Life Will Be the Death of Me with Chelsea Handler - Minisode: Big Boyfriend Problems with Yamaneika Saunders

Episode Date: July 11, 2025

A positive update from a favorite trans caller.  Then: A new boyfriend’s nether-regions overwhelm.    * Need some advice from Chelsea? Email us at [e-mail] * 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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Bell. Connection is everything. I survived nine months in captivity, and I've spent my life exploring how other people survive what should have destroyed them. I'm Elizabeth Smart, and these are The Survivor Files. Every week, I'm with survivors who lived through the unthinkable, abducted, stalked, controlled, and nearly silenced. These are stories about what it takes to make it out alive. Listen to The Survivor Files with Elizabeth Smart on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

If your bookshelf and your For You page are equally important to your personality, welcome home. Pro Society is a weekly podcast that's part book club, part group chat for anyone who thinks Pride and Prejudice and Love Island deserve the same level of discourse. Each week, we're connecting the dots between books, the internet, and pop culture with your favorite writers, book talk creators, and plenty of overthought opinions. Yeah, I'm obsessed. I'm obsessed. Listen to Pro Society on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm Hoda Kotb, host of the podcast Joy 101 with Hoda Kotb. You know, I'm always searching for inspiration and useful tools to maximize joy.

Like when my friend Henry Winkler offered advice to aspiring actors and really anybody hoping to stand out. You're not hired just to fill time and space. You're hired to fill the space with you. Listen to Joy 101 with Hoda Kotb on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hi, welcome to a mini episode. These are our mini-sodes. We have a special guest on our mini-sode. Her name is Yamanika Saunders.

Hi, Catherine. How are you today? Hi, Chelsea. Hi, Yamanika. Hi, Yamanika. Hi, Yamanika. Hi. I adore you guys.

You're so crazy. I'm good. I'm so good. Okay, bye. Bye. Okay, Catherine, what do we got with Yamanika today? All right. Well, our first thing that we have up is a follow-up from a wonderful caller we had,

Witt, who called in on our John Lovett episode. He was wrestling with whether or not to reveal to his longtime girlfriend's family that he's trans. Okay. So I checked in with him, and Witt said, oh, my goodness, hi. It's really nice timing to hear from you and give you an update. We ended up telling them, well, my partner did, in a very casual conversation back in November. Long story short, they received it very well, were honored that we trusted them with the information enough to tell them, and also said it would have been okay had we chosen not to tell them.

At first, I thought, oh, damn, maybe we didn't need to say anything, but ultimately, it was a huge weight off my shoulders. Yeah. Never in the moment, never, and he was worried about like, well, are they going to ask awkward questions? Never in the moment, nor since then have they asked any inappropriate questions and really just were happy that my partner was happy and could see the genuine love between us. And this week I proposed and we're now engaged. Prior to asking her, I had a conversation with her parents about my intentions, hoping

to have their support. They were nothing but thrilled and happy to welcome me into the family. Thank you for this insight. It helps make the decision based on what I really wanted without thinking about what their reaction would be. But it also helped me have conversations with others about the sensitivity of the topic should they be on either side of the conversation. Thanks again. Come to Canada for the wedding. Cheers, Wit. Wow, that's nice. That's a nice result. But what would they tell? Because her family didn't know that he was trans and she didn't-

The partner's family, yeah. The partner's family, his girlfriend's family didn't know that he was trans and they didn't know if they should tell them or just like leave it off the table. And I don't even remember I think I said to have her do it in a casual way if they feel inclined right like yeah they don't need to know that he's trans but like if they want to tell him that it's not really his I don't remember what the fuck I said quite frankly you know that's exactly what you said you were like if you feel you need to and I know it was this sort of thing where some things were coming up where it's like oh we're going on a beach vacation together soon so people are going to be in you know swimsuits and I will too and like there are scar you know different

things that he was like I don't know if I need to explain this ahead of time sort of thing Yeah, people be having scars and shit. I got keloids all over the place. Yeah, well, that's a little bit different than being trans, but okay. Shut up! Plus, from $94 a month, price guaranteed for two years on internet with a two-year term and auto pay credit. Visit bell.ca for details and to check availability. Bell. Connection is everything.

