On Purpose with Jay Shetty - Jimmy Kimmel: The Untold Story of Failure, Rejection & Fame (And the Rare, Unseen Side of Him as a Husband & Father!)

Episode Date: August 13, 2025

Have you ever failed at something you really wanted? What did that experience teach you about yourself? Today, Jay chats with late-night legend Jimmy Kimmel for an unforgettable live conversation at the Greek Theatre in Los Angeles. Jimmy opens the episode playfully roasting Jay, showing off his signature, sharp wit right out of the gate. The laughs quickly give way to a candid, wide-ranging conversation about Jimmy’s  life, marked by gutsy decisions, constant reinvention, and moments of surprising vulnerability. Jimmy reflects on the emotional cost of self-expression, his early struggles with being misunderstood, and how persistence (and a healthy dose of delusion) helped him find his place in the world. Jimmy shares how anxiety has shaped his life, from growing up without much money to now being someone people rely on for support, advice, and even financial help. From outrageous pranks and career missteps to a touching tribute to his prank-loving Aunt Chippy, Jimmy constantly balances humor with disarming honesty. Jimmy also opens up about the challenges of becoming more emotionally available, how therapy has helped him grow, and how being a father, and now a grandfather, has reshaped his priorities and softened his edges. In this interview, you'll learn: How to Stay True to Yourself How to Use Humor as a Tool for Healing How to Keep a Lifelong Passion Alive How to Stay Grounded When Success Finds You How to Cope With Anxiety Through Creative Outlets How Helping Others is the Key to Healing Yourself It’s not about being perfect, it’s about being honest, showing up, and continuing to try. Whether through meaningful conversations, creative expression, or simply sharing space with others, healing and connection are always within reach. With Love and Gratitude, Jay Shetty Join over 750,000 people to receive my most transformative wisdom directly in your inbox every single week with my free newsletter. Subscribe here.  What We Discuss: 00:00 Intro 04:44 Why is Putting Yourself Out There So Hard? 08:00 Discovering What Truly Drives You 09:19 The Origins of Jimmy’s Legendary Pranks 11:56 When the Pranks Never Stop 17:02 Failed Firings and Conversations That Went Sideways 18:30 Staying True to Your Creative Voice 21:42 Becoming a Grandfather for the First Time 25:55 Living With Anxiety: How It Shapes Family Life 27:29 Jimmy’s Take on Managing Anxiety 29:56 What It’s Like to Face Financial Pressure 31:17 How Jimmy Met the Love of His Life 32:31 Is Finding Love in LA Really That Hard? 33:17 The Secret to a Strong and Lasting Marriage 38:19 Why Talking About Your Feelings Is So Tough 39:16 What To Do When You’re Feeling Low 43:05 Jimmy on Final Five Episode Resources: Jimmy Kimmel | Instagram Jimmy Kimmel | Facebook Jimmy Kimmel | YouTube Jimmy Kimmel | X Jimmy Kimmel | TikTokSee omnystudio.com/listener for privacy information.

This is an I-Heart podcast. Hey, I'm Radhdi Dvlucia, and I'm the host of a really good cry podcast, and I have the opportunity to talk to Vivian too. Whether you're trying to get out of debt, build wealth, negotiate like a boss, or just finally understand how to do money right, Vivian is the person to ask. Not understanding your own money and not understanding finances, there is risk for financial abuse. Yeah.

And that is why every single woman needs to be good with money. Listen to a really good cry on the IHeartRadio app, Apple Podcasts, or wherever you get your podcast. It feels selfish sometimes to be happy. It's hard to figure out to be happy. There's no logical reason why we shouldn't be happy. It doesn't make sense. Jimmy Kimmelts been hosting his late night show for over 20 years. Jimmy, you don't do a lot of interviews.

What does it feel like to be on the other side? Putting yourself out there is hard. I started in radio. You're already halfway hidden. Nobody sees you. You don't have an audience there to not laugh if you're not funny. When everyone's firing you, letting go of you, telling you this isn't a great idea. How do you hold on to an idea when everyone's telling you it's terrible?

Pure delusion. Has talking about your emotions always been something that you've found challenging? I feel like I've matured a lot thanks to my wife. In what way? No, don't ask her. Oh, she's standing. She wants to be asked. All right, before she gets up here, Jay, I should just say,

you've been very open about your son's heart condition. And that's been something that I imagine is extremely difficult. To stop and think about someone else and their child. The number one health and wellness podcast. Jay Shetty. Jay Shetty. The one, the only. Jay Shetty.

I am so excited to be here tonight at the Greek Theater in L.A. with the one and only Jimmy Kim will make some noise, everyone. Thank you. Thank you for having me, Jay. I want you to know that my first question, as it always is, because I'm never, I'm interested. I was watching you, and when you had people stand up and you said, stand up if you've ever worried about how you looked.

And I was wondering, because I couldn't see the audience, if anyone didn't stand, buddy. And if there was a person who's never worried about how they look, that's the person I want to hang out with after the show. But I said, what is the, you know, what is the, because I, you know, I want to fit in. They said, it's elevated casual. I was like, all right, well, okay, I'll find something that seems to fit that category. And then I come here and you are dressed like Adam Sandler. I'm not wearing shorts. I'm not wearing shorts. Is this technically elevate? I mean, what is it elevated from.

