A lot has changed since our drink below with Chelsea Handler in 2017. On April 27, 2019, Chelsea Handler is coming to Detroit for her Sit-Down Comedy Tour and “A Drink With” founder and host, Hillary Sawchuk, will ask the comedian and “New York Times” bestselling author everything you want to know about her new book “Life Will Be the Death of Me.” Come laugh and cry as we talk about how vulnerability is strength, life-changing therapy and going deeper into your own life. Click here for tickets. 

Cheers to your success and your Netflix series “Chelsea” broadcasting in 190 countries.

Cheers. L’chaim!

I love your talk show because you’re having meaningful conversations and I’m actually learning because you talk about topics that matter.

Thank you. And so do I! I’m so excited that I’m learning.

How do you prepare for interviews? Specifically, the sit-downs like your conversation with Amy Schumer or Renée Zellweger?

You know what, for those kinds of interviews I do the least amount of preparation because I know so much about them. I mean I’ve grown up with Renée Zellweger. I feel like all of the questions I naturally have are going to be questions everybody has. As a conversationalist I want to have an interesting conversation with anyone I meet at a dinner party, so for those people I feel like I know what people want to ask them. There are different styles for different people. I do most of my research when I’m talking to somebody that I know nothing about, if it’s a politician or if it’s the Secretary of Education, who I had on for the very first episode. He had this insane story of his childhood and how he came to be, and his family history was so impressive. So, people like that, who I really don’t know anything about, then I do my research. But if it’s somebody that I’m comfortable with and that I follow and that I know, then I know we’re going to have a normal cool conversation, just by nature of being curious.

What’s a topic that you want to dive into that you haven’t shot yet or the producers don’t know you want to explore?

Everything is pretty much on the table. They pitch me different ideas all of the time, whether it’s related to science or math or astronomy or the moon and the sun and all of that. It’s stuff that I respond to: women’s wrestling, or, “Do you want to go to UFC, do you want to do something with them?” It’s kind of like the world is your oyster, you know? The only place that it’s really hard to shoot with is the NFL. They are very protective, they don’t want anybody saying anything negative and they don’t want a loose cannon like me involved with them. So that’s the only place. I’d love to go learn about football because I know nothing about football. I know what I respond to. If I have an interest in it then it will be interesting to watch me do it, or investigate it. If I’m not interested I can’t expect viewers to be interested in it.

Have you ever done a Native American sweat lodge?

Noo. How much weight do you lose in one day? I may … That could be interesting. That is a little ayahuasca-y.

What is something about show business that you weren’t prepared for?

I don’t know. I always felt like I was a celebrity even when I was like 3 or 4. I was like, “Why isn’t everybody trying to talk to me?” I was pretty prepared for it. I don’t have any boundaries really, so privacy for me has never been a thing. I don’t really care. I don’t take myself seriously enough, some would argue, so I don’t really have any of those issues. I don’t care if somebody takes a picture of me, unless I’m running on the beach and cellulite is visible. That’s the one thing I try not to do too much. If I’m around paparazzi I don’t get up. I’m like, “Alright, you can just sit there.” I don’t get chased or any of that stuff. I’m an open book so there’s no mystery and I’m not that kind of celebrity. I’m like a talk show host. I’m doing my thing. The only thing I haven’t been prepared for is that you start to have an unhealthy relationship with fame. That is maybe something that’s not great, but you can deal with that in a healthy way.

At what point did you feel that way?

I had taken a year and a half off and I did these documentaries [“Chelsea Does”] for Netflix, which are separate from the show, and I remember walking — you get used to people looking at you and saying, “Hi.” Like, “Hey, Chelsea!” — and I remember walking down the street in Santa Monica on Montana Avenue and somebody said, “Where has she been?” It was in such a nasty way and I thought, “Oh shit. Was I gone too long? Do I have to start up again?!” I’m like, “Wait. What?” It just freaked me out and [then I thought], “What the fuck, that’s her shit. Who cares what that woman says?” So there was a moment of like panic and then I thought, “Okay, that’s silly.”

What’s something that you had to work hard at along the way?

