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Former Chicago Bears quarterback Jay Cutler, 41, is embarking on a new chapter in his life with entrepreneur Samantha Robertson, as multiple sources confirmed their engagement to People magazine in November 2024. The couple's relationship, which became public in September 2023, has evolved from romantic European getaways to a commitment that marks Cutler's first engagement since his divorce from reality TV star Kristin Cavallari.
Robertson first caught public attention wearing a distinctive diamond ring at the "Yellowstone" Season 5B premiere on November 7, 2024, though the couple maintained their characteristic privacy regarding the engagement. Their relationship initially came to light through Robertson's social media posts, including images from a wedding they attended together in France and intimate moments captured in Montana, where she captioned a sunset photo with, "Sunsets in Montana never disappoint."
Before this engagement, both Cutler and Robertson navigated previous marriages. Robertson, a mother of two daughters, Sophia and River, was previously married to actor Trace Ayala. Cutler's seven-year marriage to Kristin Cavallari ended in April 2020, with the divorce finalized in 2022. The former couple shares three children: Camden (12), Jaxon (10), and Saylor (8).
Interestingly, Cavallari had expressed hope for Cutler's romantic future during an August 2022 appearance on the "Call Her Daddy" podcast, stating, "I hope that he finds someone, I really do. I want him happy. My kids benefit from that."
Despite characterizing their marriage as "toxic" during the same interview, Cavallari's public support for Cutler's happiness highlighted their commitment to maintaining a healthy co-parenting relationship.
The engagement news comes as both parties have moved forward in their personal lives. Cavallari recently ended a seven-month relationship with Montana Boyz star Mark Estes, citing age differences and misaligned life goals. Meanwhile, Cutler and Robertson have maintained a relatively low profile, making selective public appearances while building their relationship away from the media spotlight.
Representatives for Cutler have not officially commented on the engagement, maintaining the couple's preference for privacy. However, their appearance at the "Yellowstone" premiere, where Robertson's engagement ring made its debut, served as a subtle announcement to the public.
