Quest Love Show is a production of iHeartRadio.

Hey What's up, Everybody?

Welcome to The Questlove Show, a new era and a format for QLs.

After close to a decade of award winning podcast You Know and Love, I'm back with a new idea after a lengthy hiatus having conversations with people who always wanted to get to know on a deeper level.

This week I spoke with Chelsea Handler virtually.

She was at home in Los Angeles and I was in my office at thirty Rock in New York City, the Red Room.

We know Chelsea as a comedian, television host, and a seven time New York Times bestselling author, with her latest book, I'll Have What She's Having out this year.

Chelsea is also part of the iHeart Podcast family.

With her Dear Chelsea Show.

This year, you can catch Chelsea Handler on her High and Mighty tour along with her Las Vegas residency at the Cosmopolity.

I was really happy to have her.

On the sho as the launch of this QLs two pointoero period.

For me.

This conversation you're gonna hear why Chelsea is present.

She lives in the moment, She loves vacations, She also prides herself as a listener, which she was with some of my questions.

Chelsea is raw and unfiltered, and in this conversation we discussed perhaps traveling together.

Listening to Chelsea talk about her favorite places.

You know, sounds fun, liberating, and grateful her work ethic.

Like me, she wears many hats, and this one was for me and Chelsea.

Like a few QLs guests in the past, she was opening to random questions and jumping around a little bit.

So I hope you liked this new approach for QLs and let's get to it all right, enjoy.

Hey, Chelse, welcome to the quest Left Show.

How are you today?

How's it going?

I'm good.

I like the looks of where you are.

It looks like it is a marijuana infuse dark room.

I am so not that person.

I am.

Yeah, okay, So this is what I want to know.

What time did you wake up this morning?

Six twelve am?

Is that typically where your body clock sets off?

Or yeah?

Unfortunately I kind of would prefer to sleep a little bit later, but like, I kind of need a good two to three hours before things get going.

Just to decuntify.

Do you know what I mean like I'm a bitch and I have to wake up.

I write in my gratitude journal that's now on my phone.

So that's a lot easier than writing because I've lost the I've lost the aptitude.

For writing or the design.

It hurts.

So I do my little gratitude.

I say everything I'm grateful for, even if you know I'm not feeling great.

Then I meditate for twenty minutes.

I play with my dog, I let him out, and I just slowly.

Come to you know what I mean.

I need a good two to three hour lead time to start.

I had everyone else to start my day.

So yes, wherever I am in the world, typically I wake up pretty early.

Okay, so that's what your first fifteen minutes.

But what I want to know.

Is, what was the last half hour of your last night, of your day?

Last night?

What is the last half hour?

Huh?

Last half hour?

I went to this tech conference or like this kind of tech gathering.

So I came home from that pretty early.

I was home by like nine p thirty.

I came home from that, I got into bed, I put on Charlie Sheen's documentary and then that's like background noise.

So I'm not really watching it, but I just kind of liked the TV to lull me into sleep.

And then while that's happening, I'm checking my phone, returning my emails.

I'm doing a big stand up tour next year, so I looked at my ticket accounts because it just went on sale, so I peruse that.

Then I looked.

At my emails, look at my day tomorrow, and then I just put my eye shades on.

I put my rain machine on so that I have the thunderstorm going, and then Charlie Sheen, and then usually about like ten minutes of whatever background TV I have on.

After I put my eye shades on, I turn off, and then I'm usually down.

Okay, I was going to ask, do you sleep with the TV on or off?

So off off, but I fall asleep with it on.

I find it helpful to fall asleep, And I know that's not Everyone will say that's a bad but I don't really give a shit.

I'm fifty years old.

I know what's best for me.

There you go.

During the uh what I'll say in air quotes the first cycle, I used to always sleep to the news, just to make sure that we are all in one piece.

The next morning, right right.

But then the more I started studying about how the brain works and how the subconscious works, I realized that sleeping the doom and gloom as I was sleeping was making my day worse.

So I actually started maybe turning off the television maybe in yeah, three years ago.

Yeah, I mean, in general, it's probably a good privent, like not to watch the news at all.

I mean, there's really nothing that we're gaining from watching that.

Listening to a podcast, a political podcast, I find is much less damaging, especially while you're out and driving.

There's something about.

Driving and listening to the news that is less damaging to your system than actually just sitting on your couch and watching the news.

So the way that I take an information, for instance, like if the Roots have a difficult song to master, or if I have to do something that requires like memory, I'll actually sleep to that loop, you know, like, oh yeah, when you're in your sleepy, tired, THETA state, that's where you retain.

But I also believe that when you're driving, that's the equivalent of sleeping, because you're still in your subconscious state even though you're.

Aware in driving.

But I tend to read a lot of audiobooks and listen to podcasts while driving because I'll retain the information better.

I don't know why, but you know I love driving.

I love driving.

That is like my live in California.

Yeah, I live in LA.

So there's a lot of traffic here and that's the lamee.

But it's so nice to know when I can leave somewhere and it's like a forty five minute drive, not sitting in traffic, but an actual forty five minute drive Like that, I can go up to maulhalland and look at the views and have a long ride with myself, Like that's my kind of that's my vibe.

People are often shocked that when I get to LA, I want to drive myself.

