The Playboy Interview With Chelsea Handler

A candid conversation with the talk-show iconoclast

Nov 6, 2017    34 min read
Written by
Danielle Bacher
Photographed by
Patrick Maus

After seven years of mocking celebrities on basic cable, Chelsea Handler has discovered that she prefers to ply her exfoliating wit on issues more pressing than Kim Kardashian’s Botox. At 42, with a freshly launched talk show on Netflix, the new Chelsea is ready to get serious. She admits it’s part of growing up: With age comes maturity—and better decisions. She still cracks jokes, but now Handler wants to use her platform to take on politics, maybe even influence policy. She regularly opens her Bel-Air estate to raise money for Democratic candidates. At this year’s Politicon (often referred to as “the ComicCon of politics”), she faced off against conservative firebrand Tomi Lahren in a spirited debate on health care. She has even toured the country to encourage college students to vote. “I don’t like people who say ‘I’m not into politics,’ ” she says. “That’s bullshit. You need to be. I want to serve my country before I take off to Spain and live there forever.”

For Handler, moving to Netflix last year was an essential step in her shift away from gossip-fueled comedy. She filmed a four-part docu-series, Chelsea Does, on which she traveled the world to investigate such weighty topics as sexual abuse, drug addiction and arranged marriage. Then came Chelsea, the streaming giant’s first talk show, on which Handler balances guests like Senator Al Franken and Representative Linda Sánchez with more lighthearted celebrity fare. The first season was marked by distinct growing pains, but early this year it came back strong with a new weekly schedule. Handler grew up in Livingston, New Jersey, where her father, Seymour, was a used-car salesman and her mother, Rita, was a stay-at-home mother of six children. As the youngest, Handler often served as her siblings’ instigator and prank initiator. When she was seven, one of her sisters dared her to enter their parents’ bedroom while they were having sex and snap a photograph. Young Chelsea obliged, only to find her mother wearing a nurse’s cap; her father, curiously, had a bandanna around his neck. At the age of 18, Handler had her first one-night stand. As described in her best-selling memoir My Horizontal Life (her books have appeared on the New York Times best-seller list five times, with four hitting the top spot), the experience left her sore. Clearly Handler has no problem discussing her sexual history. She doesn’t like anal sex; she has enjoyed receiving cunnilingus from a woman; she advocates sex on the first date. Oh, and she’s less horny than you might imagine.

Handler moved to Los Angeles when she was 19 to pursue acting but ended up waitressing and living with her relatives. A week after her 21st birthday, she was pulled over in her 1985 Yugo for drunk driving. She spent the night in jail because she had an outstanding warrant for using her sister’s ID. Sentenced to traffic school for the DUI, she found herself cast in the role of class clown—and something clicked. She was awakened to the art of stand-up. A short time later she booked one of her first gigs, at Punch Line in San Francisco. Making people laugh came easily; throughout her life, Handler had dealt with pain and hardship by telling jokes.

The greatest hardship came in 1984, when Handler’s older brother Chet died while hiking in Jackson Hole, Wyoming. Handler was nine years old. In 2006, their mother passed away after fighting breast cancer for more than a decade. In both cases, heartbreak brought the family closer together. Unlike with Chet’s passing, Handler saw in her mother’s death a silver lining: This time, the family had a chance to say good-bye.

These days, Handler tries to balance her more serious perspective with simple positivity. When she’s not speaking at LGBTQ or women’s rights events, she’s using dating apps to explore commitment-free relationships with men. Closer to Handler’s heart than any boy toy are her beloved pets. Along with her Instagram-famous dog Chunk, she has adopted sibling chow pups Bernice and Bert. (She’s keeping them out of the public eye while they finish obedience camp.)

We sent contributing writer Danielle Bacher, who most recently profiled Tim Heidecker and Eric Wareheim for Playboy, to catch up with the funnywoman turned TV mainstay turned activist. Bacher reports: “Our first interview took place in Handler’s L.A. Netflix office, where she greeted me with a brisk handshake. Sporting workout gear, no makeup and blonde locks swept into a pony-tail, she talked forcefully about the presidency of Donald J. Trump and the importance of taking a stand. She was more serious than I anticipated—and more complex than I’d given her credit for. She’s strong and opinionated but also has a softer side. She’s open but can be distant, outspoken but not overbearing.