I don't know what this is, but I assume it's what you were to go to 7-Eleven. There's nothing, this is just casual. This is not, this is interesting, level casual is what it is. Jimmy, this is not the roast of Jay Shadda. I think you're at the wrong. I was told differently. I think you're at the wrong event. I think we're going to see you out.

Stand up if you've ever eaten a whole pizza by yourself. Jimmy, we're three minutes in and you started roasting me already. I'm sorry, it's my nature. I was telling you, I was why it was confusing to me because you're talking these people and everybody's got these great stories and you're hypnotizing them with your eyes. I know what you do.

You know, like, 85% of this audience is here in the hope they might get to have sex with you, right? That's why I showed up. So how does this go, Jimmy? How does that work between me and you? What sex? Yeah. Well, when a host and his guest fall very much in love,

they go into the dressing room and I'll show you from there. Yes, that's right. My wife would not approve. Thank you so much. That's the only reason. Thank you so much. I appreciate it. Jimmy, you don't do a lot of.

of interviews, but you agreed. No one wants to talk to me. You agreed to do this one. Why now, why here? And what does it feel like to be on the other side? First of all, my wife loves you. And so I become exposed to you, your magic. We have some mutual friends. And really, I said to my wife, I said, hey, Jay Shetty asked me if I would do his show. I said, what do you think? She said, well, I'd like to hear you on that. And I said, all right, well, you're not. Let's listening to me at home, so maybe we can accomplish something tonight. We'll make some magic happen. Where is she? Is she here tonight? He is here, but I don't know where she's sitting. She may be. Hello. Oh, there she is. If you guys just want to write

write on a card, what do you think of her? We'll hand them to her after. Thank you for making this happen. Jimmy, let's start there, actually. You know, tonight has been all about what we don't do because of what people think of us, the things we worry that people are perceiving about us, the judgments, the criticisms that people have of us. Talk to me about a time in your life when you really felt like imprisoned by that, if ever. Oh, very much so all the time. Not just, I mean, really, honestly, like if I'm at an event and I'm not dressed properly, I feel, in fact, I went to a wedding recently. A very good friend invited me to be in his wedding party, and he wasn't not great with the details of the party. But,

But again, another dress code situation. This one was festive attire, which means nothing to me. And I was in the wedding party, and I wore what I thought was festive attire. And I showed up and everyone else was in a black suit. And so I'm the idiot in all these wedding photos. And that, you know, that's, I feel uncomfortable with the simple things like that. But, you know, putting yourself out there is hard. And I'm not talking about show business.

necessarily. I think that there are a lot of people that I've known over years and years who are really good at something. And you try your best to encourage them to do that thing that they're good at. And they're either going to do it or they aren't. And sometimes for them, you saying they're good at it is enough. That's enough for them. And they don't want to threaten that idea. They don't want you to ever think, oh, you weren't good at that. So they leave it. And I think that's, to me, that's so sad that people will do that because I do think that there are so many people who know they have this potential or this talent or whatever it is. And they just, they don't use it because they don't want to be proven otherwise, because

everyone in their, in their little circle thinks it. And they don't want to change their minds. And I know that's an inelegant way of saying it, but you just really need to do it. you have to do it. And I, for me, I was fortunate because I started in radio. And when you're on the radio, you're already halfway hidden. Nobody sees you. You don't have an audience there to not laugh if you're not funny. So you just kind of have to assume you were. And you keep going. And I was able to take baby steps from being on the radio to being the sidekick on a game show, to being a partner on a comedy show to eventually doing my own show. And I'm not sure if I would have been

able to take that big leap. I was fortunate, really genuinely fortunate and very lucky to have been in a situation where I could take those steps one by one. Oh, yeah. I mean, it's just a lot of it is luck, you know? That's the other thing that is a sad truth, but a lot of it is luck. Now you have to be ready when you get that moment or you are lucky when you have that moment of fortune you have to be prepared and you have to do whatever it is that you need to do to accomplish whatever goal you would like to accomplish but still luck is a big part of it yeah i want to i want to get to that but i want to i want to go backwards a little bit because i read somewhere that you actually grew up wanting to be a scientist no no i don't know where you read that but that is false okay was i far

into Ziploc bags and leaving them under my sister's pillow, yes. If that's what you consider to be science, I wanted to be a scientist. But, no, science was never my thing. I wanted to be an artist when I was a kid. I liked to draw. That was my thing. I wanted to draw. And you were good at drawing?

Yes. What would you draw? I draw my classmates, which they never liked. I would draw anything. Superheroes when I was a little kid. caricatures of people, I draw my family, I draw David Letterman on the television as I was watching him. Pretty much, I still, to this day, if I'm, if I have a pen and a piece of paper, I'll just scribble whatever, whoever is sitting in front of me as we're sitting there. Wow. And so you'll still

do it today? I do, yeah. Have you done it on the show ever? A couple of times. It's hard to be funny and draw at the same time. They're like, they're totally different parts of your brain. They definitely got that wrong. The media never gets anything wrong, right? Yeah, I know. In this case, it's your fault. In this case, it's yours. I'm always fascinated by what people wanted to be when they were growing up and then what they end up becoming because I think there's so much hidden in childhood.

