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 Gossip Girl heartthrob, 22, is hot on the market since splitting from Carrie Underwood. So, whom should he date?

Michelle Trachtenberg, 22: Rumors flew last month that the two were dating – and she's called him a "sweetheart."
Taylor Swift, 18: Chace has a thing for blonde country stars. Maybe he could dry those teardrops on her guitar!
Leighton Meester, 22 They once found a love connection on Gossip Girl – could life imitate art?