“On the second day we sat down, both bagels and Belvedere were available. She turned down the vodka, grabbed a diet soda and loaded a hollowed-out everything bagel with chive cream cheese. Of all the things I learned about her in those two sessions, the one that really struck me in the moment was her extreme aversion to heat. She hates sweating. Everything, it seems, is better below 66 degrees.”

Let’s start with your childhood. You were the youngest of six. Was there a competition to be the favorite child?
I think we all believed we were the favorite child. My sister’s friend from college, who I think majored in psychology, did her thesis about our family. She interviewed us all individually, including my parents. It’s so funny, because when she asked each child who they thought was the favorite, they all said themselves. She said, “This is a really good indicator that your parents were good at parenting”—which they weren’t. Now that we look back, it’s clear I was the favorite.

In your book Are You There, Vodka? It’s Me, Chelsea, you say that your classmates in fifth grade called you names like “dog.” Were you bullied a lot?
I was a bully and I got bullied. There were times when it was really bad. I transferred schools twice because of it. I was probably bullied for being a loudmouth and for being pugnacious. I experienced both ends of that, so I’d be lying if I didn’t say I was rude growing up.

You shoplifted underwear at Sears and sold tickets to a fake raffle, the purported prize of which was a chance to meet Carly Simon on Martha’s Vineyard. What other mischief did you get into as a child?
Oh, everything. I was really bad. I had a lot of pity for myself. I was rebellious, and I always wanted to push boundaries. That was just instinctual, and I kind of always went with it.

Why was it instinctual?
I felt I was a good person but I was misunderstood. Some of my friends’ parents didn’t want their kids hanging out with me because my parents were kind of a mess and our house looked like a used-car dealership. There was shit all over the driveway. We were like the Sanford and Son of our neighborhood. I wanted to overcompensate for that. I became ashamed of my parents because everybody was driving around in a brand-new car and my parents didn’t have that. The place I grew up was kind of materialistic. I think after being jolted so much by my brother’s death, it took me a while to get my footing and understand what it means to be a good person, to be reliable and follow rules. I’ve never really been good at following rules because I like to make up my own.

You started your career by performing stand-up around Los Angeles, and you were on Oxygen’s Girls Behaving Badly. In 2005, your first book was published. How did you end up with your own television show on the E! network?
I was on E! doing commentary about pop culture. I was just a talking head. Then the people at the network were like, “Why don’t you have your own show? You have a really strong point of view.” We did The Chelsea Handler Show, which was kind of a sketch-variety series, and it didn’t do very well. The problem was it took so long to film each episode, and they wanted me to have more regular commentary on pop culture stuff. So they were like, “Why don’t we do a nightly talk show?” and I didn’t want to do that. Then we shot four or five episodes a week of Chelsea Lately. It was very under the radar. It was like one big fraternity house—so immature and stupid. But it was great, because we were outlandish and childish and got to do whatever we wanted. Why didn’t you want to do a nightly talk show?
I didn’t not want to; I’d just never thought about it. I didn’t really have a great plan for things. In terms of performing, I kind of fell into stand-up comedy because of the six months of DUI classes and the reaction everyone there had. Then I got a taste of what it felt like to be on stage and to be commanding a room and how powerful that was. I loved it, but I was scared shitless. Every time I went on stage I was scared. Almost every night I did stand-up, I had the same conversation with myself, saying, “Oh my God, I can’t believe I’m doing this. How am I doing this?” There were times I would puke and hate myself afterward. Do you suffer from anxiety?
I wouldn’t call it anxiety. If I do have anxiety, there’s nothing I’ve ever done about it. I’ve definitely taken beta blockers when I’ve been nervous and had to speak in front of a large crowd. Once you take a couple, your neurotransmitters work differently. I don’t really take them anymore. I’m into this new thing called Enneagram types. It basically gives you a number for your personality. Understanding the number you are helps you deal with other people better. I’m a number eight, which is a protector.

Did E! ever ask you to tone down your treatment of people like the Kardashians?
They definitely did, but I didn’t listen to anything they told me to do. I feel it’s important that your audience can trust you and know that you’re not being manipulated. I pushed back all the time on anything the network thought was over the line. I’ve been close to major endorsement deals, major campaigns, and then they’ve asked me to tone down my Twitter or my Instagram, and I’m like, “I’m not for sale.” I don’t get those campaigns because I’m so political. The Kardashians are antithetical to everything I stand for, so I thought it was funny to do that. I thought it was needed. I can’t believe they’re still on. I think that’s a real reason we’re in the situation we are in this country.

