The veteran radio DJ started by asking the star how fans should feel about him in the wake of his assault on Rihanna, his court case and his emerging musical comeback.
"I'm human. If people feel a certain way, I'm not going to say they're wrong. But it's not right to judge somebody when people make mistakes all the time," Chris told Angie. "I've learned from my mistakes and I'm learning from them. And I regret every moment, every second of it."
The star admitted he knew he'd "let a lot of people down."
"I won't let you down anymore," he said, addressing his fans. "That was one of the most embarrassing things for me, because of my image and who I was as a young role model to a lot of kids. It was hard for me."
While he wouldn't give details of what happened between himself and Rihanna in February, Chris said having seen domestic violence himself, he didn't want to inflict it on anyone – and separated himself from abusers.
Asked if it would ever happen again, he insisted it wouldn't.
"I can be certain, for sure, from me… Me being a kid who grew up with domestic violence, certain things in my household when I was growing up, that's something I never want to put anybody through… That's not who I am at all," he said.
But Chris did open up on Rihanna – and his feelings for her.
"We've been friends since I was like 15, we got serious when I was like, 17," he said, admitting he wasn't over her yet.
"Feelings are feelings and they don't go away overnight, especially if you sit down and be like, 'Look, I'm [going to] really be in this relationship with you, past whatever the case, past our busy schedules, past us being two of the biggest artists.' I really care about her," Chris said.
So will he date someone new?
"I'm taking my time right now," Chris said. "I'm back to square one. I still got feelings for Shorty, I gotta get over the hump."
Chris — who announced plans for a "Fan Appreciation" tour on Tuesday — also discussed his difficult comeback, thanking some fellow celebs for reaching out to him when he needed help.
"Will Smith called me and he was talking to me one-on-one, man to man. Puffy called me," Chris revealed. "[Will] reached out a hand and helped. I needed them to kind of mold me into different things."
Of a much-discussed feud with Oprah Winfrey, however, he said he wanted to clear the air.
"I don't diss Oprah," he said. "I just feel me and her did so many things together, I felt that at the time, I needed a helping hand – just talk to me and Rihanna. I'm not even saying have me on the show but… help. Just help. Because I thought that we had that relationship to where it could be like that."
Now, Chris said he's looking toward the future and his new album – and the viral wedding video from earlier this year that helped put the focus back on his music.
"That put me back on the map with the iTunes!" he said, adding his new material was personal. "I wouldn't call it a confessions album, but it's my version of my life in a nutshell."
And of the incident with Rihanna, he said this will be the "last time" he talks about it.
"This is the last one," he said, saying he wants to move past it in future interviews. "I'm going to focus on what it was and learn for it. This interview will be the last time I really speak on the subject."
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