For me, especially you know, when I'm testing music, Like I whenever an album was complete, I would go up the Pacific Coast Highway and test the material because for me, if it works on that drive, then it works elsewhere.

So it's it's a therapeutic thing for me.

But I never heard a person that lives in California.

Like I thought I was the only one.

People look at me like, wait, you like to drive, And I thought I was the only one so I'm glad to know that.

Yeah, I prefer I don'tfer I like, if I'm in New York City, I prefer to be driven.

If I'm in LA, I prefer to drive.

Okay, that makes sense.

Okay, So how old were you when you realize you had a gift?

Be it charisma or organizational skills or.

It's definitely not organizational skills.

I've never realized anything about that.

In fact, I mean, yeah, don't.

I don't have that.

I have no logistical expertise, no domesticity.

I think I realized I was precocious and that I got attention for that.

And I was the youngest of six children, so like, to me, that was an avenue to get what I wanted was to be kind of bold and brazen and say the things that nobody would accept a little five or six year old girl to say.

And I got rewarded a lot from my three brothers because they thought it was so funny because I was obnoxious, and they'd be like, go up and tell that guy that he's an idiot, and I'd be like, no problem, and then I'd go and tell them and they'd be laughing, you know, like they made me do stuff like that all the time, and I loved their reaction to that.

So then that became my commodity.

Like I became that kind of personality and I leaned into it pretty hard.

Six siblings, five siblings.

I'm the youngest of six.

Can you rank them in order?

Yes?

I can.

Rank your siblings in order.

Chat Roy, Glad Simone and Shashana Chelsea.

I don't mean by age, I mean by closeness.

Oh oh oh, sorry, I thought my brothers and sisters.

I'm like, fuck it, I hope so.

Or what skill set does each sibling have that you admire the most?

I won't make you okay.

Okay, Well, my brother, my oldest brother, not to be a bummer, but he died when I was nine years old, so he's out of the picture.

But I still account to him as my brother because obviously my brother, my second oldest brother.

Roy is a chef and he is the biggest teddy bear in the world.

He was the chef on Chelsea Lately.

He was the chef on my Netflix show.

He's the one you just always want around.

He's like a party favor.

Roy is the sweetest, most gentle man you know, Like we just all love him.

My sisters and I are like, that's our teddy bear.

Then there's Glenn, my other brother, who's very intelligent but also slightly misogynist and like he's married to a Russian woman who's a real Putin sympathizer.

So I have a little of a bit of a challenging relationship with that part of the family.

I spent my last twenty.

Five years going on vacation with my whole family, Like I take a lot of pleasure and like taking my whole family away.

And after, like, you know, like four years ago, I was like I'm wrapped.

I was like, I didn't marry this woman, Olga, you did you go on vacation with her.

I no longer want to finance a vacation where I'm listening to Russian state propaganda, So that relationships a little bit, you know, it's got some friction.

My sisters are Simone and Shashana, and my sister's a healthcare attorney, and my other sister has her own ear piercing company in New Jersey, and the.

Girls are always reyal tight.

Our whole family's pretty close and communicative.

But like, you know, are you the family alpha?

Yes, you're the organizer.

Definitely.

Okay, so Thanksgiving time.

Who's Thanksgiving time?

Thanksgiving start for you.

Well, Thanksgiving time starts for me by telling my family we're not celebrating together this year.

Leave me out of it.

I don't care about holidays.

I don't care about Christmas.

I don't like being told when to celebrate general.

Yeah, I just I.

Find that all very annoying.

Like I want to celebrate.

I want to have a life when I want to have a life.

I don't like when people are like, Okay, today's Thanksgiving.

I'm just not into it.

Butgiving whatever the hell.

I feel like I hopefully ski somewhere, but yeah, or I'll go to a friend's house, Like, I just don't like it to be I don't like the formality of that, you know.

I want it to be casual and I'm going to do my own thing.

But we do vacation several times.

I mean, we usually vacation over Christmas, like for a long week, and then in the summer we'll go to Martha's vineyard or something.

Typically speaking, although in the last couple of years, like I just said, I've kind of taken ownership over.

My holidays again.

And I'm vacationing less with my family and more with myself.

You said, now you're even preparing for your set, Like for you, like what is the process of honing your skill set as far as having fresh material for a comedian, which I know, like especially when all of you are choosing from the same subjects, like your take on where we are now, Like how do you what's that whole creative process?

Like well, I think you know, for me personally, like I've made a living by being myself.

You know, I've made a living off of my personality, which is not something as a little kid even and knew I could do.

I didn't even know that was possible.

You know, when you do stand up, you're writing your own script.

I mean some people in may of writers, but still there, Like it's so important.

Whether it's me writing books, whether it's me doing my podcast Dear Chelsea, or whether it's me doing stand up.

These are all self generative, right, I'm all like they're all coming from me, And I think that, you know, like I work really hard when I work, and then I you know, don't work really hard.

When I don't work, I go and vacation.

Really hard, and I experience really hard because I want to have experiences to talk about.

Like you have to live a life to gain the material to write books.

You have to live a life to gain the material to write a set.

You know.

I like, last year, I put out my my most recent special on Netflix, and that means you start over that you have to have a whole new hour of material.

So then you go into your life and you're like, what haven't I talked about yet?

