Boomer Apologist with Iliza Shlesin…ger

Summary

Podcast Summary: Dear Chelsea – Episode: Boomer Apologist with Eliza Schlesinger

Host: Chelsea Handler
Co-Host: Catherine Law
Guest: Eliza Schlesinger
Release Date: March 13, 2025

"Dear Chelsea" is a weekly advice show hosted by comedian and author Chelsea Handler, where she tackles diverse listener questions with humor and honesty. Each episode features co-host Catherine Law and celebrity guests, navigating topics from love and sex to family issues and personal loss. In this episode, Chelsea welcomes fellow comedian Eliza Schlesinger to discuss generational conflicts, sustainability, the intricacies of the comedy industry, and personal relationships.

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1. Introduction and Guest Arrival (00:00 - 04:19)

The episode opens with Chelsea humorously lamenting the complexities of modern television options, setting a lighthearted tone. She briefly mentions her presence at South by Southwest (SXSW) in Austin, expressing exhaustion from her busy schedule.

Notable Quote:

"I feel like someone drugged me three days ago because my head is so unclear."
— Chelsea Handler [02:43]

Chelsea shares updates about her achievements, including her recent book becoming a New York Times bestseller for the sixth time, underscoring the rewards of hard work.

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2. Welcoming Eliza Schlesinger (04:22 - 08:30)

Chelsea introduces Eliza Schlesinger, highlighting her as a talented comedian with a new stand-up special titled "A Different Animal" available on Amazon Prime. Eliza discusses her approach to comedy, emphasizing storytelling and the challenges faced by female comedians in maintaining authenticity on stage.

Notable Quote:

"As a woman, if you do have a good body and you're dressed sexy or it's revealing, especially if you're unknown, it does take the audience an extra 90 seconds to get over it."
— Eliza Schlesinger [18:37]

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3. Generational Conflicts and Sustainability (08:30 - 11:10)

Eliza delves into the tensions between Boomers and younger generations like Millennials and Gen Z. She critiques consumptive behaviors such as "sheen hauls"—bulk purchasing of cheap, fast-fashion items—and discusses the shared responsibility across generations for environmental degradation.

Notable Quote:

"Boomers didn't invent that [fast fashion]. So while they laid the groundwork, the perpetuation is on all of our shoulders, especially Generation Z."
— Eliza Schlesinger [10:11]

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4. The Realities of Shower Sex (11:10 - 17:26)

The conversation shifts to a humorous critique of shower sex, highlighting practical difficulties and societal misconceptions. Eliza shares personal anecdotes, emphasizing women's discomfort and the unrealistic romanticization of such intimate acts.

Notable Quote:

"When you're in your 20s, you're just like, yeah, I'll do that. It's hot. But you're not loving it."
— Eliza Schlesinger [14:05]

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5. Navigating Relationships in the Comedy Scene (17:26 - 25:00)

Chelsea and Eliza discuss the complexities of dating within the competitive comedy industry. Eliza shares her experiences with fellow comedians, noting the challenges of maintaining professional and personal boundaries. Chelsea humorously recounts her past relationships with comedians, including a memorable encounter with Tom Rhodes.

Notable Quote:

"If you try to date a male comic who doesn't do as well as you, they always get jealous."
— Eliza Schlesinger [24:28]

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6. Listener Advice Segment: Supporting a Trans Son-in-Law and Career Transitions (37:00 - 58:31)

Caller 1: Blake – A 31-Year-Old Trans Man (37:00 - 45:00)
Blake seeks advice on handling his conservative Christian in-laws who struggle to accept his relationship with their daughter. Eliza and Chelsea provide empathetic guidance on maintaining civility, demonstrating kindness, and navigating familial tensions without taking personal offense.

Notable Quote:

"This is your chance to show up and be like, look how dope you are."
— Eliza Schlesinger [41:42]

Caller 2: Blake – Career Transition and Creative Fulfillment (46:13 - 58:31)
Blake, a producer seeking to transition into scripted TV writing, asks for advice on balancing financial stability with creative passion. Eliza offers practical steps, emphasizing the importance of perseverance, incremental progress, and strategic networking within the industry.

Notable Quote:

"You just have to do both. You're just going to have to be exhausted."
— Eliza Schlesinger [49:16]

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7. Conclusion and Promotions (58:00 - End)

Chelsea and Eliza wrap up the episode by promoting Eliza’s new comedy special "A Different Animal" on Amazon Prime. Chelsea also announces her upcoming European tour, "Abroad," detailing destinations across Europe and additional Vegas dates, inviting listeners to join her on her comedic journey.

Notable Quote:

"We're so tired of hearing about you."
— Eliza Schlesinger [37:43]

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Key Takeaways:

• Generational Responsibility: While Boomers initiated certain consumerist behaviors, current and future generations share the responsibility for mitigating their environmental impact.

• Authenticity in Comedy: Women in stand-up face unique challenges in balancing appearance with comedic authenticity, often needing to assert their individuality against societal expectations.

• Navigating Personal Relationships: Maintaining relationships with conservative family members requires empathy, kindness, and self-assurance, especially for marginalized groups.

• Pursuing Creative Passions: Transitioning careers to align with personal passions demands relentless hustle, patience, and strategic networking within the industry.

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Conclusion

This episode of Dear Chelsea offers a blend of humor, genuine advice, and insightful discussions on contemporary issues ranging from generational dynamics to personal relationships within societal frameworks. With Eliza Schlesinger’s candid perspectives and Chelsea Handler’s engaging hosting, listeners gain both laughter and meaningful takeaways to navigate their personal and professional lives.

Don’t miss Eliza Schlesinger’s latest special "A Different Animal" on Amazon Prime and Chelsea Handler’s upcoming European tour.

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Disclaimer: This summary is based on the provided transcript and aims to capture all key discussions while excluding advertisements and non-content sections, in accordance with the user's instructions.

Transcript

[Chelsea Handler]

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[Chelsea Handler]

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[Katherine]

Morning brings a fresh new energy.

[Eliza Schlesinger]

And no matter what the day holds, we come to the Today show for all of it.

[Chelsea Handler]

We get the best start to the.

[Eliza Schlesinger]

Day because we started together. Watch the Today show weekdays at 7am on NBC. Hello? Hello?

[Chelsea Handler]

Who's there?

[Katherine]

Hi, Chelsea. Am I speaking to a number one New York Times bestselling author?

[Chelsea Handler]

Yes, you are. Yes, you are. Six times over. Number one New York Times bestselling author. The phone call I will never get tired of getting in my entire life. I can't believe it.

[Eliza Schlesinger]

Oh, my.

[Chelsea Handler]

I really didn't think I was gonna be number one this time. I don't know where I got that in my head, but I really didn't. I just thought, oh, I'm. It doesn't matter what number I am. I'll be Grateful to be on the list. And then I was number one. And then I thought, my God, it happened again. This is my seventh book and my sixth number one New York Times bestseller.

[Katherine]

Hell yes.

[Chelsea Handler]

So, yes, hard work pays off.

[Eliza Schlesinger]

That's.

[Chelsea Handler]

That's the truth.

[Eliza Schlesinger]

Yes.

[Katherine]

And you have been working hard. You've been making the rounds. You're everywhere right now, and it's really exciting to see.

[Chelsea Handler]

I'm currently in south by Southwest. I'm in Austin at South by Southwest. I feel like someone drugged me three days ago because my head is so unclear. I'm not sure what happened yesterday. I didn't even have a drink. I had four panels and I still feel like someone drugged me. So I'm like, what is. Maybe I did drug me and forgot.

[Katherine]

I was gonna say. If anyone drugged you, the most likely culprit is you.

[Chelsea Handler]

This is true. This is true.

[Katherine]

Well, congratulations. That is so exciting and I'm so happy for you.

[Chelsea Handler]

Thank you. Thank you. Thank you, everybody. Who's listening? I hope you've ordered my book or you ordered or downloaded on Audible or whatever. But get. I'll have what she's having because it's going around. And I have my European dates up. All of my European dates are officially up now and for sale on Chelsea handler.com. and I'll be in Vegas March 21st for a live new, brand new stand up show. March 21st and April 19th are my next two Vegas dates for our fans.

[Katherine]

Well, I'm so excited about our guest today. She is so fantastic.

[Chelsea Handler]

Oh, yes. This is a comedian, so you're in for a good treat and conversation. And a female comedian. Someone who I have known for years, but I've never really. Oh, no. I used to have her on Chelsea lately all the time, but I haven't seen her in years. Anyway, she's hilarious and her name is actually pronounced Eliza Schlesinger.

[Katherine]

Schlesinger.

[Chelsea Handler]

Fuck. It's Eliza Schlesinger. So. And she has a new special out. So everybody please go and watch that. You gotta support female comedy, guys and girls.

[Katherine]

And you gotta see these pants, and.

[Chelsea Handler]

You'Ve gotta see these pants. Please welcome Eliza Slasinger.

[Eliza Schlesinger]

I have a rule about hot food on a plane.

[Chelsea Handler]

What is it?

[Eliza Schlesinger]

You can't bring hot food.

[Katherine]

I hear that.

[Eliza Schlesinger]

Because everybody can smell it, right?

[Katherine]

Herbal eggs is a cold food.

[Eliza Schlesinger]

Yeah. You know what? It's just visually gross, but I guess they don't smell. It's not like sulfur, but it is. The idea of it is gross.