I’m never nervous to mix business with pleasure. I would advocate for most people to do the same.

You started dating your then boss, Ted Harbert, in 2006, the year The Chelsea Handler Show premiered. Were you nervous about mixing business with pleasure?
No, I’m never nervous to mix business with pleasure. I would advocate for most people to do the same. Okay, but were you worried people might judge you?
That comes with the territory. People are going to talk shit about you no matter what you do. If my relationship was based on me trying to get ahead in this business—first of all, I’m not capable of being with somebody I’m not into. It doesn’t jibe with who I am. But if I were going do that, it wouldn’t have been somebody from the fucking E! network. You were still working with him after the breakup. Was that awkward?
It wasn’t a great breakup. It got ugly. We’re all right now, but yeah, it wasn’t good. I think after three years I was like, “Okay, this isn’t what it was.” It was basically me just waking up one day and realizing we’d been together for four years and it wasn’t working. Which is hard, because you don’t want to break up. You don’t want to lose somebody, but you’re not in love anymore. I knew that, but I kept trying to make it work. I think all women try to do that. It’s not unhealthy to want to maintain a relationship, but when it becomes untenable, you have to let go. I’m very much an independent person. Ultimately, in terms of the relationship, I’m not the best. That’s not my best self.

Are you afraid of living alone?
My friend Shelly, her girlfriend and my brother moved out of my place three or four years ago. Before that, I hadn’t lived alone since I left Ted, and I lived in that apartment for about six months. I did fear it, and now I don’t. Once I started living alone, I was like, “Oh, this is awesome.”

It’s been three years since Chelsea Lately ended. What do you miss most about that show?
I don’t miss anything about it. My contract was coming to an end. They thought it was a negotiating tactic, but I was like, “No, I’m actually done with the show.” I just did it for a couple of years more than I wanted. I don’t want to be a bitch when I’m at work. I want to be in a good mood, you know? I was done. It was an experience, but I’m missing that sentimentality chip. I’m not a big misser of things, really. I miss Tammy, my dog, who recently passed away. But I don’t miss things, you know?

What about your mother?
I remember when my mom died, I was looking at my brothers and sisters and thinking, Thank God that’s over. She was so miserable and sick. She had breast cancer and then stomach cancer, and then it spread to her bones. She did not want to be remembered that way. I was on my first book tour in London when I got the call to come home because it was the end for her. I sat in the hospital with her for a week, and she was just like, “I need you to help me die. They’re trying to keep me alive and I’m done fighting.” I was like, “I’ve got it. No problem. I will help you die.”

That must have been painful.
My family, especially my dad, wanted to keep her alive no matter what. The nurses said something like “Once you give her morphine every four hours, you’re saying good-bye to her.” I was like, “That’s fine. Stop forcing her to eat. She doesn’t want to eat. She has no appetite. She doesn’t like it.” She was weak and she was sick of fighting. And I got it. I was like, “You can count on me.” I love her and everything, but I don’t have the kind of personality that I sit around and can’t get out of bed for days.

I once heard you say that she’s still around you and you feel her presence.
I don’t really feel that anymore, but I definitely did for a while. I felt like somebody was hanging out. I’m sure that’s just hopefulness.

Are you still close with your father? Is he still groping all the nurses at his assisted-living facility?
He’s definitely still groping all the nurses. I’m not very close to my dad, because he lives in Pennsylvania, and even when I go back East, it’s not easy to go see him. I mean, I could if I wanted to. I just don’t put forth the effort the way my brothers and sisters who live back there do. But yeah, he’s there, and he’s still harassing women.

Do you think you’ve ever gone too far with a joke?
I’m always moving forward, so I don’t dwell on that. I imagine if I ever said something super insensitive that I would feel bad about it, but I really don’t think I’ve ever gone too far. There’s a line I don’t like to cross. I don’t know how to identify that, but I think if it’s truly tasteless, I don’t need to do it. I’ve never felt compelled to make an apology about something I’ve said or done.

