Scott Disick and Sofia Richie – 15 Years

Scott Disick quite literally found fame because of his relationship with Kourtney Kardashian. They even share three children and dated from 2005 to 2015. But in 2017 Disick started making the gossip columns for a different reason when he started dating Sofia Richie, daughter of Lionel Richie.

She was 15 years younger than him, and a teenager when they met, meaning the relationship caught a lot of flack and attention. At one point they even moved in together, but in 2020 they broke up. In 2021 Disick has been rumored to be dating Amelia Hamlin, a model 19 years his junior.