Leila George and Sean Penn (With a 32-year age gap)
Sean Penn has been married to several well-known people throughout his illustrious and lengthy career. Of course, Madonna and Robin Wright are among them, but Sean is drawn to a younger target after the end of these relationships.
This resulted in a very public romance with a considerably younger woman. Layla George, an actress, linked to him in 2019, is 32 years his junior.