Former NFL Star Jay Cutler Finds Love Again: Engagement to Samantha Robertson Confirmed
Multiple sources close to the couple have confirmed the official engagement of Jay Cutler, the former Chicago Bears quarterback, and Samantha Robertson, in a glittering revelation that is capturing hearts across the sports and entertainment world.
The joyful news first came to light at the ‘Yellowstone’ Season 5B premiere in New York City on November 7, 2024, where Robertson turned heads wearing a sparkling engagement ring. The couple, who made their relationship Instagram official in September 2023, has been steadily sharing glimpses of their romance with the public.
Their love story first caught the public’s attention when Robertson posted a heartwarming sunset photo in Montana last fall. “Sunsets in Montana never disappoint 🫶,” she wrote, marking their social media debut as a couple. The relationship quickly blossomed, with the pair jet-setting to France for a destination wedding shortly before their engagement.
Cutler, 41, has been openly expressing his affection for Robertson. In a touching display of romance this January, he shared a beach photo featuring “Sam ❤️ Jay” written in the sand, letting the world know just how serious their relationship had become.
Robertson, a mother of two daughters named Sophia and River from her previous marriage to actor Trace Ayala, has seamlessly integrated into Cutler’s life. Meanwhile, Cutler brings his own family dynamic to the relationship, sharing three children with his ex-wife, Kristin Cavallari: Camden (12), Jaxon (10), and Saylor (8).
The engagement news comes at an intriguing time in Cutler’s life. Earlier this month, Cutler encountered personal challenges following his arrest for DUI in Tennessee.
His ex-wife Cavallari addressed the situation briefly on her “Let’s Be Honest” podcast, saying, “I do hope that he gets the help that he needs,” while maintaining a respectful distance from it.
Speaking of Cavallari, she’s been notably supportive of Cutler’s journey to find love again. During a 2022 appearance on the “Call Her Daddy” podcast, she expressed genuine hope for his future happiness: “I hope that he finds someone; I really do. I want him happy. My kids benefit from that, you know. I hope he remarries.”
The newly engaged couple has been making the rounds at high-profile events, most recently attending the ‘Yellowstone’ premiere together in New York City. Their public appearances have shown them looking pleased and comfortable together, with Robertson often sharing their adventures on her Instagram account.
The timing of this engagement marks a new chapter for Cutler, who ended his seven-year marriage to Cavallari in 2020 after a total of ten years together. This fresh start with Robertson seems to be exactly what the former NFL star has been looking for.
While Cutler’s representatives haven’t officially commented on the engagement news, the couple’s recent public appearances and Robertson’s notable ring have done all the talking. As this story develops, fans and well-wishers are eagerly awaiting more details about their wedding plans.
For now, it seems the former quarterback, known for his strong arm on the football field, has scored big in the game of love, finding happiness with someone who shares his zest for life and adventure.