Life Will Be the Death of Me with Chelsea Handler - Only Perfect Once with Alex Edelman

Episode Date: June 13, 2024

Comedian Alex Edelman joins Chelsea to discuss gambling together in Vegas, what it’s like when your heroes are in the audience, and balancing success with showing up for your friends.  Then: A roommate wants to cohabitate with her friend… not her friend’s boyfriend. A widowed mom of two dips her toe back in the dating scene.  And a world traveler can’t stop dating much-younger men.     * 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 iheart radio app apple podcasts or wherever you get your podcasts hi katherine hi chelsea how are you oh i'm well i'm just estoy and mallorca i know it's week two for you. I know. It's very, very relaxing here. Anything exciting that you are doing on a regular basis? Well, I'm supposed to be in full vacation mode. I could not find my LSD for this trip. So

we looked high and low in my house in LA and we could not find it. I got lost in transport. So I don't have my usual toolkit here. So it is just very much being in the present moment with my family it is very much in the present moment so a lot of them left and there's a couple still a couple stragglers still here and then i have a new group arriving tomorrow oh that's exciting the best development is that the guy that works at our house he makes sure that i have a frozen mango daiquiri every time i come home from a bike ride oh that's lovely it's like i i'm not even eating food anymore. It's just, there's so much caloric intake from those daiquiris that it's like a full smoothie meal. I mean, if it's the same guy as a couple of years ago, I mean,

he's always handing out orange drinks. Oh, hey, Aperol Spritz, daiquiris. Yeah. It's really good times. Really good times. Well, the good news is I had a great time with my nieces and nephews though. We all bonded big time. They all really, really appreciated the trip. And, um, yeah. All We're just one big fucking happy family, the Handlers. I love it. I was talking to your nieces, and one of them mentioned that you had told her whole family when they stayed with you during the pandemic that they needed to go get family therapy and that you called the therapist on them.

Yeah, I did. I did. I did. I mean, listen, if your sister can't call the therapist on you, what are you going to I was like, we're all going to do a therapy session, and I sat them all down in front of a Zoom, and then I was like, what the fuck am I doing here? Why do I have to be in this session? It's for you guys.

I'll excuse myself. I know. Excellent. Chelsea, what should people write in about this week? Roommate problems. If you're having an affair with a married man or a man who has a girlfriend or anyone who has a girlfriend or significant other, please write in. Call in. We want to talk to you.

And also roommate problems. Love those. Those are very juicy. I've had a lot of those in my life. Yes. And they always get messy because it's like that's supposed to be sort of your safe space. And I don't know. It gets very messy very quickly.

That's right. I once had a roommate who had a tramp stamp of the Cleveland skyline. I think that tells you everything you need to know about a person. No shade to our Cleveland listeners, of course. That's a pretty big tramp stamp. No? It was. She was so proud of it, too. Oh, yeah. Oh, I do have an update. One that made me respond to this caller with, hell yes, girl. Okay, great.

So this is from the Joan Baez episode that we did. And she had bipolar disorder and had to kind of like going to some treatment and was back in with mom and sort of struggling with like, what's my place in the world as I go back into the workforce. But Abigail says it's been about seven months since I was on the show and I have a wonderful update to share. Thanks to your advice, I interviewed like crazy and only applied to jobs I was genuinely interested in. After some time, I landed a position at the Museum of Fine Arts, Boston, which I just adore. It's been a great joy to be immersed in art and I feel that I've found myself again. While I'm still living at home, I will never forget what Chelsea said about being under her parents until she was in her 30s.

I'm currently in the process of rebuilding my life. Thank you for your wise words of wisdom then and now. I so appreciate you, Gail. What do you mean under her parents until she was 30? She's talking about me being under, oh, reliant on them until I was 30? But you didn't live with your parents when you were 30, right? No. You moved out.

You came to L.A. Fucking kidding me. Kidding me. I once tried to have my dad moved out here to L.A. My family vetoed it. They're like, Chelsea can't handle that. What are you doing? I was like, why?

I've got the money. I've got the space. We could just put him in the next room. And they're like, you don't even know what you're talking about. Chelsea, our guest today is Alex Edelman. I just watched his special, Just For Us. I met Alex first in Vegas. This is when you were dating Hannah Einbinder.

And I was, oh, this was the night. You were there the night I got together with Joe Coy for the first time. no no we didn't get together he was there and that was when i decided oh i'm gonna i'm gonna date him i remember that i remember you talking to us about that being like i think he's he's lovely guy yeah joe also used us i'm not sure if you remember this but joe used us all as like proxy gamblers we all went to like a blackjack table and i was like i'm gonna stay and joe was like you're gonna hit and i was like i'm gonna hit and so like joe was like and hannah's like i'm gonna stay and just like you're gonna stay and chelsea and he was like doled out like it was it

was actually like kind of amazing and at the end he was like you won eleven hundred dollars i'm like no joe you won eleven hundred dollars the real good luck charm there just so we're clear is fucking me i'm the gambler and i'm the one who wins and i'm the one who gives money to everyone so that they win okay so let's not get that fucking twisted then i knew alex of course so charming and lovely and then i kept hearing about his show which is called just for us which was playing in new york and all of my friends were talking about it everyone was going everyone was going so obviously i had to go i went with some friends and it blew i mean it blows everyone away and he recently won a fucking tony for it how fucking awesome is that it was it's so

