9. Holly Madison
via:www.glamour.com
When you end a relationship with someone as old as Hugh Hefner, any man you date afterwards is considered an upgrade in our books. How Holly Madison managed to sleep with the 89-year-old for six years is shocking and mind baffling to say the least, but the model seems to have eventually come to her senses, finding love in her now-husband Pasquale Rotella. In fact, Madison says she’s so happy that she wishes she had met him before she went on to live in the Playboy mansion — a time she deeply regrets. Also See: Top 10 illuminati signs and the celebs that use them (+Photos)
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