Charlize Theron & Sean Penn
Have you seen Charlize Theron’s 2017 film Atomic Blonde? Sorry, she’s amazing. Anyway, she was dating Sean Penn and even got engaged to him in 2014. Penn is 15 years older than her. Sadly, it didn’t work, and they split in 2015.

Charlize Theron & Sean Penn
Evan Rachel Wood & Marilyn Manson
Now, the star of HBO’s new hit, Westworld, and so much more, Evan Rachel Wood! She was dating the wild musician Marilyn Manson on and off from 2006 until 2011. Wood was just 18 years old when she began dating the musician who is 18 years her senior. Actually, the two got engaged, but still broke up in 2011.

Evan Rachel Wood & Marilyn Manson