[Chelsea Handler]

It should be more than just. It shouldn't just be hot food. There should be a list of things that are not tenable for a flight, you know what I mean? Because hard boiled eggs, perfect example. Those could be fine in a container, in a Ziploc container, but as soon as you open the seal, then everyone is exposed to that. So you need to swallow those whole.

[Eliza Schlesinger]

Or like the Mario 2. Is that gonna vibe with anyone who listens to this? Remember the egg creature that would spit out the eggs in Mario 2?

[Chelsea Handler]

Okay, I miss that game. Remember when times were so simple that you could play Super Mario Bros? I used to get up at my friend's sleepover. So we would be like 10, 11 years old, and I would set my alarm. I don't know why I was traveling with an alarm, but I would get up at 10 early. Like, got sets so that I could get on the Mario Super Mario Brothers before the other girls at the sleepover woke up. Because, like, it's like, no, no, no. I'm already on. You can't push me off.

[Eliza Schlesinger]

I've got a schedule.

[Chelsea Handler]

I'm so obsessed. I miss being that obsessed with something.

[Eliza Schlesinger]

Oh, I feel like we are obsessed and we don't realize it. Like now it's just called an addiction.

[Chelsea Handler]

Oh, the phone, you mean?

[Eliza Schlesinger]

Oh, yeah, yeah.

[Chelsea Handler]

Social media.

[Eliza Schlesinger]

I have to take it off. I have to take it off every day and put it back on.

[Chelsea Handler]

Where do you take it off of?

[Eliza Schlesinger]

I take it off my phone and then my.

[Chelsea Handler]

Take it off of your phone, take.

[Eliza Schlesinger]

It off Instagram, and then I have to do this walk of shame where I scroll back to find the password that my social media manager keeps for me. But rather than ask her, I just have it stored. Like I'm lying to her. Like it's somewhere in my phone and I just go and I get it and I just erase it every night and.

[Chelsea Handler]

Sounds like you're lying to her and to yourself.

[Eliza Schlesinger]

I am. This is so lovely.

[Chelsea Handler]

Oh, my goodness, Carlos, you. You're so. That makes me want to have a coffee. And I don't even drink coffee.

[Katherine]

And you get a little snack.

[Eliza Schlesinger]

I have my snack. I'm not going to have a snack.

[Chelsea Handler]

With that little cookie. Yeah, like we're at a nice hotel somewhere far, far away.

[Katherine]

Sure, I would love a coffee. Thank you.

[Chelsea Handler]

Okay, first of all, Eliza Schlesinger is here. She has a new special out, which is fucking funny as shit. Thank you. It's called A Different Animal. Are you the animal or is this special the animal? Both.

[Eliza Schlesinger]

I'm the. I was just. I'm. It's different. I think I'm different. I think I wanted to create something different. I have to say, first of all, your house is so beautiful and everyone knows you have so much money.

[Chelsea Handler]

Why does everyone think I have so much money? I don't understand where this archways.

[Eliza Schlesinger]

It would never occur to me to redo the arch. Like, doorways. I walked in and you're like, I watched your special. And then for a second I was like, oh, no, she saw an old one. And, like, she thinks it's the new one. Someone sent you a link, which is like, peak Hollywood elite. No other podcast had a link. And I'm like, who? Yeah. Cause you have people that get the links.

[Chelsea Handler]

That is so funny.

[Eliza Schlesinger]

I mean, you got a sneak peek. Nobody has seen this. And so I'm blown away.

[Chelsea Handler]

Okay, well, as the first person that's officially seen this special, besides, I'm assuming you. Or maybe you haven't even seen it yet because you don't even have the link. I can forward you the link if you want. I wanna say a. You're very prolific as a standup. This is your seventh standup special. This one is on Amazon Prime. Everybody and Amazon and Hulu are getting into standup specials. So, like, those are good places to watch them too. And everyone now has Amazon Prime. I'm assum. That's not as many people as Netflix, but it is prevalent and pervasive. I say that is pervasive. Amazon itself is pervasive. But you have such a talent.

[Eliza Schlesinger]

Oh, thank you.

[Chelsea Handler]

You really do. You really have a great. My standup is very much storytelling and, you know, personal storytelling. You have a very clear talent of structuring jokes, premises, punchlines, which you even talk about in the special. You mention in the special. But I love your focus on the different generations about millennials, because I don't even know what am. What am I?

[Eliza Schlesinger]

You are Generation X. X. X.

[Chelsea Handler]

Okay, so it goes from Generation X, then Millennials.

[Eliza Schlesinger]

You're hoping I'd say Gen Z. I'm like, you're Gen Z?

[Chelsea Handler]

Oh, God, I hope not. No. They're so fucking annoying. Gen Z. So then Gen X. No, I'm X.

[Eliza Schlesinger]

It goes X. It goes. Well, if you go youngest to whatever, it's Alpha, which is what my child is or will be. Gen Z. Millennial. I'm sorry?

[Katherine]

Millennial.

[Eliza Schlesinger]

Millennial.

[Chelsea Handler]

There is a Zennial.

[Eliza Schlesinger]

Please call me a Zennial. Millennial. Elder Millennial, which is what I am. Generation X, Baby Boomer, Silent generation, and then our forefathers.

[Chelsea Handler]

Okay, so I just Know that I'm not a boomer, so I'm the generation after the boomer. Okay? I really. I mean, and also, when you look up generations, it's like sometimes they say, oh, 11 to 15 years, and then sometimes it's a decade. And there's different definitions of it all. But nevermind that. In your special, you really delineate what the differences are between all of these with a lot of attitude and anger towards. Towards younger generations.

[Eliza Schlesinger]

Working title. Attitude and anger.

[Chelsea Handler]

Not picking up the baton after you guys. After millennials just, like, laid out everything for future generations. They're just like, wait, what? What do we do? The first of all, I would just like to go on the record and say boomers are the worst ones because they ruined our planet. And they. They. Did they. Well, they did well. They had a lot of babies. Can I say something about apologist?

[Eliza Schlesinger]

Well, I'm not a boomer apologist.

[Chelsea Handler]

She's an elder millennial boomer apologist.

[Eliza Schlesinger]

I have to say, there is this thing, I wrote about this in my book, like, when you accuse a generation of something, like, what are we expecting? That boomers are going to collectively come together and be like, we're so sorry when we all have those Amazon accounts, like, we all postmate stuff, we all order stuff from China overnight. So while they may have laid the groundwork in terms of, like, disruptive oil practices and stuff like that, like, we contribute to it with every frivolous purchase, with every sheen haul. Boomers didn't invent that. So they laid the groundwork. But the perpetuation of it is definitely on all of our shoulders, especially Generation Z.

[Chelsea Handler]

What is a sheen haul?

[Eliza Schlesinger]

A Sheen hall is where you buy a bunch of clothes from sheen from, like, fast fashion, and then you try them all on and then you kind of throw them away, but they were going to dissolve anyway. And that, like, rose to popularity in the pandemic. So you'd get people that weren't really mindful, didn't really, I guess, were ignorant too. Fast fashion and that, like, Sheen and H and M are like the number one pollutants of fast fashion on this planet. So you would just order like 50 pieces of clothes for like a dollar and you try them all on, and then maybe you throw them away, you know, or something like that. And so that's. That's what a sheen haul is.

[Chelsea Handler]

Okay. I thought you were going to say, then you return everything because you don't want it.

[Eliza Schlesinger]

No. Some would say that's even worse for the planet because then it's Going back.

[Chelsea Handler]

Well, anyone who's doing that isn't caring about it, doesn't care about the planet. Anybody who's ordering a bunch of clothes, trying them on and returning them is not.

[Eliza Schlesinger]

Or keeping them, and they go nowhere. Or you donate them, but nobody wants them.

[Katherine]

Cause they're so cheap.

[Eliza Schlesinger]

I feel like every podcast I do, I come back to, like, sustainability, and people are just like, turn it off. Go back to Justin Balgon. It's like, that's October 7th.

[Chelsea Handler]

Let's talk about. Oh, yeah, that's the last time we saw each other. Right after the. At a Jew event, right after October 7th.

[Eliza Schlesinger]

But can I. Can I. You came. I invited you. I put on a benefit. And they were like, who else can we invite? And I was like, I have Chelsea Handler's email, and I don't think she knows I have it. And I emailed you, and you wrote back and you came, and that, like, elevated the event. Like, I tried to already. Like, we had tried to have some cool people there, but, like, we don't know each other that well. And the fact that you were like, yeah, I'll be there. I was just like, that was such a cool moment where you definitely did not have to answer that email, and you definitely did not have to show up. And, like, I felt, like, anointed into, like, a cool comedian hall of fame. That's just you and I.

[Chelsea Handler]

Well, I'm glad I went. I'm glad I went.

[Eliza Schlesinger]

I'm glad you came, too.

[Chelsea Handler]

Okay, so I don't want you to have to talk about sustainability, but we can talk about shower sex. Let's talk about shower sex.

[Eliza Schlesinger]

Let's talk about shower sex.

[Chelsea Handler]

I want to know who is having shower sex. This is a topic that Eliza covers in her special in a hilarious way. And it's kind of a, you know, kind of calling out all men who are stupid enough to believe. I don't care how hot your relationship is or how new it is or how horny you and your partner are or you and your throuple are. You know, I don't want to discriminate. Maybe you have more than one lover in a group, but no one wants to fuck in the shower. It's not fun.

