Who Should Be Dating Whom in 2007?

After her breakup with Kevin Federline, Britney Spears has been dating music producer J.R. Rotem. But matchmaker Shoshanna Rikon of Shoshannasmatches.com doesn't see that lasting long. "Britney needs someone stable and supportive who can keep her in check, a wholesome guy like Adrian Grenier of 'Entourage,'" she said. "Her next guy has to be someone who loves kids and is responsible." Grenier, 30, has five years on Spears, and has never been married.
(AP Photo)

Nicole Richie ended the year with a highly publicized DUI arrest, and has been dogged by reports about her weight loss and wild lifestyle. "She needs someone who's made that track down recovery road, someone who knows the burden of being a celebrity kid and managed to survive," said matchmaker Shoshanna Rikon. Jack Osbourne might be her man. "He's four years younger than her. But he's also the child of a famous music star, and achieved fame through reality TV. She needs to be on his path."
(AP Photo)

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