crazy it feels like such a weird like make-a-wish thing everyone's like good for him you know good for good for this guy and gosh buddy here's a thing to keep going like it really is so so nice but yeah it's so weird to do the show and then your comedy heroes and the people that you look up to just start coming like i remember i just saw chelsea in the audience i'll never forget she was like sitting on the aisle and i heard the laugh and i was like chelsea's here tonight and then like i looked down in the audience and i see chelsea and i was like i kept having to not look at her because i didn't want to be like what does chelsea think of that joke is chelsea enjoying the story it's just and so like i did the show like this or like i was looking over well you i mean

you had legends every single night coming to your show you had everybody like steve martin and shit right like you had crazy people that you were taking pictures with that you i would see you posting every day so that must have just felt incredible to have so much support from the community that you are in it was just nuts and also i felt like a real imposter syndrome although also it's nice to do a thing that people are enjoying like i've done a couple of solar shows not all of them have resonated like this one and so and like you've experienced this we've talked about like you are so prolific in terms of like writing new material and doing new tours and it's so hard to like put away a thing that is really successful because you've you've worked so hard

in so long and i know you work things out on the road sometimes so you'll like get to a place where it's like finished and cruising in a way that it wasn't at like the beginning of a tour and then you're like time to film it and put it out like it's a totally it's a real like exhausting mind fuck experience because you were working on this show for about six years right yeah i mean i worked on it for a year and then i sort of put away for like a year to work on a television show and then And I was like, all right, I'm going to recommit myself to my show in this year of 2020. And then like after two months of like a four month tour, the whole thing shut down and we didn't come back until 2022. But like I've been working on it and massaging this thing for, you know, like Robert Kraft.

I've been massaging this thing for, you know. And now it's a special on HBO or on Max, I should say. Yeah, it's on. It's on Max. It aired on HBO. Like it really like it's the coolest thing that's ever happened to me. So I know. OK, so tell for our listeners who are not familiar, haven't seen the special yet. Let's talk about it. Why don't you tell us about it? It's very fucking funny. Well, it's obviously it's a comedy special. It's full of jokes, but there's a story at the center of it. I went to this meeting of white nationalists in Queens and eventually one of them was like, sorry, but this guy's Jew. And I'm like, yeah, I'm a Jew. And so like, that's what the show is about is like this meeting. And there are obviously tangents and stuff like that. And there's like a cute one of the white nationalists. And so there's like a little daydream about that.

But yeah, it's mostly about this meeting. And there are lots of other stuff. A lot of the twists and turns, but basically the crux of the evening is you're in a meeting with a white supremacy group, white nationalist group, and them discovering that you're Jewish and then your reaction to that, which was what? Fear? I mean, not really. It was mostly a conversation.

you know it was mostly like hey maybe there's stuff we can talk about and it turned out there wasn't but like it's just it's just an argument guys listen you just come over for shabbos we'll figure it all out you know but like uh but it really there's actually a critic once pointed out uh correctly that not much happens is that like i go to this meeting and i eat a muffin and then they find out that i'm jewish and i leave but in between it's a useful like inflection point for like conversations and like some tensions and some characters and stuff like that a lot of tension I was like terrified the entire time watching it well that's why it's so enthralling and why so many people are you know so interested in seeing it and talking about it and you're getting

awards for it is because it is touching on a subject matter that people are loathe to tackle a and you know it makes people nervous so many people are so conflict avoidant that they don't even want to hear about anything like that you know what i mean luckily there's a whole other group of people that feel the opposite but you've done that a lot like that's one of the reasons that i think you're you're uh beloved seems too simple you but like you are because you tackle difficult stuff and you're pro and not only you're prolific you like i've always preferred comedy that was like a little bit of a high wire act i've always preferred comedy that took a little bit of like we just have so much comedy and there's so many funny people and there are truly

many brilliantly funny comedians but now i think we want a little like you want great comedy but you also want a little bit of like insight or you want a little bit of daring or you want like someone to talk face to face with someone about race or about drugs and you've done this in your specials and your books and your serieses and so like i think that's a really it's like a weird imperative now for comedians who aren't just uploading short clips to instagram or tiktok which is like a perfectly acceptable fine important way to like build your following but I've always been team long form and I think when you're like team long form you have to give people like a little like you know yeah well because you want an arc right you want a beginning

a middle and an end of a story because that's what you are you're telling a story and and some comics are just telling jokes but a lot of comedians all are telling stories that that hour is one long story. So tell me about how you're dealing with all of your success and everything, because I run into Alex all the time. We run into each other at social engagements all the time. He's the first person I see every time I go anywhere. I said to him the other day at that Kevin Hart brunch that Kevin showed up two and a half hours late, too. Tell me how you're handling everything, because we've had a couple of conversations, and I'm curious. I know that you're special. I mean, my family always did say that that was a concern of theirs, that I was

