Olivia Wilde & Jason Sudeikis
Actress Olivia Wilde and actor/comedian Jason Sudeikis had an immediate connection! It took only two years of dating before the couple got engaged in 2013. Though, they never married officially, they have two lovely children. So, Jason’s nine years he has on Olivia has not proved to be a problem in their relationship.

Olivia Wilde & Jason Sudeikis
Katy Perry & Russell Brand
Though, the age gap was not as substantial as some of our other couples on this list, the 9-year difference may have been a factor in Katy Perry and Russell Brand’s relationship. The marriage only lasted for two short years. Actually, many fans speculate much of Katy Perry’s lyrics are about her ex-husband on her latest album.

Katy Perry & Russell Brand