Jay Cutler and Samantha Robertson Are Engaged


Jay Cutler and Samantha Robertson

Jay Cutler and Samantha Robertson in New York on Thursday, November 7
Noam Galai/Getty Images for Paramount

Jay Cutler and Samantha Robertson are reportedly engaged after more than one year of dating.

Sources told People on Tuesday, November 19, that the pair, who have been linked since September 2023, are getting ready to walk down the aisle. The news comes after they attended the season 5B premiere of Yellowstone in New York City earlier this week, where eyewitnesses exclusively told Us Weekly that the mother-of-two was spotted rocking a diamond on her ring finger.

Us has reached out to representatives for Cutler and Robertson for further comment.

The pair’s September 2023 Instagram debut came when Robertson, 33, posted a snap of her and Cutler, 41, looking loved up in front of a blazing sunset. “Sunsets in Montana never disappoint,” Robertson captioned the photo.

Jay Cutler Seemingly Debuts New Relationship With Samantha Robertson After Kristin Cavallari Divorce

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Jay Cutler has seemingly entered his first public relationship since his divorce from Kristin Cavallari. Samantha Robertson hard-launched their romance via Instagram last month. “Sunsets in Montana never disappoint 🫶🏼,” Robertson captioned a snap of herself and Cutler, 40, posing together in front of a sunset. Cutler left a sweet comment on the post, writing, […]

The PDA moment came on the back of another cozy post from Robertson in the days prior, which included snaps of her and Cutler holidaying in France.

Traveling to the Europe for a friend’s wedding at the time, Robertson captioned the previous post, “Vive la France 🇫🇷 Congratulations @chanelhandel @amackenzietemplar. The most beautiful wedding ❤️.”

Prior to meeting Robertson, Cutler was married to Kristin Cavallari from 2013 to 2022. The exes share three children: Camden, 12, Jaxon, 10 and Saylor, 8.

Jay Cutler Shares Sweet Message in Sand to GF Samantha Robertson

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Courtesy of Samantha Robertson/Instagram Jay Cutler is all in with girlfriend Samantha Robertson. “Sam ❤️ Jay,” Cutler, 40, shared via his Instagram Story on Friday, January 19, with the message written in the sand at the beach, tagging Robertson in the post. Robertson, 33, revealed that she and Cutler were dating in September 2023 with […]

Robertson, meanwhile, was previously married to actor and fashion designer Trace Ayala. Robertson and Ayala share daughters Sophia and River.

Robertson and Cutler’s engagement follows news that the NFL star and Cavallari, 37, and Cutler are in a great place as they coparent their children together.

“My heart broke in my marriage. And even though I’m the one that walked away, it was not what I wanted,” Cavallari revealed on the October 22 episode of her “Let’s Be Honest” podcast. “It was not what I had envisioned and I really tried everything I could.”

“You just can’t get there. And I would say my heart was broken for years in my marriage,” she added. “Again, I’m not talking s—- about Jay at all. I’m really not. I’ve publicly said some things at first. And now I don’t really talk about him at all.”




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