Julio Bazan, 49, said he spotted the billionaire media mogul sitting in her limousine outside of the Soho House hotel Sunday night and he asked her for money, the New York Post reported Wednesday.
Bazan said Oprah initially told him she had no money but changed her mind after he told her a joke.
"Hey, Oprah, why is it good to date a homeless man? (Because) when you're finished, you can drop him off anywhere," Bazan recalled telling the TV host.
"She laughed," he said.
The panhandler said Oprah handed him five $20 bills, which he spent on underwear, alcohol and a steak dinner.
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