What's happened in the last year, you know, Just like I was telling you about my family and my family vacations, like that's a topic in my stand up, Like I started editing people in my family.

I'm like, listen, I didn't marry your wife.

I'm not required to go.

I've extended my generosity for twenty five years.

I want to go on vacation with your kids, bring me your kids, but you.

Guys stay back.

Or I want to go on vacation with my siblings and none of their spouses, you know.

Like I'm actually setting different a set of rules now because I just don't feel like doing that anymore.

Like I'm a woman.

I pay for almost everything that my family does together, and now I'm making the rules to fit what I desire, and there's nothing wrong with that.

Okay, So maybe a decade and a half ago, I was in the beginning process of maybe maybe will they or won't they dating a comedian and someone put something in my ear and I couldn't get rid of it, which is basically they were like, you know, you've better not never mess up, or you'll be part of her.

Set, right, And I almost think.

That I subconsciously sabotage the relationship so I could get out of it.

Do you find it hard to sort of draw in people?

And I don't mean like your comedy circle or whoever your creative circle is, but do they often have is that apprehension or are they slow to come into your sphere for fear that they might be the subject of your life, which is the stage.

I'm sure that that is something that lots of men think about, if there's ever a chance of connecting with them.

I'm sure many men are like, oh god, I've talked.

I've spoken publicly about almost every relationship I've had, not everyone, because some people who are private, like, if you're not a public figure, I try to leave you out of it because it's not fair.

But if you know, like I dated Joe Coy.

Who's also a median, so I've spoken about that publicly, very limited.

Nobody really knows why we broke up, but you know, we were a very public relationship, so we publicly broke up.

But I didn't drag him.

You know, I would have done that probably ten years ago, but now I'm a little bit more mature, So I try not to humiliate men because I know, a my feeling is a lot of men are already turned off by me and my bold personality and the fact that I'm confident.

That turns a lot of men off sadly, you know, instead of men going, oh my god, that's a woman who knows what she wants and is confident.

Yeah.

I often say that, like, you know, we'll say like, yeah, I want to strong, will d d D D D D da da da.

But then in almost every situation, the person that tells me that we'll have some sort of buyers remorse later and I'm like, well, you got to be honest with what you really want in relationship.

Because yeah, it looks good like what.

Paper, yeah, right, what you think you may not want when it's put to the test.

And it's real, Like, you know, I'm an independent I don't really need a lot from a guy.

You actually have to be a great guy and we have to have great chemistry for you to be in my life.

I'm not like my standards are so high because I really don't want to settle or have to for anything less.

And you know that's not a threat, that's just my truth.

Like I've been through gross guys and idiots, Like I'm not doing that again.

I'm too secure and I'm totally fine also being single.

Like I'm not one of those women who's on dating apps every night going, oh, I got to hook up, I got to find somebody, I got to go on dates.

I don't operate like that.

So who's in your trusted circle then that you really trust, like that knows where the bodies are buried?

Like what's the number?

A number of people?

Probably like five people.

Okay, yeah, but you know I'm.

Not like a private person.

Obviously, I'm not precious about my privacy.

I'm a very public I've always been very public.

That's kind of part.

Of my deal.

You know, there's not a lot of mystique here because I'm always willing to talk about everything.

So it's not like I have a ton of secrets.

You know, they're out there.

It's not like I have a ton of like hidden stuff that only certain people know about.

Yeah, there's stuff that is in public.

But as far as like bodies being buried, like I would have already outed myself on.

That, who's your first like life role model, like a real life person that you know in your childhood, And then I was going to say, who's your north star?

As far as creativity?

Yeah, Like, I think my sister was my hero, my oldest sister, Timoe, when I was growing up, because she kind of played the role of my second mother.

She was my de facto mother.

My parents were you know, when you have six children, they're out to lunch.

They were exhausted.

My mom slept like a cat throughout my whole childhood.

I mean they would forget to pick me up from school.

I'd walk home, like in the middle of a blizzard, and I'd walk home and my dad would be sitting at the kitchen table reading the New York Times.

I'm like, hello, hello.

Devin, and I just walked home and a in a snowstorm.

So yeah, my sister was my hero.

Because she was kind of the one that mediated between me and my father and my parents when our relationship was more volatile as far as artists or creatives.

You know, I grew up on The Cosby Show like that was my show.

I wanted to be part of the family.

Like I considered myself to be a Huxtable.

I wanted Rudy and Vanessa to be my sister.

I wanted to fuck my brother, you know, not my real brother, but my brother.

On the show.

And I love the idea that my father was a guynecologist or an obgyn basically with those swinging kitchen doors and those sitcoms in the way, it just felt like the most idyllic childhood, right the Huxtables.

To me, that was it.

And then you know, we all know what happened with that, So there you go for heroes.

I was going to say that watching Malcolm Jamal Warner vicariously, I was him on that hill, right, And when he passed away, I had to return to like dust off my my my DVD player and break out the box set and rewatch all eight seasons as a mournful process.

And I realized how much that show kind of pushed me forward in life, you know, like I didn't know that we could live like that, and so, yeah, it is a hurtful process if you get betrayed on that level, like how do you how do you even deal or return to it?

And so I was also also this is I've told the story before, but maybe you haven't heard it.

