Dear Chelsea - From Cute to F*ckable with Dylan Mulvaney

Episode Date: April 10, 2025

Back by popular demand, it’s Dylan Mulvaney!  Dylan reveals how Chelsea helped her have her first kiss as a girl, who she’s looking for on Raya, and who in the room is a whore on the loose.  Then: A crush on a friend turns into deeper soul-searching.  A newly-married woman wonders how to support a single friend.  And non-binary babe struggles to feel like themselves out in the world. * Order a signed copy of Chelsea’s new book HERE! * 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.

Hi Katherine. Hi Chelsea. Hi, hi, hi. How's everybody doing? Good. You know what, I actually saw our friends Allison and Darling in New York last week. Oh did you? I did. Allison and Darling, yes, they're taking the town by storm. Everyone who's listening, please, this is a reminder that if you tag me when you're watching my special, my new special The Feeling on Netflix, where I wear my gold one piece, which is my golden anniversary year. I had no idea between gold bond that I was wearing gold, gold bathing suit and then my special, which I taped way before I turned 50, I was wearing my gold jumpsuit and this is my 50th year. So everything is gold and that's your golden anniversary.

So it's my anniversary with myself. I love that. I know. So please tag me for the special because I get so many tags about my books, but I'm not getting as many about my special and my special is the newest thing out. So I want to make sure all my ardent fans are watching it and tagging me and I'll repost you and yes, it's called the feeling. I love it. And Chelsea, we also wanted to ask for more couples and duos to call in or to write in for Minisodes. Yes, if you're having a, even if it's a friendship like kind of disagreement or

a relationship disagreement, we want you guys to call in for couples advice. We're going to do that on our Minisodes as well too. And also everyone can check out my European dates. I start in Reykjavik, I'm in May and I end in Lisbon, Portugal at the beginning of June. So come see me in Europe if you're one of our European fans. Also, if you guys want another inspiring book to read, I Am Maria by Maria Shriver just came out and it is beautiful. It's a book of poetry. I'm not really, but it's not your traditional poetry.

It's like stream of consciousness poetry. And there's a foreword by her about everything she's experienced in her life that is so moving. And it just blew me away. I read the entire book last night on my sofa. Yeah. Well, I just finished Dylan Mulvaney's new memoir. Yes, I've read that. Of course, for our new guest. I mean, it's so, I mean, obviously, you know, we read a lot of celebrity memoirs on the show.

And I think it's one of my favorites that I've ever read. Like, it's so beautiful it's funny, it's light, it's refreshing, like it's honest, it's great. Yeah it's a great read just like Dylan herself. She's a great read. And her brand new podcast, The Dylan Hour, just launched. I actually worked on it. It was so much fun. It has amazing episodes. It's so fun and kitschy. It's really fun to watch on YouTube also because it's like 60s themed and it has a whole pink set and it's really sweet. I would start with either like the Norrie Reed episode. It's really, really fun. There's an episode with her dad that's really touching and really fun. She's got an episode with Glennon Doyle. Go check it out. The Dylan Hour.

Which brings us to our guest. Please welcome Dylan Mulvaney. Oh, look at you. Look at how you handled that microphone, Dylan. Wow. I'm a podcaster now. Wow. Back by popular demand. Wow. By very popular demand is our favorite transgender woman,

our favorite transgender person, Dylan Mulvaney is back. Oh my God. And we have a lot of catching up to do. We have a lot to talk about. Because you've been hanging around with a lot of my friends. I saw Alan Cummings, you posted a lot of catching up to do. We have a lot to talk about. Because you've been hanging around with a lot of my friends. I saw Alan Cummings, you posted a picture of you guys last night.

I'm like, where is everybody? Well, I, more importantly, the last time I was on this podcast, the last thing I asked you, I hadn't been kissed as a girl yet. And I was like, should I do it? And you were like, yeah, hurry the fuck up. And I did accomplish a lot of that

since we last saw each other. But what I'm about to show you is very important because I was in Paris and this was, Alan Cumming was included in this evening and I went clubbing with a bunch of people like from a conference and I left the club looking like this. And I just wish that for our audio listeners that they would really get to see this. But can you describe what you see? Well, we can hold it up. Can I hold this up to a camera? Can you see that? This is Dylan. That's me leaving the club at five a.m. Looking like a whore on the loose.

This is what I would call summer whore. When you have the hot pink lipstick, it's all around her face. But that was once like maroon. And then it went, it's all around her face. No, but that was once like maroon. And then it went, it's giving clown. This is ridiculous. But basically I went into the club with- And sucked face with everyone you saw. And just one, just one. And he really did a number on my makeup.

Your face looks like my head right now. I thought I had a pimple on my forehead this morning. So are you saying my face looks like a pimple? Well, in that picture, it looks like a big pimple that popped. I said right now. I thought I had a pimple on my forehead this morning. Are you saying my face looks like a pimple? Well, in that picture, it looks like a big pimple that popped. I said right now, I said, we got a big problem if that's what I'm walking around like all the time. I thought I had a pimple on my forehead this morning

in my hotel room and I went in after it and then as I was trying to squeeze it and nothing was coming out, I realized it's a fucking mosquito bite. So I basically attacked myself. It adds character. And I went into it's like a knot on my head right now. I got into my car this morning.

We're in New York. It's like a cartoon with like a fucking piano dropped on your head in New York. And my driver's like, what's he goes, what's wrong with your head? That's what he said to me. Rafa. He can say that though. He's been my driver for a long time. Okay. So Dylan Mulvaney, the last time we spoke,

you were, I mean, first of all, I don't even know where to begin. You've been very busy. Been all over. But I was going through the ringer right when I saw you. That was post-beer gate. You were getting a lot of backlash. Getting a lot of backlash.

