Jay Cutler and Fiancee Samantha Robertson's Relationship Timeline

is off the market! After over a year of dating, the famous ex-quarterback is now engaged to . 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 ,. 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 .

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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.

Courtesy of Samantha Robertson/Instagram

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.

Courtesy of Jay Cutler/Instagram

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

Related: Jay Cutler and Samantha Robertson Are Engaged: ReportJay 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 […]

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

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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.

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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.

Related: Who Is Samantha Roberston? 5 Things to Know About Jay Cutler’s GirlfriendJay Cutler has officially entered his boyfriend era with Samantha Robertson. The former NFL star hard-launched his relationship via social media in September 2023, years after his divorce from Kristin Cavallari. Cutler and Cavallari were together for 10 years before announcing their split in 2020. They share three kids. While neither Cutler nor Robertson have […]

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  and businessman

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Jay Cutler and Fiancee Samantha Robertson's Relationship Timeline

Jay Cutler and Fiancee Samantha Robertson's Relationship Timeline

Jay Cutler and Fiancee Samantha Robertson's Relationship Timeline

Jay Cutler and Fiancee Samantha Robertson's Relationship Timeline

Jay Cutler and Fiancee Samantha Robertson's Relationship Timeline