9. Jennifer Lopez and Cris Judd, 9 months
Whoa, Jenny is way more of a heartbreaker than we thought. She started dating back-up dancer and choreographer Cris before she and P. Diddy broke up publicly. The two were married in October 2001. Then, she started dating Ben Affleck before she and Cris officially divorced in July 2002. We wonder what really happened with Marc Anthony.