And now that just seems to be the trend of my life. Okay, let's revisit what was happening. It was the beer commercial. There was a beer situation, and it felt like the whole world was after me. life. Okay, let's revisit what was happening. It was the beer commercial. There was a beer situation and it felt like the whole world was after me. And now I've really learned how to not give a fuck. And I think I learned that kind of from you. And I also just now know to roll with the punches, because if this is going to be my life, then I think that's kind of just comes with it. Yeah,

do our best. I think it's very important to build resiliency as soon as you possibly can, because if you're gonna be in a public, if you're gonna be in the public, there is no way that you're gonna get out of this unscathed being a public personality. There's just no way. So when people are really sensitive

and they can't deal with it, I mean, it's a natural reaction to have, but eventually you have to toughen up a little. Were you ever fragile? I kind of, the way I've read your stuff, like it doesn't seem like that. I don't know if fragile would be the word, but I've been knocked down a lot.

Yeah, I've been knocked over and down and thought, oh, fuck, maybe I should just disappear. Maybe everyone's sick of me or maybe this or that. And that, you know, you think that those moments are temporary. They're not permanent. And I deal with a lot of people that come to me who are fragile and want to know what to do.

I think we're attracted to you. Yeah, maybe. To help us fix our shit. A magnetism because it's like, oh, you're okay. But that becomes a lot to handle too. Like I remember, this was just last week. I was like, I had so much of my own shit to deal with. And then I had like four or five people coming to me about how to deal with their shit.

And I remember thinking, I don't have the fucking time for this. I'm not a counselor. But then I'm like, no, you are a counselor. That's actually what you like and enjoy doing. You want to help people. So it's easier to look in rather than into yourself sometimes. Have you met anyone that you're interested in like more long term? Are you just having fun with strangers? I've been, you know, in Paris bars that'll do it.

Oh, oh my God, you're going to die. I can't believe I'm telling you this on on air. I did hook up with my room service waiter in Paris also this weekend. I've always dreamt about that. I left that that picture moment and I went back to the hotel and then I got a charcuterie board and the waiter was so hot, Chelsea, and he went, Sava, and I went, Sava. And then- Does that mean sucky sucky?

What does Sava mean? It means how are you? I think. And I said, how are you? And somebody else is going to quote me that was incorrect. Then we started making out and it was amazing. I love that these things, you were making out with your room service attendant?

I didn't even know that was legal. Well, I'm trying to kind of pivot because I went on a date a few weeks ago where the person was, well, I was on a date with a woman and she was like, she first asked me, she's like, are you into me? And I was like, yeah, I'm into you. And then I was like, are you into me? And she's like, well, I was like, what does that mean? She I'm into you. And then I was like, are you into me? And she's like, well, and I was like, what does that mean? She's like, you're kind of like the baby bird

and I'm the mama bird and I don't know if I'm allowed to fuck the baby bird. And I'm like, you can fuck the baby bird. And I'm just sort of now trying to figure out how to take myself out of the cute to fuckable category. You know what I mean? So dear Chelsea, how do you go from cute to fuckable? I think it's a natural progression

and it's gonna happen very naturally. And it starts with the room service waiter. And it starts with sucking off the room service waiter. No, I don't think you sucked him off. I didn't do it, I didn't do it. Okay, good, good, because I just, yeah, yeah. I mean, you can, there's nothing wrong with that. I mean, I don't know what goes on in France,

but it sounds wonderful. This is like when masseuses go down on you. I'm like, I've had a lot of massages and that's never come off. I was gonna say, you did say it though, down on you. I'm like, I've had a lot of massages and that's never come up. I was gonna say, you did say it though. Like that was a frequent like- I would love a masseuse to go down on me. You used to get on Grindr.

Well, but I wanna just have a masseuse offer it. Like, why not? I'm relaxed, I'm not gonna fight you. You can go down on me, finger blast me. That's the perfect setting for me to get finger blasted is while I'm lying down half out of it. I want that for you too. I know. So, and I hear all these stories. I even went to this hotel that I heard they had.

Specifically, what's wrong with me? And then I was like, Oh, I guess. And my friend's like, you're just too intimidating. I go, while I'm getting a massage, I'm too intimidating. You have to go full glam. You get full glam done. We get Jamie makeup in here just to like really beat your face. Yeah. You've been hanging out with Jamie makeup a lot. Oh, I love that woman. I know, good vibes.

She's so fun. I know, she's so fun. Yeah, you got to keep the good ones around. I told her she's a personality hire. You need her personality. I was like, forget about your makeup skills. Your personality is where it's at. That's how I feel about myself too.

Okay, so tell me about your life. I want to know. So you left here and you had a lot of drama with the beer and then that subsided. And then we started Marco poloing me and you because we found that I don't like to text, you don't like to do FaceTimes or phone calls. So it's like this walkie talkie app. And I asked you about Ayahuasca, went to do that down in Peru by myself. And that really made me willing to do life again.

It was like a lot of great things came up. And then I came back to the States and finished up my book. I've got my podcast. What's the podcast called? It's called The Dylan Hour. Oh, I love it. And it's sort of like that. You deserve a podcast.

Thank you. It's like sort of this 1960s flair. You know, I love to live in the eras. And what originally came from was that there was I was getting so much hate from these like conservative extremists like right wingers had all these podcasts and I was like, well, what the fuck I want one. And and so it's not targeting those people at all. It's just kind of a celebration of femininity. And the important part is that we get to drink alcohol on it. Which do you ever do that on here?

I don't, not on my podcast, but I did Burt Kreischer's podcast, and it was around, it was at noon, and I had two vodka OJs, and it was a two-hour podcast, and I think that's pretty much how all podcasts should be conducted. It's just a very loose format, and people are more relaxed, and it's just easier to drink and talk about yourself.

And they'll tell you more things. Yeah. I mean, I don't need alcohol to open me up. You know, I mean, I already have a problem with my mouth. I give away way too much information. If you were going to come on my pod, what do you think we would drink? Like, what's your go-to? I was drinking gin for a while. I'm kind of in gin. You'll get there, honey. I'm a little bit in gin, and then I'm kind of pivoting back to vodka now. Vodka was grossing me out for a while because it tasted like, it started to taste like gasoline.

But whenever you overdo anything, it starts to taste disgusting. You ever tried Everclear? Oh no, that's really gasoline. I like that one. That's like rubbing alcohol. That'll get you. What are you drinking?