[Eliza Schlesinger]

No woman.

[Chelsea Handler]

Not sexy. It's not. And your penis doesn't. No one can feel anything. Also, nobody ever talks about the fact that you can't feel your penis inside a vagina when you're in the shower.

[Eliza Schlesinger]

When you're stressing and, like, this idea that, like, oh, let's have shower sex. I'M like, we're not two gay guys at a crunch on, like, a Thursday. Like, we're not fucking in a shower.

[Chelsea Handler]

Why do people. That's another thing I want to discuss. Thank you for bringing it up. It's like, you have espn. Why are people fudgeing at gym? Like, gay men specifically. I know some gay men who specifically go to the gym just to give blowjobs in the sauna.

[Eliza Schlesinger]

I don't understand giving a blowjob, but I understand. I feel like if you're a gay guy, it's like extra testosterone. So it's like at level 10 all the time. And you're like, I got to get it in. Because most men would. Like, my husband is like, you just tell me. You tell me when. He's like, I'm always ready. And so it's like, it's that times two.

[Chelsea Handler]

You're like, thank you. I didn't know that.

[Eliza Schlesinger]

I'm like, I know, but the showers, it's just more like you following me in here, thinking I'm turn. Like, I'm here to shave my armpits and, like, give the illusion of a bikini line. And you followed me in. I guess we have a bench in here. One person is always cold, One person's always uncomfortable. The lube gets washed away, perhaps in your.

[Chelsea Handler]

Oh, are you suggesting that you use lube in the shower?

[Eliza Schlesinger]

I guess you should.

[Chelsea Handler]

It's actually the opposite of a lubricant water.

[Eliza Schlesinger]

Because.

[Chelsea Handler]

Have you ever tried to fuck in the ocean? It's the same thing. It's the same thing. You know, you can't get anything. It's like, you need. Actually, you need a lubricant, but who's gonna bring a lubricant to the beach and into the ocean and then lubricate. When you're underwater, it's just all anti. It's like, counterintuitive.

[Eliza Schlesinger]

You have a whole contingency of, like, mermaid fans that are like, actually, I find aquatic sex. I think it all just aquatic sex. I think it just speaks to, like, a woman's comfort not being taken into account. And. And when you're in your 20s, you're just like, yeah, I'll do that. It's hot. But, like, you're not loving it. No, like, and you're cold, and you're looking down at your feet, which are. Your toes are spread apart. So you get a grip, and you've got, like, chicken feet. And your hair. I have curly hair. And so the whole time I'm just like, do I look like the monster from Barbarian. Like, which is, like, the reference, or.

[Chelsea Handler]

Does your husband care? Answer. No, he doesn't care what you look like.

[Eliza Schlesinger]

He doesn't care. And if I don't feel hot, then it can't happen. And then if I do feel sexy, I'm like, I'm too busy taking a picture of how hot I look to have sex right now.

[Chelsea Handler]

Is that why you wore those pants during your special? To show people how hot you are? You need to explain those pants to me.

[Eliza Schlesinger]

You don't like them.

[Chelsea Handler]

Well, I'm not going to pretend that I like you. I mean, you have. You have an incredible body, and I like. I like that you. I like that you show it off, and I understand that. But those pants, I was just like, why? Yeah, why? I don't. I don't know.

[Eliza Schlesinger]

I'll tell you why. Because I can. And I think as a woman, I think the more you.

[Chelsea Handler]

Come on in, Carlos.

[Eliza Schlesinger]

Come on in, Carlos. Bring that business.

[Chelsea Handler]

There's no reason you shouldn't become part of this podcast.

[Eliza Schlesinger]

This is so cute.

[Chelsea Handler]

This is so cute. I didn't even know this was available in my own home.

[Eliza Schlesinger]

It's so continental.

[Chelsea Handler]

That's how rich I am, you guys. I didn't even know I had a cafe.

[Eliza Schlesinger]

She just met Carlos. She didn't even know he was here. I saw. I'm. And I love. I love a fun pant. And the pants that I wore on my last special were like.

[Chelsea Handler]

I remember a similar outfit.

[Eliza Schlesinger]

It's a similar silhouette, and I didn't mean to fall into it, but we all, you know, you dress for your body type.

[Chelsea Handler]

What's your body type?

[Eliza Schlesinger]

Well, the thighs are like. I started doing Pilates, so it's different, but I don't know. Strong core.

[Chelsea Handler]

Excuse me one second. I don't want to cough over you. Apparently, I'm allergic to coffee.

[Eliza Schlesinger]

You don't have a strong core.

[Chelsea Handler]

Okay, go ahead.

[Eliza Schlesinger]

You just. For your body. I mean, it's just. I don't know. I don't like to wear a skirt on stage because I move around a lot. Like, there's just things that you. That you find empowering. And people were so upset about the last pant, and I was like, no, those pants are fire. These pants. I was scrolling through a rave party wear website, as one does when they're trying to conceive a child. I had had my daughter and I. I don't remember if I just gotten pregnant with Ethan or. We were thinking about it, but I saw those pants, and there was something about them. I was like, those. Do you ever buy like an article of clothing and you're like, I don't have an event now, but I know I will. Does that ever happen to you or did you have someone dress you?

[Chelsea Handler]

Oh, God, no.

[Eliza Schlesinger]

I know what you mean.

[Chelsea Handler]

I know what you mean.

[Eliza Schlesinger]

I saw them and I was like, they're just. I like that they had the micro flare. Like, I just. I was like, that's something aspirational. So I bought them and then I was pregnant for a full year and then I just worked out every day with those. Like, my trainer would be like, hips, pants, pants. Like, think about the pants. And I just. They reminded me of Cher.

[Chelsea Handler]

Like, turn back definitely.

[Eliza Schlesinger]

And I just know that there will be a day that I shouldn't wear those pants.

[Chelsea Handler]

Right.

[Eliza Schlesinger]

And I just thought that they were cool enough while not being super distracting. Do we had to iron out the bulkiness of them in Photoshop because they don't lay right? Because they're like made of cheap plastic. Maybe, But I just was like, these pants will upset enough people and enliven people and it'll at least be a talking point.

[Chelsea Handler]

Yeah, well, you're right, it is a talking point. So good for you. Mazel toast.

[Eliza Schlesinger]

Thank you. I was just. I thought they were just cool and I just liked them.

[Chelsea Handler]

Well, I like that you. It doesn't really matter if I like them or not. It matters that you take a risk and are like, you know, stepping into your own power and like, I'm gonna fucking wear these pants. That's all that really matters.

[Eliza Schlesinger]

That's what I mean. And also I do feel empowered in them. And I do. It's like an extension of who you are on stage. And I also think I come from a generation of stand up and I definitely was a huge part of this, like, just wearing a hoodie on stage. I think there's a. I think there's a video of you of like at the ice house like 400 years ago, and you're wearing a hoodie. Right? Like, I feel like we women weren't encouraged to do that. And now I look at younger girls and they're just like in a bra on stage and they don't think about it. And I think that that's great. And so I have to push myself to be like, no, you can wear these things. You don't have to cover up and you can just be yourself on stage. And so when I do large shows, I feel comfortable.

[Chelsea Handler]

Do you? When I came up, I was always trying to play down my looks. And be more tomboyish.

[Eliza Schlesinger]

That's what I'm saying.

[Chelsea Handler]

And I've never really, like, I've never really worn a dress on stage or a skirt on stage. Like, even when I used to wear heels on stage, I'm like, this is so annoying. Like, this is not who I would ever be in real life. But did you feel like you had to dial down your looks when you were coming up?

[Eliza Schlesinger]

It's something that people talked about.

[Chelsea Handler]

But I like, you can't be funny and pretty. So cool it with the pretty.

[Eliza Schlesinger]

Oh, it was more. Normally it was an accusation. Like, funny and pretty. Like, what's the catch? And you're like, I don't know. You're really ugly. So this is obviously, what's the catch?

[Chelsea Handler]

I have herpes. That's the catch.

[Eliza Schlesinger]

Pretty.

[Chelsea Handler]

And I have.

[Eliza Schlesinger]

I'm dying. I am a tomb. Like, I always grew up wearing big T shirts. And not really, you know, you. Maybe you wear a tank top to a college bar when you're out, but on stage, I just was always comfortable as that. So I never went out of my way. But I always felt like. Remember I wore white ripped jeans on stage at the Comedy store in like, 2011, and I had a bad set and I was like, must have been the jeans. We'll always dial it back. And there is. As a woman, when you come on stage, if you do have a good body and you're dressed sexy or it's revealing, especially if you're unknown, it does take the audience an extra 90 seconds to get over it. And I was always of the mindset like, nope, I need to get you right up top because I've got something to say. And I only have these eight minutes. But as an adult, I try to take more time now. Yeah. And more secure hands.

[Chelsea Handler]

I mean, you do jam a lot of material into an hour.

[Katherine]

Yeah.

[Chelsea Handler]

And I don't mean jam as a negative. I mean, you really get so much bang for your buck with every sentence, every joke, every premise. You. It's very full bodied.

[Eliza Schlesinger]

Thank you. I like full. I like that.

[Chelsea Handler]

It's very artistic. I appreciate that artist. And in the form of stand up, like, that's very, very well done.

[Eliza Schlesinger]

Thank you, Chelsea Handler. That means a lot. I do. I was watching some of Ali Wong the other day, and she's very deliberate. And she speaks, we'll say, slower than I do. I mean, most auctioneers do. And I was watching that, I was like, I could have gotten two hours out of this if I just did like a Wong pace. If I Just spoke like every other comic and just took my time.