What was the most difficult segment you’ve done on your shows so far?
Meeting with my ex-boyfriend Peter for the Chelsea Does docuseries. I dated him when I was about 20 to 22. I was not looking forward to that at all.

Was that your idea?
No, it was the director’s idea. He called me and said, “We really need to see you with an ex-boyfriend.” I was like, “None of them are speaking to me, first of all, so how am I supposed to contact them?” And then I was like, “Okay, who’s the most banal of all of them who would even consider this?” It was my very first boyfriend, who’s British. I dated him when I moved to Los Angeles, and he knew me when I was a waitress. It ended up being great and fun, but ugh, I just hated that idea. So yeah, things like that embarrass me.

Did things change on Chelsea when your show runner and executive producer Bill Wolff parted ways with the show three weeks into the first season?
Well, he didn’t part ways with me. It just wasn’t a match. For a show like this to work, you need a right-hand person. And for me, that person was somebody else. It wasn’t Bill, so it just didn’t make sense to continue. The show definitely got off to a rough start in the first year. I think it had a lot to do with that dynamic. It wasn’t comfortable for me. I didn’t feel protected. So yeah, it did change. It took a while to kind of get the wheels back on.

What are the pros and cons of being on Netflix?
The advantage is that they can give you creative license to do whatever you want. It’s kind of the perfect place. I don’t have to worry about advertisers. That’s a huge bonus. I can make episodes 50 minutes or an hour and 10 minutes. I can have dinner parties at my house and film that. I wanted to go to Tokyo, Mexico City, Russia, India, and they let me do all of that. I’ve been able to document everything I’m doing while doing it. It’s like going to school and getting paid to get an education. The only disadvantage—and this isn’t Netflix-related—is being beholden to a studio. I prefer to be outside a studio, out of my comfort zone.

Chelsea has taken a turn toward the political. Were you always into politics, or was Trump the reason for the change?
I like getting informed about politics, this election and what has transpired. I feel passionate about it. Right now, with the political landscape, there’s so much I want to do. I’ve been doing town-hall talks all over the country. I want to campaign for a lot of people in the midterm elections. I just like sticking up for the underdog. People would say, “Oh, she’s a bully. She makes fun.” No, I was calling out people who I felt were acting like assholes. When I’m calling out Lindsay Lohan and Paris Hilton, those are the people who deserve to be taken down a notch. They’re behaving badly, and they’re irresponsible. Now that this administration is behaving badly, and Trump is behaving badly, whenever I think anything’s unjust, I like to get loud about it. I want everybody to be treated the same way.

What do you think of this presidency so far?
Resign, please. Spare us the rest of your presidency. I think it’s an abomination. I think if there were a way to erase a presidency, I would. Or at least not acknowledge that this one happened. I believe he’ll be impeached. I think there’s no way he can sustain this. He’s constantly breaking laws, and he has no idea how to live in any sort of legal parameter. Everyone needs to stand up and fight right now.

When Trump won, I think you spent the entire night and the next day crying. How do you feel looking back on that?
I stand by that. I was in shock, you know? I don’t think I was crying that night. I was just apoplectic. I didn’t cry until the next day. I saw this man walking down the street in Brentwood, going to get a coffee or something with his son, and he was crying. I was like, “Okay, the world isn’t over. This man’s crying too.” I think when men join the fight—like when a man is crying because Hillary Clinton lost the election—we’re much better off than we were a long time ago. Men joining the conversation for women’s equality is a tipping point.

If Hillary had won, do you think you would be mocking her on your talk show as much as you do Trump?
No, because she’s an adult. I think she would have been a great president. I get that it’s over, but I don’t think there was as much to make fun of, other than those outfits she wears. Where are those available?

I know you enjoy drinking. I heard that back in the day you would carry around bags of lemons wherever you went just in case you needed a quick drink. Is that true?
I used to carry around a little lemon squeezer for my drinks. I have since switched to lime, but I no longer carry it around. They usually have one.

Do you recall the most intoxicated you’ve ever been at your job?
You mean on air? No, I don’t do that, usually. I’ve had a drink or a shot with a guest, but I’ve never been shit-faced on my own show. I have been when I was doing stand-up. I remember at one show, I think it was in Kansas City, somebody had given me an edible. Halfway through I wasn’t feeling great. I was paranoid. I remember reading a review of the show on Twitter or something later, and it was like, “Oh God, Chelsea was hammered.” The next show you totally behave. And then the next show you get drunk again.

