8. Kris Jenner and Corey Gamble 25 Years Apart

Kris Jenner and Corey Gamble have been together since 2014, maintaining one of Hollywood’s longest-running age-gap relationships. At 25 years her junior, Corey entered Kris’s life not long after her split from Caitlyn Jenner. Despite skepticism from the media and even her own family at first, the couple have stood the test of time. Corey appears frequently on Keeping Up with the Kardashians and has grown close to Kris’s children and grandchildren. While they keep some aspects of their relationship private, their affectionate appearances at events and mutual support have kept them in the public eye. Kris, in her late 60s, and Corey, in his early 40s, seem unbothered by the age difference and continue to prove that chemistry and connection matter more than numbers.