I don’t need to share my opinions about everything all of the time. My friend Mary always says, “You don’t need to give everybody the truth. It’s none of their business, first of all, and you only save that for the people you really care about.” And my problem is — it’s not so much of a professional problem as it is a personal problem — if somebody does something that I don’t like, I can’t not say something or I can’t say, “That really hurt my feelings,” or, “I think that’s fucked up,” or, “I think you’re fucked up.” I don’t have that gene. I’ve been getting better, but it’s really difficult for me not to say exactly what’s on my mind. I can’t be nice to people that I don’t like. I don’t have that thing either and that doesn’t work well in business situations a lot.

Who has been a woman in your career that helped build you up?

Sarah Silverman and Gloria Steinem are on the show together and they are two people I’ve always looked up to. I mean, Sarah because she is so brave and Gloria Steinem for the same reason. Gloria Steinem helped pave the way. I think it’s interesting to think about how even if you don’t like a woman… you have to give credit to all of the women that helped every single woman today get where they are. There are so many people like that. So even if you don’t like somebody but they came ahead of you and they did groundbreaking stuff, you kind of have to acknowledge that. Joan Rivers and I weren’t friends but she definitely opened so many doors for me. And for me to not acknowledge that is being an asshole. So here I am acknowledging it.

I’m about to turn 30, what was going on in your mind at 30?

Thirty is great. First of all, it’s exciting to be alive. So you can’t have any of that bullshit [thinking], “I’m old!” Fuck off. You could be dead, you could have cancer, you could be in the hospital, so just be happy you’re alive. So, you’re going to start with that. Every decade is a whole new adventure, 40 is what 30 was. I think you just have to look at everything as a new adventure. I didn’t really get my shit together in a huge way until I was 30, 31, 32. That’s when I started to get my career going and my last show on E! started when I was 32. You’re not going to get the life you want until you work for it for a while, so aging is part of getting closer to all of the things that you want.

I’m almost embarrassed for my 20-year-old self.

Yeah 20s are embarrassing. I mean I’m more proud of the way I conducted myself in my 30s than in my 20s, definitely. Twenties… oh God I could have died.

Do you believe in soulmates?

I don’t know if I believe in soulmates. I think if you do believe in that then I think my sister is my soulmate. If you believe in that then I believe in many soulmates. If I believe in souls… I don’t know, that’s the lifelong question. Do we believe in God? Do we believe in all of that shit? If you believe in God then that means you believe in souls and vice versa. They kind of go together. I don’t know. I think a lot of people you connect with and you feel like you’ve met before because there is just a special bond whether you’ve known them from a past life or not. I don’t know the answer to that. I don’t believe in one soulmate. I think there are many and they come in the shapes of dogs, animals, women, men. It’s not necessarily the person you fall in love with. It could be your mom.

I saw an interview where you said your mom was spiritual. What did you learn from her that you carry with you?

My mom was really sweet and she was religious also. She was very spiritual. She could see life in a bigger way than I could as a kid, obviously. She knew from a very early age… she said, “You’re going to have a very big life. That’s who you are and your sister is not like that. She is going to be quiet and you’re going to need to take care of her when you’re older.” My sister is five years older than me and I remember as a little girl being like, “What?! Why do I have to take care of her? She should be taking care of me!” She was so sagacious. She could see the way the world was going to work out in 20 years! Whether she made that happen or she just made that prediction, I don’t know, but she was just spiritual in that way. She just had a way of looking at things that was sweeter. My best friend from high school told me after my mom passed away that my mom was the first person who ever told her she loved her. I was like, “What?! I didn’t know my mom told you she loved you.” She goes, “She was the only person,” because her own parents didn’t tell her. I thought, “Oh my God,” but that was my mom. She just knew when somebody needed extra love. She was extra juicy and lovable. You wanted to just hold on to her little meat. She was really cute.

Was there a time when you didn’t know what you were good at? Did you ever feel a little lost and not sure what direction to go?

