Ben Affleck and Ana de Armas (16 Years)
Ben Affleck has a notorious reputation as a ladies’ man. He’s dated the whose who in the world of Hollywood and entertainment, from Gwyneth Paltrow to Jennifer Garner to Jennifer Lopez and beyond with most of them sharing the same age range, but it seems that Anna de Armas changed all of that when they first hooked up after filming the movie Deep Water. Affleck and the brunette beauty exploded into a whirlwind romance on the quick and, as Hollywood people tend to do, professed their instant love for each other, regardless of their 16-year age gap.