special um but but look i in terms of success it all first of all there's a huge amount of imposter syndrome like i said and second of all are you still feeling that imposter syndrome a little bit and also like a little bit less just because i'm doing new stand-up for the first time and like i had a show on netflix as a joke which was like an hour and a half of material that wasn't just for us so that was really like comforting to have great good for you i don't know what that'll be i don't know if it'll be like another show i'm pretty tired from doing this one for years and years and years but yeah that could be a good thing and it's amazing to meet like really interesting people like i went to this i got to be one of the time 100 this year and i had

like a really fulsome conversation with this guy motaz aziza who's like a palestinian photo journalist and we had like a really visceral intense personal conversation about like this thing that obviously he and i had probably very different opinions on you know some things we agree on some things we don't and so like it's really cool to be in new spaces meeting like new people and like it's amazing to be like a time 100 person or it's amazing to like get a tony award and so like yeah i really enjoy like getting to go to some stuff but i've also like learned to say no a little bit the last couple months i used to say yes to everything because there wasn't very much it's very manageable to say yes to everything but now sometimes like it's just not

feasible to to go and also not to be too like granular here there's something very concerning about your iteration techniques taken away i used to just like nurture things at like open mics or small work in progress shows and now you know when i try to put work in progress shows on sale it's nice that they sell in tiny rooms like very small rooms but the expectation has changed and the idea that I'll be able to sort of like labor away at something tricky for a long time until I get it right, that's changed a little bit. So like, that's the element of like success that concerns me. And also sometimes people will feel comfortable saying a lot of stuff to me that I was like, that I'm like, oh gosh, I would never say that to another person. Or I can't believe

you're saying that to me. And like, my director passed away right before we started on Broadway and he was my best friend. We were really close. And you know, sometimes people come to me in the street and want to talk about him and I'm like okay you know I want to write something about him at some point because he was because I think about him every day and he's still like you know a big part of my mental capacity but someone came up to me after a show and was like is it true that your show would have been a little better if your director was still alive and I was like oh my god it's like funny I was like I can't believe you'd say that to me and he was like exactly and by the way yes it will it a thousand percent will be better if Adam was uh here but

there's nothing i can do about that and also like yeah i'm i just people ask me a lot for my takes on israel and palestine uh speaking of motaz and like when i had that conversation with motaz someone took a picture of it and wound up in the newspaper and like that's fine but i still need to be able to have those conversations i still need to be able to talk about tricky things with like an aspect of grace that you would afford a person as opposed to an entity so like that is really tricky and really scary and also i'm stretched pretty thin so it means it's hard for me to like give correctly of myself to like friends and family in a way that i used to be able to like now it feels like a lot of times good once in a lifetime stuff is happening so even though i've

learned to say no you know i just can't show up for people in the way that i used to and i think that that will affect my friendships and affect my ability to like date and affect my ability to like be a you know like a person who is like regular as a con like a constant struggle between these like exciting new things that i get to do and the person that i still like very much want to say sorry if that i hope that answer is like i'm being extremely transparent about like my biggest insecurity about this but like but for the most part my life is very uh similar to the way it was before with the exception of like now i get to go to like the tony's or like i got to go to the met gala it's like that's a very very salubrious event to get to go to it's very but like at the

end i still like page an uber home and like wait a few minutes for surge pricing to go down until i get the uber you know it's not like i'm rich now or anything like that i think what you're saying about your family and your friends and everything i think that always finds its balance you know because you're like at the beginning not at the very beginning but you're at the beginning of a long career and when you are in this phase of excitement and offers and opportunities it is very hard to say no. And family and friends always understand that as long as that doesn't become your defining thing. Like that's all you care about. I've had that struggle before too. Like, oh, I've got this opportunity, but I'm supposed to go here with my family.

And I always err on the side of family because that really is the most important thing. And I have flown, you know, made plans where I've had to fly around the world in 24 hours to accommodate everybody, you know, but I always do find that it is worth it because your bandwidth is the most important thing. But as long as you are constantly filling your cup up, you are more readily available to give to the people in your life that deserve your attention and your space and your time. You don't ever want to give that away. You know what I mean? Like people are understanding in the beginning, but those are the people that are going to be there for you when times are good or when you're struggling with something or something's disappointing.

So it is a tricky balance, but it's totally doable. Yeah, it's just like when the special came out, there was a really intense period of PR. And so it's still intense and also very nice. You get to do things like this. You get to talk about your project. At the same time, I let a couple friends down. My friend made a trip from Boston to see me at the screening

of the special that HBO had and I couldn't like really spend any time with her because I just like done the Tonight Show that day which was amazing and like I had been on like morning television and then I got to the thing and I was pulled like hither tither and yawn and so like really didn't have a chance to like talk to my friend and then my friend called me the next day and very like appropriately was like I felt disrespected and I was like I understand because like I think I saw And I don't know if I even said thank you or if I was appropriately grateful for this huge amount of effort. And she came four hours on a train and then stayed in a hotel and went back on the train the next day. It's the day of her life.