I went to I was performing in Atlantic City doing stand up and Bill Cosby was also performing in Atlantic City.

The end of the story.

Okay, so this casino manager approaches me.

I was doing two nights.

He was doing two nights.

We were in two different rooms.

And he calls me.

I mean, we're performing in two different rooms.

Obviously we were staying in two different rooms.

But the casino manager approaches me.

She's like, oh, Bill Cosby would like to meet you.

And I'm like twenty seven, twenty eight or no, no, I was in my thirties because I was on Chelsea Lately at the time.

And I was like, They're like, Bill Cosby wants to meet you.

He's you know, he wants you to come to his hotel room at three pm.

And I was like, oh my god, are you kidding me?

Bill Cosby knows who I am?

What And so I go up and I brought the guy that was opening for me, who was also on Chelsea Lately with me in one of the comics, Chris Frangola.

I had a security guard with me, and I was like, guys, do you want to meet Bill Cosby?

Knowing nothing, knowing just like the more the merrier.

We go up.

We knock on the door and I'm like, oh my god, Oh my god, mister Huxtable's coming like this.

He opens the door.

Bill Cosby opens the door and you know, you know, he's got that great face, at least it used to be great, and it was like, you know, that jello pudding.

Smile he had on his face.

And he opens the door and he's got this big smile and he doesn't see the two guys that are standing next to me because they were like to my right.

And I jump into Bill Cosby's arms.

I'm like, dad, I'm home.

Like That's how I greeted him.

And he was holding on to me, and I was holding on to him.

He held on a little bit longer than I and then and then I said, and these are my friends, Chris, and then my security guard and.

His face dropped.

Yes, and we go in, and we go in and we sit and it's like, you know, he's got this huge suite and we're sitting.

We sit down and he's like, who are these guys, blah blah.

I'm like, oh, well, this is Chris my opener.

And he proceeds to go in on Chris Frangola for opening for a woman and telling him how he'll never be successful in comedy because he's opening for a woman.

And I was like, wait, what is this?

Like I thought we were being punked.

I was like, is this a And then you know, at a certain point, I had to stand up for my friend because he was just dragging him.

And I finally went up and I'm like, you know what, I'm sorry, We're out of here, Like we don't need to listen to this.

This isn't pleasant or fun.

Oh we got that serious?

Yeah?

Yeah?

Yeah, it was like it was really obnoxious.

So we walk out and that feeling of you know, you meet someone that you should you know, we couldn't even speak to each other, the three of us.

We walked down the hall out out of his room and we're all just like, you know, speechless.

So I'm very grateful that I had the enough intuition to bring people with me.

I think what people don't know when they look at your life as a goldfish or as a person that's separate from their lives, is that you.

Haven't met that.

It's easy.

Can I ask you what was your version of air quote making it when you were ten years old?

What was your version of what you thought success was going to be?

First class?

And like being flying first class at ten years old?

I went on my first flight and I walked past the first class section and I was like, whoa, whoa, whoa, whoa, whoa?

Who are these people right here?

Like this looks like my group?

And my mother was like, keep walking, sweetheart, that is not our group.

That will never be our group.

We have six children.

We will never be able to afford to fly first class.

And I was like, fuck that shit.

I'm like, the next time I fly, that's where I'm sitting.

And it took me about three years of saving up babysitting money and lemonade stand money.

But when I took my next flight, I was thirteen years old, and guess who sat in tuc while my family sat all the way and coach, wait.

Did you do this independent of them as well.

Yes, I went down the street.

We had a neighbor who was a travel agent.

I bought my own first class ticket.

It was something like eighteen hundred dollars.

It was like nineteen.

It would have been nineteen eighty eight because I was thirteen flying from We're flying from Newark to LA.

I had grandparents that lived in LA and I bought my own first class ticket.

And I didn't tell anyone because I was flying with my two brothers, Glenn and Roy, and I want I could not wait to see the looks on their faces when I sat down in my seat.

I couldn't wait.

And when I did, I stopped and I was like, you know, thirteen years old, but acting like I was, you know, forty.

I was like a businesswoman.

I had a briefcase.

I was like in California, I had kidneys.

I had to dress up back then, correct, Yeah.

Yeah, well you didn't have to, but I wanted to.

I was told you had to dress up.

If you said I had to wear suits until yeah, that.

Was like the SEVENTI yeah, I guess that was the eighties two when people dressed up.

But I sat down in tuc My brothers thought I was joking.

I put my little briefcase in the over had been with my little Barbie, you know, backpack and for my week in California, we were going to Disneyland, and my brothers are like looking at me, and I just showed them my ticket and I was like, I'll see you counts at the end of the flight, and then I went back to coach where they belonged.

And at one point my brother came up to the first class like we were up in the air for like an hour.

You know, I'm enjoying a glass of champagne because they don't know how old I am.

And my brother comes up to my seat and he's like, you can't do that.

You can't do that.

I go, I can't do what he goes.

You can't fly first class without giving it to You can't buy a first class ticket and not give it to one of us or mom.

And I'm like, are you I go, what are you serious?

Get the fuck out of my face.

I'm like, you're ten years older than me.

I'm thirteen, you're twenty three years old, and I figured out how to do this before you did.

No, thank you, sir.

And I'm like, I don't even know how you got up in this section.

