So True with Caleb Hearon - Taylor Tomlinson Isn't Settling

Episode Date: March 26, 2026

Welcome! This week’s guest is the hilarious Taylor Tomlinson! Taylor and Caleb talk self worth, hot people, navigating dating apps, comets, and much more! Watch Taylor’s special Prodigal Daughter now streaming on Netflix!  Join our Substack for ad free full episodes, early access to merch, our community chat, and more! https://calebsaysthings.substack.com/  Follow Taylor! @taylortomlinson  Follow the show! @sooootruepod  Follow Caleb! @calebsaysthings  Produced by Chance Nichols @chanceisloud Head to https://turbotax.com to find a store location near you and get matched with a TurboTax expert — with real-time updates in the iOS app.  Find exactly what you’re booking for. https://Booking.com, Booking.YEAH! Book today on the site or in the app. Let Rocket Money help you reach your financial goals faster. Join at https://RocketMoney.com/SOTRUE So True with Caleb Hearon is edited and engineered by Nicole Lyons. Our social media manager is Virginia Muller. All episodes are filmed in The So Trudio at Legitimate Business World Headquarters in Brooklyn, New York.  A Wave series. wavesportsandentertainment.com  Learn more about your ad choices. Visit megaphone.fm/adchoices

Wave. By the way, I'm not pro Taylor get rid of her work ethic. I think it's awesome. I'm like, we should probably meet in the middle. I probably need to be more like you, and maybe you could be a little more like me in the regards of saying yes and no. I mean, you do a lot.

I do plenty, but I'm not on your level. And I want to know, like, where do you think that comes from? What is that about? Probably from a place of inherent unworthiness. Let's go! I've been to therapy. Boom, boom, boom. Today's episode is presented by Intuit TurboTax.

Now this is Taxes. Taylor. Hello. What's up, girl? Oh my gosh. It's so crazy to be inside my favorite podcast. You're in the SoTudio. So nuts.

That is too sweet of you. It's not sweet. It's true. I really mean it. You got to stop. No, because most times I do a podcast and I'll like go listen to a few of the most recent ones to be like, okay, what's like the vibe? And with yours, I was like, I've listened to every single one.

some of them twice. Who are your faves? Who are my faves? I mean, I just listen to Chris Fleming. Of course. Obviously. You have to. Chris is like, I watched his special too.

And Chris, I mean, it's so like, it's boring to talk about what a genius Chris is because everybody. It's all we do. It's all we do. And everybody knows now and he quite frankly doesn't need it. But like, God, like every time I watch him, I'm just like, am I terrible at standup? Like, am I like the least creative, funny person in the world? Like, because that's just.

But then I put Chris in like a different category where I go like, okay, well, what he's doing is something else. Like that's like in a more special place. And I'm doing regular stand-up. It's kind of like when you do like when you do math, you have to take off the best number and the worst number. Yeah. It's like that. And you just got to take Chris out of the equation. And then you go, oh, the numbers make a lot more sense when he's not involved. Yeah. Yeah. Like I feel like that about my stand-up. Like I'll watch Chris and I'll be like, so he has access to something that I never in a million years. will get close to knowing.

Yep. And once I take him out of the equation, I go, I'm pretty good at this. Yeah. Yeah. He is so good. And it's so funny,

I did a big phone interview for like his vulture. They did like a huge vulture piece of him. Yes. Yeah. And I talked for like 45 minutes effusively about Chris. I was like,

he is like an incredibly principled person. He's so smart. He's so lovely and warm. And like I think he's like a level of brilliant that like most of us can only hope to even come close to. Just waxing glaze. Chris. And then the, I think, I didn't read the whole interview, but I think the one thing

they put in there from me was like, Chris doesn't care what parties he gets invited to. And I was like, you guys. Like you just like, what? Oh, Chris doesn't give a fuck. Chris is kind of a bitch, click. Like, I was just like, I texted Chris and I was like, hey, just so you know, I gave like really sweet comments. And then I did read a little bit more of the piece. And it was Chris being like, every podcaster is a charlatan. And I was like, Okay, well. Well, that's a big sound going around on TikTok from that episode, right?

It's like there's something waiting for me in The Divine for resisting podcasting. Do you know that? Oh, you're not on TikTok. From our show? Yes, from that episode with Chris. It's going viral right now. Oh, people are using it? Yeah.

Hey, good job, you guys. I forget you're not on TikTok, which is like, I mean, you're kind of my hero in every way. Taylor. Like, I was a fan of yours and then I met you in person and I was like, fuck. Like, God, I told everyone for the following week after I met you at that fundraiser, I was like, Caleb Heron's like, like, is good as well. we want him to be. I was like,

you guys. All the staff shaking their heads, no, solemnly, solemnly, say where you know not what you do. Like when we got coffee in LA afterward, I was like,

you guys, Caleb kind of changed my life today. Did you know you could say no? Okay, that is true. We did have a really good talk about that. You could cancel stuff? Like,

I really, I left, we hung out for like an hour and I was like, I think I owe Caleb money. You do. I do. And you invoice me.

I sent an invoice. Yeah, yeah, yeah. And I ignored it because you taught me that. Boundaries. No, that's far too sweet. We met in person finally because I begged you to come and do my benefit show.

You didn't have to beg me. That made it sound like you were saying no. Literally, I sent like a very pathetic like, I'm a huge fan. Would you please come do this benefit show? And you're like, yeah, of course. That is so funny that that was your experience because here's what happened on my end. I was on the road with my sibling brain and Sophie Butler who opened. Do you know Sophie?

Yeah, we haven't had the chance to me, but she's very funny. She's so funny. And we were on the road. We were in our hotel room. And we were like getting ready for the show or something. And your DM came in. And I went, because I was like such a fan. And I waited to open it until the show was over because I didn't know what it was about.