And there's so many experiences, so many things we hear, say the subjects we study at school. But you've had this history of pranks, always being a central pillar. And for most of us, maybe you did a few pranks when you were a kid. How many of you did some pranks when you were kids? Any of pranks? Yeah, all right, a few of you. I did a lot of pranks when I was kids, but sometimes you leave those behind, but you actually lost jobs because you did pranks on your colleagues.

Yeah, bosses, yeah. Bosses, right. Is this going to be where I crack open this junie and there's a cockroach in it or something like that? Because you planted it, the sabotage. There's a prank. Yeah, I love pranks. the reason that I love pranks is because I grew up in a family that would scream and yell when I did something and I got a great reaction out of it. I mean, really, if you don't want to be

pranked, just don't react. That's the way to go. But I grew up. My Aunt Chippy is a very loud woman. She is on my show regularly. We are still, she's 85 years old, most recently. I mean, I started by putting little explosive in her cigarettes and tying cans to the back of her car. And She would go to work or she'd be in the casino in Las Vegas smoking and pow, the cigarette would blow up. And then she'd call and curse me out over the phone and I loved it. And now that I have a TV show, I'm able to escalate. So a couple of months ago, this has been a dream of mine since I saw those Waymo cars. She doesn't know about these.

She lives in Las Vegas and she's never seen a self-driving car. so I had a guy pretend to be a chauffeur and a Waymo car pick her up at the airport he gets out of the car he opens the door for her he says I have to you might have to use the restroom and then we'll go she's like yeah no problem go ahead he closes the door of the car and off it goes

and there was some real concern that this might kill her because she's 85 So I wrote to each of our daughters, my three cousins. I said, listen, here's what I'm planning to do your mother. And I need your permission beforehand because I don't want to kill her on TV. And if I do, I need someone to blame. Within seconds, they all said, oh, definitely do it. Definitely do it.

So we've got a sick family, but a fun family. But talk to me about when you weren't, you didn't have the resources to pull it of your own show and you were losing jobs over pranking your bosses. First of all, where does the audacity come from? And second of, how do you keep doing it? I believe it wasn't just once. I wouldn't call it audacity

so much as I would call it stupidity. I thought that I was a dish jockey. I did a morning radio show and I worked at a lot of radio stations in a lot of cities. If you've lived in the city, I probably had a job and been fired in that city. And each time I thought the bosses would be on board with the idea that the listeners would think it was funny if I was torturing them because then they could drive their work and go, I love hearing these guys screw with their bosses.

I wish I could do that, but I'm enjoying it through them. And they never liked it at all. They would tell me they were going to like it when they hired me. And then when it happened, they hated it. Just dumb stuff. Once we were golfing and I unlatched their golf bags on the back of the carts and then forgot about it for like six holes and then ran over their golf clubs. Once I completely smashed the inside of, I had a hot dog.

It's a long story. But there was a hot dog that he didn't eat and he threw in the garbage. And every night I would sneak in and put it in his drawer in his desk. and each day he'd open his desk and there'd be a hot dog in there and he didn't know why and he'd throw in the garbage again and then each time I would get in there and I'd put it back in the desk and then he started locking his office so I climbed in over the you know the offices have that like kind of really cheap ceiling I lowered myself in and as I lowered myself completely the desk collapsed, the shelves collapsed.

It looked like the Northridge earthquake had happened only in his office. I knew that I'd be fired if he found out. So I just got out of there and locked the door, put the hot dog in before I left. And never mentioned it again. I don't know what he thought happened. But eventually they'd fire me. Eventually they'd have enough of my notes. How did that conversation go, the firing?

Was it a conversation or you just got a message? Like, what did that look like? Well, it would go like this. Of course, there were different situations, but generally it would go, so you know how you work here now? Tomorrow, you won't be working here. And in fact, we're going to get a box.

We're going to go in your office. We're going to get all your shit and we're going to walk you out to the parking lot. I have to say, to this day, I hate firing people. It crushes me to fire somebody, even if they deserve it, even if they've done something,

bad because I've been fired so many times. And it sounds funny. These stories are, I get that they're funny, but it wasn't funny at all at the time. I was making like $18,000 a year and then had to go home and first of all tell my wife at the time that I'd been fired again for being an idiot and that we're going to have to pack all our stuff and move to Tucson. And that happened over and over and over again until eventually I found a radio station here in LA, K-Rock, that valued my commitment to nonsense. And I also grew up a little and I learned like, okay, don't call your boss's wife at home on the air and dig into their personal life, those kind of lessons, those important lessons that you learn along the way. And I was able to keep that job until I got a job in

television. I love your commitment to the prank. I have some things going on right now that would blow your mind that I can't even talk about because they're bubbling. But what my thing is, my wife does not like when I, my wife, I got her a, um, did you know you can get a personalized license plate for anyone's car? No. How does that work? Explain that to me. Well, what you do is you fill out the forms and then you forge the person's signature at the bottom. And you write on the what you would like their personalized license plate to be. In my wife's case, I made it Weebe Jammin. And then the license plate came in the mail,

