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"I think that if she is prepared to deal with that and is prepared to help him help himself then so be it," Winfrey told Extra on Friday. "I have no judgment about it. That's why I can sit there and have such a great time with her because I do all my interviews with no judgment whatsoever. If that's how you choose to lead your life, that's really okay."
Winfrey also described a portion of her intimate interview with Rihanna, 24, in which the Barbados-born superstar recognized that her father's abuse of her mother resulted from his struggle with his own personal demons, and that, like Brown, he was a good person deep down.
"You know what I loved about that interview is that she came with a big, wide open heart," Winfrey told Extra. "She was in the space of forgiveness. And that she learned a lesson, that she was repeating with Chris Brown exactly what she needed to learn from her father."
In 2009, Brown assaulted Rihanna and left her swollen and bruised. Brown was sentenced to five years of probation.
Despite that incident, however, Rihanna and Brown, 23, rekindled their friendship -- and now it looks like they may be on the road to romance. The duo was spotted getting cozy at a New York City club last week, right before Brown broke up with Karrueche Tran, his girlfriend of two years.
"We love each other and we probably always will, and that's not anything that we're going to try to change," Rihanna told Winfrey in August. "I think he was the love of my life. He was my first love and I see that he loved me the same way."