Jay Cutler is reportedly engaged to Samantha Robertson, according to People. The former Chicago Bears quarterback has taken the next major step in his relationship with Robertson, who is a mother of two. Multiple sources close to the couple confirmed the engagement news to the outlet.
Neither Cutler, 41, nor Robertson have publicly announced the engagement, but speculation began swirling after Robertson was seen sporting a sparkling diamond ring on her left hand. The couple attended the “Yellowstone” Season 5B premiere together earlier this month, where Robertson’s new accessory caught everyone’s attention.
Cutler’s representative did not immediately request for comment on the engagement report by People, leaving fans to continue speculating based on the subtle hints the couple has dropped. While Cutler and Robertson have not been particularly open about their relationship, they have offered glimpses into their romance over the past year.
The couple first went public with their relationship in September 2023, when Robertson shared several photos on Instagram from a wedding they attended together in France. The photos showed the two looking happy and comfortable in each other’s company, signaling the start of their public journey as a couple.
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Shortly after their trip to France, Robertson posted another photo from their vacation to Montana. The snapshot, taken during a beautiful sunset, showed her cozied up with Cutler. She captioned it, “Sunsets in Montana never disappoint,” and the photo reflected the closeness between the two.
Although the couple has kept their relationship mostly private, these small social media moments have given fans a glimpse into their bond.
Despite their reserved nature, it seems that Cutler and Robertson have grown closer over the past year, culminating in their reported engagement.
Samantha Robertson was previously married to actor Trace Ayala. The former couple shares two daughters, Sophia and River, who remain a big part of her life. Robertson has continued to prioritize her family while finding happiness in her relationship with Cutler.
As for Jay Cutler, his engagement to Robertson comes two years after finalizing his divorce from ex-wife Kristin Cavallari. Cutler and Cavallari announced their separation in April 2020 after seven years of marriage, and their divorce was finalized in 2022.
Following the end of their marriage, Cutler even threw a lighthearted divorce party to mark the next chapter of his life.
Cutler and Cavallari share three children together: sons Camden, 12, and Jaxon, 10, as well as their daughter Saylor, 8. Despite their differences, the former couple has worked to co-parent their children and maintain a sense of stability for their family.
Cutler and Robertson’s engagement marks a new beginning for both of them, as they look ahead to building a life together. Though neither has made an official announcement yet, fans are eagerly waiting for more details about their journey as an engaged couple.
For now, the quiet but meaningful hints they have dropped are enough to celebrate this next chapter of their love story.
