Dear Chelsea - Boomer Apologist with Iliza Shlesin…ger

Episode Date: March 13, 2025

Iliza Shlesinger joins Chelsea to talk about facing online backlash, why you can’t have a good hookup twice, and why she chose THOSE pants.  Then: A neighbor’s misnomer may be stuck t...hat way.  A screenwriter wrestles with a blank page. And a trans man struggles to accept the way his in-laws treat him… even though he doesn’t own a ladder. * Order a signed copy of Chelsea’s new book HERE! * Check out Iliza’s new special, A Different Animal, on Amazon Prime! * Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com * Executive Producer Catherine Law Edited & Engineered by Brad Dickert * * * The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opinions of iHeartMedia or its employees.  This Podcast should not be used as medical advice, mental health advice, mental health counseling or therapy, or as imparting any health care recommendations at all.  Individuals are advised to seek independent medical, counseling advice and/or therapy from a competent health care professional with respect to any medical condition, mental health issues, health inquiry or matter, including matters discussed on this Podcast. Guests and listeners should not rely on matters discussed in the Podcast and shall not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.  See omnystudio.com/listener for privacy information.

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Starting point is 00:01:33 My name is Brendan Patrick Hughes, host of Divine Intervention. This is a story about radical nuns in combat boots and wild haired priests trading blows with J. Edgar Hoover in a hell bent effort to sabotage a war. J. Edgar Hoover was furious. He was out of his mind and he wanted to bring the Catholic left to its knees.
Starting point is 00:01:57 Listen to Divine Intervention on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts. Hello, hello. Who's there? Hi, Chelsea. Am I speaking to a number one New York Times bestselling author? Yes you are. Yes you are. Six times over, number one New York Times bestselling author.
Starting point is 00:02:17 The phone call I will never get tired of getting in my entire life. I can't believe it. Oh my gosh. I really didn't think I was going to 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, it doesn't matter what number I am. I'll be grateful to be on the list. Of course.
Starting point is 00:02:32 And then I'm with 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. Hell yes. So yes, hard work pays off. That's the truth. Yes, and you have been working hard. You've been making the rounds. You're everywhere right now, and it's really exciting to see. I'm currently in South by Southwest. I'm in
Starting point is 00:02:56 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. I was gonna say, if anyone drugged you, the most likely culprit is you. This is true. This is true. Well, congratulations.
Starting point is 00:03:20 That is so exciting and I'm so happy for you. Thank you, thank you, thank you. Everybody who's listening, I hope you've ordered my book or you ordered or downloaded an 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 ChelseaHandler.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.
Starting point is 00:03:51 Well, I'm so excited about our guest today. She is so fantastic. Oh yes, this is a comedian so you're in for a good treat and conversation. I had 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.
Starting point is 00:04:13 Schlesinger. Fuck! It's Eliza Schlesinger. So, uh, and she has a new special out, so everybody, please go and watch that. You gotta support female comedy guys and girls, and you gotta see these pants. And you've gotta see these pants.
Starting point is 00:04:30 Please welcome Eliza's Lesson Grr. I have a rule about hot food on a plane. What is it? You can't bring hot food. I hear that. Because everybody can smell it. Right, and hard-boiled eggs is a cold food. Ew.
Starting point is 00:04:42 You know what, it's just visually gross, but I guess they don't smell. It's not like sulfur, but the idea of it is a cold food. It's different. Yeah, you know what? It's just visually gross, but I guess they don't smell. It's not like sulfur, but the idea of it is gross. It's momentarily sulfur. But I think it shouldn't just be hot food. There should be a list of things that are not tenable for a flight. A no-fly list.
Starting point is 00:04:57 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 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 of Mario 2? I miss that game. Remember when times were so simple that you could play Super Mario Brothers? I used to get up at my friend's
Starting point is 00:05:20 sleepovers 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 early, so that I could get on the Mario Super Mario Brothers before the other girls at the sleepover woke up, because it's like, no, no, no, I'm already on, you can't push me off, I was so obsessed. I miss being that obsessed with something.
Starting point is 00:05:40 Oh, I feel like we are obsessed and we don't realize it. Now it's just called an addiction. Oh, the phone you mean? Oh yeah. Yeah, social media. I have to take it off. I have to take it off every day and put it back on. What do you take it off of?
Starting point is 00:05:53 I take it off my phone and then my Instagram. You take it off of your phone? Take 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.
Starting point is 00:06:06 Like it's somewhere in my phone and I just go and I get it and I just erase it every night. And then restore it. Sounds like you're lying to her and to yourself. I am. This is so lovely. Look at how beautiful, Carlos. Oh my goodness.
Starting point is 00:06:16 Carlos, you're so, that makes me wanna have a coffee and I don't even drink coffee. Thank you. You get a little snack and everything. I have my snack, I'm not gonna have the snack. With that little cookie, Yeah, I like that. This was so European. I feel like we're at a nice hotel somewhere,
Starting point is 00:06:28 far, far away. Sure, I would love a coffee. Thank you. 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 The Different Animal. Are you the animal or is the special the animal?
Starting point is 00:06:42 Both. 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. Why does everyone think I have so much money? I don't understand where this comes from. Look at these archways. 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.
Starting point is 00:07:06 Someone sent you a link, which is like peak Hollywood elite. No other podcast had a link. And I'm like, yeah, cause you have people that get the links. That is so funny. I mean, you got to sneak, nobody has seen this. And so I'm blown away. Well, as the first person that's officially seen this special besides I'm assuming you,
Starting point is 00:07:25 or maybe you haven't even seen it yet, because you don't even have the link. I just, they wouldn't like it. 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.
Starting point is 00:07:41 So like those are good places to watch them too. And everyone now has Amazon Prime, I'm assuming. I guess not as many people as Netflix, but it is prevalent and pervasive. I say that in pervasive. Amazon itself is pervasive. But you have such a talent. Oh, thank you.