Has anyone ever tried to convince you that you had a drinking problem?
I’ve never been formally told that. No one has ever staged an intervention. I mean, people know that I’m a drinker and that I’ve always kind of advocated for being up front about who you are and not trying to be something you’re not, you know? There have been nights when I definitely should have gone home a lot earlier than I did, for sure. But I don’t think anybody’s ever come up to me and said, “We’ve got to talk about your drinking problem.”

Have you ever been to Alcoholics Anonymous?
No. I had a boyfriend who said to me, “You never want to abuse alcohol because you never want to have to give it up.” And I was like, “Hey, that’s a great idea.” But I definitely did abuse it. I mean, I love alcohol. It just takes the edge off. It makes everything a little bit more fun too.

After you were pulled over for driving under the influence, what was your experience in jail like?
I got pulled over literally about a block after I’d passed my own apartment because I was shit-faced. I learned that lesson the hard way. I was in jail for about 36 hours, in the Sybil Brand Institute. It was awful. It was horrendous. It was the grossest thing I’d ever been around. I couldn’t believe it. People were trading tampons for mustard and mayonnaise. You go to the bathroom and try not to make eye contact with anybody. It was scary and depressing. I will not drink and drive ever again.

I watched you drink ayahuasca on Chelsea Does. It seemed to be traumatizing for you. Do you like psychedelic drugs?
I do. I like getting high on drugs. I love mushrooms, but I don’t do them as frequently. Drinking is my favorite. I love a cocktail. I try not to drink two nights a week. It’s such a bummer. I don’t think I was traumatized by the ayahuasca. I liked it because it brought out my relationship with my sister and made me take into account how she felt about me and the way I was treating her. But it’s not my favorite kind of drug—first of all, because you have to vomit. Then I felt completely in control the whole time. You see everything that’s positive. You’re overwhelmed with love. You see this phantasmagoria, a quick fast-forward flash of your childhood and your entire life. I did mushrooms and acid in college, and it was nothing like that.
No, this is different. It’s not social. You need to be kind of isolated, and it’s your own experience. For me, my childhood just played out with me watching myself. It was going really fast. I saw childhood animals, like Poopsie Woopsie and Mutley, that I’d forgotten about. I also envisioned my sister and me on Martha’s Vineyard in the summers. We liked to tip each other on kayaks. We were laughing so hard we peed in our pants when we were jumping off the dock. All that laughter, just watching it from afar and seeing us as kids was incredible. How was your trip to South Africa this year?
I was on a safari for about four days with Charlize Theron, her mom, my cousin and my best friend, Mary McCormack. I went for the Charlize Theron Africa Outreach Project, or CTAOP. She gives money to different grants in different parts of South Africa for young people to get sexual education and sexual protection.

What did you learn there?
That rape is rampant. South Africa has the highest HIV rate in the world. It’s frowned upon there to ask a boyfriend to use a condom because you’re thought of as a whore if you’ve had sex before. So these girls have unprotected sex because they don’t want anyone to judge them, and then they get AIDS. A lot of them have older men who are taking care of them, and they don’t have access to education like we do. CTAOP provides grants to all these communities that need an after-school place for girls to go. It’s a safe environment to hang out, motivate and support each other. My friend Mary always says, “You don’t have to be somebody’s best friend, but treat every girl like she’s a sister.”

Our society seems to have progressed in terms of women coming out and talking about sexual assault and rape. Do you think we’ll see more progress in the future?
Well, it’s nothing you can get away from. When you read the statistics, it happens all the time, every single day. It’s happening to people right now. And the idea that Betsy DeVos, our secretary of education, is overturning rules in order to protect rapists is horrifying. The conversation can’t go away. Change doesn’t necessarily happen when you want it to, but it does happen. Conversations are important, and again, having men join that conversation is important.

In my entire adult life I don’t think I’ve ever masturbated. I’m too embarrassed. I don’t even get the concept.

