Jay Cutler and Samantha Robertson Deepen Relationship Following His Divorce from Kristin Cavallari

Cavallari Expresses Hope for Cutler's Happiness, Believing it Will Benefit Their Children

Former Bears quarterback Jay Cutler has found love again with Samantha Robertson after his high-profile breakup with ex-wife Kristin Cavallari. They made their relationship official in September 2023 and have recently shared a romantic beach getaway.
Cutler and Cavallari were married from 2013 to 2022 and share three children. Their divorce process, which began in 2020, was marked by financial disputes and public airing of their issues.
Cavallari has expressed her hope for Cutler to find love again, stating that his happiness would have a positive effect on their children.
Robertson, previously married to fashion designer Juan “Trace” Ayala III, has two daughters from that relationship. She and Cutler reportedly met through mutual friends in Nashville.
Cavallari is also moving on and has joined the exclusive dating app 'Raya', though she has high standards for her potential partners due to her children.