Starting point is 00:07:58 You really do. You really have a great, my stand-up is very much storytelling and personal storytelling. You have a very clear talent of structuring jokes, premises, punch lines, which you even talk about in the special. You mentioned in the special. But I love your focus on the different generations about millennials, because I don't even know
Starting point is 00:08:17 what am I. You are generation X. X, X. Okay, so it goes from generation X, then millennial. You were hoping I'd say Gen Z. I'm like, you're Gen Z? Oh, God, I hope not. No, they're so fucking annoying. You're so young. Gen Generation X, then Millennial. You were hoping I'd say Gen Z. I'm like, are you Gen Z? Oh, God, I hope not. No, they're so fucking annoying.
Starting point is 00:08:27 Gen Z, so then Gen X, no, I'm 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. Thank you, I'm actually a Millennial. There is a Zenial. Please call me a Zenial. Zenial, Millennial, Elder Millennial, which is what I am.
Starting point is 00:08:44 Generation X, Baby Boennial, millennial, elder millennial, which is what I am, generation X, baby boomer, silent generation and then our forefathers. 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.
Starting point is 00:09:00 And then sometimes it's a decade and there's different definitions of it all. But nevermind that. You and your special, you really delineate what the differences are between all of these with a lot of attitude and anger towards younger generations. That was the working title, attitude and anger. We're not picking up the baton after you guys,
Starting point is 00:09:23 after millennials just like laid out everything for future generations. They're just like, wait, 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 did, well they did. They had a lot of babies.
Starting point is 00:09:40 Can I say something? Are you a boomer apologist? Oh, I'm not a boomer apologist. She's an elder millennial boomer apologist? Oh, oh. Well, I'm not a boomer apologist. She's an elder millennial boomer apologist. I have to say, there's 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.
Starting point is 00:09:58 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.
Starting point is 00:10:15 So they laid the groundwork, but the perpetuation of it is definitely on all of our shoulders, especially Generation. Z, what is a Sheen haul? A Sheen haul 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,
Starting point is 00:10:31 but they were gonna 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 to fast fashion and that like Sheen and H&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.
Starting point is 00:10:54 And so that's that's what a Sheen haul is. Okay, I thought you were going to say then you return everything because you don't want it. No, someone say that's even worse for the planet because then it's going back. 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, or keeping them and they go nowhere,
Starting point is 00:11:10 or you donate them but nobody wants them because they're so cheap. I feel like every podcast I do, I go back to sustainability and people are just like turning off, go back to Justin Beldon. It's like that at October 7th. Let's talk about, oh yeah,
Starting point is 00:11:22 that's the last time we saw each other right after the, at a Jew event, right after October 7th. 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. But 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.
Starting point is 00:11:36 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
Starting point is 00:11:54 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. Well, I'm glad I went. I'm glad I went. I'm glad you came too. Okay, so I don't want you to have to talk about sustainability, but we can talk about shower sex.
Starting point is 00:12:09 Let's talk about shower sex. Let's talk about shower sex. I wanna 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
Starting point is 00:12:31 or you and your throuple are, you know, I don't wanna discriminate, maybe you have more than one lover in a group, but no one wants to fuck in the shower, it's not fun, it's not sexy, it's not, and your penis, 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. When you're stressing and like this idea that like, oh, let's have shower sex.
Starting point is 00:12:55 I'm like, we're not two gay guys at a crunch on like a Thursday. Like we're not fucking in a shower. 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 fucking at gym? Gay men specifically, I know some gay men who specifically go to the gym just to give blow jobs in the sauna.
Starting point is 00:13:15 I don't understand giving a blow job, 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 and you're like, I gotta get it in, because most men would. Like my husband is like, you just tell me when. He's like, I'm always ready. And so it's like, it's that times two. You're like, thank you, I didn't know that.
Starting point is 00:13:34 I'm like, I know. But the showers, it's just more like, you following me in here thinking I'm turning, 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 life. Oh are you suggesting
Starting point is 00:13:53 that you use lube in the shower? I guess you should it's actually the opposite of a lubricant water. 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 it in and it's like, you need, actually you need a lubricant, but who's gonna bring a lubricant to the pool and into the ocean and then lubricate when you're underwater? It's just all anti, it's like counterintuitive.
Starting point is 00:14:15 You have a whole contingency of like mermaid fans that are like actually, I find aquatic sex. I think it all just speaks to- Aquatic sex. I think it just speaks to like a woman's comfort not being taken into account. And when you're in your twenties, you're just like, yeah, I'll do that, it's hot.
Starting point is 00:14:30 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 can 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 a representation.
Starting point is 00:14:46 Or does your husband care? Answer, no, he doesn't care. What do you look like? But I 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.
Starting point is 00:14:57 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. You don't like them. Well, I'm not gonna pretend that I do. I mean, you have an incredible body, and I like that you show it off, and I understand that. But those pants, I was just like, why?
Starting point is 00:15:17 Yeah, why? I don't know. I'll tell you why, because I can. And I think as a woman, I think the more- You can come on in, Carlos. Come on in, Carlos, bring that biscuit. There's no reason you shouldn't become part of this podcast.
Starting point is 00:15:29 This is so cute. This is so cute. I didn't even know this was available in my own home. It's so continental. That's how rich I am, you guys. I didn't even know I had a cafe. She just met Carlos. She didn't even know he was here.
Starting point is 00:15:39 I saw, and I love a fun pant, and the pants that I wore on my last special were like a hype. Yes, I remember, a similar outfit. 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. What's your body type? Well, the thighs are like, I started doing Pilates so it's different, but I don't know, strong core.
Starting point is 00:16:00 Excuse me, one second, I don't wanna cough over you. Apparently I'm allergic to coffee. She's like, bullshit, you don't have a strong core. Okay, go ahead. You dress for your body, I mean, it's just second I don't want to cough over you. Apparently I'm allergic to coffee. You don't have a strong core. Okay go ahead. You dress 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 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 don't remember if I had just gotten pregnant with Ethan or we were thinking about it, but I saw those pants and there was something about them.
