samantha through his Instagram Stories at one point.

On January 19, 2024, I, a devoted fan, was blown away by the ex-husband of Kristin Cavallari, Jay Cutler, as he shared heartwarming images of “Jay [heart] Sam” etched in sand and tagging his lady.

On November 7, 2024, during the Yellowstone premiere, it was observed that Samantha was wearing a ring on her left hand. Fans took notice of this.

Initially, there was much speculation that Jay Cutler may have proposed due to the eye-catching jewelry on Robertson’s finger. However, just a fortnight later, it was announced by People magazine that the pair had in fact become engaged.

Samantha shares two daughters, Sophia and River with her ex-husband.

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2024-11-22 14:37