I love vodka. I love an espresso martini. Oh, I had one of those yesterday. That's like rubbing alcohol. That'll get you. What are you drinking? I love vodka. I love I'm an espresso martini Oh, I had one of those yesterday. It'll keep you up and I love Oh dirty Shirley Temple. You ever had one of those? What's really about it with vodka? Oh, yeah, or an apparel spritz. Yeah, that's very my orca vibes Yeah, my orca very my orca and apparel spritz. So you'll come on my pod one day. Of course. What are you talking about? I'm honored to be on your podcast. And yeah, it's sort of just like a celebration of femininity and giving me a chance to get off, you know, the internet so much and kind of get in front of somebody else because so much of what I was doing online was just me in my bedroom.

And I was like, I haven't talked to someone in five days. So it's time to sit down and shoot the shit. And are you still living in your same house? I live in the cute house. Okay. The Joan Mitchell vibes. I didn't know if you had to move because you were worried about all the backlash. That was scary, but we're okay now. Now everything's good. So that's great. I'm glad to hear that.

What other backlash have you been facing? I released a song called Days of Girlhood. Did you hear about that one? Yeah, I heard about that, but I did not hear about the backlash. So I put this song out sort of as like, you ever heard of Rebecca Black's Friday? Yeah. Or like Paris Hilton's Stars Are Blind? You know, I wanted one song to give the gaze, you know, if I was going to go at any moment,

just to remember me. And so I basically put the most sort of just like stereotypical, silly, feminine things into one song. I did not think I was singing fucking, you know, I didn't think I was Tchaikovsky or anything when I went into writing this. And wow, the internet just roasted me because it first started with the TERFs

and it started with, you know, women who were so deeply offended that I would be singing about womanhood or girlhood. Wait, what's a TERF? Trans Exclusionary Radical Feminist. Oh, what's the turf? Um, trans exclusionary radical feminists. Oh, fuck. A feminist that doesn't include trans people. Okay, copy.

And... Like a J.K. Rowling, right? Yes, but the song gave them kind of like this perfect sort of like, oh, I'm going to be sad on the internet to talk about how much this song, you know, made them so upset. And then my audience had already decided that it was a bad song, but the thing about Gen Z is they will ride hard. And so when they found out it was getting hate, they were like,

well, now this is my favorite fucking song I've ever heard. But yeah, I don't think I meant for, I don't think the music industry is for me. How about you? No, no, I don't have any. I can't sing and I have no rhythm. I can't even dance. What's your go-to karaoke?

I don't do karaoke. Ever? Dylan, are you not hearing me? I cannot, you want to hear me sing? I have no rhythm. I can't even dance. What's your go-to karaoke? I don't do karaoke. Ever? Dylan, are you not hearing me? I cannot, you wanna hear me sing? Yeah, I do. Happy birthday to you. Happy birthday to you.

Like, that's it. That's good. No, that's not good. Voice lessons. I know that's not good. And I'm not taking voice lessons. You think I need to add that to my repertoire? I don't know. It sounds like you've got two months in Majorca to fucking find some cool- I have one month in Majorca,

and I'm not fucking, and I'm not recording an album. That's not what you wanna do with your time. You want me to come out with a song so I can get more, Nathan, you got. So you can do, you can- Fuck, she's onto me. You can come in and be like, look, look at Chelsea. She's a real fucking asshole. Wait till you see this one.

We should, we should, actually, I should record a song, and then we release it together called, You Thought I Was an Asshole, Watch This. Featuring, I should record a song and then we release it together called, you thought I was an asshole, watch this. Featuring, I'm gonna be featured on it. Catherine, do you sing? I do, I do sing. Oh, hell yeah, okay. Yeah, so, you know, I'll sing on there with you as well.

Thank God. Catherine sings when she talks sometimes and I have to tell her to stop. She'll be like, Chelsea! Stop singing. I'm like, Catherine, that does not go with this podcast. I can't help it, I have a song in my heart. This is not a musical theater podcast.

Mine is, get ready. I wanna talk about some heartfelt moments that you've had with fans and people that have reached out to you, because that must feel really good and meaningful, and I know that you have them. Oh my God, every day. I think so often the internet feels like the most toxic place

and then I'll open up like a DM from like a girl that just went to college that's getting her bottom surgery or a parent that like they watch my videos together and like that to me is worth it. Like I think so often I feel like social media and content creation, it's so, can feel really icky sometimes. It can feel like it's either selfish or that you don't know if it's actually helping anyone or that it's potentially hurting, you know, like I'd never want to put something out there that's a bad representation of the trans community.

But then when you've got the dolls surrounding you and rallying behind you, and that was my big takeaway from the backlash at Beer Gate was like, oh, I got so burned and the trans community and the queer community were the ones waiting to pick me back up. And I think that just told me like, oh, that's who I want on my side. That's who I want my audience to be. And, cause I tried so hard to be palatable for so long. And now I'm like, fuck it. To be appealing to all these people, right? Yeah. We were talking about that with my book title.

They were like, oh, well, this is gonna exclude men. And I'm like, but what straight men are reading my books? Like, let's be honest. I'd rather home in on the people that are my audience. All the people who feel like I do, who don't wanna have children, who are single, who is, you know, who care about being a woman and being a sister and all of those things.

It's better to focus and hone in on your audience instead of trying to appeal to everyone. Amen. And my show that I'm doing is called Fag Hag. And a lot of people go, oh my God, can I say that? I'm like, I don't know, can you? You're kind of a fag hag. I know, I know.

You like gay people. I do, I love gay people. I went out last night, I tried to set my two gay guy friends up and my one gay friend got so fucking wasted. He was such a mess at dinner. And then I had my other friend at dinner. She got off a plane from Paris. And so I'm with this guy that I know,

trying to set him up with this guy and my other friend. They're not making any sense the two of them it was like being out with three-year-olds they like each other yeah they ended up hooking up oh great what's my turn well I don't know I don't know because you like men and women so it's hard for me to focus on which one okay it's funny though because when I'm on Raya and if I'm looking for men it's a lot of these guys that'll say like mutual you you know, mutual and common Chelsea handler. And it's usually, you know, it's usually the men over 40.