Starting point is 00:16:34 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 do you have someone dress you? Oh God, no. I know what you mean. I know what you mean. 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
Starting point is 00:16:51 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, they reminded me of Cher, like turn back time. And I just know that there will be a day that I shouldn't wear those pants. And I just thought that they were cool enough while not being super distracting.
Starting point is 00:17:15 Do we have to iron out the bulkiness of them in Photoshop? Cause they don't lay right. Cause 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. Yeah well you're right it is a talking point so good for you Mazel Tau. Thank you. I thought they were just cool and I just liked them. 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
Starting point is 00:17:44 I'm gonna fucking wear these pants that's all that really matters. 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 view of like at the ice house like 400 years ago and you're wearing a hoodie right? Like I think there's a video of you at the Ice House, like 400 years ago, and you're wearing a hoodie, right? I feel like we women weren't encouraged to do that. And now I look at younger girls and they're just in a bra on stage
Starting point is 00:18:13 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. When I came up, I was always trying to play down my looks and be more tomboyish.
Starting point is 00:18:30 That's what I'm saying. 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?
Starting point is 00:18:46 I think it's something that people talked about, but I- Like you can't be funny and pretty, so cool it with the pretty. 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?
Starting point is 00:18:59 I have herpes, that's the catch. I'm funny, pretty, and I have herpes. I'm dying. I am a tomboy, like I always grew up wearing big t-shirts and not really, you know, maybe you wear a tank top to a college bar when you're out, but on stage I just was always comfortable with that. So I never went out of my way, but I always felt like,
Starting point is 00:19:17 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, it 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,
Starting point is 00:19:33 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 wear secret hands. I mean, you do jam and I only have these eight minutes. But as an adult, I try to take more time now and wear secret hands.
Starting point is 00:19:46 I mean, you do jam a lot of material into an hour. 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. It's very full bodied. Thank you. I like that. It's very artistic.
Starting point is 00:20:03 I appreciate that. Like you're an artist in the form of standup. Like that's very, very well done. 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.
Starting point is 00:20:18 I mean, most auctioneers do. And I was watching that and I was like, I could have gotten two hours out of this. Like if I just did like a long pace, if I just spoke like every other comic and just took my time. Yeah, she does speak slowly. I was like, there's an art to this. I got to slow down and I won't have to work as hard to write. Like I can just have two hours out of this one. So. Doesn't it feel like standup feels like such a hustle, right? Like it is you're constantly,
Starting point is 00:20:43 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, working. I feel hustled and I do hustle. Yeah. It is I mean you're a real stand-up 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,
Starting point is 00:21:12 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,
Starting point is 00:21:26 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, cause 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,
Starting point is 00:21:46 like are you done taking your break? I'm sure people would prefer I just take the break forever. Well, it's you're completely self-reliant. There's no like- There's no safety net. Yeah, right. Like the mortgages are in my name. But that's also kind of a nice thing that conversely,
Starting point is 00:22:01 there's like a flip side of it, which is you're not really answering to anybody but yourself. 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,
Starting point is 00:22:16 but we did get to a place 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 there was like a stutter step,
Starting point is 00:22:35 especially as a woman, because we're expected to be kinder and empathetic at every turn. Meanwhile, guys were like, oh 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.
Starting point is 00:22:52 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 respond. Well, now that Trump is pregnant,
Starting point is 00:23:09 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,
Starting point is 00:23:28 like when Eliza's husband's friend or stranger. Stranger, usually stranger. Right, finds out that you're pregnant, especially with a boy. Especially, they love to know there's a boy in the world. But men will, 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
Starting point is 00:23:52 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. 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. Way to go because men love to know other men are having sex.
Starting point is 00:24:18 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. We don't want anyone having sex. We want, and men are just like, just however you gotta get it in. And it's primal and it's the way they are, but I want the congratulations as well.
Starting point is 00:24:35 Have you, did you have sex with a lot of, or did you have a lot of boyfriend comics? No. Ever? No. None. You never dated a comic. I did, but so long ago, and I kind of just stayed out of it, but a big reason I did,
Starting point is 00:24:47 and I think you can probably relate to this, I became a headliner so early in my career. From winning last comic standing? 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,
Starting point is 00:25:08 but that, I didn't need that from a man. And I certainly didn't want to date a coworker 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. I'm trying to think if I made out with any of them. I don't even think so.
Starting point is 00:25:30 I once had sex with Tom Rhodes. Do you know who Tom Rhodes is? I just canceled on a lineup he was on the other night. Oh my God. Oh, I was like, did he do something? Was he canceled? He's very nice. He's a sweetheart. I once had sex with him. He's good looking. Yeah. And yeah, he is still good looking. He came up to me, we were at an airport lounge the other day, and he- Which one?
Starting point is 00:25:48 American. And I was with my cousin and he was like, "'Hey, Chelsea, just wanted to say hello.'" And I just thought he was- He shook your hand? 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.'"
Starting point is 00:25:59 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 Joe Coy, 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.
Starting point is 00:26:25 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 of months later. Is this after you were you or is this before your book?
Starting point is 00:26:45 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.
Starting point is 00:27:00 And then we tried to recreate it in LA and I met him at the comedy store here in LA and it was a, 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 have one good night with a person doesn't mean you should ever see them again.
Starting point is 00:27:18 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. I feel that way with an entree. I'll be like, I want to order another one. Yes. You can never have two Egg McMuffins. The first is so delicious. Yes.
Starting point is 00:27:33 I love Egg McMuffins. The second one? I love them. Instant diarrhea. What they need to do is make Egg McMuffins a little bit bigger. 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 going to be able to go to McDonald's and I fucking love Egg McMuffins. Stock up.
Starting point is 00:27:50 Stock up. Were you freezing them? Well, yeah, I was freezing them and they are not as good when you freeze them. No! They are so good. Turns out fast food doesn't last. Nothing got me off of them quicker than freezing them. I'm like, these are not good at all.
