The New York Post reports that Julio Bazan approached the talkshow host, who was sitting in her limo outside Soho House in New York's Meatpacking District, and asked her for money.
Winfrey told the 49-year-old panhandler that she didn't have any cash on her person and showed him an empty purse, which is when Bazan decided to tell her a joke instead.
He quipped: "Hey, Oprah, why is it good to date a homeless man? [Because] when you're finished, you can drop him off anywhere!"
She then allegedly rewarded him with five $20 bills through her limo window.