Go back to your robe.

Please behind the curtain.

Yeah, get back on the garden.

What unfair rule was implemented in your childhood?

Don't go out past eleven?

You know?

Well, I don't know.

If this wasn't I don't know if this was unfair, but I got caught.

I got when my girlfriends and I were like eight years old, we did what was called the feeling, where you would basically masturbate but over your clothes so everyone would call.

You would just like rub your vagina but over your genes.

Actually, the thicker the material, the better the traction, so you wanted more attraction, so you would never actually touch your vagina directly, but we would do it in school.

We would use rulers.

We would just all be like, are you going to get the feeling?

During math class?

Like whenever we could try and hide it.

So I got pretty confident about getting the feeling.

I'd go home and I'd lie down in front of like an ottoman and kind of shade my body so that I could, like, you know, just watch General Hospital and masturbate the whole time.

And then my parents caught me, and I guess they had known for some time that I was.

Doing it, but I thought it was unfair, and they.

Were like, you cannot masturbate in the living room anymore.

They shamed you.

Yeah, yeah, totally shamed me because I was starting to use appliances like spoons, like a wooden spoon or you know, I would see a corner of a wall and I'd go up to that.

I was getting a little carried away in truth.

So they told me I couldn't masturbate at home anymore, or.

No in the living room.

They're like, if you want to do that, save it for the privacy of your own room.

And I thought that was unfair because I was just experimenting with my body and finding out what my desires were.

Wow, this is not the answer I was expecting.

Wow.

So no master being with our utensils or I know.

And also I felt like keeping my clothes on was the first step, you know, like, that's pretty respectful being.

Yes, you're being respectful.

Absolutely.

Are there any mementos or toys from your childhood that you've kept this entire time?

Not toys, I would to say, but mementos, yes, like you know, school pictures or family lots of family stuff, like when you have such a big family, We had like a lot of fun ridiculousness, you know, it was always chaos.

And we had this summer house in Martha's Vineyard and so we have a lot of.

Fun up there.

So yeah, Like and we always had dogs, like, we always had a family dog.

So I have a lot of like memories from that and mementos like pictures of my childhood dogs and stuff.

But as far as like actual mementos or toys, no, I don't think I'm not like sentimental like that, Like I'm not somebody who saves a lot of stuff.

All I care about is anything that's in writing, like a card or a photo.

Those are the things that mean the most to me.

Well, wait, you can't say that you're not sentimental, because I would assume that for you.

I mean you've written seven books, correct, yes, seven books, and what you do for a living is recalling the past.

So I mean there's a part of you that has to be somewhat sentimental.

Well, I mean sentimental it lends that that word kind of means that you're holding onto the past in this kind of Yeah.

Well, it's just like you know, it's like I miss it.

You know, it's more of a reflective than it is sentimental, Like it's more of a I mind it for material.

I mean, there are parts of it that I am sentimental about, you know, like my brother who passed away.

Of course I'm sentimental about his stuff, and I do have a couple of his things actually, But like I find the word sentimental to mean, like, oh, I get emotional when I think about things, Like a lot of things are just references and reflections that I take with me, and my past is so much a part of who I am, Like I had to be salty to survive.

I had to have a big personality to be heard, and so it's part of the fabric of who I am.

Can you tell me a story of the worst time you ever got in trouble in your childhood?

Oh?

Well, I mean there were a couple.

I once had a party at my house.

My dad was actually in the hospital, and I was like perfect, and we have the house free.

And I was like in seventh grade and I had a huge party at my house and everyone just started taking stuff from my house, and the cops came.

Like people were.

Stealing stuff like pieces of furniture and then the cops came.

And when the cops came out, I was like, I'm out of here too, and I left my own party and went and hit at our elementary school in the woods until they left, because I didn't want to get in trouble.

So you thought you could get her away with so obviously you raised on like eighties, nineties teen movies, like you thought you could get away with us.

Yeah, totally.

I was like, Oh, if they don't see me, then they can't prove I was there.

And it's like, where are your parents?

Did you?

What did your parents do for a living?

My dad was a used car dealer and my mom was like a home health care nurse, but she didn't work.

She only worked when my dad's business was doing pretty badly, which was quite often because he was he was a used car dealer, but he didn't have like a place of business.

He just sold cars out of our driveway.

So our driveway was like this big circular driveway covered in these terrible geloppies, like there would be tire irons and tires and everything was just strewn.

It looked like like the front yard of Sanford and Son.

So they were sentiment.

Well, my dad was I mean or he just couldn't sell a car, depending on how you look.

At it, got it.

So wait, what happened when when you got found out?

Oh, I mean I got in trouble.

I mean the police found me in the woods, like we were all gathered there together.

We had no experience in like dodging the police or anything.

Another embarrassing thing.

I got caught shoplifting at Sears.

Remember Sears.

I don't know Sears still exists, maybe.

But I got caught shoplifting.

But bras and underwear.

First of all, it's like a home appliance store, so buying bras and underwear from Sears.

Is already off.

And my girlfriend and I, Jill, got caught shoplifting and then I had to go and that was really shameful, Like my mom wouldn't even talk to me for a week.

She was like, that is so gross that you went and stole.

And my dad had to take me to these shoplifting classes where you had to get up and the father was like, I am the father of a shoplifter.