Starting point is 00:28:03 You know what else would get you off of them? Having two on like a regional flight in the Northeast. Regional. You're like, I just, my treat. You lost me a regional flight. It was my treat. How depressing. For years when I, when I was first traveling, my, you know, get there to the airport
Starting point is 00:28:15 and I was like, okay, I never eat McDonald's, but this is 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.
Starting point is 00:28:33 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 wanna date you. Like 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. And it's a good lesson to know.
Starting point is 00:28:48 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. Sometimes it's okay just to read a good book and let it go. You don't have to keep rereading it. I will say, you don't know who this person is There was a a total power reversal. I was playing somewhere
Starting point is 00:29:09 I'm not even gonna say the city or anything and it was I was a comic a younger comic that I had known forever and I they'd Opened for me rent like guest sets at this in this city and I'd see them as every few years and He came over and he just went down on me I don't 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.
Starting point is 00:29:36 And I just, after you're done eating me out, you can eat whatever you want out of the mini bar. And it was great. And I, and it was, and I felt like a real headliner and it just, it's like a nice memory and I 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 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 it's not necessarily all about us. It's like, well, that's also like, you know, friendly.
Starting point is 00:30:05 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 because 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.
Starting point is 00:30:19 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. I keep in touch like over DM and he 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, 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
Starting point is 00:30:35 who also has to go down on me. How did you meet your, how did, every family member needs to go down on you. How did you meet your husband? That was him. I met him on Raya. Oh, really? A Raya success story.
Starting point is 00:30:48 Have you been? Of course. I had lots of different sex on Raya. Different countries. I find Raya to be great for when you're in the UK or New York or it's a nice hotspot and it gives you a, I mean now it's opened up a little bit more
Starting point is 00:31:03 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? Continental. More continental buffet. It gives you more of a grouping of people that are actually a little bit slightly elevated than what you're going to find on Twitter, I mean, not Twitter, sorry, Tinder or like Hinge or whatever. It's just like a little bit more of a guarantee
Starting point is 00:31:25 that you're not gonna find curated. That was the word I was thinking of. Thank you. Not the unwashed masses. Well, you know, people will grimace at, will bristle at that, but like, if you have a public profile, like if you are a celebrity at all,
Starting point is 00:31:37 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.
Starting point is 00:32:08 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 yours, cause it's a vulnerable thing to go out with someone. Well, of course, of course, especially when they, yeah. Especially when you are a celebrity
Starting point is 00:32:24 and they know who you are and you're putting yourself out there. I'm of the ilk that you just let go of all of that. Who gives a fuck? You're gonna 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?
Starting point is 00:32:39 I'm like, easily. I'm trying to get some action. Right, we are also at this. Who cares? I don't care if they know that I'm on this site. That doesn't bother me. Right, especially not now. I think like the stigma of online dating
Starting point is 00:32:50 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
Starting point is 00:33:02 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. Wow. I was his first riot date. He was like, I don't know, like my fifth or something.
Starting point is 00:33:16 Like I hadn't been on it that long and it just worked. Wow. He was so lovely. And that was like day one. And like, that was it. And so what kind of artist is he? He's a chef. Oh, artist is he he's a chef Oh, but he's a I should have brought you a book
Starting point is 00:33:27 he's a cookbook author and chef and And a writer and so he writes a lot of you know articles freelance, but he is a chef and cookbook author That's cool. It was cool. And when I met him he was he had opened Are you a regular eater or do you eat not eat meat or anything? No, I'm a regular regular person He was the opening chef for blood Sows Barbecue on La Brea, which is like an LA staple. And he has his cookbooks, he writes cookbooks, he has one coming out.
Starting point is 00:33:53 Do you ever eat at Found Oyster? You're very far west over here, so I don't know. No, but I've heard of Found Oyster, I love oysters. So Ari Collender, 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,
Starting point is 00:34:07 I wanna do a cookbook, he will capture your voice and write that with you and recipe test. That's such a nice refreshing vocation. It's so, it's great. In this town especially. Yeah, he's not like a fake chef. Or a photographer or a producer. I mean, photographers at least can take photographs,
Starting point is 00:34:23 but producers is a little bit of a gray area, as we all know. Yeah. Okay, on that note, we're gonna take a break and we'll be right back with Eliza Schlesinger. Our iHeartRadio Music Awards are coming back Monday, March 17th on Fox, starring Bad Bunny, Glowrilla, Kenny Chesney, Money Long, Nellie, your host, I Heart Radio, LL Cool J.
Starting point is 00:34:48 Are you guys ready to have some fun tonight? Plus I Heart Innovator Award recipient, Lady Gaga. I Heart Icon Award recipient, Moriah Carey. And I Heart Breakthrough Award recipient, Gracie Abrams. Watch live on Fox, Monday, March 17th at 8, 7 Central. Do you remember what you said the first night I came over here? How goes lower?
Starting point is 00:35:09 From Blumhouse TV, iHeart Podcasts, and Ember 20 comes an all new fictional comedy podcast series. Join the flighty Damien Hirst as he unravels the mystery of his vanished boyfriend. And Santi was gone. I've been spending all my time looking for answers about what happened to Santi. And what's the way to find a missing person?
Starting point is 00:35:28 Sleep with everyone he knew, obviously. Mm, pillow talk. The most unwelcome window into the human psyche. Follow our out of his element hero as he engages in a series of ill-conceived, investigative hookups. Mama always used to say, God gave me gumption in place of a gag reflex.
Starting point is 00:35:45 And as I was about to learn, no amount of showering can wash your hands of a bad hookup. Now, take a big whiff, my brah. Listen to The Hookup on the iHeart Radio app, Apple podcasts, or wherever you listen to your favorite shows. ["POD OF REBELLION"] Welcome to Pod of Rebellion, our new Star Wars Rebels rewatch podcast. I'm Vanessa Marshall.