[Chelsea Handler]

She does speak slowly.

[Eliza Schlesinger]

I was like, there's an art to this. I gotta slow down and I won't have to work as hard to write. Like, I can just have two hours out of this one.

[Chelsea Handler]

So doesn't it feel like stand up feels like such a hustle? Right? Like it is. You're constantly. If you're a standup comedian and that's your main vocation. I mean, obviously we all have ancillary things we do. But like if that's your main vocation, it is constant fucking hustle traveling.

[Eliza Schlesinger]

I feel hustle and I do hustle. Yeah, it is. I mean, you're a real standup. You get it. Like it's not like something that you picked up once you became famous, which a lot of people do. I don't think people fully understand. Like, especially when you're an artist versus just a joke teller. Like when you actually do bleed for this and this is something that you, that is, you're married to, in a sense, you are the engine. And I was actually thinking about that on the way over here. Like, if I don't write, if I don't push myself to work out and to write this, there's no one writing it for me. There's no studio calling, being like, we're going to put a team together, what's your next thing? If you don't write your books, if you don't create these things, especially when you're a funny woman, because no one can create the funny for you. People could of course write you some jokes, but like the engine is me and when I take a break, like, there's no one knocking at the door, like, are you done taking your break?

[Chelsea Handler]

Yes, yes.

[Eliza Schlesinger]

I'm sure people would prefer I just take the break forever.

[Chelsea Handler]

Well, it's. You're completely self reliant. There's no, like, there's no safety net. Yeah, right.

[Eliza Schlesinger]

Like the mortgages are in my name.

[Chelsea Handler]

But that's also kind of a nice thing. Conversely, there's like a flip side of it, which is you're not really answering to anybody but yourself.

[Eliza Schlesinger]

Yeah, I think so, yes. Because I can take those breaks, I can take that vacation. But I do feel that we've. I think we're coming away from it now. But we did get to a place in, in comedy where you were answering to a very loud minority on the Internet. And that's. Those are the people that were canceling people. People that had nothing and were angry at you for trying and Those voices got amplified, so I was never answering to them. But you. There was, like, a stutter step, especially as a woman, because we're expected to be kinder and empathetic at every turn. Meanwhile, guys are like, yeah, I got this underage hand job, and it felt great. And, yeah, maybe women shouldn't be allowed to read. And it's just like, oh, more of that, please. And I get up here, and if I'm like, oh, yeah, I chose to have two kids, it's like, why didn't you have three? Do you hate women who don't have kids? And you're just like, all right. You're constantly having to answer for what you have done and haven't done as a woman. And I think that we're swinging the other way, where now you can kind of just make statements and not have to.

[Chelsea Handler]

Well, now that Trump is pregnant, now that he's been pregnant for quite some time, but now that Trump is president, I'm sure all that political correctness, everything's out the window. Something else you talk about in your standup is. Which I think is so great when men congratulate other men for impregnating their wives. Like, when Eliza's husband's friend or stranger.

[Eliza Schlesinger]

Stranger. Usually stranger.

[Chelsea Handler]

Right. Finds out that you're pregnant, especially with a boy.

[Eliza Schlesinger]

Especially. They love to know there's a boy in the world.

[Chelsea Handler]

Right.

[Eliza Schlesinger]

But men will. There's. It's the weirdness. The dystopian weirdness of standing there while one man congratulates my husband, not me, on the pregnancy. I'm like, he played the smallest part. Like, I am doing all the work. And it's like, congratulations. Six seconds. Well done. And you're just standing there. It's Super Handmaid's Tale. And you're just like, well, I was just glad to receive. It's not their party.

[Chelsea Handler]

And what are they congratulating each other on? Seriously, though, when you think about it, it's like, yeah, way to go. Fuck your wife and get her pregnant. Way to go.

[Eliza Schlesinger]

Way to go. Because men love to know other men are having sex. And like, two guys at a bar, if a guy leaves with a girl, a guy will just high five and be like, nice job. Women are like, don't go with him. That doesn't feel safe. Like, we don't want anyone having sex. Yeah, we want. And men are just like, just however you got to get it in. And it's. It's primal, and it's the way they are. But I. I want the congratulations as well, have you.

[Chelsea Handler]

Did you have sex with a lot of. Or did you have a lot of boyfriend comics?

[Eliza Schlesinger]

No.

[Chelsea Handler]

Ever?

[Eliza Schlesinger]

No.

[Chelsea Handler]

None. You never dated a comic?

[Eliza Schlesinger]

I did, but so long ago. And I kind of just stayed out of it. But a big reason I did, and I think you can probably relate to this. I became a headliner so early in my career, so.

[Chelsea Handler]

From winning last comic standing.

[Eliza Schlesinger]

Yes. And so that was like 25. And so that's the time of your life where you are looking to at the time, mostly men who were in positions of power for validation to take you on the road. And it's not that women always sleep with those guys, but that I didn't need that from a man. And I certainly didn't want to date a co worker or someone who was less funny or successful than me. So that pool was pretty much shot. And I think men, you know, you try to date a male comic who doesn't do as well as you, they always get jealous. So I just never. It was never my dating pool. Trying to think if I made out with any of them. I don't even think so.

[Chelsea Handler]

I once had sex with Tom Rhodes. Do you know who Tom Rhodes is?

[Eliza Schlesinger]

I just canceled on a lineup he was on the other night.

[Chelsea Handler]

Oh my God. Oh. I was like, did he do something? Was he canceled? He.

[Eliza Schlesinger]

He's very nice.

[Chelsea Handler]

He's a sweetheart. I once had sex with him.

[Katherine]

He's good looking.

[Chelsea Handler]

Yeah. And yeah, he is still good looking. He came up to me, we were at an airport lounge the other day and he American. And he. I was with my cousin. And he was like, hey, Chelsea. Just wanted to say hello. And I just thought he was.

[Eliza Schlesinger]

You shook your hand?

[Chelsea Handler]

I thought he was a rando. Like, I just thought he was a fan or something. And I said, oh, hi, nice to meet you. He goes, it's me, Tom Rhodes. And I'm like, oh, hi. Like, because I did fuck him many, many years ago in San Francisco. And it was one of those great experiences where you have a kind of fun one night stand. Like, I never really dated that many comics. I mean, I know I dated Jo Koy, but that was like postscript of like comedy coming up time. And he's one of those comics I had sex with. And when he walked away, Molly's like, who is that? I'm like, oh, this comic, Tom Rhodes. I had sex with him like many, many moons ago. And I didn't say moons ago. Cause I don't say that. But I remember having a great interlude with him. We had sex. We Had a fun night in San Francisco. We were fucked up, drinking and whoever, who knows whatever else. And then we tried to reenact it in la and he like a couple months later.

[Eliza Schlesinger]

Is this after you were you or is this before your book?

[Chelsea Handler]

I was coming up. I wasn't. No, I was like, you know, starting out and I think I was opening for him at the San Francisco Punchline. Probably, like, I was probably the opener. There was a middle and he was the headliner. And so we ended up having, you know, a great night on our last night of the week. And then we tried to recreate it in la and I met him at the Comedy Store here in la. And it was a dis. I think I got my period. Like, it was one of the worst hookups ever. You know what? Sometimes you just have to leave something alone. Like never speak to. Just cause you had one good night with a person doesn't mean you should ever see them again. It's like when you go to a really good restaurant when you're on vacation, don't go back there the next night because it was so good the first night. It will only disappoint you.

[Eliza Schlesinger]

I feel that way with like an entree. I'll be like, I want to order a another one. Or like the. Like, you can never have two Egg McMuffins. Like, the first is so delicious.

[Chelsea Handler]

You're like, I haven't had. No, I love Egg McMuffins.

[Eliza Schlesinger]

The second one, instant diarrhea. What they need to do is make Egg McMuffins a little bit bigger.

[Chelsea Handler]

When we went through Covid, I had my housekeeper. I'm like, just go stock up on as many Egg McMuffins as possible, because I'm not gonna be able to go to McDonald's. And I fucking love Egg McMuffins. Stock up, stock up.

[Eliza Schlesinger]

Are you freezing them?

[Chelsea Handler]

Well, yeah, I was freezing them. And they are not as good when you freeze them. No, they are turns out of them quicker than freezing them. I'm like, these are not good at all.

[Eliza Schlesinger]

You know what else will get you off of them? Having two on like a regional flight in the Northeast.

[Katherine]

Regional.

[Eliza Schlesinger]

You're like, I just.

[Chelsea Handler]

You launched me a regional flight.

[Eliza Schlesinger]

It was my. For years when I. When I was first traveling, my, you know, get there to the airport. And I was like, okay, I never eat McDonald's, but this is my. My allowance at the airport. I'll have it. And then one time I had two. Never again. Yeah, I definitely agree with you about the. Sometimes you have these Wonderful moments, like sexual encounter. And it's just. And no one's jealous. It's not weird. And I feel like women so rarely get to have those where you're like, I don't even want it again. I don't want to date you. Like that. That hit the spot. And even though I didn't get off, like, that was still great. Thank you so much. You don't need it again.

[Chelsea Handler]

And it's a good lesson to know, like, for our young listeners. It's a good lesson to know. Just because you have a great night with somebody doesn't mean that you need to have another great night with them. Like, sometimes it's okay just to, like, read a good book and let it go. Like, you don't have to keep rereading it.

