George Clooney

George Clooney, the quintessential Hollywood bachelor, has been romantically linked with everyone from Anna Friel to Renee Zellwegger.  He's only been married once, to actress Talia Balsam from 1989 to 1992. He famously declared that he would never marry again, much to the disappointment of female co-stars.  Nicole Kidman and Michelle Pfeiffer famously wagered Clooney that he would settle down and start a family someday to the tune of $10,000 and $100,000 respectively.  Despite all the A-list hook-ups attributed to Clooney, he's spent most of the 21st century romancing three women—Lisa Snowden, Krista Allen, and Sarah Larson.