Starting point is 00:36:11 Hi, I'm Tia Sircar. I'm Taylor Gray. And I'm John Lee Brody. But you may also know us as Harrison Dula, Spectre 2. Tabin Wren, Spectre 5. And Ezra Bridger, Spectre 6 from Star Wars Rebels. Wait, I wasn't on Star Wars Rebels. Am I in the right place?
Starting point is 00:36:26 Absolutely. Each week, we're going to re-watch and discuss an episode from the series. And share some fun behind the scenes stories. Sometimes we'll be visited by special guests, like Steve Blum, voice of Zabarelio Spectre 4, or Dante Bosco, voice of Jai Kell, and many others. Sometimes we'll even have a live way debate.
Starting point is 00:36:42 And we'll have plenty of other fun surprises and trivia too. Oh, and me? Well, I'm the lucky ghost crew Stowaway who gets to help moderate and guide the discussion each week. Kind of like how Kanan guided Ezra in the Ways of the Force. You see what I did there? Nicely done, Jon. Thanks, Tia. So hang on, because it's going to be a fun ride. Cue the music! It's gonna be a fun ride. Cue the music. ["Pomp and Circumstance"] Listen to Potter Rebellion on the iHeart Radio app,
Starting point is 00:37:11 Apple Podcasts, or wherever you get your podcasts. Hey, y'all, it's your girl, Cheekies, and I'm back with a brand new season of your favorite podcast, Cheekies and Chill. I'll be sharing even more personal stories with you guys. And I know a lot of people are going to attack me, why are you going to go visit your dad? Your mom wouldn't be okay with it.
Starting point is 00:37:29 I'm going to tell you guys right now, I know my mother. And I know my mom had a very forgiving heart. That is my story on plastic surgery. This is my truth. I think the last time I cried like that was when I lost my mom. Like that, like yelling. I was like, no. I was like, oh, and I thought, what time I cried like that was when I lost my mom. Like that, like yelling. I was like, no.
Starting point is 00:37:46 I was like, oh, and I thought, what did I do wrong? And as always, you'll get my exclusive take on topics like love, personal growth, health, family ties, and more. And don't forget, I'll also be dishing out my best advice to you on episodes of Dear Cheekies. So my fiance and I have been together for 10 years. In the first two years of being together,
Starting point is 00:38:08 I find out he is cheating on me, not only with women, but also with men. What should I do? Okay, where do I start? That's not love. He doesn't love you enough, because if he loved you, he'd be faithful. It's going to be an exciting year,
Starting point is 00:38:21 and I hope that you can join me. Listen to Cheekies and Chill, season four 4 as part of the My Cultura podcast network available on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. And we're back with Eliza Schlesinger. Okay, Catherine, what do we have? What's happening? We actually have two Blakes today. Oh my God.
Starting point is 00:38:44 Is it with Blake Lively calling in for advice? If she calls in one more time, I swear to god. She's like, I'm your neighbor, Chelsea. My god. 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.
Starting point is 00:39:06 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?
Starting point is 00:39:27 I don't know what to do. Hi. Hi, Blake. Hi, Blake. I think you're muted. I think you're muted. It's the carrot at the bottom next to the microphone. Got it.
Starting point is 00:39:37 Ah, look at that. Hi. That's one millennial helping another. Just doing what I can. Hi, Blake Lively. How are you? I'm good, thank you. How are you guys today?
Starting point is 00:39:47 We're so tired of hearing about you, Blake Lively. Okay, so your wife's parents, they know you're trans. Correct. And that's the big issue? Yeah, when her and her ex-husband, he got mad and he went and told her family about me. Doesn't matter. Were you guys having an affair?
Starting point is 00:40:08 No. So what does he, I'm confused. Why was he even in the picture? Just a jealous ex. 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 do?
Starting point is 00:40:20 He started dating and then he was like, well, I'm still bitter about this. Oh, so he went, oh, oh. 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 micro penis.
Starting point is 00:40:33 And are they, they're nice to you other than what you're talking about? Like, is it civil when you see them? 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.
Starting point is 00:40:57 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 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. That's exactly right. And to just be like this great person in their lives and show all your great qualities and not judge them for their ignorance. That's right.
Starting point is 00:41:21 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 fuck. 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.
Starting point is 00:41:38 You know what I mean? That's on them. I think, because it's 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 perceived That you're being treated like there's a weight to that if someone says anything to you You're always gonna be wondering is it because I'm trans in the way that we're like is it because I'm a woman is it?
Starting point is 00:42:00 Because of my color is it because of this whatever 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, it 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,
Starting point is 00:42:27 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 wanna 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
Starting point is 00:42:45 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. Like prove them wrong, basically. Yeah, I mean, what do they think? The knock is that you used to be a woman
Starting point is 00:43:02 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.
Starting point is 00:43:16 You are probably the only trans person they know. I was, yeah. Oh, is there another, is your wife now trans? 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 we live in the woodworks. But yeah, I'm still the only one they personally know.
Starting point is 00:43:41 This is the only one fucking their daughter. Yeah, that's right. That you know of, yeah. I was the only one fucking their daughter. Yeah, that's right that you know of yeah, I Sure, hope so 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 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. Yeah, and just rise above that. You know what I mean?
Starting point is 00:44:08 Their problems are not your problems. You should just, it's almost like anything, any feelings or opinions they have about you is just not even part of who you are. It has nothing to do with you. You wanna move through the world and move through your relationship with them just as a nice beacon of light,
Starting point is 00:44:25 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, maybe it's hurtful of course, but as long as it's not abusive or they're treating you in an unkind way,
Starting point is 00:44:52 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
Starting point is 00:45:09 rather than having that be some sort of onus though, it kind of gives you a sense of purpose. 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.
Starting point is 00:45:22 So like, and the good news is you don't have to worry about anything because like men don't do anything. Like you don't have- Do to borrow a ladder? Like you're their son-in-law. So like, and the good news is you don't have to worry about anything, cause like men don't do anything. Like you don't have to. Do you have a ladder? I have a step ladder. No, you're a grown man. Go get you a ladder from the home depot.