And I don't even know. So it's a thing where it just requires a lot more intention than I'm used to expanding. And so I'm going to have to be more thoughtful and intentional in a way where I used to just be like, oh, yeah, I'll go to that thing because it's the only thing I'm invited to this week. when you have like a project every day feels like your birthday a little bit people are like oh look at this thing you made and you're like yeah look at this thing i made and then but like after like two weeks of that yeah because you don't want to take yourself that seriously a thousand percent and on that note we're gonna take a break and we'll be right back the jonas brothers are running it back we live the burning up tour and celebrate the biggest

jonas brother hits that have defined a generation one incredible celebration one unforgettable night see the jonas brothers live at rbc amphitheater september 28th get tickets now at ticketmaster.ca jonas brothers the burning up tour all over again 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 gonna have to look up this story. I'm obsessed. I'm obsessed. From best-selling 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. and we're back with alex edelman whose special is on max called just for us so if you haven't

seen it go see it it is very eye-opening and hilarious and you see how talented this person is okay alex on this podcast i know i know you're jewish so you've been to a lot of therapy all jews have and we are going to use that therapy and spit it back out i'm so excited for this And I know kind of your thing is you love to use comedy to sort of tackle tough issues. So we're going to put that a little bit to the test today, starting with our first question. So Courtney says, Dear Chelsea, I'm a big fan of the podcast. I lost my husband two years ago to suicide. I was 29 at the time and he was 33.

I found comedy and dark humor to be a very helpful tool, as well as therapy and support groups. I was pregnant with my second baby when he passed away. I now have a four-year-old and an 18-month-old. I've done lots of work on myself and have started a fundraiser in memory of my late husband. I've started dating again and feel very out of my depth. I don't want to waste my time and I tend to overshare. I don't want someone who can't handle my situation, but I know I need to balance the information I'm sharing. I also need to have someone who can understand that my late husband will always be a big part of my life.

Any tips for dating after trauma? Courtney. Alex, what do you think off the top of your head on that? I think that it's a really, this is like a really tough struggle that comes down to a thing that's actually very universal, which is, I am a certain way, I feel certain things at a cellular level. Some of those things may be more socially valid than others, right? Like someone's political opinions might be as, you know, ingrained in them as a trauma, right? Like, and so you make allowances for a trauma where you wouldn't make them for, you know, various

political opinions. Do you know what I mean? People have a thing about themselves that is who they are. And the big question is, can other people handle those things? And how much of myself do I have to hide? How much of myself am I comfortable sublimating in order for someone to see me? How much do I gradually reveal of myself? And I think the answer is, it's the personal comfort thing, right? If you feel like it's really important for you, for someone to be able to understand how you relate to your late husband right off the bat, even if it makes them uncomfortable, you will find that person. That person exists. But also, I think this person should be progressing with the comfort level that they feel, but they should be fully aware that

that is a thing that may be difficult for some folks who aren't as secure or evolved or sensitive in the right way to handle. I agree. I think you have to like gauge all of us individually when we're dealing with trauma or whatever, have to gauge when we are ready to get back on the scene. And it sounds like you think you are ready to get back on the scene.

And a good test of that is, this is such an important issue to you that it has to be kind of at the forefront of any dating scenario it sounds like. It doesn't sound like something you could hold back and like tell somebody about three months into a relationship because that's not fair. You really are dealing with trauma. And circling back to what Alex said about trauma is like there are more allowances made for people who have been traumatized and have been through something difficult. And this is as difficult as it gets. Your husband committing suicide while you have two young children pregnant with one and have another. It's all crazy. No one is prepared for that.

So Mazel Tov, that's Jewish for congratulations on getting it this getting this far and for being a parent to those two children by yourself, because nobody signed up for that. And I know you didn't. And you're doing it. And I'm sure you're doing a hell of a job. So as far as the dating goes, I would say, really, it's a great way to weed people out. You know what I mean? Somebody who doesn't get them out of there right away. And somebody who does, you keep them around and you grow into a friendship, hopefully like a love ship or whatever ship you're looking for. But I would be front loading this information with with potential dates, not on the apps or whatever. But like once you meet them and get to know them, like on the second or third date, explain, you know, if you really think that there's a spark there and there's some chemistry, you'd be surprised by other people's capabilities to deal with situations like this. Just like you're surprised in the in in the disappointing sense, you can also be surprised in the other way.

People will surprise you with how capable they are at dealing with something like this or someone else who might have had some sort of similar experience could be out there. And that would and that would be amazing for you or someone, you know, who lost their wife and wanted children. You know, there's just so many different variations of what could possibly be your future. So I would just try to step toward that and really get out there and start dating as your schedule permits. You know, you don't have to go on five dates a week, but because it's also good practice for you to understand your comfort level with discussing this issue. And and the more you talk about it, the easier it will become. And the farther away the sharpness of the trauma. So, yeah, I agree.

