Jay Cutler and Samantha Robertson Are Engaged: Sources (Exclusive)

Mar. 15, 2025

Jay Cutler and Samantha Robertson.Photo:Samantha Robertson/Instagram

Samantha Robertson/Instagram

Congratulations are in order forJay CutlerandSamantha Robertson!The former Chicago Bears quarterback and mother-of-two are engaged, multiple sources close to the couple tell PEOPLE exclusively.Cutler, 41, and Robertson attended theYellowstoneseason 5B premiere on Thursday Nov. 7 where she donned an sparkling engagement ring.Jay Cutler and Samantha Robertson at the Yellowstone season 5B premiere on Nov. 7, 2024.Noam Galai/GettyA representative for Cutler did not immediately respond to PEOPLE’s request for comment.Cutler and Robertson went Instagram official in September 2023. The couple posed in front of a brilliant sunset looking cozy together. “Sunsets in Montana never disappoint 🫶,” Robertson captioned the picture.Days before,Robertson shared pictures of them togetherin France, traveling for a destination wedding. “Vive la France 🇫🇷 Congratulations @chanelhandel @amackenzietemplar. The most beautiful wedding ❤️," she wrote.Jay Cutler in 2019.Nuccio DiNuzzo/GettyNever miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer​​, from celebrity news to compelling human interest stories.Cutler was previously married toKristin Cavallarifrom 2013 until 2020. They sharesons Camden, 12, Jaxon, 10, and daughter Saylor, 8.Cavallari, 37, previously said that she hopes Cutler remarries one day. “I hope that he finds someone, I really do,” theHillsalum said inAugust 2022while on theCall Her Daddypodcast. “I mean, I want him happy. My kids benefit from that, you know. So I hope that he gets remarried. I mean, I really do.“Samantha Robertson.Samantha Robertson/InstagramRobertson, meanwhile, was married to actor Trace Ayala. Though their relationship timeline is unclear, they both have posted about each other on their Instagram pages.Robertson and Ayala share two daughters, Sophia and River, who are occasionally featured on herInstagramaccount.

Congratulations are in order forJay CutlerandSamantha Robertson!

The former Chicago Bears quarterback and mother-of-two are engaged, multiple sources close to the couple tell PEOPLE exclusively.

Cutler, 41, and Robertson attended theYellowstoneseason 5B premiere on Thursday Nov. 7 where she donned an sparkling engagement ring.

Jay Cutler and Samantha Robertson at the Yellowstone season 5B premiere on Nov. 7, 2024.Noam Galai/Getty

Noam Galai/Getty

A representative for Cutler did not immediately respond to PEOPLE’s request for comment.

Cutler and Robertson went Instagram official in September 2023. The couple posed in front of a brilliant sunset looking cozy together. “Sunsets in Montana never disappoint 🫶,” Robertson captioned the picture.

Days before,Robertson shared pictures of them togetherin France, traveling for a destination wedding. “Vive la France 🇫🇷 Congratulations @chanelhandel @amackenzietemplar. The most beautiful wedding ❤️,” she wrote.

Jay Cutler in 2019.Nuccio DiNuzzo/Getty

Nuccio DiNuzzo/Getty

Never miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer​​, from celebrity news to compelling human interest stories.

Cutler was previously married toKristin Cavallarifrom 2013 until 2020. They sharesons Camden, 12, Jaxon, 10, and daughter Saylor, 8.

Cavallari, 37, previously said that she hopes Cutler remarries one day. “I hope that he finds someone, I really do,” theHillsalum said inAugust 2022while on theCall Her Daddypodcast. “I mean, I want him happy. My kids benefit from that, you know. So I hope that he gets remarried. I mean, I really do.”

Samantha Robertson.Samantha Robertson/Instagram

Robertson, meanwhile, was married to actor Trace Ayala. Though their relationship timeline is unclear, they both have posted about each other on their Instagram pages.

Robertson and Ayala share two daughters, Sophia and River, who are occasionally featured on herInstagramaccount.

source: people.com