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More Than Friends

Originally posted Thursday October 20, 2005 06:00 AM EDT

Jennifer Aniston and Vince Vaughn Photo by: Malibu Media

That's exactly how some pals have reacted to the news of the yoga-loving Friends megastar linking up with the Wedding Crashers goofball, a stalwart guy's guy who prefers flannel shirts to red-carpet glam. "Vince and her? Really? I see them as very different types of people, with different interests," says Vaughn's friend and Swingers costar Jon Favreau. But others see why Vaughn might attract the ex-Mrs. Pitt. "He's as funny and charming offscreen as he is onscreen," says his Be Cool producer Stacey Sher. "He's well-brought-up, he's polite, he's thoughtful, he's kind."

Adds Crashers costar Keir O'Donnell: "He has an old-world quality about him, like a Frank Sinatra." Still, "he hasn't had a relationship with somebody in a while," says a friend. Vaughn's only prior high-profile romance was with actress Joey Lauren Adams, whom he dated in 1998. But like his Crashers character, Vaughn seems to be mellowing with age. "Some of his friends are having babies and growing up," says the pal. "Maybe he is maturing."

Aniston would certainly know. She returned to Chicago for the final stop of Vaughn's Wild West Comedy Show tour (in which Vaughn emceed for stand-up acts) Oct. 11 at Chicago's Vic Theatre. The actress laughed and looked on as Vaughn glanced up at her balcony seat and waved. Once the show ended, Aniston stuck around for the wrap party. At first she and Vaughn kept their distance, but they quickly warmed up to one another, holding hands and stroking each other's back before kissing while boogying on the makeshift dance floor to "Funkytown."