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The thing about playboys is, they like to play. And avowed bachelor George Clooney was doing just that as he broke bread—actually, chicken and shrimp fajitas—at Tortilla Flats in Manhattan on Oct. 12 with old pals including Rande Gerber, Cindy Crawford and Tate Donovan. There was laughter, there were Herradura Añejo margaritas ... and there was a stunning brunette rubbing Clooney's neck. Las Vegas cocktail waitress Sarah Larson lip-synched to pop tunes with Cindy, did a chilled shot with Rande and covered George with kisses—a make-out session similar to one they enjoyed a few days earlier at Harry Cipriani. "He seemed very proud to show her off," says a Cipriani staffer. "He liked the attention."

A continent away, fellow player Matthew McConaughey was practicing his own version of ladies'-man living: At Les Ombres restaurant in Paris on Sept. 24, the Texan greeted the maître d' with a "bonsoir," then spent the next several hours holding hands with Brazilian model Camila Alves as they watched boats pass on the Seine. Over the next few days, the two were inseparable while he filmed a Dolce & Gabbana ad. "He was playful, but very gentlemanly," says one witness. Sums up another: "Très cool."

And alas, ladies, très taken. After years of devotion to the buddies they play ball with—and pull pranks on—PEOPLE's current and former Sexiest Man Alive both seem to have found keepers in women who can match them in spirit and stride. Alves, 24, a native of Rio de Janeiro whose family moved to L.A. when she was young, met McConaughey about a year ago. Since then, she has been the gung ho girl at his side, riding the waves this year from Australia, where he filmed Fool's Gold, to the Bahamas, where he shot the comedy Surfer Dude. Meanwhile, Larson, 28, who heralds from Kent, Wash., and has worked at several of the N9NE Group's nightspots in Vegas for several years, got more than a thrill riding shotgun Sept. 21 on Clooney's Harley Davidson in Weehawken, N.J. When a car in front of them took an unexpected turn, they took an unexpected face-plant onto the sidewalk. He fractured a rib and she broke a toe, but that didn't stop them from attending the New York City premiere of his film Michael Clayton three days later. Clooney, 46, was proud of his lady, who gamely limped down the red carpet in one high heel, an ace bandage and crutches. As he told PEOPLE, "She seems like she can take it, huh?"

She's not the only one. Bliss for McConaughey is his $100,000 Airstream trailer—an upgrade from the model he used to trek across the country in 2005 doing press for Sahara. His costar and then girlfriend Penélope Cruz skipped the road trip, but Alves has been a regular at the Malibu Beach RV park where McConaughey camped until recently, showering in the public facilities and washing dishes outdoors.

"She likes roughing it," says a close McConaughey source. "She doesn't complain when they go hiking for 10 days without clean clothes or a shower." Which may be why he took a break from filming in April and brought Alves to meet his family in Texas. In September the two took a serious step forward by moving into a $1.1 million modular home in Malibu. Both now sport mystery matching rings, but "they're not engaged," says a source. Still, says another McConaughey friend, "everyone is convinced he'll be with her for a long time, if not forever."

Clooney's romance with Larson, whom he has known casually for years, took off when they cozied up at the Ocean's Thirteen Las Vegas premiere party in June. Smart, sweet and athletic, she is, says a Clooney friend, "totally his type." He's not shy about letting people know it. During an August stay at the Hotel Cipriani for the Venice Film Festival, says a source, "He couldn't keep his hands off her." Ditto in New York, where, after their accident, he was also protective, cautioning well-wishers at a party, "I have an injured person on the couch."

Signs of long-term tenderness? "Priorities do change as you get older," Clooney told reporters in August. Then again, some things may never change, as he made clear recently to an artist in Venice who offered to do custom paintings as wedding gifts. "Don't say weddings around me," Clooney responded. "No weddings!" All together now: Whew!

  • Contributors:
  • Jennifer Garcia/Los Angeles,
  • Lesley Messer/New York City,
  • Alyssa Shelasky/New York City,
  • Jeffrey Slonim/New York City,
  • Michelle Tan/New York City,
  • Alicia Dennis/Austin,
  • Peter Mikelbank/Paris,
  • Courtney Rubin/Venice,
  • Monique Jessen/Venice.