Hollywood's Best & Worst Boyfriends

JAKE GYLLENHAAL, 27
HOT—AND SO SWEET!

STATUS: Dating Reese Witherspoon, 32, since March 2007.

HE’S KID-TESTED: “He really enjoys spending time with” Witherspoon’s kids from her marriage to Ryan Phillippe—Ava, 9, and Deacon, 5—says a source close to the couple. The actor even flew from a London movie set to Los Angeles to celebrate Deacon’s 5th birthday.

NOW THAT’S LOVE: He’s willing to try anything—even yoga!—to make his lady happy.

JAKE’S BOYFRIEND RATING: [4 hearts]

JOHN MAYER, 31
THE LADIES’ MAN

STATUS: In October he reunited with Jennifer Aniston, 39, after a break. Exes include Jennifer Love Hewitt and Jessica Simpson.

THE MAYER MOJO: “He makes you feel like you’re the most beautiful woman on the planet,” says a source. The singer told PEOPLE he is “very appreciative” of Aniston, adding, “to have somebody who knows you in this world, that’s a really nice thing.”

THE DOWNSIDE: Don’t expect him to keep a secret. In August Mayer blabbed to paparazzi about his split from Aniston.

JOHN’S BOYFRIEND RATING: [2½ hearts]

People.com Readers poll

Would You Date John?

YES 30%

NO 70%

RAFFAELLO FOLLIERI, 30
ANNE HATHAWAY‘S CRIMINAL EX

STATUS: Single since Hathaway ended their four-year romance shortly before he was arrested for fraud.

ARRIVEDERCI, BABY: Chartered planes, private yachts, trips to Capri—fun, for sure. Not fun? Seeing your ex (who posed as a sharp Italian businessman with ties to the Vatican) sentenced to 4 1/2 years in jail for scamming investors with bogus real estate deals.

RAFFAELLO’S BOYFRIEND RATING: [Broken Heart]

TONY ROMO, 28

THE ALL-STAR

STATUS: Girlfriend Jessica Simpson, 28, has been his No. 1 fan for nearly a year.

TOUCHDOWN: The Cowboys quarterback loves kids, dotes on Jessica’s maltipoo pup Daisy and is willing to talk on the phone for hours every night they’re apart. No wonder the singer can’t stop gushing about him. This fall Simpson told the crowd at the state fair in Texas that she’d dated some “butthead” guys in the past—and Romo is “an amazing boyfriend . . . the calm of the storm in my life.”

TONY’S BOYFRIEND RATING: [4 hearts]

GEORGE CLOONEY, 47
THE UNCATCHABLE CATCH

STATUS: Single (don’t believe rumors that he’s reunited with former flame Krista Allen).

HE’S GOT IT ALL: Looks, smarts, an estate on Lake Como . . . but above all, that old-school elegance. Says a pal of his ex Sarah Larson: “He is over-the-top polite. He holds doors, pulls out chairs, gets drinks. He is a rare breed.”

THE HITCH: Marriage. He’s not interested. At least he’s honest.

George’s BOYFRIEND rating: [3 hearts]

Would You Date George?

YES 62%

NO 38%

LOVE LIVES OF THE GOSSIP GUYS

Their Gossip Girl characters sizzle—but how do they score offscreen?

CHACE CRAWFORD, 23
STATUS: Single. “He’s very caring,” says a pal. He even gives girlfriends homemade gifts! For one, “I did a beautiful drawing,” he says.

ED WESTWICK, 21

STATUS: Single, but spotted kissing costar Jessica Szohr, 23. “I like the challenge of keeping the sparkle in something,” says the Brit.

PENN BADGLEY: PENN BADGLEY, 22
Blake Lively: STATUS: Dating costar Blake Lively, 21. He’ll write songs and serenade his dates.

PLUS: “I rarely cook, but I would for a girl.”

ZAC EFRON, 21
THE HIGH SCHOOL SWEETHEART

STATUS: Dating his High School Musical costar Vanessa Hudgens, 20, since 2005.

GOING STEADY: He has stuck by Hudgens despite the pitfalls of youth, fame and elaborate dance sequences. And, yes, Hudgens admitted to Ellen DeGeneres, he’s “a good kisser.”

ZAC’S BOYFRIEND RATING: [3 hearts]

HE’S GETTING SERIOUS!

JUSTIN TIMBERLAKE: JUSTIN TIMBERLAKE, 27
Jessica Biel: He and Jessica Biel, 26, spent Thanksgiving together in his hometown of Memphis; in October they attended her friend Beverley Mitchell’s Italian wedding. After nearly two years of dating, the pair seem like—dare we say it?—a married couple. “I give Jess the right to choose where we eat all the time,” Timberlake said recently. “I know where my bread is buttered.”

CHRIS BROWN, 19
YOUNG AND HAVING FUN

STATUS: Dating Rihanna, 20, since early ’08.

IN TUNE: With their romance now public, the singers love to cuddle at clubs. She’s “down-to-earth, real cool,” Brown says. But he shoots down rumors they’re cohabiting: “I’m 19! I don’t want to move in with anybody yet.”

CHRIS’S BOYFRIEND RATING: [3 hearts]

LANCE ARMSTRONG, 37

THE GLOBE-TROTTING PLAYBOY

STATUS: Single since the end of a fling with Kate Hudson, 29, in July.

DATESTRONG: The champion cyclist and cancer activist keeps busy with his Lance Armstrong Foundation and just announced he will compete in the 2009 Tour de France—but he still makes time for romance. He’s dated Sheryl Crow, fashion designer Tory Burch and Hudson and flirted with Ashley Olsen, but anyone looking for a soulmate should proceed with caution. “He probably makes a better buddy than a boyfriend,” says a pal. “He loves the ladies.”

LANCE’S LOVE RATING: [2 hearts]

Would You Date Lance?

YES 26%

NO 74%

JACK WAGNER, 49

THE STEADY PARTNER

STATUS: Dating former Melrose Place costar Heather Locklear, 47, since March 2007.

SEXY AND SUPPORTIVE: Wagner stood by Locklear through her battle with depression and recent DUI arrest. “He’s very nurturing,” Locklear told PEOPLE last year. Plus, she says, “he’s very hot!”

JACK’S LOVE RATING: [3 hearts]

BOYFRIEND RATING STAY AWAY [Broken Heart] DATE AT YOUR OWN RISK [2 hearts] HE’S A KEEPER [3 hearts] MARRY HIM! [4 hearts]

Updated by Jennifer Garcia,

and Jeffrey Slonim