Chelsea Handler’s Surprisingly Serious ‘Next Chapter’ Chat

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Leave it to Oprah to get a handle on comedian Chelsea Handler's not-so-funny side. The "Chelsea Lately" host recently sat down with Oprah Winfrey for an "Oprah's Next Chapter" chat, and while there were a few laughs (and one or two awkward moments!), the interview was surprisingly serious.

Check out how Oprah handled Chelsea.

On the loss of loved ones

The 38-year-old comedian experienced great loss at a young age. Chelsea was only 10 years old when her older brother fell off a cliff and died while hiking, and in 2006, her mother died after a battle with breast cancer. "I thought I had dealt with it in the right capacity, because I had so much lead time," she said of her mother's death, but six months later had a wake-up call when she went to call her mom on the phone and realized she was gone. Sometimes there are days where she says, "I just want my mom."

On finding her way home

The self-described "Fresh Princess of Bel Air" admits she once had $40,000 in credit card debt but vowed that someday she'd make enough money to pay it off. (Mission accomplished!) But she knew she made it really big when she bought a posh pad in Bel Air, a place she'd always dreamed of living. Speaking of money matters, Chelsea hates it when friends split checks at restaurants. Her mantra -- and Oprah's -- is "whoever has the most money should pay."

On being a hopeless romantic

What's the status on Chelsea Handler's love life? Surprisingly, she's a hopeless romantic.

"I always wanted be with a man who thought the world of me," she confessed. Meanwhile, her on-and-off relationship with hotelier André Balazs is currently on, and yes, she's a woman in love. "We're trying to figure out how to live a life together," Chelsea said. "I've met my match."

But she drew the line at being married with children. "I don't really have any value on marriage," she said. "I don't want children." But she'll take a dog or two anytime!

On being the anti-Oprah

Time magazine once called her "the anti-Oprah," to which Chelsea said, "Everybody loves Oprah, not everybody loves me." (Oprah didn't agree with that assessment!)

"It takes a long time to warm up to me … People who behave badly, I will make fun of," she explained, but she added that she avoids being mean to people are helpless and have personal issues going on. You can watch Chelsea Handler talk about being a cruel queen bee here.

"Oprah's Next Chapter" airs on Sundays at 9 PM ET on OWN.

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