[Eliza Schlesinger]

I did. I will say, you don't know who this person is. There was a total power reversal. I was playing somewhere. I'm not even going to say the city or anything. And it was a younger comic that I had known forever. And they'd open for me, like, guest sets at this. In this city, and I'd see them every few years. And he came over and he just went down on me. And I've never shared the story. And it felt so powerful because normally it's the other way or you have some weird sex. And I just let him. And it was great. And I had to leave early the next morning. And I was like, you can eat whatever you want out of the mini bar. I gotta go. And I just.

[Chelsea Handler]

After you're done eating me out, you can eat whatever you want out of the mini bar. And it was great.

[Eliza Schlesinger]

And I. And it was. And I felt like a real headliner. And it just. It's like a nice memory. And I never really talked to this person, but, like, yeah, that was nice.

[Chelsea Handler]

Of you to let them do that. Yeah, that's what I think. That's nice to let somebody go down on you. Like, that's the way that women should be viewing that. That's a nice thing to do for another person. It's not necessarily all about us. It's like, well, that's also like, you know, friendly.

[Eliza Schlesinger]

Yeah, you're gonna love this. And it felt, like, powerful and cool. And it didn't feel like anyone was taking advantage. And I definitely. Then it was weird. Cause, like, that person brought their family to see me. Like, two years later, I'm like, here's some tickets. No problem. Like a nice relationship.

[Chelsea Handler]

Did you feel like. Did you feel when that happened and they came back around with their family. Did you feel any ick at all? Like, oh, no, keep in touch.

[Eliza Schlesinger]

Like, over dm. And he's like, hey, my family's. Can I get tickets? I'm like, Andy's a fan. Great. Of course you can have tickets for your sweet family. Who also has to go down on.

[Chelsea Handler]

How did you meet your. How did you. Every family member needs to go down on you. How did you meet your husband?

[Eliza Schlesinger]

That was him. No, I met him on Raya.

[Chelsea Handler]

Oh, really? A Raya's success story.

[Eliza Schlesinger]

Have you been.

[Chelsea Handler]

Of course, yeah. Lots of different sex on Raya. I find Raya to be great for, like, when you're in the UK or New York or, like, it's a nice hotspot and it. And it. And it gives you a. I mean, now it's opened up a little bit more and expanded more, but when I was using it a lot, it gives you a more. What is the word that I'm thinking of?

[Eliza Schlesinger]

Like, continental. More.

[Chelsea Handler]

Continental Buffet. It gives you more of a grouping of people that are actually a little, slightly elevated than what you're going to find on, like, Twitter. I mean, not Twitter, sorry, Tinder or like, Hinge or whatever. It's just, like, a little bit more of a guarantee that you're not going to find. Curated. That was the word.

[Katherine]

I was thinking of the unwashed masses.

[Eliza Schlesinger]

Well, you know, people will grimace at or bristle at that, but, like, if you have a public profile, like, if you are a celebrity at all, you can't open yourself up to just going out with whomever. And so for the longest time, for me, like, I was never so, like, I wasn't famous enough that I was, like, at Denzel's. Denzel. Why would we find Denzel Washington? Oh, my God. Or like, I just wasn't at famous people's houses, but I was famous enough that I couldn't just pick up a random person. So you would rely on, like, friend recommendations. You know, I dated someone I knew in college and you just would find these people sort of natively. And then Raya came along and so it wasn't necessarily other celebrities, but it was, like, verified. Like, oh, I'm an artist too. Like, I get it. So you don't leave your. It's a vulnerable thing to go out with someone.

[Chelsea Handler]

Well, of course, of course. Especially when they, you know. Yeah, especially when you are a celebrity and they know who you are and you're, like, putting yourself out there.

[Eliza Schlesinger]

I'm.

[Chelsea Handler]

I'm of the ilk that you just let go of all of that. Like, who gives a fuck? You know, you're going to walk around being this person in your real life regardless. So when people who are friends of mine are like, how could you go on those sites? I'm like, easily. You know, I'm trying to get some action, right? It's like, who cares? Like, I don't care if they know that I'm on this site. That doesn't bother me.

[Eliza Schlesinger]

Right. Well, especially not now. I think, like, the stigma of online dating is completely gone. Everybody does it. It makes a lot of sense. You can't go out every single night. But I do think, you know, when you're younger, you're just trying to, like, sort it out and you don't know what someone else's intention is, right? When they go. And then you bring them to your house or you go to, like, it's just weird. But I did meet him. He was not a celebrity. And I was like, who let you in here? But he was just so funny and so easy to talk to. And then that was that.

[Chelsea Handler]

Wow.

[Eliza Schlesinger]

I was his first riot date. He was like, I don't know, like, my fifth or something. Like, I hadn't been on it that long, and it just worked.

[Chelsea Handler]

Wow.

[Eliza Schlesinger]

He was so lovely. And that was like, day one. And like, that was it.

[Chelsea Handler]

And so what kind of artist is he?

[Eliza Schlesinger]

He's a chef. Oh, but he's a. I should have brought you a book. He's a cookbook author and chef and a writer, and so he writes a lot of articles freelance, but he is a chef and cookbook author.

[Chelsea Handler]

That's cool.

[Eliza Schlesinger]

It was cool. And when I met him, he had opened. Are you a regular eater or do you not eat meat or anything? No, I'm a regular, regular person. He was the opening chef for Bludso's Barbecue on La Brea, which is like an LA staple. And he has his cookbooks. He writes cookbooks. He has one coming out. Do you ever eat at Found Oyster? You're very far west over here, so I don't know.

[Chelsea Handler]

Yeah, no, but I've heard of Found Oyster. I love oyster.

[Eliza Schlesinger]

So Ari calling her. He wrote Ari's book, and that comes out called how to Cook the Finest Things in the Sea. So he's the guy that. He's got James Beard's award. Like, he's the guy you go to if you're like, I want to do a cookbook. He will capture your voice and write that with you. And recipe test.

[Chelsea Handler]

That's such a nice, refreshing vocation. It's so it's great in this town especially.

[Eliza Schlesinger]

Yeah, he's not like a fake chef.

[Chelsea Handler]

Or a photographer or a producer. I mean, photographers at least can, you know, take photographs, but producers is a little bit of a gray area, as we all know. Yeah. Okay. On that note, we're going to take a break and we'll be right back with Eliza Schlesinger.

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[Eliza Schlesinger]

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[Eliza Schlesinger]

Morning brings a fresh new energy.

[Chelsea Handler]

This is today with and no matter.

[Eliza Schlesinger]

What the day holds, we come to the Today show for all of it.

[Chelsea Handler]

When things are tough, we talk about it. When there's something to figure out, we dig into it. And when there's joy, we celebrate it.

[Eliza Schlesinger]

Because today is where it's all happening. We get the best start to every.

[Chelsea Handler]

Morning because we Start it together. Watch the Today show with Savannah Guthrie and Craig Melvin, weekdays at 7am on NBC. And we're back with Eliza Schlesinger. Okay, Katherine, what do we have? What's happening?

[Katherine]

We actually have two Blakes today.

[Chelsea Handler]

Oh, my God. More. Is it Blake Lively calling in for advice?

[Katherine]

If she calls in one more time.

[Eliza Schlesinger]

I swear to God, she's like, I'm your neighbor, Chelsea.

[Chelsea Handler]

My God.

[Katherine]

Well, our first Blake of the day. He says, dear Chelsea, I'm a 31 year old trans man who lives in northern Ontario, Canada. I grew up very liberal, where being who you are was not a crime or shameful. And now I'm married and I've been with my wife for almost six years now. She comes from a very conservative Christian home and her family took a while to warm up to me. They never came to our wedding because it's a sin, quote unquote. And they don't agree with our lifestyle. They still aren't on board with us to this day. But then they claim to love us and all of that fun stuff people say, should I continue to be the bigger person and continue to just visit them like they haven't done anything wrong? I don't know what to do.

[Chelsea Handler]

Hi.

[Katherine]

Hi, Blake.

[Eliza Schlesinger]

Hi, Blake.

[Chelsea Handler]

I think you're muted.

[Eliza Schlesinger]

The carrot at the bottom next to the microphone.

[Blake (Caller)]

Got it.

[Chelsea Handler]

Look at that. Hi. That's one millennial helping another.

[Eliza Schlesinger]

Just doing what I can.

[Chelsea Handler]

Hi. Hi. Blake Lively. How are you?

[Blake (Caller)]

I'm good, thank you. How are you guys today?

[Eliza Schlesinger]

We're so tired of hearing about you.

[Chelsea Handler]

Okay, so your wife's parents, they know you're trans?

[Blake (Caller)]

Correct.

[Chelsea Handler]

And that's the big issue?

[Blake (Caller)]

Yeah. When her and her ex husband split, he got mad and he went and told her family about me.

[Eliza Schlesinger]

Doesn't matter.

[Chelsea Handler]

Were you guys having an affair?

[Blake (Caller)]

No.

[Chelsea Handler]

So how. What is he. Why? I'm confused. Why was he even in the picture?

[Eliza Schlesinger]

Just a jealous ex.

[Chelsea Handler]

Yeah, but if you weren't in the picture, then how did he know about her? How do you already know about this story? Before I.

[Eliza Schlesinger]

He started dating and then he was like, well, I'm still bitter about this. Oh.

