· though he is not married in 2025, jay has been in long-term relationships and remains a private figure in his personal life. · jay cutler is off the market! After over a year of dating, the famous ex-quarterback is now engaged to samantha robertson. · before divorcing in 2020, jay cutler was wed for 7 years to his ex-wife, kristin cavallari. His current partner is samantha robertson, who has two children from a previous marriage. His influence continues through coaching, motivational speaking, and social media, where he inspires millions worldwide. Heres everything to know about the former nfl stars fiancée. While attending his high school at wachusett regional, jay met kerry cutler, whom he dated for almost 10 years. The former nfl quarterback recently went instagram-official with new girlfriend samantha. · it was known to the public that jay had a first wife before meeting angie. · jay cutler and samantha robertson went instagram official in september 2023 and are currently engaged. · former nfl quarterback jay cutler is now living with his girlfriend samantha robertson after his divorce with kristin cavallari. · jay cutler has a new lady in his life three years after he and kristin cavallari called it quits.