Rudy Giuliani

A member of the Roman Catholic Church, Rudolph Giuliani has been married 3 times.

First, Giuliani married Regina Peruggi, his childhood sweetheart. They separated (informally, not legally) after 7 years. Giuliani moved alone to Washington, but did not divorce his wife until he met Donna Hanover, a pretty local TV personality in 1982. They began dating, and subsequently Giuliani and Peruggi split, with a civil divorce and an annulment from the Catholic Church. How does one get an annulment after nearly 14 years of legal marriage? By proving that you were actually second cousins all along, so it doesn't count. (They would have needed dispensation from the church to marry in the first place.)

Now free to marry Hanover, Guiliani did so in 1984, in a Catholic ceremony of course. They had two children, Andrew (1986) and Caroline (1989). By 1996, the marriage was on the rocks. Hanover rarely appeared at Giuliani's public events. In 1997, Vanity Fair reported that he was having an affair with City Hall communications director Cristyne Lategano. Giuliani denied the affair.

Soon enough, he'd found another woman -- Judith Nathan. In 1999, he began an affair with her, charging his police protection while at her home to the city, and arranging for her to receive chauffeured rides from the police department at taxpayer expense. By 2000, Giuliani and Nathan appeared together in public everywhere, to Hanover's chagrin. Local papers broke the news of their affair, making it official. When he finally announced he was divorcing Hanover, he did it at a press conference -- but neglected to mention it to Hanover first. She found out he was divorcing her when the press did. Giuliani left Hanover, taking refuge in the home of his gay friends.

After an acrimonious divorce from Hanover, Giuliani married Nathan in 2003. (It was, incidentally, her third marriage as well.)

Guiliani is estranged from his children.

On May 3, 2009, Rudy was a last-minute no-show at the wedding of the gay friends who took him in during his divorce from Hanover. Only days earlier, he told the NY Post "Marriage, I believe, both traditionally and legally, has always been between a man and a woman and should remain between a man and woman." It is unknown whether he sent a gift.