And and I'm like, do I want to be? Do I want to be sisters with her on this one? And then I sometimes I'm like, should I text her? And I'm like, he's not hot enough to really go to bat for this one. Yeah, right. But I will start vetting through you. Yeah, just send me a screen. They always say, no, you can't take a screenshot.

I know, but I do it all the time. I do it. You're not supposed to. No, they're going to ban your ass so fast. They're not going to ban me. They need you. If they haven't banned me by now, they're not going to ban me.

And sometimes I need to take a screenshot, because I'm like, wait, I don't know if I've already met this person. Or sometimes they'll be like really hot, and I'll be like, good for Chelsea. And I can only assume. Maybe it's like your fucking pool boy. I know, this person. Or sometimes they'll be like really hot and I'll be like, good for Chelsea. And I can only assume, maybe it's like your fucking pool boy. I know, I know.

I use Raya a lot when I'm, and yeah, in spurts. There are periods of my life where I am all about Raya. Oh, I love it. Because it's just so fun when you're in a different city and you're just wanting to hook up and nothing more serious, it's perfect tool. Oh, the best. And you can, like I've seen guys from high school

that, like, I had a crush on, or I've seen, like, my favorite actors, and that, it's good. On that note, we're going to take a break, Dylan, and we'll be right back with Dylan Mulvaney. If you'd like advice from Chelsea, write into us at dearchelseapodcast.gmail.com. We'd love to hear your questions for any juicy story you'd like advice on.

But this week, we're especially looking for questions about parenting. So if you are a parent and have problem children, please write in and tell us your story at dearchelseapodcast.gmail.com. And we're back with Dylan Mulvaney. Catherine, are we ready to rumble today? We are so ready to rumble. We've got our collars hanging out. We've got questions.

And our first question comes from Audrey. I think this fits very much in to what you were talking about with dating and dating guys or girls. So Audrey says, hi, Chelsea. I'm a 22-year-old trans woman from the South. I have a doozy for you. I've been with a man for four years, and we got together a couple months into my transition.

I love him, and he is my best friend. But I've recently come to the realization that I am attracted to women. I think I just made myself believe I was attracted to men because I liked how validated and feminine it made me feel to date a man. But I've come to realize my femininity is just as valid being with a man or a woman.

After thinking about all of this, my attraction to men has gone way down. It's like once I discovered the truth, my brain wouldn't let me see men the same. My attraction for women is now greater than it is to men. Should I tell him I want to experiment with women? Should we break up? I don't want to hurt my best friend that I love so much, but I want to make some changes. Audrey. Dylan? Well, I think it's very common for trans people to expand their sexuality, you know, after a gender identity shift, because I think once you unlock one part of yourself, you're like, oh my gosh, there's this, why would I limit myself? You know, it's like, I think we put sort of parameters on ourselves and once you open one floodgate, you're like, fuck it.

And I think that's kind of what happened with me is like, as far as like, oh, why am I limiting myself? But I also think, and it sounds like it's more so just based on her attraction to women and less of like her disdain for men, because I more so am like, wow, this grass isn't greener because I had never been with straight men before and now I have. And it's actually not the it's not amazing.

Yes. Gay men. I know it's not amazing. And that's why so many women are becoming late in life. A lot of friends make that change. Yeah, it's totally normal. And then like in getting really serious, really fast, which they getting really serious with with women Uh-huh, and I think for Audrey it sounds like maybe if there's nothing going on with the relationship that feels toxic or unsafe

And she still really does enjoy this person. It sounds like maybe an open relationship might Yeah option if he's if he's gonna be open for that But I really don't think you have a choice. When you love someone and you respect them, it is really kind of imperative that you are honest with them. Oh, absolutely. So either way, I mean, if he's not open to it,

you'll find out right away. But either way, you need to be honest about your desires and give him the opportunity to say yay, or if he rejects it, and then you have a decision to make. Right, Catherine, did she write specifically that she's met another woman that's kind of interesting to her yet?

No, just I think in general. Well, that's a good timing situation. It sounds like a conversation with the boyfriend or the man friend to see how he feels about what this relationship could look like. Yeah, yeah, you should definitely address it though. It's good practice to address these uncomfortable conversations as early as you can

because life is filled with them. And the better you are at being honest and upfront and direct without it being acrimonious or you're screaming or yelling, like the more evolved you become and the better skilled you are to actually handle difficult situations. Yeah, and Audrey is only 22, so like very young,

just starting to experience these things. And she also mentioned best friend a couple of times. And there's maybe some examination there of, our relationships change over time. And maybe you do feel about this guy more that he's a friend than a real partner, or maybe the romantic feelings have shifted. Gen Z is so fluid with everything. And I think that my advice to her would be like,

don't try to put a label on what this attraction is for you until you do a little experimenting and you put your... You know, like, you might like being with women more than you expected or it might not. But I think in the meantime, having this conversation with the guy and going from there, because I don't think anyone in that age group

is gonna be judgy. I also think it's a great time in your life to be experimenting with your femininity. I liked what you said in her letter about, she's realizing that her femininity isn't reliant upon a male presence. Yes. I did get a little nervous. I thought about, you know, being with a woman, would that make me feel like I had to, like, step up and put on sort of these, like, masculine qualities?

But it's never been that way. And I think that as long as it's not giving you dysphoria, it can be really beautiful because a woman honoring a transwoman's existence in a romantic relationship is really special. What ended up happening with you and this older woman? Or this woman you were just talking about? Oh, with the baby bird? The mama bird? The mama bird. Sorry, not only.

We kissed, but then I think it was... Then you regurgitated into your mother's mouth? Well, then I said, because I asked her, I was like, well, how do I go from cute to fuckable? And she was like, you need to have more sex. And I was like, how do you know I'm not having more sex? And she was like, well are you? And I was like, no. And so I think it was kind of like doctor's order situation and then I'll circle back, you know, with like, so.

Doctor, come back in two weeks after you've taken. Find me some, it sounds like your pairing skills are great. Well, I mean, I've been on a roll lately. I've hooked up. I've actually set three people up in the last six months. Well, maybe find me... I could go with the man. Okay.