[Chelsea Handler]

So he went.

[Eliza Schlesinger]

Because I'm in Ontario with nothing else to do. I know what I'll do. I'll go fuck up her life because she left me. It didn't work. I had a micropenis.

[Chelsea Handler]

And are they. They're nice to you other than what you're talking about? Like, is it civil when you're. When you see them?

[Blake (Caller)]

Yes, it is civil. It's just the fact that I know the things that have been said. And I guess that's just the bitter aspect of it where it's like, you've never apologized, but it's also. I shouldn't have to carry that, I guess.

[Chelsea Handler]

Yeah, no, I mean, I always have a different kind of feeling about this day to day, but I just feel like as long as you can be civil with each other, it's kind of an opportunity to demonstrate love and kindness.

[Eliza Schlesinger]

That's exactly right.

[Chelsea Handler]

And to just be like this great person in their lives and show all your great qualities and not judge them for their ignorance.

[Eliza Schlesinger]

That's right.

[Chelsea Handler]

You know what I mean? Because I think you can get a lot farther by that with that attitude. I am always like, fuck off, Shut it down. If someone is an asshole, then. But if they're not being abusive to you, if they're not being nasty to you to your face anyway, who cares what they say behind your back? That's really not your business anyway, you know what I mean? That's on them, I think, because it's.

[Eliza Schlesinger]

Easy for us as like heterosexual people to be like, whatever, big deal. But like, you also carry whatever comes along with being trans and what you think the world thinks of that and the way that you either are treated or perceive that you're being treated, like there's a weight to that. If someone says anything, anything to you, you're always going to be wondering, is it because I'm trans in the way that we're like, is it because I'm a woman? Is it because of my color? Is it because of this, whatever? We all have that. And I think you're absolutely right. It's your chance to show them all the kindness and love that the queer, trans, whatever community always preaches. And it definitely hurts and hurts your feelings, but you want them to feel so bad that they weren't the kind loving Christians that they talk about. When you leave, you want to be, and you don't have to be fake, but you don't let them take away who you actually are. Don't let them decide for you that you are all the awful things that they've decided you are, or trans people are, and you just keep demonstrating it. And if they want to be man enough to say it to you, then you can have that conversation. But I think a lot of times we come at people with very charged with anger when they have an idea about who we are, and then we end up proving that. And this is a chance to sort of deflate some of that ignorance.

[Katherine]

Like prove them wrong? Basically, yeah.

[Eliza Schlesinger]

I mean, what do they think? They just. The knock is that you used to be a woman and you're with their daughter. That's the knock. It's not that you're a bad person and they can't handle that. It is a foreign concept, like gay we've all sort of wrapped our minds around, but it is if you consider where they're coming from. Like, that's a lot to take on. You are probably the only trans person they know.

[Blake (Caller)]

I was, yeah.

[Eliza Schlesinger]

Oh, is there another? Is your wife now trans?

[Blake (Caller)]

What a plot twist. No, it's just a small community that they live in. There's others that have come out of the woodworks, I guess you could say, since, you know, we live in the woodworks. But yeah, I'm still like the only one they personally know though, I guess.

[Chelsea Handler]

You're the only one. Their daughter.

[Eliza Schlesinger]

Yeah, that's right. That you know of.

[Blake (Caller)]

Yeah, I sure hope so.

[Eliza Schlesinger]

This is your chance for them to be like, I know my son in law's trans and he's great. Yes, we token is we do it with everyone. We're like, well, I've got a Filipino friend, she seems cool, so they all must be. I've got a Jewish friend and they don't seem awful. They all must be. This is your chance to like show up and be like, look how fucking dope you are.

[Chelsea Handler]

And just right, like be. Rise above that. You know what I mean? Their problems are not your problems. You should just. It's like almost like anything any feelings or opinions they have about you is just not even part of who you.

[Eliza Schlesinger]

Are, has nothing to do with you.

[Chelsea Handler]

You want to move through the world and move through your relationship with them just as like a nice beacon of light, as like a joyful reprieve from the rest of their life, so that they're slowly understanding that you're just like anybody else, that you're a real person with real feelings and real emotions and without an agenda. You know what I mean? But really don't get stuck on what they're saying or what their attitudes are. As long as it's not hurtful or. Sorry, not. Maybe it's hurtful, of course, but you know, as long as it's not abusive or they're treating you in an unkind way, just keep pushing through. Because I think you should carry with you. Like you're speaking for lots of trans people. You know, your interactions with them are emblematic of all the trans people in your community. So like, unfortunately, keep that in mind. But I find that rather than having that be some sort of onus, though, it kind of gives you a sense of purpose.

[Eliza Schlesinger]

It's. But by the way, you don't have to do anything extra. But you're their son in law. You know what son in laws do? They call up, they're like, hey, you need to borrow a ladder. Like, you're their son in law. So, like. And the. The good news is you don't have to worry about anything because, like, men don't do anything.

[Chelsea Handler]

Like, do you have a ladder?

[Blake (Caller)]

I have a step ladder.

[Eliza Schlesinger]

No, you're a grown man. Go get you a ladder.

[Chelsea Handler]

I think you need to get a real ladder.

[Blake (Caller)]

I just hired people, so I don't need ladders.

[Chelsea Handler]

Okay, well, then hire someone to bring them a ladder, I think is what Eliza is saying.

[Eliza Schlesinger]

Or next time you go to their house, start knocking on studs and be like, this is a solid wall. Just start trying to fix things in their house. Be like, can we readjust this door? Bring a level. Just start seeing if everything's. Just start critiquing all the masculine stuff.

[Katherine]

And then you take the stud finder and you put it to your own chest, and you're like, found one.

[Eliza Schlesinger]

Here I am.

[Blake (Caller)]

That's literally what I can do.

[Chelsea Handler]

Okay, well, I mean, that's one step in the right direction.

[Eliza Schlesinger]

Just be a boy.

[Blake (Caller 2)]

Thank you.

[Chelsea Handler]

Yeah. I have a question for you. Are you guys affectionate in front of her family?

[Blake (Caller)]

We don't hide it. We don't, like, make it something that we try to hide or flaunt it. And, like, we're not trying to do something that's not us at the same time.

[Chelsea Handler]

Right.

[Eliza Schlesinger]

This holiday season, it's time to amp it up.

[Chelsea Handler]

And the holidays are right around the corner because we're in March.

[Eliza Schlesinger]

Yeah.

[Chelsea Handler]

So get back.

[Eliza Schlesinger]

Plenty of time to prepare. A lot of caressing, a lot of neck kissing. Just let him know on the ladder.

[Chelsea Handler]

You wanna do all of this on.

[Blake (Caller)]

The ladder while critiquing everything, right?

[Chelsea Handler]

Yes. Yeah.

[Eliza Schlesinger]

Just be a man.

[Chelsea Handler]

But you know what we're saying, right? You got what we're saying, Blake?

[Blake (Caller)]

With all of the toxic masculinity going around on the news right now, I think I can convey some of that.

[Eliza Schlesinger]

Thank you. That's what we're.

[Chelsea Handler]

This is the answer.

[Eliza Schlesinger]

This is what we want. Make Ontario great again.

[Blake (Caller)]

You know what? Canada might be the best state if it happens.

[Eliza Schlesinger]

Guys, welcome, welcome. Number 51.

[Blake (Caller)]

Don't worry. Chelsea already has a place here, so it's not even like she really has to move.

[Eliza Schlesinger]

Right.

[Chelsea Handler]

It's not like I'm even immigrating. I'm just like going from Canadian passport. I don't. I have a housing in Whistler, Canada, but I don't have a passport.

[Katherine]

She won't need one.

[Chelsea Handler]

But I marry a Canadian if I have to, but I don't need to marry a Canadian.

[Eliza Schlesinger]

No.

[Chelsea Handler]

Yeah, Everyone knows. Always, like before the election, I was like, oh, you can just move to Canada. I'm like, I have a feeling he probably thinks he's getting to invade Canada and take Canada over. Like, Canada is not far enough away.

[Blake (Caller)]

I don't think he can get that tan up north.

[Eliza Schlesinger]

Can't get it here. It's not a real tan.

[Chelsea Handler]

It's from a bottle.

[Blake (Caller)]

That's what I mean. But we don't sell it here, so I don't know.

[Eliza Schlesinger]

Well, especially if it's American made. You won't be. Rip Tito's Vodka. Sorry about that.

[Chelsea Handler]

Anyway, Blake, good luck with everything. Congrats.

[Blake (Caller)]

Thank you so much.

[Chelsea Handler]

Congrats on your relationship. And I think you're going to. I think you're actually going to be a great example for your in laws and that whole family to, you know, open minds and expand horizons.

[Blake (Caller)]

Well, thank you. I appreciate everything, guys.

[Chelsea Handler]

Okay, thanks, Blake.

[Blake (Caller)]

Bye.

[Chelsea Handler]

I couldn't resist taking a bite of that. It was like calling my name.

[Katherine]

All right, onto our next Blake.

[Chelsea Handler]

Oh, this is Blake. Back to back Blake.

[Katherine]

Back to back Blake. So our Next Blake is 28. He's here in LA. He says, Dear Chelsea, I need some big sister energy. And who better than you? After over a decade of producing unscripted content spanning editorial, TV commercials, presidential campaigns, and the wild west of social media, I'm ready for a change. I've worked for iconic brands across the Conde Nast portfolio, produced for Hillary Clinton and Stacey Abrams, and even helped Applebee's snag a can lion.