You were sexual even at a young age. In the third grade you went to a masturbation party and got yourself off every chance you could. Do you think that shaped how you express yourself sexually?
It turned into a masturbation sleepover party. We called it “the feeling.” It was a bunch of eight-year-old girls, and we were just learning how to masturbate. We were rubbing our vaginas over our clothes. It wasn’t a vagina party at all. It was basically like playing doctor, but no one was touching each other, thankfully. Do you masturbate?
In my entire adult life I don’t think I’ve ever masturbated. I’m too embarrassed. If I have it’s been more than 10 years. First of all, I don’t have the fucking time. Second, it seems depressing. If I have 10 minutes, I’m sleeping; I’m not fucking jerking off. It seems depressing to jerk off in your bed, come and then what? I don’t even get the concept. And I’m not that horny, so it’s not part of my repertoire. I’m horny if I’m into somebody, but I’m not horny if I’m not. I’m not boy crazy. You said on an episode of Chelsea Does that you never wanted to get married and that it was nausea-inducing to think about. Do you think if you found the “right person” you would feel differently?
I think that by remaining single for so long I definitely dodged a bullet. If I were to meet somebody I was that in love with now, I would be more open to the idea. I think the older you get, the fewer obvious mistakes you make. But I don’t think the older you are, the better the decisions you make when choosing somebody. If I were to date somebody now, they would have to be a spectacular human being for me to even consider marriage. I’m not saying it’s not going to happen, but I’m not somebody who is waiting and hoping.

Have you ever been in love?
Yeah, absolutely. I was in love with Ted. Four years, I better have been. I was totally head over heels in love with him. I didn’t marry him, but I was young, you know? That was my first big love affair. And then I was in love with another guy I dated. People fall in and out of love all the time. It’s hard to maintain that level of adoration, especially when you put everything into it and then people grow apart.

How much did sex matter to you at 21, and how much does it matter now?
It mattered a lot more to me at 21. It was more of a conquest thing back then. Now I can take it or leave it. I don’t hang my hat on it. If I go on vacation and don’t hook up with a guy, I’m not like, “Oh, that was a failure.” When I was 21, it was like, “I’ve got to hook up, I’ve got to hook up. Who’s this guy? Who’s this guy?”

You use dating apps like Tinder and Raya. Has anything gone terribly wrong on one of those dates?
I definitely go to extreme lengths to get rid of some men, and it’s not necessary. I make up too many stories. I just need to be more direct. I have a hard time saying “I’m not into you.” The last time I made a big spectacle out of trying to blow somebody off, it bit me in the ass. I was in New Zealand, and I lied to a guy because I realized I wasn’t into him after he’d flown there to meet me. I told him my relative was dying and I had to fly back to California. I told him I’d taken off two hours before, and he walked right by me while I was sitting at a dock having a drink with my assistant. He walked right up to me and was like, “I thought you were going back home.” I told him the plane was delayed. At that point it was like, Keep walking. You should’ve seen the look on my assistant’s face. I’ve learned the hard way that I shouldn’t lie. The only time I lie is when I’m trying to get away from a guy. It turns into a fucking nightmare. I mean, I’ve planned weddings that haven’t happened. It’s ridiculous.

Would it be an issue for you to date a man who is less famous or less successful than you?
I want somebody who’s got their shit together. I don’t need someone who has more money or more success than I do, but I need you to not be trying to figure out what you’re going to do with your life. You’ve got to have a job, have ambition, drive and be passionate about things. I would love to date somebody who has nothing in common with me. But it’s not hot when somebody’s not into life.

Do you have rules for yourself, such as not sleeping right away with somebody you really like?
No, I have no rules. I want to sleep with them as soon as possible to find out if I want to sleep with them again, or if there’s anything at all to talk about.

You claim to feel terrible for men who have small penises. Have you ever had sex with a man who wasn’t well-endowed? Did you enjoy it?
I have, and I did not enjoy it. It was horrifying. I was doing it to make an ex-boyfriend jealous, and it was even worse. I couldn’t believe it. He had absolutely no penis. This is when I was 19 or 20. I must have told everyone I know because I was so worried. I was wondering how many small penises are in the world. Like, what if half the men out there have small penises? But I’ve run into only two small penises in my entire life. Like really small. Ones that were unmanageable or unworkable.