When I was 14 years old, I was kidnapped and held captive for nine months. I survived, and I've spent my life exploring how other people survive what should have destroyed them. I'm Elizabeth Smart, and these are the Survivor Files. I just remember this low, taunting voice next to my ear saying, shut up, don't say anything. Every week, I'm with survivors who live through the unthinkable. I knew if he woke up, without a doubt, he was going to hurt me. I started feeling that there was someone at the end of my bed, and I just started screaming. They are abducted, stalked, controlled, and nearly silenced.

but these aren't stories about what's taken from them. They're stories about what it takes to make it out alive. Listen to The Survivor Files with Elizabeth Smart on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. If your bookshelf and your For You page are equally important to your personality, welcome home. This is Prose Society, the weekly podcast

that's part book club, part group chat for thought daughters, pop culture obsessives, and anyone who thinks Pride and Prejudice and Love Island deserve the same level of discourse. I'm Eli Rallo, and every week we're connecting the dots between books, the internet, and the conversations everyone can't stop having. I'm going to have to look up this story. I'm obsessed. I'm obsessed. From bestselling authors and your favorite book talk creators to the latest pop culture moments, nothing is off the table.

It's like if you can hide some real messages inside compelling characters, then that is a Trojan horse. Whether you're looking for literary deep dives, smart pop culture conversations, or a community of readers who love to think a little too much, you're in the right place. Listen to Pro Society on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. See you between the pages. On the new podcast, Solita, we share the messy reality of traveling alone as a woman. I can wait four hours for the next bus or this random dude is offering me a ride on his motorcycle. I chose option B.

I'm Julie Pinheiro, and I travel by myself because it's a rare space where I can say yes without asking anyone else first. I'm on a mission to reclaim the word solita, trading the pity for possibility. Every time I tried to be alone, I kept meeting people and they were like, you smiled at us. Not a lot of people smile around here. It's when you're alone that you're most receptive to the world as it is and not the lies you're sold about it. It can be a time where you push your limits, change your mind, or wake up to a new version of yourself. So whether you're a solo travel veteran or you're too nervous to book your first trip, I hope you listen to Solita on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Anyway, anything else, Catherine?

Well, we do have a caller, and Yamanika, I'm very interested to hear, well, actually, both of your advice on this. Okay. Here we go. So Michelle says, Dear Chelsea, I've had your email address saved in my drafts for like two years. I've had many things that I've wanted to consult with you about, but things come and go. I'm currently reading your newest book. I'll have what she's having and wanted to tell you how much I love it. I just read the chapters on Poopsie, Woopsie, and Oopsie and shed a tear.

This coming from a girl who never cries. I do have one dilemma currently in my life, and if you've ever experienced this, maybe you'll have some insight. I just started dating a man who seems great on a lot of accounts, except for one small or not-so-small problem. He has a really huge penis. I don't say that in a lighthearted way or a joking way about how some women want a big cock. I joke with him and tell him he has a double dick. It's literally double the girth of a quote-unquote normal penis.

We've tried to have sex a couple of times, but it just doesn't work. If it goes in, it hurts after a few seconds for me. He's age-appropriate, has an education and a good job, and is loving, sweet, and communicative. So I would love if this would work, but I also can't wreck my body for it. Any advice or experience, Michelle? God, I've never had a penis that was so big that it didn't fit, that it didn't hurt. So you can't even get it. And are you, like, lubricated and ready to rumble?

