Jay Cutler Engaged To Samantha Robertson, Sources Confirm

Former NFL quarterback Jay Cutler is reportedly engaged to Samantha Robertson, a mother of two, according to sources close to the couple.

While neither Cutler, 41, nor Robertson has publicly announced the engagement, Robertson was recently spotted wearing a dazzling diamond ring during the premiere of Yellowstone Season 5B earlier this month.

The couple first publicly announced their relationship in September 2023, when Robertson shared photos of them attending a wedding in France.

Days later, she posted a snapshot of the pair enjoying a sunset in Montana, captioning the image, “Sunsets in Montana never disappoint.”

Despite these glimpses into their relationship, the couple has largely kept their romance private over the past year.

Robertson was previously married to actor Trace Ayala, with whom she shares two daughters, Sophia and River.

Cutler, on the other hand, was married to reality TV star Kristin Cavallari for seven years before their divorce was finalized in 2022. The former couple shares three children: Camden, 12, Jaxon, 10, and Saylor, 8.

Cavallari has described her past marriage to Cutler as “toxic,” but during a 2022 interview, she expressed her hope that he would find love again. “I want him happy. My kids benefit from that,” she said.

While Cutler has embraced a new chapter with Robertson, Cavallari has also moved on from her most recent relationship with Mark Estes, a 24-year-old social media star. The pair dated for seven months before splitting in September due to differences in long-term goals.