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


The Laguna Beach alum, 22, proved he can still set hearts aflutter on The Hills. But whom should he date?

Lauren Conrad, 22: They went on a date on The Hills – and she's clearly still interested.
Lo Bosworth, 21: They're old schoolmates – but with a clean slate and room to grow.
Kristin Cavallari, 21 Stephen's first love, she's also pursuing a film career.