Courtesy of E!Chelsea Handler's in the hot seat! The funnywoman is used to being the one asking guests the questions, but on Sunday's Oprah's Next Chapter, it was Handler's turn to offer up some answers. Oprah Winfrey visited the Chelsea Lately host's home in Bel-Air, Calif., to talk fame, romance and her past. And of course, there were a few laughs along the way, with Chelsea jokingly accusing Winfrey of name-dropping moments after stepping into her posh pad.
WHAT WE LEARNED
A Kindler, Gentler Chelsea: She's been called the anti-Oprah, but just what did Chelsea have to have to say about her "cruel" rep? "It takes a long time to warm up to me," Handler told Winfrey. And that while "everybody loves Oprah, not everybody loves" her. However, the After Lately star revealed that she's made an effort not to be so mean to people who are helpless, but will make fun of bad behavior.
Friends in High Places: As Oprah pointed out, Chelsea's star has made quite the ascent. But she reveals that now that she's a Hollywood "insider," her jokes haven't changed much. While her famous friends—including A-listers like Jennifer Aniston, Reese Witherspoon—have made appearances on her show, she maintains that these are celebs she wouldn't make jokes about anyway. Lady Gaga and Lindsay Lohan, though, are a different story.
Laughter Is the Best Medicine: After opening up about her brother's death—he died when Handler was 10—Chelsea dished that humor helped her get through tough times. And speaking of tough times, the funnylady showed a vulnerable side as her voice cracked while telling Oprah that sometimes she just wants her mom, who passed away in 2006. Chelsea dished that while chatting about the future with boyfriend André Salazs recently, she just felt the need to talk with her mom.
Going to the Chapel?: Sure Chelsea's in love, and Andre's her match, but when Oprah asked if there are wedding bells in the future, Chelsea wasn't so sure. "I don't really have any value on marriage. I mean I guess it would be fun to do for the sake of it once." And as for kids? "I don't want children," Handler said. And as Oprah pointed out, Chelsea's dog are enough. Chunk, one of her adorable pooch's even had a cameo during the special.
Mo Money, Mo Problems: Handler fessed that even before she made it big, she lived large, often treating her pals to dinners. However, living so high on the hog had its side-effects. After finding herself $40,000 in debt, the comedian vowed that she'd pay off her bills on her own. And now that's she's found success, she still foots the bill while out with friends. Um, how do we get sign up for a girls' night with Chelsea? And while we're at it, how about drinks and dinner with Oprah, who seemed on board with Chelsea's paying-the-bill M.O.?!
The Fame Game: "You don't feel like, 'Oh I'm famous," Chelsea laughed. Though many of her superstar pals have to deal with the paparazzi on their everyday errands, Handler told Oprah she maintains her regular life, saying that she goes anywhere and heads to restaurants by herself.
And Then Things Got Awkward: After dishing on the hard-hitting topics, Oprah brought up Chelsea's er, intimate, relationship with The Oprah Winfrey Show. The talkshow queen asked Handler about passages in her book where she talked about masturbating while watching O's show. "I'm really quite embarrassed," Chelsea offered up, sending Oprah in to another fit of giggles. "That was probably a time in my life when I didn't have a big social life," Handler confessed.
Secret Time: "I'm completely empathetic to anyone, I don't even have to know them," Chelsea told Oprah when asked about the side of her people might not know about. And though she can be crass, when it comes down to it, Handler's secret hope is all about love. "I always wanted be with a man who thought the world of me," she revealed to Oprah. Looks like she's found him!