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.

Sign up for our daily newsletter and other special offers.
    Choose your newsletters
Thank you for signing up! Your request may take up to one week to be processed.
    see all newsletters