and I went out in the garage, and I screwed it on to the car. And I waited until she was, you know, until she came out to the car, and she wasn't happy. But I've done that with a lot of people. My band leader, who plays the saxophone, I made one that says, Senor Saxi. I put that on his car I got the idea at a U2 concert

somebody had a license plate said U2 fan I thought oh okay maybe I'll do that in a bad way what's a firing conversation that went wrong what's the worst time you've fired someone and you're like oh I shouldn't have done it like that oh well one time it went on for like three and a half hours

it was me hugging and them crying and just kind of of going around in circles over and over again and until finally i was like all right i got to go pick up my kids so wait you fired them then hugged them oh yeah right yeah there's always some hugging involved yeah it's you know it's not great i got fired one time and i'd been fired now so many times i knew what was i knew was coming because the way do you know is they stop yelling at you and um once they stop yelling at you you're in trouble they're like ah forget And we don't need. Why bother we're firing them in three weeks? But I went in and it was me and my partner on the radio and they sat us down. They said, listen, you know, we're going to go in a different direction and, you know, all that bullshit that they say to you. And this is probably best for you guys too. And I'm thinking, no, it's not. And then they gave the whole spiel and they were nervous. And I said, listen, here's what we're going to do. We're going to come to work on Monday morning and we're going to pretend like none of this ever happened.

And there was a long moment of confused and terrified silence. Yeah. And then I started laughing and gave him the finger and left, I think. Before we dive into the next moment, let's hear from our sponsors. Welcome to the U versus you podcast. I'm Lex Barrero. And every week we sit down with some of the biggest names in entertainment to talk about the real stuff, the struggles, the doubts, and the breakthroughs that made them who they are.

We go deep, exploring childhood trauma, family, overcoming loss, and the moments that shape their journey. These honest conversations are meant to take the cape off our heroes, with the hope that their humanity inspires you to become a better you and therefore set you free to live the life of your dreams. Here's a sneak peek. I'm trained to go compete. I'm trained to eat harder. But sometimes that mentality stops you from stopping and smelling the flowers in your own garden. Is it wrong to want more? We migrated.

Our family migrated here. I'm like second generation. Who will have a trauma vying from a country, exanjero, and you're going to States? Listen to you versus you as part of Michael Tutta Podcast Network,

available on the IHard Radio app, Apple Podcasts, or wherever you get your podcast. And back to our episode. On a serious note, what's beautiful about that is you were able to hold on to a really authentic part

of self-expression that was your comedy or something you feel. found funny. It was something that you really believed it was something everyone would find funny. You didn't give up on that. You were able to hold on to it and find a place eventually that allows you to pull off these crazy things. How did you stay true to that when everyone's firing you, letting go of you, telling you this isn't a great idea, it's pushing people the wrong way? Like, how do you hold on to an idea when everyone's telling you it's terrible?

Pure delusion. Just, like, a lot of the things I thought were so funny weren't even funny. Like, they weren't funny. Like, you know, I wasn't that good at my job. And, I think that's an important thing, too, because I look back at these jobs and I go, well, it wasn't all their fault, you know, like, on one hand, I feel like maybe they should have recognized that I was always a very hard worker and that I did have some talent. I think every one of them would tell you that. But on the other hand, like, I was kind of crazy, you know, I was doing antisocial things. And they didn't get it and they didn't want to deal with it. There were adults and I was this asshole, you know, this kid. And they didn't want to deal with it. But I do have this thing where I, just kind of figure like, well, if I think it's funny, then surely there will be other people that think it's funny. And it applies to other people, too. You know, one of the best things about my job and really about, even when I was on the radio, is I've been able to identify and help other people who I saw as talented and who didn't quite know how to do it or make their way in or stay there once they got in. And that to me is very sad, even just putting my aunt chippy on television,

right now I'm not the first person to put one of their relatives on television but I just kind of looked around and go like well I think she's funny and so I think other people will think she's funny and the same with my uncle Frank her ex-husband who was my security guard on the show before Guillermo was there and then they were there at the same time he was just this weird very neurotic very um anxious former cop from New York who only arrested six people in 20 years and had this strange outlook on life where he would take $200 out of his ATM at the beginning of the week. And then he wanted to have zero dollars in his wallet at the end of the week. And it had to be that way. And so if he had any money left in his wallet on

Sunday, he'd just give it to people like strangers. He just handed out to people. And he was always doing this like weird stuff and I you know I one time my bandleader on my show is my best friend since I was nine years old we grew up across the street from each other and I didn't know my relatives were funny until he thought they were funny I was like oh they're annoying they're always yelling at each other they're you know it's like oh they're coming over he's I said my aunt chippy and uncle frank are coming over he's like oh can I come I was like what it's like oh they're hilarious I was like they are and that clicked for me I was like oh yeah they all yeah they all hilarious. And it turned out he was right. And I've just kind of operated by that principle

for my whole life. Yeah. Talking about family, you just became a granddad too, right? I did. My daughter, Katie, had a baby, a baby girl. Probably should have got more applause for that. But, um, thank you. I mean, I feel like almost killing my Aunt Chippy got more applause than having a... A granddaughter. But yeah, we're very excited. She's what, like, maybe like eight days old or something. Yeah.