Starting point is 00:45:33 I think you need to get a real ladder. I just hired people so I don't need ladders. Okay, well then hire someone to bring them a ladder, I think is what Eliza is saying. 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?
Starting point is 00:45:50 Bring a level. Just start seeing if everything's, just start critiquing all the masculine stuff. And then you take the stud finder and you put it to your own chest and you're like, found one. Here I am. That's literally what I can do.
Starting point is 00:46:02 Okay. Well, I mean, that's one step in the right direction. Just be above it. Thank you. Yeah. I have a question for you. Are you guys affectionate in front of her family? We don't hide it.
Starting point is 00:46:13 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. This holiday season, it's time to amp it up. And the holidays are right around the corner because we're in March. Yeah. So get ready.
Starting point is 00:46:28 Plenty of time to prepare. Yeah. A lot of caressing, a lot of neck kissing. Just let them know. On the ladder. You want to do all of this on the ladder. While critiquing everything, right? Yes.
Starting point is 00:46:41 Just be a man. But you know what we're saying, right? You got what we're saying, Blake. With all of the toxic masculinity going around on the news right now, I think I can convey some of that. Thank you. Great. That's what this is. That's the answer. This is what we want. It. Make Ontario great again. You know what? Canada might be the best state if it happens, guys. Welcome. Welcome number
Starting point is 00:47:04 fifty-one. Welcome number 51. Don't worry, Chelsea already has a place here. So it's not even like she's really has to move right? It's not like I'm even emigrating. I'm just like going from one- Do you have a Canadian passport? I don't, I have a house in Whistler, Canada, but I don't have a passport.
Starting point is 00:47:17 She won't need one when she's moving in. But I can marry a Canadian if I have to, but I don't need to marry a Canadian. No, yeah. Everyone knows always like before the election, it 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.
Starting point is 00:47:34 I don't think he can get that tan up north. He can't get it here. It's not a real tan. It's from a bottle. No, that's what I mean. But we don't sell it here. So I don't know. Well, especially if it's American made, you won't be.
Starting point is 00:47:45 RFP Tito's vodka. Sorry about that. Anyway, Blake, good luck with everything. Congrats. Thank you so much. Congrats on your relationship. And I think you're gonna, I think you're actually gonna be a great example
Starting point is 00:47:57 for your in-laws and that whole family to, you know, open minds and expand horizons. Well, thank you. I appreciate everything guys. Okay, take care. Thanks Blake. Bye. I couldn't resist taking a bite of that.
Starting point is 00:48:10 It was like calling my name. All right, onto our next Blake. Oh, this is Blake, back to back Blake. 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?
Starting point is 00:48:25 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 Condé Nast portfolio, produced for Hillary Clinton and Stacey Abrams, and even helped Applebee's Snag a Can Lion. Feels like his LinkedIn bio. Seriously, dude. I mean, you know. Look at his board back there. But despite all this, I've hit a wall of unfulfillment.
Starting point is 00:48:54 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.
Starting point is 00:49:11 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 dewy high camp, and I've 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.
Starting point is 00:49:50 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. Hello, hello. Hi Blake. Hi Blake. Hi Blake. Hello, hello. Hi Blake.
Starting point is 00:50:06 Hi Blake. Eliza, do you wanna take this? This is our special guest, Eliza Schlesinger. Hello, hello, I'm very familiar. Was that good? No, in a good way, in a very good way. I mean, I am no stranger to the analysis paralysis, but also the actual act of putting one foot
Starting point is 00:50:24 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?
Starting point is 00:50:42 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 your creature comforts outweigh that? Some people are, for me it is paramount,
Starting point is 00:51:04 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? 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.
Starting point is 00:51:23 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
Starting point is 00:52:09 that would be because I'm doing it at night. I'm doing it on my lunch breaks at my full-time job. It's it you're writing a scripted show. There's only two scripted shows. Yeah, two scripted shows right now. 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 show runner, 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. Yeah, I mean, that's what I'm getting from you.
Starting point is 00:52:39 You're doing all of it. And I mean, I think you're looking for like a way out of doing all of it together, 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.
Starting point is 00:53:04 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.
Starting point is 00:53:27 And the good news is you have that fire in you, but I'm gonna 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.
Starting point is 00:53:44 Oh, she had a baby. And then they'll pick it up, but we're gonna do it in the summer. Okay, well, it's actually gonna 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
Starting point is 00:54:00 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. To make a deal for a show you had not created. Hadn't created, it was a blind script deal
Starting point is 00:54:14 and in the end we didn't take it. It 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. Yeah, and that's kind of where I think I felt inspired to write in because I actually, I'm loving this process.
Starting point is 00:54:34 I never thought, I wanted to get it in descriptive, 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 seemed so simple. And I actually fell in love with the writing process, and it became really great. And then, you know, 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
Starting point is 00:54:55 fun and exciting. But, you know, 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 like 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 It's not a 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,
Starting point is 00:55:28 but there's actually very little to be done once you've written it. And it's gonna 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,
Starting point is 00:55:42 and this industry is moved so slowly. So the hardest thing to do is nothing. And that's what's happening right now. You just got to 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.
Starting point is 00:55:57 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 slowly start to take off. Yeah, Sean Hayes once gave a piece of advice that was like, he for himself when he was coming up, he said, and I think he actually still does this, but do one thing every day
Starting point is 00:56:19 that's toward the career you wanna have. So 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. 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,
Starting point is 00:56:45 do you have a rep, do you have reps? No, I don't. That's the other thing. You gotta get that rep. I've always been in-house, like when I was at Con Day, 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.
Starting point is 00:57:00 And I got advice earlier on that was sort of like, 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 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 wrapped, 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- 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
Starting point is 00:57:19 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 tugging away. Like 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,
Starting point is 00:57:38 or it's like overwhelm or I don't know what to do next. It's like- No one's coming to save you. Yeah. What's your next step? You have two scripts? So I have two concepts. I'm starting to script them right now.
