Jay Cutler is off the market! After over a year of dating, the famous ex-quarterback is now engaged Samantha Robertson. Cutler, 41, is best known for his time in the NFL, where he played 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 divorced in 2020. Robertson also has two children and was previously married to an actor Trace Ayala.
September 2023
While it is 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 it another photo of the couple posing for the couple, this time from Montana.
“Montana sunsets never disappoint 🫶🏼,” Robertson wrote in an Instagram caption, alongside a photo of her cozying up with Cutler.
January 2024
It was a new year, a new relationship for the lovebirds, with Cutler drawing a romantic line in the sand for the couple.
On January 19, Cutler posted a beach photo in which he wrote the words “Sam <3 Jay" in the sand and tagged Robertson.
April 2024
The couple showed their shared passion for hunting in one joint Instagram post with Jay Cutler’s company ‘Outsider’.
“Some hunting stories are better than others. Shoes off, no pants and long beard down,” they wrote in the caption, referencing the video of Robertson hunting without shoes and a sweatshirt wrapped around her waist. “Our new semi-dressed pro fighter, @samanthajrobertson, with a great shot from 45 yards.” The second video shows the couple explaining how Robertson ended up in that specific situation.
November 2024
The wedding bells are ringing for Cutler and Robertson!
Robertson wore what appeared to be a large diamond ring on her ring finger during a performance at the Yellowstone Season 5B premiere afterparty. Although neither has spoken publicly about the engagement, sources confirmed the upcoming nuptials 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 @goldstone for letting me come along to the premiere of Yellowstone for season 5. It’s going to be one hell of a ride!” The two were photographed as a couple and next to each other Real Housewives of New York City Bethenny Frankel and businessman Tom Villante.