Yeah! I used to do temp work. I used to get fired from every job. I thought, “What if this doesn’t happen for me? What if I don’t become successful in this medium and what am I going to do? Because I have no skill set.” There were many times, even throughout my career. When I left E! I thought, “I’ll probably just go travel for a few years and then maybe come back to the business and figure out what I’m going to do.” And then that didn’t happen because all of the stuff started happening and people were saying, “Take this meeting,” and then before you know it I’ve signed up to do another show. I thought, “Okay, well if I want this to be meaningful then I have to really take a year off and go find myself and find out what this show is going to be about and what I’m interested in and do something that I’m going to be proud of.”

Did you ever feel like giving up?

No, I don’t think I was ever going to give up. I think I always said to myself, “If I’m still waitressing at 30 I’m going to stop and try and find another career,” and I wasn’t waitressing when I was 30. That was my thing. I came out here when I was 20, so I thought, “Ten years of waitressing is a signal that you are going to be waitressing for another 10.”

What do your friends who have healthy marriages say is the key to a successful marriage?

I think honesty. You’ve really gotta be honest about everything. One lie turns into 15. And you know that from being a person. I think couples who stay together that have healthy marriages are open and they are friends. You have to be buddies.

What kind of guy do you want to date? Do you want someone in the entertainment industry so they can relate to your world or do you want someone that isn’t even a part of that?

I don’t know what the fuck I want. I don’t know! Sometimes I think, “I’ll never date an actor,” and then sometimes I think, “Well who else am I going to meet?” And then I’m like, “We need politicians on the show; I want to date a politician.” I’d like to not date somebody in this business. I want somebody who is really smart and educated, not that actors aren’t, some are actually very educated but I just want somebody who has a completely different life than me. I think that’s exciting.

Somebody you can learn from.

Yes! I don’t want more of this shit.

If you could have a drink with anyone, who would it be?

Probably Barack Obama. I’m really crushing on him right now. Big time. I fucking love that guy.

Where would you want the drink to take place?

Here! Alone. Nobody watching. I just love Barack Obama. I would do anything with him. I wouldn’t even want to be filmed. I just want to talk to him alone. I just want to talk about his marriage. I like a man who is honorable. He’s so thoughtful and inspiring. I’d want to talk about his family and the things that his mom said to him when he was a little kid that instilled such character, things that he remembers from his childhood. I’m curious about that. I’m curious about his relationship with his girls and the impact he has on them because when you have such a huge impact on the whole world, not just our country like a global impact, you must really measure how you’re going to have an impact on the people that are the closest to you because a lot of people miss that boat.

I also want to know, what’s his morning routine? How many cups of coffee?

Yeah I want to know all of that shit, too. I want to know exactly what’s going on. How often they have sex— all of the questions that nobody would answer.

What would you ask Hillary Clinton over a drink?

I would want to have drinks with Hillary with her daughter. I want her to just chill out and have fun because I’ve heard she’s fun and gregarious and she can throw back. People I trust have told me, “You don’t understand at dinner she is a totally different person.” I think around her daughter she’d be more relaxed and I’d like to see their relationship.

I wonder what she drinks.

Yeah, I don’t know. Most people drink vodka, don’t you think? Vodka soda.

Where are you the happiest?

Right now I’m the happiest at work. I like being here. It’s really fulfilling and I really feel like I’m busy all day. I just feel like I’m really doing something. If I’m dating somebody I’ll probably be like, “Fucking,” but I’m not dating anybody so I’m really happy working.

What’s your morning routine?

I get up, I harass my dogs and I wake them up. I get up early at 6:30, 7 a.m. and then I take a shower usually before I work out. That’s my special way. I have a special approach to that. Then I come to work, I go to my meetings and then I go the gym here on the lot with my trainer. Today I did Pilates. I don’t drink coffee.

No caffeine?

No. Sometimes I’ll have a hot tea. I don’t need caffeine. I don’t mind it, I don’t like the taste of coffee. It’s boring. I like an iced blended mocha Frappucinno. I think that’s fun, but I’m not going to drink that every day.

Watch “Chelsea” on Netflix | New Episodes Weekly

Photography by Tyler Curtis at Sony Pictures Studios lot in Los Angeles.