My one thought is and I haven't used the apps, but well, you're married. Yes, I've been married for a long time. so I'm not is Ashley Madison still available is that still an app or did they go to jail I think yeah

there was a big but I think they still exist I interviewed them once for one of my Netflix specials yeah I went up to Toronto where they're based out of and they're a couple

I was like looking at this woman I'm like really this was your husband's idea stupid ass she's like we're monogamous though and he's like

yeah I think he I think he got caught a couple weeks later after our interview for having multiple affairs anyway so we think she should

not preempt the conversation on the apps right like so I'm a widow I've got two kids I don't think widow is a good word to be using that that I just don't think that old no it does I agree it's not inviting widow is you can say I'm a single mom with two kids and then when you meet in person you talk about the real stuff you can you can just say you can just say two kids I would even be more concise because they're going to be like well that makes it unless they're unless it's Ashley Madison that you're on people are going to assume that you means you have two kids but yeah the word widow through no fault of widows themselves has become uninviting based on its association with

various unbeloved superhero movies and the most poisonous spider known to man yeah or single mother of two looking to get after it that sounds upbeat i love that that's fun but chelsea's right like congrats to you for like getting back out there after a thing it requires so much like unseen courage to actually like being the parent of two small children that alone is enough and to be with and to be a widow that alone is enough to be in a widow in that fashion having to to deal with so much that that is truly a feat so mazal tov indeed i have a question for you do people ever compare you to woody allen uh yeah but only for the artistic aspect yeah but only no i was kidding well only because i love the clarinet so much and i know it's kind of yes i

I get, I get compared sometimes artistically to it. Let's hope it ends there. Let's keep it that way. But yeah, no, I, I do. I love some of his movies and also the anecdote and I also love your anecdote. Wow. You can cut it out if you don't want, but it's my favorite thing. You've done it. You've mentioned, you've said this. I've mentioned it. People will hear, will have heard it. I love it so much, but yeah.

Thanks. I'm going to throw that into my next special. Okay. What's next, Catherine what do we got all right we have a caller things get lighter from here I call her he's can be heavy he's he can be heavy or light you're doing great I'm not happy with it I don't nothing he's very he's very bright yeah and emotionally adept that's very clear well let's see let's talk to Jessica next Jessica is calling in from Mexico City she says I'm a 42 year old woman who's lived outside of the United States for six years I've been single for seven years after a bad breakup and have been chronically dating men under 30 for far too long each year i make a resolution to not date anyone younger than 35 but here are the problems one i'm young

at heart and older guys my own age seem like they want to be my dad yes possibly abandonment and daddy issues there i still go to music festivals concerts and quote younger crowd places and i want someone who can keep up. Two, guys my age who are single are either absolute trash, not actually single, or want kids. I'd rather collect passport stamps and burn through my disposable income. So I end up going out a few times with these young guys, and of course they are always too immature in one way or another, except the bedroom, and that's where they excel, and it ends. I really want to get married eventually, but I'm stuck in this vicious cycle and I can't seem to get out. My questions are, should I give up the Gen Z dating life even though I'm very popular for

those more aligned to my maturity. Jessica. Hi, Jessica. Hi, Jessica. Hi, guys. This is Alex Edelman, our special guest today. We need a male's perspective. How old are you again? How old do I look? I'm 42. 42. And you like guys that are under 35. Is that the right bracket or under 30? I'm 35, but over 30. But right now it's like late 20s, early 30s. But my goal is 35 and over but it hasn't happened that frequently but i'm curious what you're you say that you're looking for you're looking for marriage but you're not looking for children yeah so you're looking for your person and you also like guys who who know who like Dua Lipa is listen like i travel a lot and i go to music festivals and shows all the time like i said

And so when, you know, I try to go to like maybe restaurant bars that have older people in it and they're either married or I don't know, it feels like there's no one left my age anyways. Like I've been trying to wait for these divorces. That's not true. I'm so sick of people saying there are no men around. There are men everywhere. They're falling out of trees, Jessica.

They are. You have to change your dating, your number on your app. What apps are you on? You're right. I, my friends made me do this last year, two years ago. So my dating range is 35 to 45 on my, on my dating apps. But you know, the ones that I meet out, which are end up being more successful for me just happened to be younger.

And some of the younger guys are like, they kind of are nicer. And I like how, you know, there's more consent talk. There's more like talking about your feelings. Like, there's more respect in some ways, whereas, like, men who are older, like, think that they know more than me, and it's not true. Okay, but you're generalizing everybody. You realize you're generalizing younger guys, that they're the only ones that are good and bad and that are communicative and emotionally sound or have an emotional IQ. And then you're saying that all guys older than you are idiots or chauvinistic or whatever. Neither of those things are true.

You're right. You don't want children. Is that right? Correct. Okay, so there's no rush for anything right now. A, you should be having a good time any way that suits you. You don't have to like find your partner at 42 years old. I'm 49 years old and I still haven't found my partner and I'm not fucking stressed about it.

I've got lots of options. I'm just trying to figure out if what is worth my time. You know what I mean? You don't have to look at everything like there's a time frame because that's not being present at all. And present was where all the joyfulness comes from. being absolutely present-minded enjoying the sex with these younger guys let's try not to go below 30 i mean that's just not necessary that's true we can't get mad at men for behaving that way when we're all also going to behave that way or the opposite argument is it's our turn but i think

just for what you're looking for you do want a companion more like you are looking for a steady guy i think just keep going doing what you're doing like you don't have to judge yourself But just like, you know, set it up so that you're going to have success between the ages of what is it? Thirty five and forty five is what you decided. I think that's perfect. Alex. I mean, look, I've dated older people. I was in a relationship with someone who was seven years older than me. And then I was in a relationship with someone who was six years younger than me. And like the people I've dated since then have been pretty much two or three years older than me. So like everything. So like I understand in terms of like maturity.

