Oprah Winfrey continues to get the big names on Oprah’s Next Chapter Season 2 on OWN and now she goes for the comedian riding a high right now Chelsea Handler. Oprah gets the harsh comedian to sit down and open up about her love life, marriage and children. We all know that Oprah brings out the softer side of people on Oprah’s Next Chapter 2013 and I’m sure that will happen with Chelsea Handler on Oprah;s Next Chapter Season 2.

Chelsea Handler on Oprah

Time magazine has called Chelsea Handler the anti-Oprah, which is amazing. I love this woman and they meet at Chelsea’s home in Bel Air, which is gorgeous.

They start out talking about how Chelsea grew up and wanted to have a place in Bel Air and now she is here. She said she had an a-ha moment and she was driving in her beautiful car and going to her beautiful home and she took it all in.

Oprah said Chelsea always knew she was going to be famous. Chelsea said her parents were hippies and she was the youngest of six and compared to everyone else it was embarrassing. Her mother was Mormon and her father is Jewish and she said they were the Sanford and Sons of her neighborhood. Chelsea said she had a big mouth and she had a lot to say and wanted people to hear it, but she knew she could never be an actress. The first time Oprah saw Chelsea on TV that she was going to be successful and her show was going to be renewed and a big success, which I guess did come true.

Chelsea said she feels deep down she is a good person, but as far as the anti-Oprah thing it would be Chelsea is not politically correct and it takes a long time to warm up to her. She said some people love her and some people hate her. Chelsea said people that are behaving badly she will be mean to, but she has become nicer. On Oprah’s Next Chapter Season 2, she said she doesn’t talk about the people she hangs out with or people she has on the show.

Oprah asks if she thought she would be where she was at and Chelsea said she knew she had something else to offer, but she never thought she would do stand-up. At age 21, Chelsea got a DUI and in her drug class is where she realized she could entertain a crowd and she loved it.

Chelsea’s brother died when she was ten years old when he fell off a cliff and she said she used humor to get through it and it deflected some of the attention off of it. Her Mom passed away in 2006 after battling breast cancer and this past weekend she said she wanted her Mom to be there. When she passed away was when Chelsea’s show was starting and she didn’t have time to grief.

Chelsea has dated Andre Balazs on and off for a few years and they are trying to figure out how to live a life together. She said she is in love now and she has met her match and they couldn’t be more opposite. She said she doesn’t have any value on marriage and it might be fun to do once, but she doesn’t want children and her dogs are enough. The dogs can’t talk and that is what she wanted!

For Oprah’s Next Chapter 2013, Oprah asks her if she drinks as much as she claims in the books that she has written and her fifth book will come out later this year. Chelsea said that whoever is at dinner that makes the most money should pay. She said it is hard for her to let people pay for things. Chelsea said she doesn’t feel famous.

Oprah asked if Chelsea has a thing for black men and she said she is just open for it, which included a relationship with 50 Cent. Chelsea said he is a great guy and his persona is nothing like how he is in real life and she wants to hang from his neck. She said it was fun and not one of the most serious relationships.

Chelsea said that she always wanted to buy her Mom a beautiful home, but she passed away before she could do it and now she does it for her family and she knows that her Mom can see that.

She said she always had high self-esteem and she always thought she deserved this. She said it is important to think about everyone around you and not just how she is coming across. She said she has no regrets and usually picks up the pieces quickly. She said she has always dreamt that she would be with a man that thought the world of her and would move mountains for her. She always wanted a beautiful love story.

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