Rudy Giuliani's 10-year age gap with his third wife, Judith Nathan, is somehow the least messy aspect of their relationship. According to New York Magazine, the 55-year-old politician was a married man when he ran into 45-year-old Nathan at the Club Macanudo in New York in 1999. At the time, Giuliani had been married to Donna Hanover for nearly 15 years, and they had already welcomed two children.

However, they apparently weren't on the former New York Mayor's mind when he met Nathan, as he told the New York Times in 2003 that he was drawn to her the moment he laid eyes on her. By their third meetup, Nathan was telling her mother that he was the one. "We simply were two people in love — never mind the extracurricular stuff that went on around us," she said, in apparent reference to he

See Full Page