Starting point is 00:57:50 Cause 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.
Starting point is 00:58:06 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. No, it is scripted for sure. One of them's a thriller drama, one of them's a dramedy. So I think they're- And these are hour long? Both of them are eight episodes, one hour each per season.
Starting point is 00:58:24 Not only do you need the script, I mean, you can do a pitch. Some people are for 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.
Starting point is 00:58:39 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 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? Yeah, I was planning on writing it.
Starting point is 00:58:52 I sort of was getting into like putting the pitch material and series Bible together. And then I've been getting feedback and people are like, oh, you sort of just need more of a script with this as well. 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
Starting point is 00:59:14 It's bulletproof then give it to your rep who will give you their critiques and then you go from there But you got a you have to actually write it. Otherwise, you're just a person who says that they're a writer Yeah, I don't call myself a writer. I know I'm a producer, and I think that's been the other hesitation is like, I've done producing, I've directed a little bit, but writing is very, I haven't done it since college. And this is actually something
Starting point is 00:59:38 that I'm finding I'm falling in love with. Enjoy it, enjoy falling in love with it. Thank God Eliza was here today. She's giving you great advice. I can't tell you that I've read Save the Cat in love with it. Thank God Eliza was here today. She's giving you great advice. I can't tell you that I've read Save the Cat in a long time. Their screenwriter podcast, like write it and then you'll rewrite it and then step away.
Starting point is 00:59:54 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. That's fair enough. Any kind of Bible. Heard, heard.
Starting point is 01:00:07 Heard, heard, heard. Okay, well, thanks for calling in. I mean, that's some good advice. So good luck with everything. Beautiful, thank you all so much. Check back in in like six months, Blake, okay? Yeah, let us know how you're doing. Yeah, from your mansion after you sold the show.
Starting point is 01:00:22 And I'm jealous. I wish, so awesome. Thank you all so much I appreciate it. Bye It's such a it's such a brutal that was good I'm like, I don't fucking know what to tell you. I don't really know Let's put one foot front like all I can say is hustle hustle hustle But it's like that was good too because it got into specifics Yeah, it's it's But it's like, that was good too, because it got into specifics. Yeah, for sure.
Starting point is 01:00:45 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,
Starting point is 01:01:00 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. Yeah. This is hard. Let's take a quick break and I have a little wrap up question. Great.
Starting point is 01:01:13 We'll be right back with Eliza. I keep saying Schlesinger. We'll be right back with Eliza Schlesinger. Is Hanley really Schlesinger? Schlesinger. Is it grr? Yeah. I've been saying Eliza Schlesinger. I know. I'm so sorry. Everybody does. Oh my God. It's Eliza Schlesinger? Schlesinger. Is it gr? Yeah. I've been saying Eliza Schlesinger. I know.
Starting point is 01:01:26 I'm so sorry. Everybody does. Oh my God. It's Eliza Schlesinger, everybody. Schlesinger. It's Eliza Schlesinger. There you go. Now you're Jewish.
Starting point is 01:01:34 Eliza Schlesinger. I'm so sorry. Isn't it so much better that way? Yeah, it is. Schlesinger. Nope. No. That was a test. Our iHeart Radio Music Awards are coming back Monday, March 17th on Fox, starring Bad Bunny,
Starting point is 01:01:53 Glowrilla, Kenny Chesney, Money Long, Nelly, your host, iHeart Radio, LL Cool J, are you guys ready to have some fun tonight? Plus iHeart Innovator Award recipient, Lady Gaga,. I Heart Icon Award recipient, Mariah Carey. And I Heart Breakthrough Award recipient, Gracie Abrams. Watch live on Fox, Monday, March 17th. At 8, 7 Central. Do you remember what you said the first night I came over here?
Starting point is 01:02:19 How goes lower? From Blumhouse TV, I Heart Podcasts, and Ember 20 comes an all new fictional comedy podcast series. Join the flighty Damien Hirst as he unravels the mystery of his vanished boyfriend. And Santi was gone. I've been spending all my time looking for answers about what happened to Santi.
Starting point is 01:02:38 And what's the way to find a missing person? Sleep with everyone he knew, obviously. Hmm, pillow talk. The most unwelcome window into the human psyche. Follow our out of his element hero as he engages in a series of ill-conceived, investigative hookups. Mama always used to say,
Starting point is 01:02:53 God gave me gumption in place of a gag reflex. And, as I was about to learn, no amount of showering can wash your hands of a bad hookup. Now, take a big whiff, my brah. Listen to The Hookup on the iHeartRadio app, Apple podcasts, or wherever you listen to your favorite shows. I started to live a double life when I was a teenager,
Starting point is 01:03:20 responsible and driven and wild and out of control. My head is pounding. I'm confused. I don't know why I'm in jail. It's hard to understand what hope is when you're trapped in a cycle of addiction. Addiction took me to the darkest places. I had an AK-47 pointed at my head. But one night, a new door opened, and I made it into the rooms of recovery. The path would have roadblocks and detours, stalls, and relapses. But when I was feeling the most lost, I found hope with community, and I made my way back.
Starting point is 01:03:58 This season, join me on my journey through addiction and recovery, a story told in 12 steps. Listen to Krems as part of the Michael Udda Podcast Network, available on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hey y'all, it's your girl, Cheekies, and I'm back with a brand new season of your favorite podcast, Cheekies and Chill.
Starting point is 01:04:23 I'll be sharing even more personal stories with you guys. And I know a lot of people are gonna attack me. Why are you gonna go visit your dad? Your mom wouldn't be okay with it. I'm gonna tell you guys right now, I know my mother. And I know my mom had a very forgiving heart. That is my story on plastic surgery. This is my truth.