Yeah. Smoking already, which we're concerned about. How does that feel? What is that like psychologically, internally, mentally? I feel like, I don't know. People seem to think, like, first of all, people approach you cautiously in a way about it. Like, oh, so you're having it like, like, I'm going to be upset about this. Like, what kind of an asshole would be upset about it?

having a grandchild, but I guess people don't want to be thought of as old, and I don't really care that much about that. I'm just excited to have a little, and also being a grandparent, I think is going to be, first of all, an incredible way to get revenge on my children. Tell me how, what are the pranks that are brewing? Not even pranks, just all the things they did to me that they're going to say, I know they're going to go, don't give, please, put them the bed. before 11 o'clock, you know, don't give them a bunch of Reese's pieces. And I'm going to nod, just like my parents do,

and then I'm going to do all the shit they don't want me to do. And I think that's one of the guys where the circle of life, you know. But it's fun. And it's exciting and it's strange to see my daughter as a mom. I think that for me is that it's not really about how I feel because I've always felt like the same person, I feel like I'm the same person I was when I was nine years old. But to see, like, your daughter holding a baby and smiling is, it's, you know, people know, it's great. Yeah, absolutely. Give it up.

It's, it's beautiful to hear about that because, yeah, it's, I have no experience about it. You have no grandchildren? I don't have kids, no grandkids. And it's really fascinating watching someone you love grow into becoming someone else. Like you said it was strange watching her do it. What are you noticing in her that feels? that way well she's breastfeeding which she'd never done before you know she's um just seeing my daughter is very funny my all my kids are really funny my daughter katy is very funny she's got a

very strange sense of humor she's an artist she makes these funny ceramics her name is katie kimmel you could see her on instagram and she you will get you will understand what i'm talking about she does like today she sent me like i sent her text this morning. And I said, you're not posting enough pictures of the baby on the stream. And so she just posted a bunch of pictures of the baby screaming and crying. And the baby's wearing a onesie that says, I'm 11 years old. So I know she's going to, you know, she's not going to be a traditional mom, but just seeing her be a mom is, it's just funny. I think it's like anything. Like when I try to remember,

how old I am. I don't know if you ever forget how old you are. I have to remember how old my sister is and add three years. That's how I get to it. And just seeing my kids become adults and both of my older kids are married and having to pay rent and to and be a husband and a wife is weird. It's just weird, you know, it's great, but it's weird. Yeah, they obviously inherited your comedic gene it sounds like I don't I wouldn't necessarily classify it as genius but they are very funny and just very good people I think

more important no funny's more important let me rank it hold on a second yeah funny definitely more important than good but both important super important yeah what's a part of you that you didn't want them to inherit um my nose um I didn't want want my daughter to have my beard for sure.

My anxiety maybe, of course, you know, kids, they inherit that whether you want them to or not. But I think anxiety, yeah. And I think, like, growing up without any money adds a measure of anxiety. But then you realize, like, you know, my older kids, I didn't have any money when they were growing up. And now my younger kids, I do. It's interesting because they somehow managed to get to the anxiety like they find different paths to it it has nothing it turns out it doesn't like for me like when i was a kid and i love to draw i told you i i would get a like a set of pens for christmas and i would never want to use them because if i use them they'd run out and so i'd have these pens that i never used and eventually they just dry out because we lived in las

Vegas and what a terrible thing. So now you know what I do? I buy a million art supplies and the house is like a dick blick, you know, my house is just full of these art supplies. And I know that I will never, I will not live long enough to use all this stuff. But knowing it's there makes me feel like I've conquered that anxiety in some way. By hoarding. By hoarding. So the reason why anyone else can't get art supplies is Jimmy Kimmel. That's right. Walk me through what anxiety really feels like at this point now in your life, how your relationship with it's changed over that time,

from going from being anxious about not having money, not having resources, not having a job. What does that look like as the externals change? What happens on the inside? Well, it's a lot simpler when you don't have any money because the things you're thinking about are, you know, do I have enough cash in my checking account? to have lunch today, to get a $20 bill out.

And like, it's like, oh, I have $21.18. Great, you know. And that's significant, certainly. But then you get in a, it might have been a position where a lot of people rely on you for a lot of things. And, you know, people will come to you with very serious needs, serious requests. Your relationship with people changes. It's hard to navigate that. it's hard to even find people to talk about it with.

There are, as far as I know, no books on how to handle it. And wind up having these kind of like intimate conversations with famous people. You don't even really know that well. I mean, like, I know a guy who is a real, like, family guy, who is a very wealthy guy, is a very famous actor. And I said, how many houses have you bought for your family? and he thought about her for a second and he goes, 17.

That was my reaction too. And you can't be the nephew anymore at that point. You're the person that people go to when they need something. And it can be a lot. You know, it really can. I mean, I shouldn't complain. Now it sounds like I'm complaining.

