40.George Clooney and Lucy Liu

Everyone once thought that George Clooney was the kind of man who would never settle, until = Amal Alamuddin entered his life with her sophistication and brains. While everyone was happy about their union, some viewed Mr. Clooney is their one who got away.Ever since the actor started his career, his dating life was always a hot topic. Prior to meeting his lawyer wife, he was notoriously known for his bachelor lifestyle and his fear of commitments. Clooney was not afraid to admit his involvement with women, but his rendezvous with Lucy Liu was an exemption.

He and Liu were rumored to date in 2000 since they were often spotted together, yet they never admitted to having a relationship despite being captured locking lips on New Year’s Eve 2006. Apparently, things were a bit off for both of them as Clooney started dating Lisa Snowdon. As years went by, both of them walked down different paths. Liu has never married but has a son via gestational surrogacy, while Clooney ended up getting married at becomes a father at the age of 56.