The 61-year-old media mogul was photographed as she attempted to deal with the man, Calvin Mitchell, during the awkward encounter outside Colbert's New York studio.
Mitchell told Radar on Wednesday that Winfrey once asked his mother to adopt him at age 11 after he and the billionaire mogul met on the 1992 set of ABC's movie-of-the-week, There Are No Children Here.
In the interview which labelled him Oprah's 'long-lost secret son', Mitchell claimed that he has been estranged from Oprah for 20 years.
Mitchell said:
'I want to ask Oprah, "Why did you leave me? Why did you leave me?" I'm still empty. I'm still searching. I don't have closure to this. I just don't understand.'
Oprah was seen acknowledging Mitchell outside the studios following her October 15 TV appearance and pressed her hand against his chest in the familiar way she frequently does with fans - before he left his phone number with her reps for further contact.
When he was younger, Oprah would allegedly send gifts to the boy with notes addressed: 'To my son Calvin, I love you.'
She also allegedly paid for Mitchell to attend the private Christian boarding school, The Piney Woods School, in Mississippi until he dropped out at age 17.
'I was young. I made a dumb decision, and Oprah wouldn’t forgive me. I feel like what she did was wrong,' said Calvin, who later became suicidal after she 'abandoned' him.
'She told me, "Calvin, just try to work it out. You can do it. Just hang in there." She was trying to inspire me to do what was right. But even after the long pep talk she gave me, I still left.'
He added: 'I just wanted to come home, and Oprah didn't understand that.'
Oprah has always been incredibly generous in donating money to young students, having given 400 scholarships to Morehouse College in Atlanta, Georgia and the school she opened for girls in South Africa.
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