Heartbreak is never easy!

Rihanna recently sat down with Oprah Winfrey for an interview on Oprah's Next Chapter , and the talk show queen asked the pop star all the hard questions!

When O brought up the "Rude Boy" singer's past relationship with Chris Brown, the Grammy winner got emotional and confessed, "It was embarassing. It was humiliating. I lost my best friend."

After splitting with the R&B star, the 24-year-old Barbadian beauty still had lingering feelings over the unfortunate turn of events. "I was resentful. I held a grudge. I was dark," she admitted.

The controversial bad girl was quite the opposite of what the OWN founder expected. "I thought she would have been kind of a bad-ass kind of a rocker hard-edge woman - nothing could have been farther from the truth," Miss Winfrey revealed.

We wonder what CB's current girlfriend Karrueche Tran thinks of this public confession?