3) George Clooney
George Clooney's dating history is one thing of a laundry list of significant-name relationships boasting his wit and sense of humor. But before marrying Amal Alamuddin in 2014, the actor dated many actresses and models. He was also rumored to pursue Kelly Preston in the late '80s and even steady with Lisa Snowdon in the early 2000s.
Clooney had also been pretty serious with other celebrities, such as Elisabetta Canalis and Stacy Keibler, apart from his affair with Bar Refaeli. His reputation as a Hollywood bachelor was finally written in stone when he vowed never to get married until he met Amal Alamuddin, a human rights lawyer who impressed him not just with her intelligence but also with her activism, and to whom he got married and had their twins in 2017.