Starting point is 01:04:42 I think the last time I cried like that was when I lost my mom. Like that, like yelling. I was like, no. I was like, oh, and I thought, what did I do wrong? And as always, you'll get my exclusive take on topics like love, personal growth, health, family ties, and more. And don't forget, I'll also be dishing out my best advice to you on episodes of Dear Cheekies.
Starting point is 01:05:05 So my fiance and I have been together for 10 years. In the first two years of being together, I find out he is cheating on me, not only with women, but also with men. What should I do? Okay, where do I start? That's not love. He doesn't love you enough. Because if he loved you, he'd be faithful. It's going to be an exciting year, and I hope that you can join me. Listen to Cheekies and Chill, season four, as part of the My Kultura podcast network
Starting point is 01:05:30 available on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. And we're back with Eliza Schlesinger. There you go. That's totally the way to do it with a pause in the middle. I like it. Like a hyphen. Yup. Em you go. That's totally the way to do it with a pause in the middle. I like it. Like a hyphen. Yup. Emphasis.
Starting point is 01:05:48 Yeah. Not an umlaut, a hyphen. I wish. I wish I came from a culture that had umlauts. We're anti-umlaut. Oh, we are? I think so. Umlauts haven't been canceled.
Starting point is 01:05:56 This writer says, Dear Chelsea, my 97 year old neighbor of six years who is thriving calls me Kimberly. My name is Kendall. Do I tell her? Xoxo Kendall. No. No. No, just tell her your name is Eliza Schlesinger. And she'll have an aneurysm trying to pronounce it.
Starting point is 01:06:14 No, I love that she calls you the wrong name. That's fun. Have fun with it. Yeah, what's to be gained? Yeah. How much longer could she possibly be calling you by this name? Okay, Eliza, everybody can watch Eliza Schlesinger's new special. It's on Amazon Prime, okay?
Starting point is 01:06:32 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? Probably. I mean, I don't even know how to get on Facebook at this point. Can I plug my podcast? Yeah, absolutely. Because my producer and co-host is always like, you need to tell people you have a podcast.
Starting point is 01:06:50 It's called Ask Eliza Anything. And by the time this comes out, we will have our new home on Lemonada. And what we do here is the audience is the guest. So we give life advice. Perfect. Oh my God, how funny. Yeah. So Ask Eliza Anything. Check it out.
Starting point is 01:07:05 Love it. Thank you, Eliza. Thanks for having me, Chelsea. Thank you. Thank you. Yeah. Do do do do do do. Drum roll, Catherine, please.
Starting point is 01:07:15 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 help out of this country. And it's not as easy as you think. So I'm coming to Reykjavik.
Starting point is 01:07:39 I'm coming to Dublin. I am coming to the UK. I'm coming to Brussels, Paris, Belfast in May and June. I'm coming to Oslo, Stockholm, Copenhagen, Manchester, London, Glasgow, New Zurich, Vienna. I've never ever been to Vienna. Berlin, Barcelona, Lisbon. I'm coming. Abroad is abroad.
Starting point is 01:08:03 That sounds like fun. I'm going to go see you abroad. I know. I want to go see me abroad. There I'll coming. Abroad is abroad. That sounds like fun. I'm gonna go see you abroad. I know, I wanna go see me abroad. 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.
Starting point is 01:08:22 If you'd like advice from Chelsea, shoot us an email at dearchelseepodcast.gmail.com and be sure to include your phone number. Dear Chelsea is edited and engineered by Brad Dickert, executive producer, Catherine Law. And be sure to check out our merch at ChelseaHandler.com. Are you hungry? Colleen Witt here and Eating While Broke is back for season four every Thursday on the Black Effect Podcast Network.
Starting point is 01:08:48 This season, we've got a legendary lineup serving up broke dishes and even better stories. On the menu, we have Tony Baker, Nick Cannon, Melissa Ford, October London, and Carrie Harper Howie turning Big Macs into big moves. Catch Eating While Broke every Thursday on the Black Effect Podcast Network, iHeart Radio app, Apple Podcast, wherever you get your favorite shows. Come hungry for season four. Do you remember what you said
Starting point is 01:09:14 the first night I came over here? Ow, goes lower. From Blumhouse TV, iHeart Podcasts, and Ember 20 comes an all new fictional comedy podcast series. Join the flighty Damien Hirst as he unravels the mystery of his vanished boyfriend. I've been spending all my time looking for answers about what happened to Santi. And what's the way to find a missing person?
Starting point is 01:09:33 Sleep with everyone he knew, obviously. Listen to the hookup on the iHeartRadio app, Apple podcasts, or wherever you listen to your favorite shows. Dressing. Dressing. Ohressing, dressing. Oh, French dressing. Exactly. Ha ha, oh, that's good.
Starting point is 01:09:50 I'm AJ Jacobs and my current obsession is puzzles. And that has given birth to my podcast, The Puzzler. Something about Mary Poppins? Exactly. This is fun. You can get your daily puzzle nuggets delivered straight to your ears. Listen to the puzzler every day on the iHeartRadio app, Apple Podcasts, or wherever you get your
Starting point is 01:10:12 podcasts. Hi, I'm Bob Pipman, Chairman and CEO of iHeartMedia. I'm excited to introduce a brand new season of my podcast, Math and Magic, Stories from the Frontiers of Marketing. I'm having conversations with some folks across a wide range of industries to hear how they reach the top of their fields and the lessons they learned along the way
Starting point is 01:10:31 that everyone can use. I'll be joined by innovative leaders like chairman and CEO of Elf Beauty, Tarang Amin. Legendary singer-songwriter and philanthropist, Jewel. Being a rock star is very fun, but helping people is way more fun. And Damian Maldonado, CEO of American Financing.
Starting point is 01:10:47 I figured out the formula is you have to work hard, then that's magic. Join me as we uncover innovations in data and analytics, the math, and the ever-important creative spark, the magic. Listen to Math and Magic on the iHeart Radio app, Apple Podcasts, or wherever you get your podcast.

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