Leila George and Sean Penn (With a 32-year age gap)
During his famous and long career, Sean Penn has married a number of well-known personalities. Among them, of course, Madonna and Robin Wright, but it seems that after the end of these relationships Sean was attracted to a younger target.
This resulted in him entering into a public relationship with a much younger woman. Layla George, an actress who was linked to him in 2019, is 32 years younger than him.