You seem comfortable with your body, and you even post naked photos of yourself. Are you as confident as you seem?
I have insecurities, but I’m pretty confident. I know that insecurity is a feeling and not a reality. I know when to shut up the voice in my head, and when I’m being irrational or childlike. But overall, I have a lot of confidence in what I’ve learned; also, the way I look, the way I take care of myself and the way I push myself physically to work out and eat right. I don’t nail that, but I’m confident in my friendships and the way I treat people. When you really get a handle on yourself, you know the things you’re good at and you amplify them.

You told Barbara Walters you aren’t a lesbian. But have you ever been with a woman?
Yeah, but I was really fucked-up. I don’t know if I would be with a woman when I was sober. It was more of, you know, being really drunk, and we were with a guy. But yes, I’ve been with a girl. More than once, when I was younger. I haven’t done that in a long time. But I get why people do it. It’s fun. It’s like when you’re really sexual and you’re experimenting and seeing if that’s what you’re into.

What was it like to go down on a woman?
I don’t know that I ended up doing that. It definitely happened to me. When it was my turn, I was like, “I’m going, good night. That’s what you have the guy there for.” That memory is foggy, so.…

Are you into anal sex?
No, I’m not. I did that once or twice, and for a week after my ass was broken. Eeek. But a lot of girls love it. I mean, regular sex sometimes hurts. So I don’t know what my butt’s doing.

I’d feel like an asshole if I accidentally got pregnant at 42, but I would still have an abortion, on the lawn of Capitol Hill.

You penned an article in playboy last year about having not one, as previously stated, but two abortions, which became a headline all over the internet. What did you think of that response?
I was trying not to think of the response and trying to really be honest, not just for Planned Parenthood but for women who have been through a similar situation. I’m so grateful that I had access to an abortion. I’m not proud of it, but I think it’s important to disclose that kind of information and let people know they’re not alone. Other girls have had that experience or have had it more than once. And you’re not a slut, you’re not a whore, you’re not anything. You’re just somebody who made a mistake and you weren’t responsible. Do you remember how you felt when you were going through that at 16?
I was an idiot. I was so mad at my dad. I was dating some drug dealer. I don’t know what I was thinking. I think I was hoping for twins, I was so delusional. My parents were like, “There’s no way you’re having a child. You’re getting an abortion.” Then the second time I just went and got it. I didn’t even tell them. I was on the wrong path in every way. Do you think you would have an abortion if you got pregnant now?
Oh my God, yes. I don’t feel because of my age I’m required to have a baby. I would feel like an asshole if I accidentally got pregnant at 42, but I would still have an abortion, on the lawn of Capitol Hill.

You said on your new show that everyone is talking about women’s empowerment, but it’s not about women taking over the world; it’s just about being equal. What if we did take over the world?
I think the world would have a lot less crime. There would be a lot less guns, and there would be a lot less war. I think we have more empathy and compassion. I don’t think women want people to suffer as much as men do. Women are just saner. I don’t think we need to fire rockets overseas to show that we have a big vagina.

Why do you think things aren’t equal?
I just think men get away with a lot more than women do. Men run all these companies, and men are at the top of every industry. If you look at Silicon Valley or Wall Street, or if you look at Hollywood, there are just more men than women controlling things. I don’t think that’s the end of the story, but it is a fact, and to not acknowledge that fact is to be delusional. Women have been fighting for equality since the beginning of time. Women have always been thought of as less than. It’s only in very liberal, progressive circles that men can acknowledge that women belong and that we’re an addition and not a takeaway, that women can be equal. Hillary didn’t win, but she certainly got it ready for the next woman who’s going to run.

Would you ever consider becoming a politician?
I will never, ever try to run for office, but I will definitely help get people elected.

What has been your biggest failure?
I wouldn’t regard this as a failure, but I would like to have handled myself with more aplomb when getting out of different relationships. I would like to have been more dignified instead of cutting people off without letting them know what was happening and throwing fits or looking through a guy’s phone. That behavior to me is embarrassing, but I don’t know that it qualifies as a failure so much as growing up.

Are you emotionally immature?
Yeah, I was, and I probably still am. It’s been a while since I’ve had a serious relationship. I’m more mature now, definitely. I have a pretty good group of close friends who are in healthy relationships. That’s taught me a lot. I think if I were to find myself in a relationship again, I would take from all the close friends I’ve watched and definitely be a little more mature than I was the last time.