[Eliza Schlesinger]

It's like his LinkedIn bio.

[Chelsea Handler]

Seriously, dude.

[Katherine]

I mean, you know, look at his board back there. But despite all this, I've hit a wall of unfulfillment. After a layoff in nyc, I moved back to LA and landed a job in programming management at a live streaming giant. While I'm grateful, I've realized I want to return to my first love, producing, specifically in scripted tv. Cue a mentor's advice. If you can't find the project, create it. So I started writing work that began as a cathartic way to process a breakup. Yes, I Taylor Swifted the shit out of it and reflect on chaotic work situationships. Imagine a flirtatious gay CEO in advertising. Harder than it sounds has turned into something I'm genuinely proud of. I've drafted two stories, one rooted in raw gay emotions, the other dripping in jewy high camp. And I have shocked myself by how much I love this creative outlet. Here's where I need your advice. I feel this pull to pursue writing and producing scripted TV full time. But the thought of freelancing and giving up financial stability. Hello. Student loans. Terrifies me. Everyone in LA seems to have advice, but now I'm stuck in analysis paralysis. How do I take the next right sized step toward a career I'm passionate about without losing myself in the process? How do I balance humility, creative ambition and the rent checks with love and kindness? Blake. Hi, Blake.

[Blake (Caller 2)]

Hello. Hello.

[Chelsea Handler]

Hi, Blake. Eliza, do you want to take this? This is our special guest, Eliza Schlesinger.

[Blake (Caller 2)]

Hello. Hello. I'm very familiar.

[Eliza Schlesinger]

Is that good?

[Blake (Caller 2)]

No, in a good way. In a very good way.

[Eliza Schlesinger]

I mean, I am no stranger to the analysis paralysis, but also the actual act of putting one foot in front of the other. And it's tough because you got a taste of normalcy with a steady paycheck and you're like, oh, look how cozy this is. If you were just an artist from the start and you were used to flying by the seat of your pants, then that would be very comfortable for you. I am that, like, I am a freelance person, right? These are the things that I do. I don't have that backup job. The answer is, you're just going to have to do both. You're just going to have to be exhausted. And the question that I can't answer for you is, will you be okay being not artistically fulfilled in this life if you, if your creature comforts outweigh that some people are, for me, it is paramount, but some people can live that way. And are you willing to keep that job so you can keep your lights on and then just write at night and just hustle and have two jobs until one edges out the other?

[Blake (Caller 2)]

Short answer is yeah. So, like, for me, I originally moved away from LA to go to New York because I, at my core, am a hustler. And so I, while I was doing a lot of those other projects, like, I always had a full time job and like, I was able to freelance and sort of navigate it. And what happened to me is I got a job and got a really nice salary. I was still living paycheck to paycheck at the time because New York was just crazy. But I didn't freelance anymore. And then when I had the layoff happen, it just shook everything up and terrified me. And now I'm back in a place where I have a full time job again. I came back to LA and I'm really sort of leaning into this creative outlet that I really love, but I don't have side hustles. And that's kind of where I'm like, I know I need to get back into the side hustles, but sort of writing has taken the spot of what that would be because I'm doing it at night, I'm doing it on my lunch breaks at my full time job.

[Eliza Schlesinger]

Is it. You're writing a scripted show? It's on like two scripted shows.

[Blake (Caller 2)]

Yeah, two scripted shows right now.

[Eliza Schlesinger]

Well, all you have to do is create those and then it's about just getting somebody to read it. Like, you're not a showrunner, you're not producing these things. So if you've done that, the next step is connecting it to the right people. And then the idea is that that gets made so you can leave your other job. But it sounds like you're already doing both of them.

[Chelsea Handler]

Yeah, I mean, that's what I'm getting from you. You're doing all of it. And I mean, I think you're looking for like a way out of doing all of, like some sort of jackpot. The truth of the matter is that you do have to fucking hustle. You do. And it's brutal sometimes, but like, it is a means to an end. It does pay off. So while it might not be like the most glamorous part of your life right now, it deserves your focus and attention so that it can become your source of income as well.

[Eliza Schlesinger]

But also, I mean, yes. And it has to be something that, like. And it sounds like it is, like you can't live without it. Like, I wrote a movie that's on Netflix called Good on Paper. And that movie is something that I wrote every time I didn't get the audition, every time I had an off night and I didn't have sets when I could have been going out, but I didn't. Like, I always returned to that document. And the good news is you have that fire in you. But I'm going to tell you right now, and it seems to happen for everyone but me. There is no moment where they knock and they're like, hey, we're making it. You will submit this. Hey, we'll read it next week. Okay? It's in three weeks. Oh, the executive got Sick. Oh, she had a baby. And then they'll pick it up. But we're going to do it in the summer. Okay. Well, it's actually going to be for digital. Like, you have to become so accustomed to just eating shit for breakfast because these things take forever. I just took a blind script deal with a major network that took eight months. I'm sorry. I didn't take it eight months to even get the deal. And in the end, we didn't take it because it was so bad. Eight months just to make a deal for a show I hadn't created. So I'm just letting you know.

[Chelsea Handler]

To make a deal for a show you had not created.

[Eliza Schlesinger]

Hadn't created it. It was a blind script deal. And in the end, we didn't take is such a slog. So you have to be so in love with your characters and your process, and then you have to be okay with them dying. When someone buys this and it sits on a shelf, you have to love the process so much.

[Blake (Caller 2)]

Yeah. And that's kind of where I think I felt inspired to write in because, like, I actually. I'm loving this process. I never thought, like, I wanted to get into scripted, but that was kind of elusive. And then I had a mentor just be like, then just go write it. And it seemed so simple. And I actually fell in love with the writing process and it became really great. And then I was so consumed by one project that I started another. And now I have these two projects that are just kind of building. And it's been really fun and exciting, but I do kind of want to pivot into this. And it sort of became like this thing of fear where I'm like, oh, I actually have to now continue to push this onward and stuff. But I think the fear is sort of coming from, like, feeling like I'm being consumed by just making it all happen and doing the hustle and doing everything, which isn't something that I'm necessarily foreign to.

[Eliza Schlesinger]

It's not. It doesn't sound like fear to me. It sounds like anxiety because you're wanting it all to happen. And I get it, like, all at once right now, but there's actually very little to be done once you've written it. And it's going to be sending these emails like, there's actually nothing to fear here because nothing is happening. You don't have to leave that job yet. What you are is bored. You're like, I'm ready to go. And this industry moves so slowly. So the hardest thing to do is nothing. And that's what's happening right now. You just gotta go to work, polish your draft, make sure that when it's sent, it's the best version. Don't just fire it off. And I'm the worst at that. Like, I will send a network draft with typos. Like, I don't even. I didn't proofread my college essays. It's just slow. And that's the hardest part is remembering to live your life while your dreams, like, slowly start to take off.

[Katherine]

Yeah. Sean Hayes once gave a piece of advice that was like, he. For. For himself when he was coming up. He said, and I think he actually still does this, but do one thing every day that's like, toward the career you want to have. So, like, you feel like, oh, I gotta be taking meetings, I gotta be doing all these things. Even if every day you do one thing that's advancing your career or one contact, you're still making progress.

[Eliza Schlesinger]

The biggest mistake you can make is thinking other people are working for you and then you find out that they're not. Read the trades, find the executive at the streamer. What's your dream network? How do you get to that person who can you befriend that could read that? Do you have a rep? Do you have reps?

[Blake (Caller 2)]

No, I don't. That's the other thing.

[Eliza Schlesinger]

You gotta get that rep.

[Blake (Caller 2)]

I've always been in house. Like, when I was at Conde, I was in house and advertising. And so, like, when I was freelancing, it was just me getting tapped by people within my network. But I've never had a rep. And I got advice earlier on that was sort of like, you know, you don't really need a rep if you don't have anything to be repped. But now I'm sort of at a spot where I'm like, is this the tipping point or do I need to actually get.

[Chelsea Handler]

Yeah. Now this is how you get representation with the material that you've written so far. And there is something that separates people who succeed in this business and people that don't. And I think you're at the crescendo of that, or at the tipping point of that, I should say. You gotta just keep fucking chugging away. Like, it. It is hard, it is arduous. It's all of those things. But that's what separates people from being successful in this industry and people who aren't. Is the people that give up at this point. Or it's like overwhelm or I don't know what to do next.

[Eliza Schlesinger]

It's like, no one's coming to save you.

[Blake (Caller 2)]

Yeah, right.

[Eliza Schlesinger]

What's your next step? You have two scripts.

[Blake (Caller 2)]

So I have two concepts. I'm starting to script them right now.

[Eliza Schlesinger]

Because some people won't want you to do that. There's nothing wrong with having a script in your back pocket. And you need a concept is very hard to sell if it's not packaged. So right now it's just you. If you were. If you walked in and you're like, I've got these three pieces of talent attached and someone loves it. Nobody wants that. Have that script and maybe you show it to, maybe you don't, but at least you can show it to your rep. Like, you need proof of concept. If it's a scripted.

[Blake (Caller 2)]

No, it is scripted, for sure. One of them's a thriller drama, one of them's a dramedy.

[Eliza Schlesinger]

So I think these are hour long.

[Blake (Caller 2)]

Both of them are eight episodes, one hour each per season.

