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Former NFL quarterback Jay Cutler is reportedly engaged to girlfriend Samantha Robertson two years after his divorce from reality television star Kristin Cavallari was finalized, multiple sources with knowledge of the situation told PEOPLE.com.
Robertson, a mother of two, was spotted wearing a diamond ring when she and Cutler attended the Yellowstone Season 5B premiere earlier this month. The couple went public with their relationship in September 2023, after Robertson shared several photos with Cutler after they attended a wedding together in France, which was followed by a photo of them together during a trip to Montana days later.
“Sunsets in Montana never disappoint 🫶🏼,” Robertson wrote in the caption of the Montana trip photo.
Robertson was previously married to actor Trace Ayala, the father of her two daughters. Cutler and Cavallari, who share two sons and a daughter, announced they were separating in April 2020 after seven years of marriage and finalized their divorce in 2022.
“I hope that he finds someone, I really do,” Cavallari said during an appearance on the Call Her Daddy podcast in 2022. “I want him happy. My kids benefit from that, you know. So I hope that he gets remarried.”
Cutler was a Pro Bowler in 2008 and selected as one of the 100 greatest Chicago Bears of All-Time during the team's centennial anniversary in 2019, ranking first in franchise history for passing yards (23,444), passing touchdowns (154) and QB wins (51). The Indiana native finished his 12-year NFL career with 35,133 yards, 227 touchdowns and 160 interceptions on 3,048 of 4,920 passing.
Cutler was selected by the Denver Broncos at No. 11 overall in the 2006 NFL Draft and spent his first three seasons with the franchise before being traded to the Bears in 2009. The former Vanderbilt standout initially retired in May 2017 before signing with the Miami Dolphins months later for one final season.