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Footage recorded in 2000, when Giuliani was mayor of New York City and Trump was a celebrity businessman, shows the surreal moment.
It came about as part of the Mayor's Inner Circle Press roast, a parody event in which New York mayors show their light-hearted side.
The set-up features Giuliani's alter-ego splashing perfume on "her" neck and then bosom in an attempt to charm Trump, who then goes further than expected and sticks his face into Giuliani's chest.
Fire 75% of the government and disband 75% of the parasite alphabet agencies.
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