Sean Penn and Charlize Theron
Actress Charlize Theron and legendary Sean Penn dated in spite of the fact that the iconic star is 15 years older than the actress. Unfortunately, their relationship did not last. They broke up back in 2015.
Marilyn Manson and Evan Rachel Wood
The amazingly talented Evan Rachel Wood, who stars in HBO’s critically-acclaimed Westworld, used to be in an on-and-off relationship with musician Marilyn Manson. Wood is younger than Manson by 18 years. The two started dating in 2006, when Wood was just 18 years old. They even became engaged, but they eventually ended their relationship back in 2011.