And then I had to go out.

You had to take the photo in like the were they hanging in the back?

Yeah, And then I had to get up and be like, I'm a shoplifter, and then you have to talk about what you shoplifted.

And mine was like a red bra and underwear panty set.

And I was in seventh grade.

I didn't.

I mean, who's buying launcherie from Seers?

Like none of it made any sense at all.

Ah, Okay, what's the last thing that you cooked for yourself?

Oh?

This is I did this the other night.

I was staying with a girlfriend because my house is under construction, So I was staying with a girlfriend and she cooks, she can cook.

I was staying with her for about a month, and I wanted to not leave until she taught me how to cook at least one thing.

I am terrible in the kitchen.

I'm very bad with instructions.

If you'd give me the instructions, it's very hard for.

Me to follow through.

So I wanted to cook chicken pacata, and we cooked it together with her help.

She did probably about seventy percent of the work.

I did about thirty percent, and it's still tasted like garbage.

Got it?

What restaurant would you fly across.

The world for Kespatra March.

Is that that's.

That's a restaurant in Mayorca in Day of Mayorca.

I have a house in Myorca and we go there.

We ride our bikes to this restaurant.

It's up this huge hill and then you ride down and it's right on the water, so you're sitting on the Mediterranean while you eat the most fresh fish and fried onion.

They put these little fried onion rings on everything that they serve, so you get this beautiful like dorado fish or sea bream or whatever you're into.

And then they have these crispy onion rings that they put everywhere, and then you can jump off from your table into the sea and it's this beautiful cave.

I mean, it's just heaven on earth.

I want to go to this.

Yeah, come anytime.

I'm going for the month of October quest You're welcome to join me.

So you're big on vacations and break and self care, yeah, I take it.

Yes, Okay.

So I'm a person who is notoriously known for, you know, filling up every second of the day with I don't see it as work.

It's a passion to me, but I was.

You know, when you start dating, you you're forced to go on vacations, and it was hard for me to not work.

Convince me why taking vacations are important.

Oh my god, I mean, listen, there's always a little work, like I'm always always a little bit working, Like I need.

To just decompress.

I need My life is crazy, as I'm sure yours is.

All of our lives are crazy.

It's just so important to get to a point where you feel recharged, where you feel like where you can just take your stress.

Because first of all, you go on vacation for a week, you don't start relaxing until like the fifth or sixth.

Day, and then you're leaving the next day.

That's why I go on vacation for a month, because I take a first week to adjust, and then I can actually chill out.

I can read a book and concentrate.

I can go on a bike ride for two hours without thinking about a million things.

Like.

To me, vacation is letting your mind not run you.

To me, vacation is like getting so relaxed that it doesn't matter which way the wind blows.

You might go to dinner that night, you might just sit at home.

You might stay in bed all day and watch TV.

You might be out in the ocean all day.

Like to not have a plan and let see where the day takes you.

That's my idea of a vacation, to not have anything regimented.

What is your preferred month of not working?

It could be any month.

I mean, I like working during the summer because it's gotten so hot, so it's like I don't enjoy that.

Being in the heat and vacation.

But I love the winter to ski.

I go to Canada in the winter to do my skiing, So I base myself out of Whistler, Canada for like four months in the wintertime.

That's also part vacation.

I mean, I do my podcast from there, and I'll be on tour from there.

But it's just a different kind of I like to change the channel a lot, you know what I mean.

I get bored being in the same place.

I find La to be a little bit sleepy.

I find New York to be much more stimulative.

And then I split my time between Spain and Canada.

All right, So have you ever gotten lost in another country?

Yeah?

All the time.

I got lost on a vespa in France for an hour and a half in a bathing suit on a freeway with eighteen wheelers driving by me because I couldn't even follow direction.

With my friends, We're all on vespos, and I was like, just had my head in the clouds.

I was like, oh, I guess I'll make a left here when no one else made a left and I got on a major freeway.

I was in beer Ritz, France, and I got on a major freeway and could not get off of it for miles and miles, and a vespa only goes like forty five miles an hour at tops, and these cars are blowing past me, beeping like, get out of the lane, get out of the lane.

So I was a very dumb American on that trip.

But I get lost all the time.

Quest I have no sense of direction all right?

When traveling?

Are you a window or an out seat person?

Doesn't really matter.

I'll probably because I have to pee a lot, so it's easier for me not to walk over anybody.

Okay, when all is said and done, what city would you like to retire in?

Probably I mean somewhere.

I'd probably like to live out my last days in my Orca.

Yeah, that's pretty much in my happy magic place.

What is it about it?

Yeah, it's just.

So I love to be on the water.

I love to hear water when I'm sleeping.

I love to be in the water.

I love to sail.

I just love that whole vibe like outdoorsy.

And the great thing about my house in my Orca is it's got this huge outdoor terrace, so it's like you kind of don't even have to leave the house to feel like you're part of Like there's this little port and all these shops and restaurants and people are always walking back and forth.

I'm bringing my dog this time so he can experience like the magic of it.

We got him a life jacket so we can go into the Mediterranean and throw him off of a paddle board or a catamaran, whatever we decide.

But also New York I think like in terms of you know, New York is so stimulating that I think as you get older, that really is the place to live, because you can't really La is too sleepy to get older, you know what I mean.

