Jay Cutler, former NFL quarterback and ex-husband of Jana Kramer, is reportedly engaged to his girlfriend, Samantha Robertson. The couple, who went public with their relationship in September 2023, has been making headlines after Robertson was spotted wearing an engagement ring at a Yellowstone screening on November 7, according to People.
Cutler was previously married to Laguna Beach star Kristin Cavallari, with whom he shares three children. The couple tied the knot in 2013 and announced their divorce in 2020. Robertson, meanwhile, has two daughters, Sophia and River, from her previous marriage to actor Trace Ayala.
The engagement comes amid legal troubles for Cutler, who was arrested in October in Franklin, Tennessee, on charges of driving under the influence, possessing a handgun while intoxicated, and failure to exercise due care. Authorities reported that Cutler’s vehicle rear-ended another car, and officers at the scene detected alcohol on his breath.
According to reports, Cutler refused a field sobriety test, prompting officers to obtain a search warrant for a hospital blood draw. During the investigation, police also discovered two firearms in Cutler’s vehicle, including a loaded pistol.
Cutler was released on a $5,000 bond, and the charges against him are classified as misdemeanors or civil offenses under Tennessee law. Despite these legal issues, Cutler and Robertson are moving forward with their relationship.
Robertson’s connection to Cutler became public on Instagram last year, and their relationship appears to have grown stronger over time. She was seen supporting Cutler at public events, and the engagement has further cemented their commitment to each other.
As they prepare for their future together, Cutler’s legal situation adds a layer of complexity to their story. However, both Cutler and Robertson seem focused on building a life together, leaving the past behind.
The engagement marks a new chapter for the retired athlete, who continues to make headlines both on and off the field. For Robertson, the relationship represents a fresh start following her previous marriage, as the couple embarks on their journey together despite the challenges ahead.