Celebrity Bachelors Matchmaker! Play Cupid for Chace, John, Kanye, George and more single stars. Tell us: Whom should they date? By Cara Lynn Shultz By People Staff Published on June 11, 2008 11:00 AM Share Tweet Pin Email Trending Videos 01 of 08 CHACE CRAWFORD P.Hawthorne/Startraksphoto;D.Herrick/ZUMA;Theo Wargo/WI;G.Binuya/ABACA 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? 02 of 08 JOHN MAYER Doug Peters/PA Photos/ABACA;J.Kopaloff/FM;M.Caulfield/WI;J.Merritt/FM 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. 03 of 08 KANYE WEST J.Mayer/WI;LYDIE/SIPA;G.Flores/CelebrityPhoto;J.Ufberg/WireImage The multiple Grammy winner, 31, is newly single. But who can share in his success? • Alexis Pfeifer, 30: He remains friends with his ex-fiancée.• Keyshia Cole, 26: He's written tracks for the reality star who lives – could they collaborate on love?• Alicia Keys, 28: A multiple Grammy winner herself, she has the star power to match Kanye's. 04 of 08 RYAN GOSLING Ray Mickshaw/WI;Vera Anderson/WI;George Pimentel/WI;Dara Kushner/INF The Academy Award nominee, 27, keeps a low profile. But whom should he veg out with? • Rachel McAdams, 31: Ryan spent two years with his Notebook costar, whom he's called "kind" and "stunning."• Michelle Williams, 27: The pals together in Manhatttan. Could they be the next Reese and Jake?• Kelli Garner, 24: She costarred with him in Lars and the Real Girl – for which he landed an Oscar nod. Could she be his lucky charm? 05 of 08 JOHN KRASINSKI J.Mayer/WI;Jane West/INF;M.Brown/Getty;Andrew H. Walker/Getty The actor, 28, is the resident romantic on The Office. But whose picture should be hanging in his cubicle? • Jenna Fischer, 34: They have incredible chemistry as Jim and Pam – and who didn't get goosebumps when he kissed her?• Rashida Jones, 32: The on-and-off couple were recently spotted stepping out to lunch.• Mandy Moore, 24: His License to Wed costar fits that "girl next door" quality he's said he's looking for. 06 of 08 SHIA LABEOUF D.Charriau/WI;J./WireImage;Juan Rico/Fame;Brad Barket/Getty This quickly rising star, 22, already has two blockbusters – Transformers and Indiana Jones – under his belt. But who should be on his arm on the red carpet? • Sarah Roemer, 23: His sexy Disturbia costar has seen her own star rise as well.• Megan Fox, 22: They had steamy chemistry in Transformers – and like him, she'll be back in the sequel.• Christina Ricci, 28: Like Shia, she's a former child star – and they're costarring together in the new film New York, I Love You. 07 of 08 STEPHEN COLETTI J.Vespa/WI;J.Strauss/WI;R.Walsh/Landov;Jordan Strauss/WireImage. 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. 08 of 08 GEORGE CLOONEY XPOSURE/RAMEY; F.Micelotta/WireImage; J.Furniss/WI; Getty The ultimate bachelor, 47, is again single. But with whom should the two-time Sexiest Man Alive share his life? • Sarah Larson, 29: Rumors of an engagement flew before the couple split. Was the breakup a sign of cold feet?• Renée Zellweger, 39: His longtime friend has called him a "good man."• Ellen Barkin, 54: Like Clooney, the sexy Ocean's Thirteen costar is a Hollywood vet. Is it time for an older, seasoned woman?