I could die early here just from being so lazy.

When I come here, it's almost like a rehab.

Like I sleep a lot, I get healthy, I work out all the time.

New York I'm out and about, you know, there's a lot more fomo there.

What time do you normally go to bed?

I go to bed pretty early in LA, Like I go to bed around ten ten thirty in LA.

I mean, listen, this weekend, let's be honest.

I went out to a party and I got home at six am on Saturday morning.

But that was an anomaly for me.

I usually don't do that, so that was really fun because I hadn't done that in a long time.

So you don't go as heavy as he used to go in.

Your oh oh no no.

I like day partying, Like I like to go out to a fun lunch.

I'd like to go do something.

Early at night.

It's kind of why I love ski culture, because you get up early, you go skiing, you have a little margarita juice boost at around eleven thirty in the morning, then you have app ray around three thirty, and that kind of counts as my dinner, and then I'm home and bed by like eight o'clock, and I get up in the morning and do it all again.

So I kind of like that lifestyle.

But I mean there's a lot of lifestyles I like.

Okay, So practical Advice twenty twenty is what I consider to be.

You know, we might be living through another type of pandemic, a spiritual pandemic.

But twenty twenty for me was a crucial year of what I consider like my BC eighty years in terms of I wasn't the same person now than I was before then.

So twenty twenty was a pivotal change for me.

What was different for you in your life now post twenty twenty that you're still implementing.

I mean, I don't think anyone is really recovered from that.

I mean I don't think you know, the work ethic is not the same for a lot of people.

People don't want to go back to work.

They didn't want to go back to work for a while, so there's.

That in the air.

In general, there's a kind of malaise about working hard.

So you're not as hustle based now as you were before twenty twenty.

No, I didn't impact me as much.

Like I mean, I grew up as a hustler.

So I'm from New Jersey, Like, you're not going to get that out of me.

What city, Livingstone and they it's by like Montclair, Like we's Caldwell.

Okay, No, but I mean I think just the reflection of so many like whether it's gen Z or what you know, millennials or their attitude from COVID.

You kind of absorb it, or you're constantly exposed to the fact that people liked not going into work, people liked the virtual life, people liked talking like this rather than being in person.

I would always choose to be in person with people.

That's just my preference.

I feel like there's much more of a connection.

So but my life, my life has a change.

I mean, I would say I'm busier now than I was before twenty twenty.

That was, like, you know, I'm.

Busier now without a talk show than I was when I had a talk show, which doesn't really make a lot of sense to me, but.

Somehow it's true.

So I don't know.

I mean, that whole pandemic, it just changed our country and our like you know, it changed the whole world.

But on a personal level, I don't feel so changed by it.

I felt more of an observer of it rather than in the thick of it.

I wasn't upset by it.

It didn't freak me out, I wasn't scared.

I welcomed the break quite frankly.

I liked it.

I read a lot of books, and I took a lot of mushrooms.

Same.

All right, we're going to be friends, Chelsea.

What book would you say probably changed your life?

What was a paradigm shift for you?

Hmmm, or at least the author that pushed you.

Yeah, letting Go.

There's a book called Letting Go by David Hawkings that I always talk about.

That book.

Have you read that.

Somebody was explaining to me, you know, like his enlightened, like his number system that he has as far as our vibration.

Yes, okay, So someone was explaining that to me and they sent me a clip and then the next thing I know, I fell down a vicious rabbit hole and damn near his So I'm reading his entire anthology, if you will, and anything he's ever written I've read over.

Like him and Neville Goddard are my two go tos?

Oh Okay, I don't know him.

Nevill Goddard.

I'll have to look him up.

Well.

Number one, I'm working on a movie right now in which the lead subject it's a documentary, but he believes in metaphysics and you know, the idea of positive thinking, affirmations, breathing, meditation, all those things, and so in order to understand that subject, I had to at least I took about a year off just to read all the metaphysical so between like Joe Despenza and but David Hawkins to me is God of them all.

So yeah, yeah, it's fascinating stuff.

It's fascinating to stuff to be like because it's scientific, but you know, it doesn't get as much airtime because it's not as easily measurable.

You know what the ideas that he's talking about, even though they are scientific and they are measurable.

Do you find it hard to talk about this with other people?

Well, I mean I just frame it in the way that energy is.

You know, like you're going there's a magnetic attraction.

If you're going to put out positive energy, that's usually what you're going to get back.

If you practice being positive, if you practice being upbeat, that becomes infectious and contagious.

If you're negative, that's what you attract.

Like, I mean, how many times have we sat around feeling sorry for ourselves or being negative and and then you just draw more negativity towards you.

So it is like, it's it's pretty powerful to understand like the laws of attraction, and to understand that you can like higher your frequency, like you can get on a higher frequency, and the higher your frequency is, the more good that comes your way and the more people that you're able to positively impact.

I find that to be just like the kind of point of that.

Whole book is to really let go of the negative, like let things go, do not resist reality.

Something doesn't work out your way, that's okay, make a left you know what I mean, that didn't work out.

Don't sit there and bemoan that it didn't work out over and over and over again.

Move forward.

So you're big on pivots.

Yes, I'm big on pivots, all right.

So how do you handle what I call the F word?