Oh, Jesus. We all have problems, right? I mean, some of them are just different than others. Yeah. What do you do about that anxiety, too? What do you do with it? Just buy more houses? For the most part, yeah.

Yeah, yeah. Yeah, it depends, you know, but I'm hopefully getting better about it, you know, because it's hard to explain to people when they want money, but your relationship with them is more important than that money. And then sometimes you realize like, oh, wait, their relationship with me is not more important than the money. And that's when you have to reevaluate the relationship. That's tough. Yeah, it's hard. that's that's really really tough I mean yeah

is there someone in particular or someone specific that you think about when you when you share that my wife she's sucking me dry jay how much do I get for this do I get paid no no shit

no she made you do this for free no there's no in particular it just it comes up you know it happens yeah in my small journey with it I've definitely experienced that as well losing people that you thought you were close to, yeah, realizing what standard or frequency of relationship you had with someone.

You put them up here and you thought you had this bond and actually you realized it was just based on finances or access or whatever it may be. Yeah, and that happens very quickly. Sometimes you get an email from somebody you went to the sixth grade with asking for a huge amount of money for something nonsensical. It's not even for a charity. No, never. Never.

It's crazy. Any crazy requests? you can share. You know, yeah, I've had a lot of raise your requests. I mean, you know, people think you can wave a magic wand and make all their problems go away. And it's not true, you know, even if a lot of times you give them what they want, they still have to deal with whatever got them there in the first place. So, you know, trying to keep that in mind, I think is important. But these are not the kinds of things that occur to people when they're in a pinch. Yeah, absolutely. You've been talking about your wife a lot tonight. And how long have you been together now?

We are celebrating our 12th anniversary in July. We've been together, I don't know, like 16 years or something like that. That's beautiful. And I believe you met on the show. I did. Yes, we met on the show. My wife is the executive producer, one of the executive producers of the show. And we made love.

And I asked her to marry me. So it wasn't you and your guest. It was, yeah. I got right to it. Yeah. No, she was not a guest, no. It wasn't like us. Yeah, it wasn't like us.

A bit different, yeah. This is terrible. This is terrible, Jeremy. It won't be that bad. I'm very gentle. This is what my, this is, this is all my British friends worry about L.A. being like, this is, this is what they all worry about. You mean all the friends who got buggered and boarding school are worried about? No, they're all like, what are all the parties in L.A. like, and,

You know, they're going to be like, what's Jimmy Kimmel actually like? And I'm going to have to show them this. Yeah. Let them know, invite them over. Apart from the pranks, what have been the, there's a lot of people out here either looking for love who've, we're still searching. You know, everyone always says it's always hard to date in L.A. Yeah. Is that true?

I think it is. I mean, I've never really been in that position. I've gone from one long-term relationship to another. But certainly people close to me. and my life of, I've seen them have a really hard time and even, like, think like, well, maybe I should move back to Chicago and that kind of thing. And I go, well, wait a minute, but there's, there's just people here and there, whatever. And obviously, the apps have changed that a lot, sometimes for the better, sometimes for the

worse, I guess, depending on what your intentions are. But, yeah, sometimes I feel bad for people because it does seem to be hard. Yeah, what's been the secret for your connection? and what's been the secret source to the 16 years and the 12 years of marriage? Left of my own devices, I'm not great, okay? But my wife is very good. She will say, she wants to,

I'm just checking in with you. And I'm like, what is this checking in? She probably learned it from you. That sounds about right. Yeah, that sounds about right. There's four check-ins. There's one every week, one every month, one every quarter,

yeah. And I get nervous. I'm like, well, what are you checking in about? Like, when what am I a motel? It's like, no, just how are you? How are you doing? I'm like, oh, I'm fine. What did you hear? I don't know. I have a very, I have tunnel vision, you know. I'm like, I got stuff I need to get done and I want to get it done. And sometimes I forget there are other human beings around me that, you know, would like to check in from time to time. So I've learned a lot and I'm still not great at it, but I am better at it than I was. And I feel like I've matured a lot thanks to my wife. In what way? In what way have I matured? Oh, Jesus Christ. You don't get

away with saying a statement right now. I knew you would do this, Jay. I knew it. I knew coming in here. What ways have I matured? Now when we hold hands, I don't take hers and put it behind me and fart on it anymore. And that's a big step for me. All right, let me get serious here. It's hard. I make jokes when I'm confronted with a serious situation. No, don't ask her.

I don't know if she wants to be asked. Oh, she's standing. She wants to be asked. I need a mic. All right. Before she gets up here, Jay, I should just say, I haven't matured. I was lying.

I just wanted to sound, I wanted to fit in with the podcast. Oh, this is what it was, yeah, right. Hi, sit on my left. Yeah. Not going to sit on your lap. I'm not going to sit on your lap. He gets uncomfortable when we talk about serious things.

He's definitely maturing in that area. Oh, I don't see any evidence of that. I'd like to say, first of all, I'm very proud of you coming here and being here. Oh, thank you. Because I think that's mature of you. Oh. See, okay, there's that. Jimmy is incredibly self-deprecating, if you can't tell.

