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

JOHN MAYER photo | Jennifer Aniston, Jessica Simpson, John Mayer

JOHN MAYER

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.

2 of 9

2 of 9

CREDIT: Doug Peters/PA Photos/ABACA;J.Kopaloff/FM;M.Caulfield/WI;J.Merritt/FM

PUBLISHED: MONDAY JUNE 16, 2008 06:00 AM EDT

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