I gotta think. I gotta start thinking. 30 to 60. 30 to 60? What kind of range is that? What kind of window? I like older too. I want somebody very sure of themselves, successful, tall.

I could see you with an older man actually. That makes sense. I'm the first wife, no I'm third wife vibes and then he's my first husband vibes. Especially with like the way you're vibing now. I know you're dressed to go to the theater, right? No, I wear this all the time. You never know what 60 year old man you're gonna meet

on the streets of New York on his way home from Wall Street. On his way home from his podcast. I had to think about what Wall Street was. Oh God, that's my one condition no man podcast. Unless it's something really boring talking about money management. Okay, Catherine. Money management. Well, our next caller is Jerry.

Jerry is... Is it Jerry Seinfeld? It's not Jerry Seinfeld. He's always calling in. You can't keep him off the line. Jerry is calling in from Chicago and Jerry uses pronouns they them. Dear Chelsea, I'm a 42 year old non-binary

genderqueer person assigned male at birth. But if you knew me in my day to day, you would only know this from my standup. That's because certain open mics are the only place I feel safe dressing or acting feminine. Probably because I can claim that I'm just joking. I don't enforce my pronouns at work because after numerous attempts, I've lost hope.

When I see a cute blouse, I will always talk myself out of buying it. And when I do muster the courage to wear, quote, women's clothes out of the house, part of me still feels a little strange. My standup hobby has been a great way to cope. I joke that I've always looked like a daddy, but talk like a mommy

and how it unnecessarily confuses people. But I know this is just a bandaid on the real problem. I hate to admit it, but I'm so ready to give up and conform again. Ever since I had to, I don't know. Ever since I had to stop being a lawyer for my health, confronting anyone about any issue, big or small, has triggered my fight or flight response, and mine is usually freeze.

And it feels so lonely because the only people my age coming out as non-binary are celebrities like JVN or Sam Smith. When you wore a jumpsuit in one of your specials, Chelsea, I bought a jumpsuit to wear to my open mics. Everyone who went up after me made fun of it. And I didn't even care because I kind of felt like I was channeling your confidence.

Maybe I'm hoping you can work your magic on this problem I honestly don't see a solution to. You're devoted, but not in a creepy way, fan, Jerry Vaitham. Hi, Jerry. Jerry will join us here. Oh, perfect. Oh, what a conundrum.

It is really just, it's just brutal. How in these streets. I know. I mean, it's just so hard to even be what people expect of you. And then you want to be something that people don't expect. And then you have to, you're consumed with what other people think. And I hate that. I hate that everyone is so consumed with what other people think and how they're going to view them and how you get rid hate that. I hate that everyone is so consumed with what other people think

and how they're gonna view them and how you get rid of that. People are always like, how are you so confident? I'm like, I don't feel like I'm that confident, but I just, I'm not interested in negative opinions about me. Do you ever feel like you might have a she, they in your bio?

Something like that is happening. Wow. Something like that. The coming out episode. Hi, Jerry. Hi. We love you already. I'm Dylan, by the way. Something like that. The coming out episode. Hi, Jerry. Hi. We love you already.

I'm Dylan, by the way. Dylan Mulvaney is our special guest. Yeah, yeah. No, I'm familiar. I've seen your videos on TikTok. They're really moving. Okay, talk to us. So you're feeling pretty low

and not able to express yourself. I can't enjoy being feminine. There's just always like a fear attached to it. And you did say, you know, you wore that jumpsuit, which I'm so obsessed with already. But you said that other people commented negatively about it. Oh, yeah. But I mean, that wasn't so much gender related so much as like, oh, yeah, are you off to like construction work or something? I think it's iconic. My worry for you is that I don't want you to use stand up as a way to self deprecate about yourself, because I think a lot of comedy

can go in that direction. And especially if the crowds you're performing for are more of the straight or tourist crowd. What I really want you to try to focus on is finding those like specifically queer or trans or non-binary open mics, because that's where you can make light of a situation without having to be the butt of every single joke. And I got back in a standup recently

since I had transitioned and I found myself in these rooms where they were only laughing when I was putting myself really down or, you know, referring back to myself as a gay man or what like it. And I think as much as it might feel good to get that laugh, I just don't want you, especially in such a sensitive time where you are truly finding your true self. And I don't want it to hinder that in any way. I want you to protect yourself. And I also, I went by they, them pronouns for about a year and three months

before I fully transitioned. And I just wanted to confirm with you, like it can be so lonely because people, some people just don't get it. What do you think, Chels? I think that you have to, I understand, and I can't, you know, I haven't been through this myself, but I think it's really important to have strong conversations with yourself every single day

about who you are and what you're putting out there, you know what I mean? So that you have confidence in your decision-making and that other people aren't having such an impact on the way that you feel about yourself. You're not looking for their validation. You have the desire to express your feminine side. That has nothing really to do with any of them. And if they don't like it, that's also not your problem. You need to go where the light is.

You know what I mean? Like the people that love you, the people that understand you. And when you're on stage, I agree with what Dylan said, listen, a lot of comedy is self-deprecating. I'm self-deprecating, but I think it's important to recognize the difference between making fun of yourself to fit in versus making fun of yourself because it's- You already love that part of yourself

and it's safe territory to make light of. Yeah, it seems like you're missing a chunk of self-love. And if I were gonna give you any advice, I would say to fill yourself up every single day before you leave the house, whether that's with like affirmations, a gratitude journal, or looking in the mirror and telling yourself that you're a fucking rock star, that you're beautiful,

that you're kind, that you're capable, and that you're intelligent. And keep having these ongoing conversations with yourself because I know Dylan, you had to do that for a very long time too. Oh, it can be so lonely. And still, you know, like I think what was sad was when I did transition back onto the binary in some ways,

it was like a little bit of relief because people at least knew where to put me or what, you know, where to slot me. And just don't give into that pressure right now because I want you to put yourself in spaces, whether that's queer bars or open mics or meetup groups, activities that like, you know 100% that the people there

are gonna honor your pronouns. They're going to compliment your fun, feminine outfits. Find someone to go shopping with that you feel really safe and is going to like make you feel euphoric. I know dating can also be really tricky, but you've got to. Honey, I don't I fucking know it. And you have to right now prioritize your identity and not your comedy career, not relationships, not any. This is your time to really explore, because if you don't go all the way in to whatever it is you're interested in or what you are looking to find, you might shut yourself off

from a lot of beautiful things. Do you have a small community there in Chicago that's separate from your work? Not really. I need to look harder. Right. I think it can be expensive, but I know Second City and the Groundlings. And there's a bunch of comedy theaters

there that have a bunch of classes. And I imagine that they attract some queer folks. And although that's not necessarily a queer meetup by any means, I do think that there might be some really cool, safe people there to get to know. And especially like, you might not need group therapy, but I think a group laugh can be a great thing.