And also, if you're going to generalize, I have found that maturity can be, like, tied to different things, especially in, like, urban environments, right? You meet people who are in an urban environment. They have, like, a preternatural hardness to them. Like, every Los Angeles person feels, like, 25 years older because they're all, like, smoking cigarettes and, like, jaded with the business already. So, like, but at the same time, like, maturity is so multivariate. varied someone can be mature in an economic way but not mature in an emotional way or mature in an emotional way but not mature in in a communication way and like or mature in a communication way and not mature sexually and so like you have to figure out which maturities are like most important to

you because if you're not stressed about children then what is the stress about dating someone who is you know 33 instead of 35 is this like an imposed thing is this a or are you looking for someone to keep pace with you yeah it's it's two things i've been single for seven years so like not any dating for more than like three months for seven years so like no i love yous you know no like cuddles at home i travel all the time but i want to be with that person and absolutely i work really hard on being in the present and I have a lot of fun for sure. And it is something that's always in the back of my head that I know I have to stop worrying about it. I've been telling myself that for years. My therapist tells me that too, but at seven years, especially after seeing

all of your friends partner up and I'm like, I was the 17th wheel to my own birthday, you know? And you're just like, all right, I'm freaking tired of this. My thing is like, yes, I am looking for someone to have to share my life with but I'm in this like hamster wheel of like meeting a young guy and they don't want the same thing as me and then yes they are out there but I haven't met the older guy that wants the same thing as me either like they're they're either fucking off from like their divorce or nobody wanted them in the first place that's just been my opinion and I haven't lived in the states for like six years and so dating is even a little bit more complicated when there's language barriers and cultural differences and I'm really tall.

Where are you living? I live in Mexico City now and I lived in Indonesia before this. That's fun. I mean, it sounds to me, Jessica, like you have a pretty peripatetic lifestyle, right? Like you travel a lot and it's like you're on the go. In a macro sense and a micro one, right? Like you, I assume your days are full of fun and activity and stuff like that. They sure are.

And you're not like tethered, but also what you're looking for is an anchor. And so I have this exact same problem because I'm a touring comedian. And so if you're looking for someone to be an anchor, you might also have to like anchor yourself a little bit. You might have to like spend time in a way, in an environment that's like a little more interior focus. You might have to like not be going

to a bazillion events constantly because it feels like you have two desires and they may be like slightly competing. And that's my two cents. Very sagacious advice and a great vocabulary. I love all of the things you're saying, Alex. Do you hear what he's saying, Jessica? I totally agree with that. It seems like what your desires and your actions are in conflict. Yeah. I mean, I've lived in the same apartment for three years. So when I say I travel, it's like weekends or like for the summer, I'm going to Europe tomorrow for like the summer. but that's a big thing that's jessica that's like a big it's like you're like i look i live in the same apartment but i am gonna leave to go to uh halfway across the world i know but i'm very

popular in europe you guys and they're so much taller i'm looking for a husband over there there's a lot of sex to be had in europe so definitely have a great time over there i feel the same way about europe but what are you gonna do you're gonna meet a guy in like france or albania or croatia or something and then like at the end of the year i'm going to croatia tomorrow alex okay i understand but then you're gonna like meet a guy after that that is the plan and then i can move there because i'm remote so i'm like so i'm like i'm not trying to like read you to filth here jessica but i'm just saying like out of the many countries in europe i picked the two that i thought were the most sort of like far-flung and impractical i thought like i'll say estonia

that'd be too much but like montenegro but so you're gonna meet these you're gonna meet these guys but presumably you go and meet someone and you're only there for the summer and then like what you you take them back to mexico city you move to croatia like these are not like this is it is it is hard to and by the way which doesn't just say you shouldn't do it like you're living your life it seems like you really enjoy your life and this is like not a front burner of your brain problem all the way through but like it is it does make it difficult and i'm only saying this because of way too much experience it does really make it difficult to like maintain a relationship when like there is a deadline and where you're leaving and so like if you go for

the summer let's say you're going for like three months or three and a half months and you meet a guy like two weeks in that's still like a lot of pressure to put on a three-month relationship be like hey do you want to move to mexico city with me mr croatia like and you're not even staying in croatia you're going to albania so like that's two countries anomaly it's an anomaly i somehow I would doubt that, if I'm being honest with you. Some of us are only the two months of the year. Like, I'm in Mexico City the rest of the year. It's only two months of the year.

Okay, listen, I'm going to reroute you. Just lean into your lifestyle. Yes. Until you're home and grounded in a place for a long period of time. I mean, you can do a lot of inner work, and you can meditate, and you could write down what you're looking for. And I find all of that manifestation stuff is impactful. As long as you believe in it, it works.

