The Moment: Starting a relationship with rapper Common
The Date: Sometime in 2008
Why It Was Crazy: We're not sure exactly when these two started seeing each other, because they kept it very quiet at first. But, after dating Jackie Long and Brett Ratner, Serena started dating Common and their relationship lasted for about two years before they called it quits in 2010. Since then, Serena has also been linked to Drake.