And that's his defense, which is beautiful and wonderful. and we all get to enjoy it, but I get to tell people how wonderful you are, and I love to do that. And I think one of the things, the most beautiful things you've done and evolving as a human is sharing your story regularly on the show, fighting for health care for children, fighting for people. I think maybe you went from being a little more inward to outward. over the last decade of your life and I think it's been beautiful to witness and... Well, thank you for bringing it out of me.

You're welcome. Thank you. All right. You have a lot of more work to do though, so I'll just... Jimmy, Jimmy, now it's your turn. We need, you know... Yeah, Jimmy. Turn this into a session.

Yeah. Okay. Now it's your turn, please. Well, first of all, is it just me or does it suddenly smell like toast? It does. You're having a stroke. He's having a stroke.

Oh, wouldn't you love that? Well, you know, I'm always amazed at how easily these kind words come out of my wife, and not just for me, but for others. Like, there's nobody you'd rather have, give a toast at your birthday dinner, because she really speaks from the heart and speaks very beautifully and makes people feel really good. And I don't think there's any better quality than that. that. Thank you. I love you and I love you. I love you too, Molly. Thank you so much. Your eyes really are beautiful. Which one of us do you love more? Well, we'll see how the night goes. No, I love your wife too. All right. Thank you. Give it up for Molly everyone. Thank you, Molly. Thank you. Thank you. Oh, you really put me on the spot there, Jay.

Whoa, she saved you. She saved me. She's saved me. you. I mean, you know, I put you on the spot, but she said you. No, you're right. Okay, so now we're going from couples therapy to individual therapy. Oh, okay. Great. Um, has talking about your emotions always been something that you've found challenging. Yes. Not useful. Like, where, on that spectrum, talk to me about that. What, what spectrum is it? Like, what does that look like? Well, I think my dad's the same way because I hear my mother yelling at him about it. But, um, yeah, it's very, you know, I can write a nice letter. I'm good. with that, but there's something about

expressing myself in a very honest way that is difficult for me. Why is it? The answer's within. The answer's not within here. Only you can answer.

There's a lot of stuff in there. Yeah. I'm not sure I want to go rummaging around. Do you... There's a whole pizza in there. But first, here's a quick word from the brands that support the show. I'm Radhidivlukaya and I'm the host of a really good cry podcast

and I have the opportunity to talk to Logan Yuri. Logan is a dating expert, a behavioral scientist, a bestselling author and someone who is seriously changing the way we think about love and dating. In our conversation, we talk all things dating, that Logan has studied and tested from what to put in your dating profile, the pictures you should and shouldn't be using, to the conversation starters that actually work. And the huge no-noes that people probably do not realize are reducing their chances of success on apps.

Whether you're single, dating, or just trying to be more intentional in love, Logan offers the kind of clarity we all need. Relationships do require work. And the best relationships are people who really work on them together. They're so focused on, if I find the perfect person, then I'll have the perfect relationship. Instead of understanding, really, that they can choose someone great and then build that relationship together. They don't need to keep searching for perfection. Listen to a really good cry on the I Heart Radio app, Apple Podcasts,

or wherever you get your podcast. All right. Thank you to our sponsors. Now let's dive back in. When was the last time you felt like you accessed that part without a letter? And you were able to share that part of yourself? About 86 seconds ago. No, but your emotions, your emotions, not about someone else,

but how you feel about something. About someone else. No, no, not how you feel about someone else, how you feel about your own emotions or feeling an emotion that may be uncomfortable or difficult or challenging. When was the last time you feel you did do that? With our therapist last Friday at 918 a.m. It's easier with the therapist. You know, I was listening to you with Bert Kreischer. Yeah. He had him on your podcast. Yeah. And he said something. He said that after after, after,

He and his wife go to therapy. He declares a winner. Do you do the same thing? No, but I like that a lot. Who wins? You know, I don't think anybody wins, really. No, I think it's just helpful. I think it's really a good thing.

I find it very uncomfortable, but I'm never, I'm never not glad that I did it afterwards. I think it's just a good thing to talk. I mean, maybe it's the reason why we can talk as humans because we're supposed to. And I think it's good. And I think a lot of guys don't like to go to therapy and then they're looking for somebody who's going to be on their side and they're looking for a referee more than a therapist and that's probably not the way to go in it.

I will say from my own personal experience that I recommend it both individually and together. And I think that it's helped me a lot of my life to sort things out, you know. And I think what you do is, you know, is very helpful for people because, I mean, obviously, you know, there are a lot of people here just trying to figure out who they are and how to go about their lives and how to be happy. And it's hard. It's hard to figure out to be happy. I mean, there's no logical reason why we should, it should be happy. It doesn't make. sense. There are so many people suffering and there are so many sad and bad things happening. And it feels selfish sometimes to be happy. It's like, oh, yeah, great. Things are going great for

you. But look what's, you know, kids don't have lunch. And I think that it takes a lot to to remember that that's not good for you and it's not helping anybody. And if you really want to do something, do something. Don't just worry about it. And so that's something that I think is important. And I also found that, like, you know, sometimes people want advice and sometimes I want advice and sometimes people who are asking you for advice don't really want to, they don't want advice. They just want something. And I always think that when you're really down, when you're, when you're feeling low and when you're looking for answers, helping other people is always a help. It always makes you feel better. So if there's a situation where you're feeling worthless or