You know what I mean? That's all we all need to do is believe what we're doing. It sounds to me a couple of the things that you've said is that you're comparing yourself to all of these other people around you instead of leaning in and enjoying your life. Your life is your own life. You're on a different path. None of your friends are going from Mexico City to Croatia, Albania, Montenegro, Estonia, you know, for the summer, right? Well, besides the ones going with me, but yeah. I mean.

All right. I think you should just stop putting pressure on yourself. Yeah, that's the thing, yeah. Yeah, stop that. Stop looking outside of your own life. That's what social media is for, and that's why it is so damaging because people look and see,

oh, I want to do that. I should be doing that. And that's what you're doing in your real life, it sounds like. And just because someone else has had a partner and you haven't had one for seven years, you're on a different path. That's okay.

Do you know who, you know the IRA, the Irish Republican Army? They were like Irish terrorists and all that stuff? Um, kind of. Do you love during the troubles in the 80s? Yeah, yeah. They were trying to kill Margaret Thatcher. And a reporter asked someone to, this goes somewhere, I promise.

And a reporter asked the head of the IRA how they felt. And they went, you know, pretty good, actually, about our chances. And they said, why? And they said, well, she needs to be perfect every time. We only need to be perfect once. And so I think this about, like, dating in high-stress environments. in the sense that like you are looking for a specific type of person and you only need to be right once and so like i think that takes a little bit of pressure obviously you're the irish

republican army like you don't you know and the world and the dating pool is margaret thatcher right like they like you need to just find your one target parallel yeah you need to find your one target and um and that one target is a person who also is mature in the ways that you value and kinetic and fun and young at heart and cool with uh going to albania for the summer you'll fucking you'll figure it out you'll find that person and in the meantime you'll have like a good amount of time so i totally agree with chelsea and that like should like not pathologize you're like yeah yeah it's not it's not even 100 the comparison it's sometimes it's just like it's just what i it is what i want inside but but the incongruency is exactly the thing because

what i'm entertaining isn't exactly gonna serve me in the long term but also maybe it's not as front burner as i thought it was because fun is like my number one value and like freedom is my number one value and all this you know so maybe you're gonna meet a 30 year old who's an old soul you know i think yeah i think what chelsea said about i thought we're on 35 to 45 when did we go back to 30. I gave you 30. Okay, forget it. I take it back. I was wrong. I wasn't even paying attention to what I was saying. No, I think I think that's right. Also, there's a lot of self love that needs to go into having a fun life. Like I've take fun very seriously. I know. I know you do. I look up to you. And that's the right attitude. But you there's also a lot of self

respect and self love that you have to instill in yourself to not feel the pressure that of these outside sources because you're just looking around feeling pressure. I understand you're saying that you feel it within yourself, but like when you love yourself enough and you have all of that going on, that is like, oh, that would be a great addition, but it's not necessary. Right. And that is what I hope I come across as. I don't want to just date anyone. Otherwise I would have by now, right? Like it has to be, he has to be additive to my life because my life is full and complete and i have a bunch of girlfriends and i you know i have all the fun in the world listen you're gonna be fine go have fun in albania go fuck your brains out or have fun with your

friends whatever you want is fine but just be in a place of acceptance instead of craving you know what i mean accept your life you've said like five times in this short time how much fun you have focus on that yeah yeah you're right consider that you've waited this long because you're waiting for the right one right as they would say in his in espanol divertirte okay thank you so much for calling in bye bye thank you adios okay that was all over the shop what what that was great actually i loved that i know it was funny yeah i like it when it's light you know what i mean sometimes things get very serious and then i have to go and smoke a big fatty yes great we'll take a break And we'll be right back with Alex Edelman.

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. And we're back with Alex Edelman for our last caller. We are back. So Amy says, Dear Chelsea, I have a bit of a situation at home. My roommate and I have lived together for two and a half years and I absolutely love our living situation.

We get along great and we haven't had any issues aside from her being late on rent a few times. Unfortunately, the past couple of weeks, she has been bringing this guy she's dating home every single night. A year ago when they first tried dating, she'd come home constantly in tears about him. He'd start arguments in public, the works. Now, out of nowhere, she is back with him and she's taking a break from drinking. I didn't think much about it. A break is always good, but now I know why. He's in her life and if they're going to date, they cannot drink around each other per his terms. She's gone out with him and partied with other friends, something she very much enjoys, being social and hanging out with groups of

friends and going to shows. Now she can't do that as much as she'd like because every single night around 10 or 11, she sneaks him into our home and he stays the night. I should note she goes for the bad guys and not the nice ones. So to me, this isn't worth her time. He's a scrub. Women's intuition is screaming inside me that he has to control her. I can't even acknowledge his presence when he's here. He says hi and I can't even look at him, let alone say hi back. It's extremely uncomfortable for me and I don't trust him in my home. I've lived here for five years and it's my safety net where I can relax, chill out and feel comfortable. But now because I'm getting so angry every night he walks in with her, it has ruined my nights for the past couple of weeks. Oh, that's

