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

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

Updated: Monday Jun 16, 2008 | 06:00 AM EDT

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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.
Single & Sexy Men of '08

Single & Sexy Men of '08

Mario! David! Andy! See the sexy – and available! – men who made PEOPLE's list last year

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