When you think Hollywood cougar, Demi Moore most likely comes to mind. After making a relationship with Ashton Kutcher work for a surprisingly long time, we're sure this 52-year-old can have another successful relationship with a tot. Most people don't meet their boyfriends through their children, but that's exactly what happened when Demi Moore met Rumor's friend Sean Friday. The 28-year-old has been with Demi for almost a year.
[Photo via @radargram]