Giuliani has been married three times. On
October 26, 1968, soon after he graduated from law school, he married his second cousin, educator
Regina Peruggi, whom Giuliani had known since childhood. In the mid-70s the marriage was in trouble and in 1975 they agreed to a trial separation. Peruggi did not accompany him to Washington when he accepted the job in the Attorney General's Office. Giuliani met local
television personality Donna Hanover sometime in 1982, and they began dating when she was working in
Miami. Giuliani filed for
legal separation from Peruggi on
August 12, 1982. Giuliani and Hanover started living together later that year in
Washington, D.C.
The Giuliani-Peruggi marriage was ended in two ways: a civil
divorce was issued by the end of 1982, while a
Roman Catholic Church annulment of the Giuliani-Peruggi marriage was granted at the end of 1983, according to Giuliani, because he discovered after 14 years of marriage that he and his wife were
second cousins, Washington Post,
March 8, 2006, p. A04.</bgref> rather than third cousins, and they did not have the Church dispensation thus needed. Giuliani and Peruggi did not have any children.
Giuliani and Hanover then married in a Catholic ceremony at St. Monica's Church in New York on
April 15, 1984. They had two children, son Andrew (born
January 30, 1986) and daughter Caroline (born 1989). Andrew first became a familiar sight by misbehaving at Giuliani's first mayoral inaguration, then with his father at
New York Yankees games, of whom Rudy Giuliani is an enthusiastic fan; Andrew also was an accomplished
junior golfer.
Beginning in 1996, Giuliani and Hanover's public relationship became distant, with Hanover appearing at few public events. In 1997, a
Vanity Fair article report that Giuliani had a romantic relationship with
Cristyne Lategano, the mayor's communications director. The mayor and Lategano denied the allegations. On Father's Day, 1995 Giuliani had told reporters that he was returning to Gracie Mansion to play ball with Andrew. However, he instead went to City Hall, to a basement suite with his press secretary. Three hours later, Hanover, angered, appeared at City Hall; yet a mayoral aide prevented her from entering the suite.
In May 2000, the
New York Daily News broke news of Giuliani's extramarital relationship with
Judith Nathan, a sales manager for a pharmaceutical company. Giuliani then called a press conference to announce that he intended to separate from Hanover.</bgref></bgref></bgref> Hanover, however, had not been told about his plans before his press conference,</bgref> an omission for which Giuliani was widely criticized.</bgref>
Previously, Giuliani had hinted at the relationship by referring to Nathan as his "very good friend."
Giuliani now went on to praise Nathan as a "very, very fine woman", and said about his marriage with Hanover, that "over the course of some period of time in many ways, we've grown to live independent and separate lives." Hours later Hanover said, "I had hoped that we could keep this marriage together. For several years, it was difficult to participate in Rudy's public life because of his relationship with one staff member," a reference to Lategano. Giuliani, Hanover and Nathan appeared on the cover of
People magazine in the aftermath.
Giuliani then moved out of
Gracie Mansion and into an apartment belonging to two gay friends. Giuliani filed for divorce from Hanover in October 2000, and an unpleasant public battle broke out between their representatives. Nathan was barred by court order from entering Gracie Mansion (where Hanover still lived) or meeting his children before the divorce was final. In May 2001, in an effort to mitigate the bad publicity from the proceedings, Giuliani's attorney revealed (with the mayor's approval) that Giuliani was impotent due to his
prostate cancer treatments and had not had sex with Nathan for the preceding year. "You don't get through treatment for cancer and radiation all by yourself," Giuliani said. "You need people to help you and care for you and support you. And I'm very fortunate I had a lot of people who did that, but nobody did more to help me than Judith Nathan." Giuliani argued in a court case that he aimed to introduce Nathan to his children on Father's Day, 2001, and that Donna had prevented this visit.
Giuliani and Hanover finally settled their acrimonious divorce case in July 2002, after his mayoralty had ended, with Giuliani paying Hanover a $6.8 million settlement and granting her custody of their children.
Giuliani subsequently married Judith Nathan on
May 24, 2003, and thus gained a stepdaughter, Whitney. It was also Nathan's third marriage after two prior divorces.
By March 2007,
The New York Times and the
New York Daily News reported that Rudy Giuliani had become estranged from both his son Andrew (now a golf team member at
Duke University) and his daughter Caroline (graduated from
Trinity School in 2007, attending
Harvard University), missing major events in their lives, such as graduations, and sometimes going long stretches without talking to them, and that neither of them was taking part in his presidential campaign. Caroline uses her mother's surname, Hanover, rather than Giuliani's, and according to reports, she did not inform Giuliani when she was accepted to Harvard. Caroline apparently linked her personal
Facebook page to the campaign of Democratic presidential candidate,
Senator Barack Obama. However, after a
slate.com contributor reported this link, Caroline removed this link from her "Facebook" page.
He is the godfather to former New York City police commissioner
Bernard Kerik's two youngest children.