Winfrey had recently interviewed the 'Diamonds' singer on her show 'Oprah's Next Chapter' about her relationship with the R&B singer who assaulted her in 2009, reported Contactmusic.
"You know what I loved about that interview is that she came with a big, wide open heart. 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," she said.
During their interview, Rihanna spoke about her memories of her father Ronald Fenty being physically abusive to her mother and how she learnt to forgive him.
"I think that if she is prepared to deal with that and is prepared to help him help himself then so be it. I have no judgement whatsoever. If that's how you choose to lead your life, that's really okay," Winfrey added.
Brown reportedly broke up with his girlfriend Karrueche Tran last week to give his relationship with Rihanna another chance.