I'm a reform perfectionist, and so for me, I would take failure very hard, like obsessively reading every record review, every show review, writing angry letters to you know you want you know.

And it took me maybe half a decade like to finally not to let that go.

But for you, how do you so now when something doesn't work?

I almost I think I've convinced myself that when I see the F work, failure is a gift because technically it's it's a teachable lesson.

But for you, how do you handle failure?

Well in the lightest way.

You're a comedian, so sometimes every joke doesn't work, and so how do you handle it in that sense?

And then I want to know, how do you handle a major perceived failure?

Yeah, I mean a joke not working is not a huge failure.

That's a part of the work.

Like, that's a part of trial and error, you know, that's my job is to test things out, see if they work, and then you know, let go of something if it doesn't work.

As far as a failure.

Like you know, trying to do something it not working, Yeah, those hit they can hint a little harder.

But it's also like, you know, I just have this kind of philosophy.

You know, it's a bummer.

You can be okay, you know, bummed out for a day or two, but I'm not going to get angry.

I'm going to get motivated.

I'm going to like, you know, re pivot.

I'm going to figure out what the next thing is.

Like you can't, you know, I just don't have the patience or the time.

To be in victim mode for too long.

So if something doesn't work out.

First of all, most things, you know, I understand a review is personal or feels personal, I should say, but most of that shit isn't personal.

Most of that shit is about somebody else's bullshit.

And like if someone doesn't like me, or if I don't sell a project that I'm going out to sell, it's like, Okay, well it didn't work at the right time, that person doesn't like me, or then look over where the light is, Like go where the light is instead of focusing on the negative.

So I just always try to practice that, you know.

I mean, I've had lots of failures, but that's part of the process.

You're not just going to be good all the time.

You know.

Things can really irk me, Like if I find out someone doesn't like me, I'm like, wait what, I've never even met that person or I've never done anything to that person.

And you know, when I was younger, I used to get a little bit upset about that.

You know, if someone would be like, oh, we don't want her on the show, she's not for us, or I would hear something like that, I'd be like.

What, Like what do they think of me?

You know?

But then you just kind of outgrow all of that.

It's like that really has That's really not on me, you know what I mean.

I haven't done anything wrong to hurt people, you know, like, I'm just doing my thing.

Either it's for you or it's not for you, that's fine.

If you don't like it, don't listen to it.

Kind of a dark question.

Who would you want to deliver your eulogy?

Probably?

Well, God, who would I want to delive for my eulogy?

I guess it would have to be someone who do You would probably be my sister Simone.

She wouldn't be able to do it though, because she can't even give me a birthday toast she gets too emotional.

So I would say either my sister Simone or my friend Michael Tiberi and Dean Ward.

They've been my writers for since Chelsea Lately days, and they know me inside and out and they know everything about me and my gardener.

I wouldn't mind him chiming in because he knows a lot about me too.

Do you believe in bucket list?

And are there is there anything that you've not checked off your bucket list for your life?

I don't really believe in bucket lists.

I'm not like that.

I'm not a planner.

I don't have goals.

I just am like I kind of fly, just kind of fly by the seat of my pants.

Like you know, my plans change all the time, and I always just kind of go with that.

I don't make huge plan I don't have like a five year prospectus or anything like that.

But is there anything that?

I mean?

All I care about really is traveling and seeing as much of the world as I possibly can and meeting as many interesting people as I possibly can.

Those are the things I care about the most.

I'm very into people and I'm very into experience.

Okay, what's the best compliment you've ever received.

That I'm a good listener?

Really?

Are you?

Yeah?

I am when I'm interesting.

Okay, it comes with the all right, okay, cool.

Comes with the caveat.

You have to write to be one of two things interesting, compelling or funny.

My last question for you, what's more important to you?

Respect or love?

Love?

But I care about being respected, absolutely, it's close.

But love is obviously more important than respect.

Yeah, but love requires a certain amount of guard dropping.

I think as we get older, it's harder to drop our guard.

You know, yeah, maybe yeah, or it becomes easier depending on you know, how self actualized you become as a as a grown person.

I think I was probably much more guarded in my twenties than.

I am now.

Okay, you know, at the end of every conversation I have, I have to figure out what it is that I've learned from you, and I will say that probably people are always saying live in the present, and to me that sounds like a good sound bite, and I'll be like, yeah, yeah, sure, live in the present.

But you know, I'm such a meticulous planner.

And of course I'm a meticulous planner because of whatever trauma is in my rear view mirror in the past makes me think, oh, I got to plan my future out.

And so for me, one of the hardest things ever is living in the present.

But more than that, you're the first person that I've heard that really makes not working sound appealing to me.

Yeah, so I might have to seriously take you on your offer.

I'm getting your information when we're done this taping, but I will absolutely take you on your offer because I just I need advice on I don't know where to go or who to I mean, for a person that did at least two hundred and fifty days, like I've traveled the world at least fifteen times over as a musician.

But you know, I don't feel comfortable unless I am doing a three hour show or DJing at night, So like to go, nothing is like terrifying for me.

So I think this kismet that we're.

Talking right now because I need someone to convince.

Me of that.

I thank you for that.

Text, Quest, I appreciate it for you.

Thank you so much, Chelse.

The Quest Love Show is hosted by me Amir Quest Love Thompson.

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