Yeah, I mean, we've tried it a few times. I mean, I can't even get my hand around it. Oh, God, that's too big. That's too much. I mean, hello, what do you have to say, Yamanika? Have you ever experienced a penis that was too big for your Pikachu? The ways in which my vagina has other stories that could be told is crazy. The way in which your vagina can adapt to a large penis?

Is that what you're trying to say? I have a very tight vagina, okay? And so a lot of times it's hard for things to get in there. But I also have a competitive go-getter spirit. and does he know that he is too like are you you've told him this right you know he's like he played it off at first like it's not that big come on and i'm like what after a few times i'm like has this been a problem in the past and he's like yeah it's been a problem and he feels bad and he really is trying and i am trying and we haven't had one successful session um how did that go yeah

what was going on there do that so well i i think it's like a combination i quit drinking for about a year just it just wasn't serving me but i decided i needed to try drinking again yeah yeah well yeah he got that hennessy dick so i had a few drinks i also did some research and i found this herb called damiana and basically it's like a supplement that you take every day and it's supposed to help your lining and your wetness and everything. And I feel like the combination of that, my nerves were settled a little bit from the alcohol and not being nervous at this thing coming at me. And it still hurt a little bit. And I feel like if we keep trying, I'll just adapt more. But it's huge. I believe you. I believe that it's very big. And I understand

that that's unpleasant. But if you really like this guy, I mean, you can warm up your vagina to a bigger penis. It works. You know what I mean? Like you can get your vagina acclimated. I just worry after the honeymoon phase is over and you're really like, then what do you do with that big dick that's coming at you all the time, you know? Well, I'm more worried like if I move on to another person. Not that that's the plan. No, it retracts. It retracts. Yeah, don't worry. It goes back. It's like when you have a baby, your vagina goes back. You know what I mean? Like it can recover from a big dick. I've definitely had bigger penises

and then it's gone down and it's like, oh, I can still feel when I have sex with somebody who doesn't have such a big penis. It's not like my vagina is stretched out, you know? Can you close your mouth?

Are you getting ready to open your mouth and put that dick in your mouth? Because it looks like you want a dick in your mouth right now. Is that what you want? I was just, I didn't,

I looked at you the second you said something about your pussy being stretched out. God bless whatever's going on. you have to be comfortable with him it's you know and like I agree with everything Chelsea said after the honeymoon phase and you got to keep you know what I'm saying seeing him around with this nonsense it's gonna be like get out of here you know scram you and your penis got to get out of here but I've never had a dick that I there's been times that I definitely thought

maybe I felt him in my throat but never a dick that like made me tap out I feel bad for him I mean, this won't even go down my throat further than this. And the thing is, it's more like triangular shape. So, like, the base is wider. Oh, God. Oh, okay. I've never seen anything like it. And you're really, are you really into him?

I really like, everything else about him is great. And it's so rare for me to find. Yeah, tell him to eat it first and then see what happens. Yeah, he does. Yeah, he got to put, okay, yeah, he got to put the work in. Yeah. Oh, my God, this is a real dilemma. I wish we knew how to open up your Pikachu more.

Yeah. Well, have you tried a lot of different positions and, like, lots and lots and lots of lube? Yes. Yes, both. And so I think we've ruled out that we cannot do mission. It's just, it goes too deep. And, like, from behind is perfect because it can't go in all the way. Yeah.

And you can kind of move so it's not, like, going as deep sort of thing. Yeah, yeah, yeah. Okay. You know. Well, that's progress. Yeah. I like that. At a certain age, you like doggy style.

You ain't got to look at them. You can do other things. You can do your accounting. Yeah. You can go through Instagram. Yep. Yeah, yeah, be one hinge looking for another man with a smaller dick. You know, you could do all this kind of stuff.

Exactly. But I've got that same go-get-em attitude. Like, I want to. Yeah, yeah. I mean, I hope it works out. I wish we had better advice for you. Well, this, I mean, if anyone has the same problem. It's called Damiana?

