Bachelors Matchmaker!

Play Cupid for Chace, John, Kanye, George and more single stars. Tell us: Whom should they date? By Cara Lynn Shultz

01 of 08

CHACE CRAWFORD

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

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

KANYE WEST
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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

RYAN GOSLING
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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

JOHN KRASINSKI
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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

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

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

GEORGE CLOONEY
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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?

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