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Denise Richards

Track record: She’s had her fair share of dating older Hollywood men ( John Stamos, Charlie Sheen, Richie Sambora, you get the picture), but maybe it’s time to try change it up a little. There’s got to be a boy toy out there looking for a Bond girl. Cougar role model: Linda Hogan. Sure she did the marriage thing, had the kids and starred in a reality show, but it’s never too late to start over. Jason Merritt / Getty Images