Jay Cutler Engaged to Samantha Robertson

Former NFL quarterback Jay Cutler is reportedly engaged to Samantha Robertson, with multiple sources confirming the news after she was seen wearing an engagement ring at the 'Yellowstone' Season 5 premiere on November 7. The couple, who went public with their relationship in September 2023, has not officially announced their engagement yet. Cutler, 41, shares three children with ex-wife Kristin Cavallari, while Robertson has two daughters from her previous marriage. In September, Robertson posted on Instagram about their romantic trips, including a wedding in France and sunsets in Montana. This engagement comes after Cutler's tumultuous past, including a DUI charge and his divorce from Cavallari, who has expressed hopes for his future happiness. The couple's relationship timeline remains somewhat vague, but they are now celebrating this new milestone together.