Damiana. I feel like this is really helping me. Okay, so that's to get your juices flowing a little bit more. Like, loosen things up. Yeah, because I am at, like, a perimenopause age, too. Yes, of course. And everybody, there's a lot of people that can't have sex when they're going through perimenopause where it feels like razor blades. Like, you really want to.

Also, are you on estrogen and progesterone? No, I can't take any hormones. Oh, you can't? Mm-mm. So you're supposed to just go through perimenopause with no help? I don't ever want to get to the point where Dick feel like razor blades. I know, but sometimes that can happen when you go through perimenopause. So she needs all the help she can get.

I'm at perimenopause. I know. I know. I'm the one who told you you were. I knew I was at perimenopause the day before you told me. Okay. Somebody, you told me second, not first. Okay.

This is not about you. This is about our caller. She's got an amazing problem. I know. She has the biggest penis in the world. You do have a good problem, okay? Oh, man. I really feel for this guy because if it's been a problem before, like, I know girls

who can't deal with big dicks either. Like, I've heard this story before. I don't know if it's the same guy. but anyway i mean i wish i wish you well i wish you luck and i hope that it works out for you guys i hope it does thanks yeah okay yes blessings to y'all blessings yeah you need a blessing okay take care you too bye and that concludes our minisode for today i think right katherine i think we're done with yamanika here she's sitting here did you see her mouth open as soon as this woman described the dick and the girth of it did you see yama's mouth just become a jar it was open

waiting for this she was ready to receive it immediately you open your mouth i mean that's what kind of sick fuck you are if you didn't have any type of reaction to what she was describing there's something wrong with you there's a whole lot wrong with you i had a reaction i didn't open my mouth that wasn't my reaction about it it was so much to think about i couldn't even hold my mouth out i want to thank you for having me thank you for coming bye so i added a couple of new dates i'm not on tour yet but i added a couple of dates just because i felt like we need a little bit more laughter and a little bit more medicine for the end of the year and i was wrapping things up but i thought maybe let me do a couple more so i'm adding three more dates in addition to my vegas

residency. I'm doing West Hampton Beach, August 21st. I'm headlining the Rochester Fringe Comedy Festival, September 13th. And I will be in Napa on October 3rd. So those will be my last dates of the year. Do you want advice from Chelsea? Write into DearChelseaPodcast at gmail.com. Find full video episodes of Dear Chelsea on YouTube by searching at Dear Chelsea Pod. Dear Chelsea is edited and engineered by Brad Dickert, executive producer Catherine Law. And be sure to check out our merch at chelseahandler.com. I survived nine months in captivity, and I've spent my life exploring how other people survive what should have destroyed them.

I'm Elizabeth Smart, and these are The Survivor Files. Every week, I'm with survivors who lived through the unthinkable, abducted, stalked, controlled, and nearly silenced. These are stories about what it takes to make it out alive. Listen to The Survivor Files with Elizabeth Smart on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. If your bookshelf and your For You page are equally important to your personality, welcome home.

Pro Society is a weekly podcast that's part book club, part group chat for anyone who thinks Pride and Prejudice and Love Island deserve the same level of discourse. Each week, we're connecting the dots between books, the internet, and pop culture. with your favorite writers, book talk creators, and plenty of overthought opinions. Yeah, I'm obsessed. I'm obsessed. Listen to Pro Society on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm Hoda Kotb, host of the podcast Joy 101 with Hoda Kotb. You know, I'm always searching for inspiration and useful tools to maximize joy.

Like when my friend Henry Winkler offered advice to aspiring actors and really anybody hoping to stand out. You're not hired just to fill time and space. You're hired to fill the space with you. Listen to Joy 101 with Hoda Kotb on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. A podcast about what happens when a small town becomes the site of a social experiment and fights back. Guess you didn't move in on a bunch of dumb hillbillies now, did you? Listen to Our Town on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

This is an iHeart Podcast. Guaranteed human.