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Some people have a preference when it comes to picking a mate and Kimora Lee Simmons is certainly one of them.
The Baby Phat founder married into hip-hop royalty by tying the knot with Russell Simmons in 1998.
Their relationship sparked a controversy because she was just 17 at the time while he was almost 30.
When that relationship went sour, she found love again with heavyweight boxer Wladimir Klitschko, who was even older than Ventimiglia by a couple years.
Eventually she was able to find love again with financier Theodore Fortsmann.
They remained together until he passed away from brain cancer in 2011 at the age of 71; she’s now rumored to be dating Richard Gere.
Although he dedicated a novel to her and even based one of the central characters after her, the couple divorced three years later.
Mary Kate and Ashley Olsen grew up in the public eye.
But after five years and a son together, they split up and she moved on to investment banker Tim Leissner whom you can tell has at least a few years on Kimmie.
Hayden Panattiere’s first big role was on a soap opera but she grabbed Tinsel Town’s attention as the indestructible cheerleader on the hit show “Heroes.” She also found herself in love with her co-star Milo Ventimiglia.
Eleven years and two children later, she and Simmons, who’s almost two decades older than the long-legged model, divorced.Soon she moved on to Djimon Hounsou, who’s only a mere 14 years older than her.