a bummer. Hi, Amy. This is Alex, our special guest today, Alex Edelman. Hey, Amy. So it sounds like you're going to have to ask, you're going to have to just tell your roommate you don't feel comfortable with him in the house and if she wants to continue dating him then she's gonna have to get a new place okay or find a new place to live i mean you you should never feel unsafe in your own house that's just thank you never ever ever ever that's like the one place that like i've made it for her and myself like yes safe safe zone safety net and i've just been like how do i handle this i don't want to be polite because in a way i'm like this is like i need to be strict about this what are your conversations been like super agreeable like i love living here i don't

want it to be uncomfortable for anybody let's make this a safety place and then and then she's sneaking him in right and then yeah like four times in the past like six days does she think you don't know that he's being snuck in i'm right there oh you're because you're saying hi well he's saying hi to you and you're not responding right okay well it's very reasonable for you to want to feel safe well the conversation will go probably something like this you'll say this and then she'll say how could you feel unsafe around him it doesn't matter why you feel unsafe it matters that you do yeah and it matters that she respects that because that's what a friendship is okay see and I didn't want to be like push you be like I know this is your place too blah blah blah I want

to be able to come home and walk around in my underwear and t-shirt yes and not have to worry about whatever and are you prepared to have someone else come and like you know I know this is new but are you prepared to have somebody else if she does choose to move out i'm like financially stable enough to like wait like that distance between transitioning and also can't she go to his house isn't that an option not allowed to she's not allowed his roommates are like no amy can i ask you a question is a bit yes are you conflict avoidant no all right well then i would how hard would it be for you wait wait can you move in with his roommates and she and him just move into your place oh my god that's amazing seems like the obvious solution no that's so

funny i mean if i knew them it might have it might be work but i'm also like not in my you seem together and mature alex what go ahead i interrupted you this time what were you going to say we've had two bits of advice so far that were like long difficult drawn out things and like not that this isn't difficult but like this is fairly simple you don't feel safe in your own home your roommate's not respecting your wishes by the way if you if it hasn't been made clear to your roommate that these are your wishes then it's incumbent on you to do that but if you have made this clear then you guys have to stop living together it's like not a compatible situation and like roommates is actually like a very it's an intimate thing it's a very intimate it's it's

very serious relationship you are living together you are huge parts of each other's life and there is a huge incongruity here this situation is like completely untenable and like you need to be like hey can you leave or be like hey this is how i feel i it's not okay with me i'm really sorry chelsea's chelsea's idea of just being like look this is how it's got to be otherwise we're gonna have to just go our separate ways i think it's very simple i should have just said uh chelsea's right that's literally that's literally that's how this podcast is it's always like i've been super cut and dry here i i believe in you amy i know you're gonna handle this and you're strong and that you have nothing to worry about so go have the conversation and you know it'll take her

a minute to digest it i'm sure but that's not your problem it's not your problem you're your problem exactly okay well have a great day and thanks for calling in thank you so much take care that was easy yeah that was nice that was a nice way to end our day together our afternoon together our morning alex i loved your advice you're so bright you're so smart i mean i i've already i already knew that but it's nice to hear it's nice to hear it within the podcast and giving advice to people in a very fruitful way i love it and i by the way it's so funny in each of these bits of advice i see like little problems that i've dealt with or little situations where i've been like deficient or little situations where i like you should have

been clearer or spoken up for myself or in the case of that of the peripatetic person i was like lady i totally hear you and also feel that maybe you either need to make a lifestyle change or just be comfortable with the life that you're living and so like it's amazing how many people who ask tough questions you're like i've had a little bit of that somewhere so i don't know yeah yeah and also it's always nice to know like it's always nice to get an outside opinion of a situation where people who don't know anything about you are telling you objectively what the situation looks like like that's what a counselor is you know okay so alex we're gonna bid you adieu congrats on your special thanks so much for having me guys true anytime honey anytime i love you and

the special is called just for us and it's streaming on max yes and please watch it if you're listening please do watch yeah watch it it's worth it okay take care okay so upcoming shows that i have you guys auckland new zealand wellington new zealand melbourne australia brisbane australia sydney australia we've added second shows to places that have sold out the 1st. And then I'm going to be in Hawaii on Maui, Kahului, and Honolulu. I will be there in July. Also in July, I'm coming to Niagara Falls on July 27th. I'm coming to Hollywood, Florida for my only show in Florida on July 28th. I'll be in Auburn, Washington on August 1st. And then Santa Rosa, California for my second show, August 2nd. August 17th is the Santa Barbara Bowl. You do not

want to miss that. And then I will be all over Maine, Charlotte, North Carolina, Charleston, South Carolina. I'm coming to Texas. I'm coming to St. Louis and Kansas City. And then I will be in Las Vegas performing at the Chelsea Theater inside the Cosmopolitan Hotel. My first three dates in Vegas are September 1st, Labor Day weekend, and then November 2nd and November 30th. I'm coming to Brooklyn, New York at the King's Theater on November 8th and I have tickets on sale throughout the end of the year in December. So if you're in a city like Philadelphia or Bethlehem or San Diego or New Orleans or Omaha, check ChelseaHandler.com for tickets. Okay. If you'd like advice from Chelsea, shoot us an email at DearChelseaPodcast at 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. 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 live 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 iheart radio 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. This is an iHeart Podcast. Guaranteed human.