[Eliza Schlesinger]

Not only do you need the script, I mean, you can do a pitch. Some people prefer a pitch, but this pitch needs to be like, you need a one sheet, you need a pitch deck. And you need these things to be, like, grabbable. And I would ask someone, you know, who's a writer for other examples of a pitch deck. Unless you already have that. It's the hardest part. I always find it's easier to just write the script. I hate pitching. It's a great way to have people tell you to fuck off, but you should be writing the script. Were you planning on writing it?

[Blake (Caller 2)]

Yeah, I was planning on writing it. I sort of was getting into, like, putting the pitch material and series bible together. And then I been getting feedback and people are like, oh, you sort of just need more of a script with this as well.

[Eliza Schlesinger]

You should just write the script. Because it is in that script that you will find all the problems. Have people read it. Have people you trust, not your friend, but like, real writers, read it, rewrite it, rewrite it, get it to a place where you think it's bulletproof, then give it to your rep who will give you their critiques, and then you go from there. But you gotta. You have to actually write it. Otherwise you're just a person who says that they're a writer.

[Blake (Caller 2)]

Yeah, I don't call myself a writer, if any. I know I'm a producer. And I think that's been like. The other hesitation is like, I've done producing, I've directed a little bit, but, like, writing is, like, very. I haven't Done it since college. And, like, this is, like, actually something that I'm finding I'm falling in love with.

[Eliza Schlesinger]

Enjoy it. Enjoy falling in love with it.

[Chelsea Handler]

Thank God Eliza was here today. She's giving you great advice.

[Katherine]

Yeah.

[Eliza Schlesinger]

I can't tell you that I've read Save the Cat in a long time. There's screenwriter podcasts, like, write it and then you'll rewrite it and then step away. Write it again. Then you can get. Your agent can't represent you unless they have something to actually read. Otherwise, it's just like a fun concept. Nobody really wants to read a Bible.

[Blake (Caller 2)]

That's fair enough.

[Eliza Schlesinger]

Any kind of Bible.

[Blake (Caller 2)]

Heard, heard, heard, heard, heard.

[Chelsea Handler]

Okay, well, thanks for calling in. I mean, that's some good advice. So good luck with everything.

[Blake (Caller 2)]

Beautiful. Thank you all so much.

[Katherine]

Check back in in like, six months. Blake. Okay.

[Chelsea Handler]

Yeah. Let us know how you're doing.

[Eliza Schlesinger]

Yeah, yeah. From your mansion after you sold the show. And I'm jealous.

[Blake (Caller 2)]

I wish. So awesome. Thank you all so much. I appreciate it.

[Eliza Schlesinger]

Bye.

[Katherine]

Bye.

[Eliza Schlesinger]

It's such a. It's such a brutal path.

[Chelsea Handler]

That was good. Especially right now.

[Eliza Schlesinger]

Thank you.

[Chelsea Handler]

I mean, I'm like, when they. People call in with career stuff, I'm like, I don't fucking know what to tell you. I don't really know. Let's put one foot in front of, like, all I can say is hustle, hustle, hustle. But it's like, that was good too, because it got into specifics.

[Eliza Schlesinger]

Yeah, for sure. And it's like, it's a super granular thing, but, like, that's what's so great about standup, is like, just go up. Just go. You don't need someone to okay it. No one has to call. Like, you can just. You can create it every night. The writing is tough, but plenty of show creators, like, were. I think, like, Mark Platt was like a lawyer and then he created shows. Like, a lot of people just start as something else and just move into writing so it can be done.

[Katherine]

Yeah.

[Eliza Schlesinger]

It's just hard.

[Katherine]

Let's take a quick break and I have a little wrap up question.

[Chelsea Handler]

Great. We'll be right back with Eliza. I keep saying Schlesinger.

[Eliza Schlesinger]

Schlesinger.

[Chelsea Handler]

We'll be right back with Eliza Schlesinger. Is Hamley Schlesinger.

[Eliza Schlesinger]

Schlesinger.

[Chelsea Handler]

Is it gur.

[Eliza Schlesinger]

Yeah.

[Chelsea Handler]

I've been saying Eliza Schlesinger.

[Eliza Schlesinger]

I know.

[Chelsea Handler]

I'm so sorry.

[Eliza Schlesinger]

Everybody does.

[Chelsea Handler]

Oh, my God. It's Eliza Schlesinger, everybody. It's Eliza Schlesinger.

[Eliza Schlesinger]

There you go. Now you're Jewish.

[Chelsea Handler]

Eliza Schlesinger. I'm so sorry.

[Eliza Schlesinger]

Isn't it so much better that way?

[Chelsea Handler]

Yeah, it is. Schlesinger.

[Eliza Schlesinger]

Nope.

[Chelsea Handler]

No, that was a test.

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[Eliza Schlesinger]

Yes.

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[Chelsea Handler]

A mother's love deserves a gift like no other. Celebrate her love, strength and style with heartfelt jewelry from Pandora. From iconic charms to sparkling necklaces, rings, earrings, and more, there are so many ways to say, thank you, mom. Pandora even has in store engraving so you can treat your mom to a trip to the store and have your pieces engraved together with your own handwriting. So on Mother's Day and every day, tell her how much she means to you with a gift from Pandora. Visit Pandora in store or [e-mail] Every.

[Katherine]

Morning brings a fresh, new energy.

[Eliza Schlesinger]

This is today with and no matter.

[Katherine]

What the day, we come to the.

[Eliza Schlesinger]

Today show for all of it.

[Chelsea Handler]

When things are tough, we talk about it. When there's something to figure out, we dig into it. And when there's joy, we celebrate it.

[Eliza Schlesinger]

Because today is where it's all happening. We get the best start to every.

[Chelsea Handler]

Morning because we start it together. Watch the Today show with Savannah Guthrie and Craig Melvin, weekdays at 7am on NBC. And we're back with Eliza Schlessen Gurr.

[Eliza Schlesinger]

There you go. That's totally the way to do it. With a pause in the midd.

[Chelsea Handler]

I like it like a hyphen.

[Eliza Schlesinger]

Yep.

[Katherine]

Emphasis.

[Eliza Schlesinger]

Yeah.

[Chelsea Handler]

Not an umlaut. A hyphen.

[Eliza Schlesinger]

I wish. I wish I came from a culture.

[Chelsea Handler]

That had anti umlaut.

[Eliza Schlesinger]

Oh, we are.

[Chelsea Handler]

I think so.

[Katherine]

I don't know. Umlaut canceled. This writer says. Dear Chelsea, my 97 year old neighbor of 6 years who is thriving, calls me Kimberly. My name is Kendall. Do I tell her Xoxo Kendall?

[Chelsea Handler]

No, no, no, no. Just tell her your name is Eliza.

[Eliza Schlesinger]

Schlessinger and she'll have an aneurysm trying to pronounce it.

[Chelsea Handler]

No. I love that she calls you the wrong name. That's fun. Have fun with it.

[Eliza Schlesinger]

Yeah. What's to be gained?

[Chelsea Handler]

Yeah.

[Eliza Schlesinger]

How much longer could she possibly be calling you by this name?

[Chelsea Handler]

Okay, Eliza, everybody can watch Eliza Schlessinger's new special. It's on Amazon Prime. Okay. And it's called A Different Animal. And if you need to know more about her, go to her Instagram, go to her Facebook. Are you still on Facebook?

[Eliza Schlesinger]

Probably.

[Chelsea Handler]

I mean, I don't. I don't even know how to get on Facebook.

[Eliza Schlesinger]

I don't have my password. Can I plug my podcast? Yeah, absolutely. Producer and co host is always like, you need to tell people you have a podcast. It's called Ask Eliza anything. And by the time this comes out, we will have our new home on Lemonada. And I do what we do here is I, the audience is the guest. So we give. We give life advice. Perfect.

[Chelsea Handler]

Oh, my God, how funny.

[Eliza Schlesinger]

Yeah. So ask Eliza anything. Okay.

[Chelsea Handler]

Love it. Thank you, Eliza.

[Eliza Schlesinger]

Thanks for having me, Chelsea.

[Chelsea Handler]

Thank you.

[Katherine]

Yeah.

[Chelsea Handler]

Do do do do do do. Drum roll, Catherine, please. Chelsea Handler. Abroad. Abroad is my European tour, which I just announced. Tickets go on sale tomorrow or today or there's a pre sale code. Chelsea. So I'm coming to obviously find a husband abroad. I need to get the hell out of this fucking country. And it's not as easy as you think. So I'm coming to Reykjavik, I'm coming to Dublin. I'm coming to the uk I'm coming to Brussels, Paris, Belfast in May and June. I'm coming to Oslo, Stockholm, to Copenhagen, Manchester, London, Glasgow, New Zurich, Vienna. I've never ever been to Vienna, Berlin, Barcelona and Lisbon. I'm coming abroad is abroad.

[Katherine]

That sounds like fun. I'm gonna go see you abroad.

[Chelsea Handler]

I know I want to go see me abroad. And there I'll be there I'll be excellent. Okay. All upcoming Vegas dates, March 21st, April 18th, July 5th, August 30th, November 1st and 29th at the Cosmopolitan of Las Vegas.

[Katherine]

If you'd like advice from Chelsea, shoot us an [e-mail] and be sure to include your phone number. Dear Chelsea is edited and engineered by Brad Dickert Executive producer Kathryn Law, and be sure to check out our merch@chelsea handler.com.

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[Eliza Schlesinger]

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[Chelsea Handler]

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