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Just two months after their trip to a Las Vegas chapel, Nicky Hilton and money manager Todd Meister, 33, are working out a separation agreement that could lead to an annulment, says a source close to the Hilton family. The reason for dissolving the marriage? First, the couple’s bicoastal relationship—she’s mostly in L.A. and he’s in New York City—wasn’t working, and second, they wed on a whim. The source says what’s holding up the agreement is that Hilton wants to keep her diamond wedding ring, which belonged to Meister’s late mother. A rep for the duo will only say that the couple “is working out issues, but there is nothing to announce right now.” Money matters didn’t dampen Hilton’s spirits last weekend in Vegas however, as she celebrated her 21st birthday with her family and close friends—including her ex-boyfriend actor Kevin Connolly (Entourage)—at the Hard Rock Hotel & Casino. Paris, meanwhile, was seen in Sin City hanging out with performer boyfriend—video playmate Rick Salomon.


Continuing to make people’s dreams come true, Oprah Winfrey threw a lavish wedding at her Montecito, Calif., estate Oct. 16 for her longtime personal trainer Bob Greene, who married Urania Orozco. The black-tie affair, held on the lawn of her 23,000-sq.-ft. Georgian, was a gift from Oprah to Greene. Strings greeted guests in the afternoon, and trumpets signaled the start of the wedding. “This is very much an Oprah production,” said one guest. And befitting the talk show queen, the timing was perfect. No sooner had the couple been pronounced man and wife than rain poured down. On cue, the party moved indoors, where the celebration continued until 11 p.m.


Not a lot of directors say “No, thanks” when George Clooney lobbies for a role in their movie, but that’s what happened when the actor met with Alexander Payne (About Schmidt). Clooney wanted to play the washed-up soap star in Sideways, Payne’s midlife-crisis buddy comedy based on the novel by Rex Pickett. The two met at Bob’s Big Boy in Toluca Lake, Calif., where Payne had to tell Clooney he wasn’t right for the part. “I said, ‘You’re a wonderful actor, but I wouldn’t believe that one of the world’s most handsome, most famous movie stars can play one of the world’s biggest loser actors,'” says Payne. The part eventually went to Thomas Haden Church.


Despite their 2002 stink bomb Swept Away, Madonna and Guy Ritchie are ready to work together again. A source says the pop star will be one of several featured cameos in Ritchie’s latest crime caper, Revolver, which began shooting in London this week…. Putting to rest rumors of an impending breakup, Leonardo DiCaprio and supermodel Giselle Bündchen were spotted holding hands in a stairwell at the Oct. 18 Hollywood Awards Gala, where the actor was honored for his upcoming Howard Hughes biopic, The Aviator.