I would like to ask one piece of advice on behalf of Jerry. So as far as like the outfit goes, right? Jerry is, you know, channeling Chelsea and wearing like a Chelsea type outfit with the jumpsuit. But is there a way that Jerry can preempt those sorts of jokes when they do come up and sort of like talk about how they look fabulous, like before anybody else comes up and makes a big deal about it? I have a friend, a comedian friend named Michael Fulk, who dresses like he likes to dress

like a woman and he goes by they them. He's non-binary and he sometimes wears dresses I'm they they like to wear dresses. They like to wear dresses. Thank you they like to wear dresses and and They have a great attitude about it because it's just part of who they are They're not ever explaining themselves. And if anyone does probe or lean in They're just like there's no question like there's such a confidence in, they're just like, there's no question. Like there's such a confidence about what they're doing that there's no question.

And it doesn't matter because you can't be doing this looking for everybody's approval. It's outside of a lot of people's comfort zones. Again, that is not your problem. That is their problem. That is their issue. Let people figure out how they're going to talk to you. You know, and you can't expect everybody to like fall in place with, you know, how you want to identify because it's so out of touch with them. But you have every right to identify however you want. So you've got to like really instill in yourself whatever confidence you were able to come up with to say, this is who I am. This is what I'm going to do. And you're going to either love me or you're going to come up with to say, this is who I am, this is what I'm going to do, and you're going to either love me or you're going to hate me, and neither one of those things are my problem. Amen.

And I think when you really do lean into who you are and what your desires are, there is a magnetic field that you kind of create around you that attracts like-minded people because you're living out loud in a brave way. Yes, and when you start vetting some of those people out, I think that makes room for the good ones to come in because what I did early on were, I could, you can sometimes just tell when people, you know, are, if they're not catching up

with your pronouns after, you know, months of years of knowing you, or if they're making snide comments about your outfits or whatever that might be, that's when you start hitting the sort of do not disturb button on that friendship, because that then expands for more people to come in. Absolutely. I believe that to be true for sure. It's about creating your own magnetic field.

And the more you are true to yourself, the more you shine, the more ebullient you can be. I know I had to throw that in there because it's really the right descriptor. You know, you want to be a ball of light, like teach people how to how to treat you. Even I remember with my family, you know, we took a little bit of time apart and I had to have some real tough conversations, but they got it when they realized how important these things were to me. And again and this is repetitive which I'm very good at you can't rely on other people's reactions to you to fill your cup up. That is not how you get your cup filled. That is an inside job you have to fulfill yourself you have to fill yourself up. I mean

sometimes you can have somebody fill you up. Hopefully one day soon that will happen for you. And I love to get filled up. But on this notion, it is a, you know, it's you're self-employed. You have to take care of your own happiness. And once you have that, then nobody can take that from you, no matter what their reactions to you are, and no matter what their judgment is.

And the more comfortable you are with yourself, the more uncomfortable people become around you. What she said. Okay, problem solved. Problem solved. Well, we have another caller joining us shortly, and we had a bit of a curve ball. This caller is L.K.

Is that L. King? Is she calling in again from her last episode? I mean, I wouldn't put it past her. I love L. King. She and I have been texting. Have you? Oh, that's great. Yeah, I like her attitude. She's a country star. She was on the podcast last year. L.K. says, I'm a 37-year-old divorced lesbian. This takes a turn, so stick with me here. I'm a 37-year-old divorced lesbian living in Alabama.

I've managed to meet a lovely woman by happenstance who is in all regards a 10. We've become fast friends and I'm digging the friendship but damn am I into her. I find myself stumbling over my words and acting like a child with a crush. This is not normal territory for me. I'm usually much more confident and direct but this woman is special.

I know she had a tough breakup in maybe the last year and I also know when we met in February she mentioned she hasn't been interested in dating since the breakup. What do I do? Continue building the friendship or make my intentions known? Will I ruin the friendship if I tell her my feelings and she's not feeling it?

I just don't know what to do. And then, so LK reached out today and said she's had a bunch of stuff kind of come up in therapy. And this is like still sort of a part of her story, but is taking a bit of a backseat. So I thought we could talk a little bit about multiple things kind of going on in our lives at once. But LK says, I wrote in about having a crush and I looked forward to talking to you about that. However, since first writing in, I've had some major developments in therapy. One of them being a slow uncovering of childhood trauma. I've lost both my parents

since 2020 and my last grandparent passed last month. I'm unsure if part of me was protecting the elders in my life, but it seems something in my brain unlocked after my grandmother passed. How do I maintain my job, myself, and my sanity as I work through these muddy waters? Any advice would be greatly appreciated. Thanks, LK.

So a lot to unpack. Hi. Hi there. Hi Al. Hi. Hi cutie, how are you So a lot to unpack. Hi. Hi there. Hi, L. Hi, cutie. How are you? Chelsea fucking Hamler. Good, how are you? Ha ha ha ha.

Fucking love her. This is Dylan Mulvaney, our special guest today. Ah ha, what's up? Hi, LK. Nice to meet you. Nice to meet you. Nice to meet you, too. What a beautiful big smile you have on your face.

