Kris Jenner and Corey Gamble, 25 Years
The momager, 64, and her boyfriend, 39, have been dating since 2014 after her split with longtime spouse Caitlyn Jenner. While he gets along with most of the Kardashian clan, he did butt heads with Kourtney after he tried to give her parenting advice.
Steven Tyler and Aimee Preston, 39 Years
Tyler, 71, is engaged to Aerosmith's 30 year old assistant, Aimee Preston. They went public with their relationship in 2016. She also used to work for Victoria Beckham and the Trump family.