Don McLean & Paris Dylan – 49 Years Difference

One of the biggest age gaps you will see on this list is the one between singer Don McLean and his girlfriend, Paris Dylan. Dylan is reportedly 49 years younger than McLean. Dylan is a model and sources say they’ve started dating sometime in 2016. This was the same year McLean’s divorce from his second wife Patricia Shnier McLean was finalized. McLean became a popular singer in the 1970s, thanks to his song called American Pie. His latest album was Botanical Gardens which was released back in 2018. He boasts of having 21 studio albums, nine compilations, and four live albums.