I love it. Thank you. First of all you too. What a beautiful big smile you have on your face. I love it. Thank you. First of all, what's going on with the girl? Are you still? Just totally took a backseat. I mean, she's a friend and I was looking forward to talking to you about that. I was kind of in that like giddy, like, you know, felt like a little kid, like just kind

of tickled. And then it was like, I'm in therapy like working on some stuff and just like out of nowhere therapy just like hit me like a truck and was like no you got more important things to think about okay well this is all good okay because this is all good it's better that therapy took a front seat that's a good sign because it is it needs to take a front seat before any real normal healthy relationships happen. Therapy is what you do

to have normal healthy happy relationships, especially. Well, let me say this. I think that when you're, the second question you ask, which is how do you remain connected to your work and be productive and be engaged in all the things that life requires from you while you're going through therapy.

And the answer to that is easily, because you are doing the work that is going to make you an even more whole person and an even more healthy person. So all of these things that you have going on while you're going to therapy, actually compliment your therapy, because you're doing it while you're facing all of your responsibilities.

And while you, so all of it is good. You can do all of it at the same time. Therapy is not meant to like, you're supposed to take two years off from life. I mean, only people can do that, you know, like I did that because you know why, but you know what I mean? That's not realistic.

That's awesome, but yeah. I don't have that. Can't, I'll do it. Not relatable, not relatable at all. But- Can't relate, but. But the other great thing about going to therapy while you're living your life

is that you can integrate your therapy and what you learn into your life in real time. Whereas I took two years off just to go to therapy and travel, so when I was done with therapy, I'm like, how do I match all of this stuff into my life when I'm working? So you actually have an advantage that you don't even really see. Sure. I like that. Because you're going to be incorporating the things you learn

as you're living your life in a real way. Sure. Sure. Go into therapy weekly. Like, don't miss. Right. Well, no, don't miss. Right. Well, no, don't, you shouldn't. I mean, hopefully, you know, you'll go and then at a certain point you'll be like, okay, you know,

I can take a break or I'm ready for a relationship. It also sounds very healthy that you recognized that this crush you had is not as important as you dealing with your childhood issues. Yeah, no doubt. That's healthy. Yeah. Because if you were more still focused on that while you were doing this, it would mean

that you had your priorities a little bit out of whack. Yeah, I was. I was focused on the kind of the stuff that was coming up and I was like, oh, shit, I was talking to Chelsea Handler about a crush. I was like, I still want to talk to Chelsea, but it doesn't feel as important as to talk about. I think sometimes people make up problems to call in. They're like, what color should I paint my... I'm like, what?

And did you just lost some loved ones too? Yeah, I lost my mom in 2020 and my dad in 2022. I'm so sorry for your loss. Thank you. Thank you. I think that while you're navigating the grief and the new sort of therapy of it all, I still want you to be able to find the joy because sometimes we go zero to 100, especially in something that's so intense as mental health

can be and we go in that direction. We forget to be silly. We forget to be in love, we forget to treat ourselves to the frivolous things. So I actually am kind of pro you still, you know, maybe not as heavily engaging a crush, but sometimes having a crush is really fun and can kind of help you take your mind off serious things and not to disassociate and put all your eggs in that basket. But I like to think of dating kind of as like an iPhone game. Well, cause so much of it is, you know, on swiping, but you know, just that thing that I'm like, oh, I don't have that much, you know,

I already did my therapy for the day. I've already had a good cry. What can we do next? Let's try to fuck someone. But I actually wanted to ask you, I wanted to ask you about this friendship thing cause I've been in that situation too, where, you know, you're friends with someone and you think, oh, maybe this could be more, but it can be a little

awkward about trying to get there. Do you think there's, are you the kind of person that would be willing to, you know, say something or do you think you would need a really clear sign? I think I would need, I mean, I don't have any problems being direct, but at the same time, it was the first time in my adulthood where I got kind of like that giddy, just like kind of stupid, you know. The best.

The best feeling in the world. That is really, truly. Just like I am now, I'm just fumbling over my words. It's like, I don't know. You don't wanna ruin the friendship. So what do you say to somebody who like... Well, what is the vibe? Break it down a little bit more specifically.

What has been the vibe of late? We don't live in the same town. So I haven't hung out with her in person. And so, I mean, it's a new girlfriend. I don't think she doesn't strike me as really interested in anything right now, not just with me, but like in general. But I don't know if I'm reading that wrong or not. Well, I think the important takeaway from this is you're getting yourself healthy, and you're creating like a better version of you that that will be like the net result after this therapy. It's gonna make you sexier. It's gonna

make you everything better. And you're gonna and then you're gonna gonna be in a better place and maybe she'll be in a different place and you can pursue that down the road. But I think your focal point should just be you right now. And it sounds like you're doing that. And that's only good. That is only good. Nothing bad is gonna come out of that. You're gonna get through your therapy sessions.

Some are gonna be tricky and some are gonna be less tricky. But you're gonna go through the gamut of emotions. And when you come out on the other side, you're gonna be a better person. You're gonna be a better fuller version of yourself. And I love that you said you're direct. Most people can't fucking be direct. So great, you have that advantage too.

I'm an Enneagram 8 too, so. You can just go up to her and be like, I like pussy. Do you like mine? You know, it's simple. Well, the time is right. You ever said that to someone? Do I like pussy? Do I like pussy? Do you like pussy?

Do you like mine? You said it like it wasn't the first time. That's all I'm saying. Okay. You want pussy? Come and get it. Oh, fuck. My mom can't listen to this one.

I was just thinking about my sisters. I was like, they're going to be like, fuck, my mom can't listen to this one. I was just thinking about my sisters. I was like, they're gonna be like, oh. My mom and sister. Anyway, you're a love, you're joyful and happy and I'm happy for you and you're gonna be fine. And yeah, keep doing what you're doing. Thanks, Chelsea.

Oh, you're so cute. We love you. Okay, love you. I love you all, thanks so much. Oh, cute. Bye. Her accent reminds me of Fortune Feimster. I love you. Okay, love you. I love you all, thanks so much. Oh, cute. Her accent reminds me of Fortune Feimster. I love it. Yeah. Well, let's take a quick break

and we can wrap up with a quickie. Okay, well, take a break and we'll be right back to wrap up with Dylan Mulvaney. And we're back. We are back. So one last little question to wrap up. Kara is in her 30s and she writes in and says, Dear Chelsea, a situation I've been dealing with lately is one of my best friends is single and longing for someone special.