you're, you know, you're feeling unloved or whatever, the best thing you can do is to help someone else because, and for yourself, not even for them. It's almost a selfish thing to do. And I think it always works. I agree. I love that. I love that. Jimmy, you've been amazing tonight. We end every on-purpose interview with a final five, these questions have to be answered in one word to one sentence maximum. So Jimmy Kimmel, these are your final five. The first question is, what is the best advice you've ever heard or received? Well, it's not be yourself. We learned that earlier. Listen, listen, that's the best advice. Who did you hear that from? I heard it from a priest. yeah a friend of mine who's a priest yeah i said what do you do when people come to you and they say

you know my my son is dying and i don't believe in god he said i just listened to them good advice speaking about that you've been very open about your son's heart condition yeah and that's been something that i imagine is extremely difficult well not anymore because he's he's doing great but um it was yeah for sure yeah what what helped you at that time what what helps you in in such a difficult dire situation and well number one children's hospital here in los angeles help help me the support the support from family and strangers and I'm a religious person.

I grew up going to church, Catholic, and all those things. And I think that the thoughts and prayers that gets thrown around a lot, people when they say they pray for you, that's to take a moment of your day to stop and think about someone else and their child. It's a small sacrifice, but it's a meaningful one. Whether you believe in prayer or not, I just think it's powerful and meaningful. And I know that's more than one sentence, but that's the answer. Thank you, Jimmy. Thank you so much. That was actually just question number one.

I just snuck another one. Oh, no. Question number two, what is the worst advice you ever heard or received? You know, I don't really have an answer to that. I think that the worst thing you can do, and I've done it, and it's something that I've learned, is to lash out. You've got to take a beat and think about what you're saying, because you'll wish you had. Yeah. So sometimes there are people that, you know, just want you to bring down the hammer of Thor.

And that's not usually the way I go. I like that. All right. Question number three. What's the first thing you do in the morning and the last thing you do at night? Well, brush my teeth. You mean besides pee? I guess, yeah.

You know, we have an eight-year-old and a 10-year-old in the house. So he comes and our eight-year-old. and pounces on us in the morning and I'd just like to snuggle with him and then he wants us to come to bed with him at night and put him asleep every night and we know that we shouldn't do it every night but we just want to

and we want to get in there with him and most of the time we're very easy to convince so those are the best in the morning with the kids in the bed and then again at night with the kids in the bed I love that all right last two questions

question number four Or what's something that you used to value, that you no longer value? My parents. No, I love my parents. You know what? I don't drink much anymore. I used to, you know, I never, like, had a problem or anything like that. But I just, it's less interesting to me now.

Why, why is that? Because I'm so high all the time. We call that California sober, I believe, yeah. All right, fifth and final question. We asked this to every guest who's ever been on the show. If you could create one law that everyone in the world had to follow, what would it be? It's the golden rule due unto others. That's it.

That's the whole thing. That's all you, if we all did that, we would be doing great. Yeah. Yeah. Jimmy, you've got one special segment to wrap it up for you. Okay. I want to show you something behind you, if we can get the first one up. Take a look.

That's me. What advice would you give to your younger self? To that self, that younger self. To young Jimmy Kimmel in the seventh grade? Play the saxophone instead of the clarinet. You're never getting late. I love it. Can we get a second up?

Looking very dapper. What does Jimmy Kimmel need to hear right now? Get away from that young boy. You mean me, right? Both of you. And then let's get the last one, courtesy of my team. You know, honestly, I never even thought I'd own a suit, So I'm ahead of the game right now, I think.

Oh, is that AI me in the future? Yes. Why is my beard the same color as it is now? You're aging well. You're aging well. What do you hope you'll feel about yourself at that age? I hope I don't look like that, number one. I do hope I have that much hair.

I have a feeling I am going to be replaced by an AI me at some point. in the future. I hope I wind up like my grandfather. And by that, I don't mean dead. I mean, it's just somebody that everybody thinks of and loves. Give it up for Jimmy Kimmel, everyone. The best.

Thank you so much. Thanks, Jay. If you love this episode, I need you to listen to one of my favorite conversations ever. It's with the one and only Tom Holland on how to overcome your social anxiety, especially in situations

where you're not drinking, and everyone else is. We talk about his sobriety journey and so much more. He gets really personal. I can't wait for you to hear it. It's going to blow your mind. The quote is, if you have a problem with me,

text me, and if you don't have my number, you don't know me well enough to have a problem with me. I'm Radie de Vlukia and I'm the host of a really good cry podcast and I have the opportunity to talk to Logan Yuri. If you're out there trying to date right now, being ghosted on hinge or want to create a dating profile that gives you a solid chance of matching with someone you actually want to go on a date

with, then this episode with Hinge's Director of Relationship Science, Logan Yuri, is definitely for you. Relationships do require work. The best relationships are people who really work on them together. Listen to a really good cry on the Iheart Radio app, Apple Podcasts, or wherever you get your podcast. This is an IHeart podcast.