Rudy Giuliani’s daughter has told of her love for threesomes, describing sex with a couple as an ‘ecstasy of unbridled self-discovery’ which was ‘metamorphic’.
Caroline Giuliani, a 31-year-old filmmaker, wrote in graphic detail about exploring her own sexuality.
She said she knew she was bisexual, but had been in monogamous relationships that were ‘not conducive to personal and sexual growth.’
Giuliani is the daughter of Donald Trump’s former lawyer and his second wife, journalist Donna Hanover – who found out during a 2001 press conference that the then-mayor of New York was leaving her.
Her brother Andrew, 34, worked at the White House and was a frequent golf partner of the former president but Caroline is estranged from her thrice-married father, and in October wrote a damning indictment of his policies in Vanity Fair.
Caroline Rose Giuliani, 31, wrote in Vanity Fair on Thursday about sexual exploration
Caroline and Andrew Giuliani are pictured with their father, Rudy, Trump’s former lawyer
On Thursday the magazine’s website published another of her features, in which she told of her sexual exploration and why she did it.
‘I now understand that my curiosity, open-mindedness, and sense of adventure are three nonnegotiable, defining elements of my identity,’ she wrote.
‘But it wasn’t until I started sleeping with couples that I shed my shame about those qualities, let alone embraced them in all areas of my life.
‘Finding the strength to explore these more complicated, passionate aspects of my personality became the key to harnessing my voice and creative spark, which in turn helped me better cope with depression, anxiety, and the lingering cognitive effects of adolescent anorexia.’
Giuliani described what it was like to be ‘a unicorn’ – a person joining in with a couple, and ‘entering a power dynamic where they are the only one without an established teammate.’
The Los Angeles-based filmmaker described her sexual adventures as thrilling and liberating
Giuliani is estranged from her father and has been highly critical of him in the press
She told of her search for sexual fulfilment, writing: ‘Once I was single, I immediately began to make up for lost time.
‘I took soul-nourishing psychedelic trips into the desert with friends.
‘I broke my stainless steel bed frame with tons of great (and safe) sex.
‘Of all of the variants of ecstasy I experienced during that period, the ecstasy of unbridled self-discovery was the most metamorphic.’
The Los Angeles-based filmmaker told how, via Google, she discovered the app Feeld, where ‘the sexually adventurous can go to find one another,’ she said.
Giuliani wrote: ‘As with any online forum, I had to weed out the occasional creep, but in general, the people I connected with were clear communicators and more transparent about difficult subjects like STD status than I had ever encountered before.’
And she said that going on a date with two people was more challenging, stimulating and rewarding than with with one – describing it as ‘volleying a beach ball with no net and no playbook.’
She said: ‘The fluidity of the situation made autopilot impossible, which made me realize how often I do go on autopilot, in dating and otherwise.
‘I thought more consciously about what I wanted to do or say in each moment. At whom did I want to bat my new eyelash extensions? Did I want to ask questions about him, her, or their relationship? Even small details like the seating arrangement required more active attention.’
Giuliani said that she still hopes, ultimately, to find a ‘monogamish’ relationship, but was enjoying finding her way there.
Her father, who is not mentioned in the article, has not commented.
Giuliani, 76, served as Donald Trump’s lawyer – to the dismay of his daughter
Rudy Giuliani’s November 19 press conference is etched in the memory for many Americans
Giuliani dressed in drag for a skit with Donald Trump in 2000
The 76-year-old is known for his own unusual romantic arrangements.
He married his second cousin, Regina Peruggi, in 1968 – a marriage that lasted until 1982.
In 1984 he married Caroline’s mother, Donna Hanover.
By the late 90s, Cristyne Lategano, his press secretary as mayor, had been widely assumed – despite her vehement denials – to hold a special place in his heart.
In May 2001 Hanover, found out at a press conference that he was leaving her.
Giuliani then made a public announcement referencing his long-rumored mistress, Judith Nathan, who he had met in 1999.
He had taken her everywhere with him since they first met – to Yankees games in the summer of 1999; to eat openly at restaurants; to the millennium celebration in Times Square; and to Town Hall meetings.
‘Judith Nathan is a very, very fine person,’ he said at that press conference. ‘And I’m going to need her more now than maybe I did before.’
Hanover called in the divorce lawyers and kicked him out of Gracie Mansion, the mayor’s residence – much to the delight of the tabloids at the time.
He married Nathan, a former nurse, in May 2003: his third wedding was held at Gracie Mansion and was one of only two performed by Mayor Michael Bloomberg. Among those attending was Trump.
Their wedding proved fiery and frequently excessive, with stories of lavish living and a wild jet-setting existence.
She filed for divorce in 2019, and their messy divorce and rows about money again captivated New York gossip columns.
‘It’s ugly, it’s operatic,’ reported The New York Times. ‘What did you expect?’