I'm newly married, so it's difficult for me to give dating advice without sounding lame and tone deaf. I remember being the only one of my single friends before I met my now husband, surrounded by married friends, constantly hearing don't worry you'll find someone. Honestly, it got annoying after a while and it didn't help. I do not want to come off that way to my friend and want to support her in any way while she looks for quote the one. My friend is one of the coolest people I have ever met. We're both outdoorsy, and she does pottery and other art and is incredibly talented. Most importantly, she has a huge heart that I know would be appreciated by the right person.

She's been going on dates that seem promising at first, and then after a couple dates, they end up acting weird, and I think it's discouraged her quite a bit. She always asks what's wrong with her when it isn't her at all, it's just men being men. It takes everything in me to stop myself from finding these men and beating the shit out of them for being so stupid and hurting one of the best people I know. I don't want her to give up when I know she wants a partner for life and a family.

If any of your listeners happen to be a straight man who loves art, the outdoors, and who isn't an asshole, then do I have the woman for you. Until then, what advice would you give my friend if you were me, Kara? It doesn't have to be that kind of pat. That's so meaningless to be like, you're gonna find your person, you're gonna find someone. There's so nothing in that. What I think is just to keep motivating your friend

to keep trying, to keep going out there, to meet men that you might think are appropriate for her, or if you do meet a guy that you're like, oh wait, actually do it and encourage your other friends if you have other friends in your friend group to do the same for her in supporting her to meet that guy. I know whenever my friends try to set me up, I find that I'm, well, actually, let me take that back.

Some of my friends, when they wanna set me up, my good close friends, then that's okay because they know me well enough. And they are close friends. And you have every right just to be as encouraging and as upbeat as possible about it. And I loved that she even pitched her friends, you know, her friend to people. She's like, if anybody's looking, now that's a cool friend. Right.

That's that right there is the energy. My favorite thing when like a friend of mine, I don't love the whole you're going to find someone, I love the how the fuck are you still single? Like that's fucking crazy. I like when there's sort of this energy of like, well, that's just fucking why. Like, because I do that a lot with my other single friends where it's like, how is this possible? Like, we're so hot and fun. And so maybe kind of like leaning into that a little bit, build her confidence up in herself, in her personality and her looks and make her feel like the fullest version of herself

as a friend rather than putting so much emphasis on what she's gonna be like when she has a relationship. Yeah, and making it dating fun and being an energetic, when you look at the subject matter of dating, it can be depleting if you have that attitude, it can be exhausting, right? dating fun and being an energetic like when you look at the subject matter of dating, it can be depleting if you have that attitude, it can be exhausting, right? Or it could be fun and hopeful and happy. And I think as a friend, it's you sound like you really care about your friend. So you're the person to keep her bolstered up, you know what I mean?

Keep her going and and be energized when she's on a date. And if it's disappointing, okay, that's okay. Well, that's okay. Well, that's out of the way. Let's get to the next one. The more people she says no to or that say no to her, the closer she is to finding the person that she is gonna wanna spend more time with. So I think she's very, very lucky to have a friend like you

and you can just be an even better friend by helping her through this and not looking at her being single as some sort of losing a game. There's benefits to being single and being in this phase looking for your love too. This is an exciting part while you're looking. It's like, enjoy the journey,

not the result of the journey. That's kind of hard to do when you don't understand or you haven't been through it and understand, oh yes, it is about the way that you're getting there. It's not always about the end result. Or give a constructive piece of advice of how you found someone or what worked for you or back in the day, however long ago that was. My best friend, Lily, will go out and I'll start talking someone's ear off that I think

is hot and she's like, pull back, pull back. That kind of stuff. I think that's fun. I think that off that I think is hot. And she's like, pull back, pull back. And like that kind of stuff. I think that's fun. I think that's what I like to hear. I'm gonna, I wanna watch you on a date and see what happens. Oh bitch. I drive the car and it goes, it gets in a wreck real fast. Goes right into a brick wall.

Oh, I do have a place though. I like to go dance, get Davey Waynes in Hollywood. Oh, Davey Waynes, I haven't been there in years. Oh, I point to the hottest person on the dance floor and we just make out to obits. You're gonna love it. Watch out. Yeah, Chelsea, I love what you said about

not the person you're gonna wind up with, but the person you wanna spend more time with. I love looking at it that way. It's just about finding somebody who liked being around. And I think also, don't forget for Kara, don't forget to go out and be girlfriends together. Ditch your husband, go do some fun things together and also like maybe read her this beautiful letter

that you wrote about her and how much you love her. That will be a shot in the arm. Yeah, okay. That wraps up our episode of Dear Chelsea. Next up is Dylan's podcast called One Hour with Dylan, An Hour with Darwin. The Dylan hour. Darwin, Darwin or Dylan?

The Dylan hour. The Dylan hour. Chelsea Hanley will be singing on it. An Hour with Dylan, An Hour with Darwin, Darwin, Darwin or Dylan? Darwin. The Dylan Hour. Chelsea Handler will be singing on it. And I'll be there performing live music. I can't wait to ask you your favorite Broadway show. Oh, I can't wait to tell you. I love you Dylan Mulvaney.

I love Chelsea. We love you. Thank you. Thank you everyone. Drum roll, Catherine, please. Chelsea Handler. We love you. Thank you. Thank you everyone. Drum roll, Catherine, please. Chelsea Handler Abroad Abroad is my European tour. So I'm coming to obviously find a husband abroad. I need to get the help of out of this fucking country. And it's not as easy as you think. So I'm coming to Reykjavik, I'm

coming to Dublin, I'm coming to the UK, I'm coming to Brussels, Paris, Belfast in May and June, I'm coming to Oslo, Stockholm, to Copenhagen, Manchester, London, Glasgow, New Zurich, Vienna, I've never ever been to Vienna. Berlin, Barcelona, Lisbon. I'm 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. Upcoming Vegas dates, April 18th, July 5th, August 30th, November 1st, and 29th at the Cosmopolitan of Las Vegas.