Bachelors 2008

Bachelors Matchmaker!

Play Cupid for Chace, John, Kanye, George and more single stars. Tell us: Whom should they date? By Cara Lynn Shultz


He's dated Hollwood's elite. But whom should the troubador, 30, settle down with?

Jennifer Aniston, 39: The couple have been spotted getting cozy in Miami – and she smooched him backstage at his concert.
Jessica Simpson, 27: He famously defended his ex on his blog – do old feelings die hard?
Sheryl Crow, 46: A fellow musician, they've spent months touring on the road together.