Do you think men are intimidated by you?
I would say “turned off” is a better description. I think men are pretty turned off by me. Older men get me, but men my own age are like, “Ugh, get her away from us.” I’m just so loud, and I think they find that gross. They’re definitely not knocking down my door. It’s not like I’m bombarded with people asking me to go out. Men don’t love women like me who are out there and outspoken. It’s not necessarily the most attractive quality.

I disagree.
Well, thank you. You are not a man, unfortunately.

What’s your favorite sexual experience?
I think the best sex you have is when you really love someone. Fooling around is fun, and it’s great to have sex. I once hooked up with a guy in England, and we were in bed for 24 hours straight, having sex. It took my body probably four weeks to recover from that. So while I thought it was amazing at the time, it was painful afterward because it was just a marathon of sex. It was fun, because it was impromptu and I didn’t know the guy, but it wasn’t intimate.

Do you have a conversation about sexually transmitted diseases and condoms before you have sex with someone?
Yeah, I try to. I can’t say that I’ve done it every single time. I feel like everybody has an STD at this point. Everyone’s got everything, so it’s almost like mixing batter again. I try to be responsible, but I’m not always the most responsible person. I have an IUD. If you’re going to have sex without a condom, then all options are on the table. You either have to do it or not do it. I would advocate having the conversation and then using a condom. Did you make the decision not to have children a long time ago?
I’ve never wanted any. I don’t get it at all. I can’t believe so many people want that. Like why? It’s such a pain in the ass. My dream was just to have a great house. I wanted a clean house because my house growing up was always such a pigsty. I wanted cleaning ladies. I wanted a staff. I wanted to be able to go home and smoke a joint on my bed and listen to Neil Young. I do that all the time now. One night it was really windy and stormy, and I went home and lit a joint and just got super stoned. I thought, Oh fuck, I’d better go lie down. So I went upstairs to my bedroom and was like, “You know what would be great? That fucking Neil Young music.” When I was growing up, my brothers and sisters always listened to Harvest Moon. I just went up there and was lying on the bed with the doors onto my balcony open, looking out on my pool. The drapes were blowing, and I was like, “This is fucking awesome.” I was just sitting there with my dogs, going, “This is exactly what I hoped adulthood would be like. Not carpooling.”

Are you a feminist?
Yeah, for sure. I associate feminism with activism, you know? I like being strong for women, being a proponent of women, surrounding myself with women. I like being supportive of all minorities. You need to be supportive of everybody in this world who’s up against something. Feminism to me encompasses much more than just females. It’s about being there for Muslims, Mexicans, refugees, the handicapped, the LGBT community, the learning disabled. To me that’s what feminism is.

Did those ideals ever conflict with making fun of other women on television?
No one’s perfect. You’re going to say things that aren’t necessarily highbrow. As you get older, you definitely try to do that a little bit less, and before you open your mouth, you go, “You know what? That’s not a necessary comment to make.” Especially when Hillary lost the election. We have a real problem with women supporting women in this country. Forget sexism; it’s women too. So I think being a feminist is about all those things.

I envisioned you being wild and crazy. You seem a lot more serious than I thought you’d be. Is that intentional?
Yeah, maybe. I feel seriously about the subject of politics, so I’m sure I come across as more serious. I’ve seen that change in myself. I’m serious when I need to be. I’m also stupid when I need to be. But yes, when I’m at work, I like to get shit done.

You wrote your first book more than 10 years ago. What would the Chelsea then say to the Chelsea now?
Don’t worry, because you’re going to have a lot of money. You don’t need to stress out about everything. Also, you’re going to be able to take care of all the people you want to take care of.

Do you fear death because of what happened to your family?
No. After you’re 40 you start to go, “Okay, wait a second. I’m not going to be here forever.” I definitely felt immortal for a long time, and I don’t feel that way anymore. I just hope it’s quick. But even if I died tomorrow, I really fucking feel like I’ve hit it out of the park in terms of what I wanted to do and where I came from. To be honest, I never really struggled. I’m a white, blonde-haired girl who’s halfway decent looking, so life has been pretty fucking sweet for me. Now I’m at a point in my life when I’ve realized, “Okay, you need to talk more to people who have had different experiences and champion them and be responsible for that. Use your platform for something good.” It’s just that when your whole life is about you, it’s nice to get away from yourself.

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