Jay Cutler and Samantha Robertson’s Relationship Timeline

Jay Cutler is off the market! After over a year of dating, the famous ex-quarterback is now engaged to Samantha Robertson. Cutler, 41, is best known for his time in the NFL, playing as a quarterback for the Denver Broncos, Chicago Bears, and Miami Dolphins.

Cutler was previously married to Laguna Beach Star Kristin Cavallari,. The exes share 3 children together: Camden, Jaxon and Saylor and were divorced in 2020. Robertson also has two kids, and was previously married to actor Trace Ayala.

September 2023

While it’s unknown when the couple actually started seeing each other, the duo made their relationship Instagram official on September 20, 2023. Robertson, 33, posted a photo of the couple in Paris, France, attending a wedding.

Three days later, she shared another photo of the pair posing for the couple, this time from Montana.

“Sunsets in Montana never disappoint 🫶🏼” wrote Robertson in an Instagram Caption, alongside a photo of herself getting cozy with Cutler.

January 2024

It was a new year, new relationship for the lovebirds, with Cutler drawing a romantic line in the sand for the couple.

On January 19, Cutler posted a beach picture where he wrote the words “Sam <3 Jay” in the sand, tagging Robertson.

April 2024

The couple showed off their shared passion for hunting in a joint Instagram post with Jay Cutler’s company “Outsider.”

“Some hunting stories are better than others. Shoes off, no pants and longbeard down,” they wrote in the caption, referring to the video posted of Robertson hunting with no shoes, and a sweatshirt wrapped around her waist. “Our new semi clothed pro hunter, @samanthajrobertson, with a great shot from 45yds.” The second videos show the couple explaining how Robertson got into that specific situation.

November 2024

It’s wedding bells for Cutler and Robertson!

Robertson was wearing what appeared to be a large diamond ring on her ring finger during an appearance at the Yellowstone season 5B premiere after party. While neither have spoken publicly about the engagement, sources confirmed the impending nuptials to People on November 19, 2024.

Cutler also posted about the event on his instagram account, captioning a photo of the couple:
“Thanks to @paramountnetwork @101studiosco @yellowstone for having me out to the Yellowstone premiere for season 5. Going to be one hell of a ride!” The two were photographed as a couple, and alongside Real Housewives of New York City’s Bethenny Frankel and businessman Tom Villante.