Oh, I love playing that game. And I was like, oh my God. Okay, we're going to open it later. And then I opened it. And you were just like, hey, it came off so breezy. You were like, hey, if you happen to be available, we'd love to have you. You know, Kansas City Tennis. You need if you're around, smiley face.

And I was like, well, I got to do that. Yeah. Got to do that in between tour dates. I had checked your touring schedule and I knew that you had that night like technically free. So I was like, hey, if you want us, I wanted to make it sound breezy because I didn't want you to feel like I would think you were some bad person if you didn't use your night off to come to a benefit show. So I was like if you're available, like I know you're going to Phoenix or whatever, but I try to make it that, you know, it's a benefit show. So I don't ever want people to feel like they have to come to do it. And I was like, Caleb knows how powerful he is that he could get anyone to fly to Kansas City.

That is not true. I would love that though. On a Wednesday night. I think you kind of are. I want you to come and stay at my house for a little while. I would love to. That was such a nice offer too. You were like, you can stay at my house. Like, and I was like, he doesn't mean that. So I'm not going to. Oh, I mean that. Do you really? I want you to come stay. You know who's at my house right now? Who's at your house? My house in Kin City. I'm obviously not there. There is a lesbian in her dog. There is a gay man in his cat. There is a punk band from L.A. And then there is a non-binary couple from Chicago passing through. And they're all just, I just put them on a group message and I was like, figure it out, you guys. That's the reality show I want to watch. You should pitch that and call it Caleb's house. I'm going to set up cameras.

You're never there. No. But it's just cameras. It's just you watching the people staying in your house. Truly. Pynopticon. And then they have to do like, what are those confessionals? Yes. About each other.

They don't know each other. Because how many bedrooms is it? It's like 10 bedrooms. Oh, no. I wouldn't probably say that. Oh, yeah. Sorry. It's like three and a half bedrooms, right?

You're so down to earth. studio, really? No, you have no money. You're a man of the people. No, it's a nice place. And I'm so glad the people get to stay there, but I don't ever get to be there. So it's turned into this funny, like, thing where my friend Addie, since she's staying there the longest right now, she's taken over on the message being like, hey guys, here's how you get in. Let me know if you need anything. I can put out some towels. Like, it's just become kind of like a self-running Airbnb where nobody makes money. I saw, I saw on Instagram, you did a story where you were like, I want to do like an artist's retreat at my house. I thought that was. I thought that was. so cool. I really want to. I want to get my artist friends to come and eventually I'd like to pay people for it but I want people to come and make their work there because I have this dream for this house that like but the house is like a hundred something years old and I'm like in the next like however long I have it I want to like infuse it with like a bunch of creative energy and have people make their stuff there

and like I'd like to maybe put like a recording studio or something in the basement so people could like record there all for free I just want people to I just want the energy in the house of like people making stuff, you know? That's so cool. I think it'd be neat. See, this is what I love about you is every time I hear you talk, I'm just like, Caleb's like living life the way you're supposed to. Taylor. You know, like sorry. And speaking of, like, speaking of living life the way you're supposed to. Well, you're not going to succeed in making this episode about me. Though I know that you would like it. And I entertained it for a second because it's early and I'm kind of like, it's a little cozy to have you be nice to me.

But you're not going to get your way. I am bad at that in interviews. I'm always like, what about your childhood and they're like, I'm a journalist. Like, leave me alone. Taylor, literally yesterday, I had an interview. I won't say the publication because then people know who it is and I don't want to make her uncomfortable, but I had an interview with a big outlet for press stuff I have coming up and I, because

we're curious people, you and I, and I was like, she was like, oh yeah, you know, English isn't my first language, so I didn't understand something that. And I was like, oh my God, what's your first language? And she was like, no, you're not going to interview me. And I was like, oh. She's like, nice fucking try. I know that trick. I'm not trying to put it off of me.

I just am like, I am curious. And then she gave me 30 minutes after we went off. When we stopped the interview, she was like, all right, ask your questions. And I was like, okay, your kids. Like I was like, she gave me time to get into it. Okay, good. That's nice. But yeah, it is a deflection tactic as well when you don't want to answer the question they have.

So I'm sure that's part of it. Is they're like, don't do that? I don't, the funny thing is like using it as a deflection, like, I've never met a question I didn't want to answer. Really? You've never met a question you didn't want to answer. I'm like, what would I? I don't think I can think. of a chance can you think of one that I'm like there I will say the only thing we come close to

what did you think of just things about like your family certain things about like there there's like one to two things about my family that people really push on that I'm like I have said what I want to say about that situation I to me it's not that I won't answer anything it's like whatever answer I give is the answer yeah that it's not for you to poke and prod and find more if I want to give more I'll give more because I'm an open person but I think other than that it's just sometimes when you're doing interviews, like the 17th question about the same viral bit. It's like, people know you from, it's like, stop. We already have done this.

Well, every video of you, people are quoting your viral jokes that you've made, like on TikTok. Like, all the top comments are just things you've said in a way that like, you know, like straight guys in high school used to quote the office all the time. Like it was their joke. I'm that for non-binary teenagers. I'm stepbrothers for they-them teenagers. Yeah, the new, the new that's what she said is, looks like he broke into the bakery and ate all the pie.

That's the new, that's what she said. God, whatever. One thing that you and I have talked a lot about, and as you know, everything is cuttable. We don't have to talk about this if you don't want to. But you work so hard. That's so nice. You really, and it's a fact. Like, you really do work so hard and say yes to so much.

It's because I'm not naturally gifted. That's not true. If I had your personality, I'd be co-eat. You try. You try to deflect from my compliment, but it's not working. You have to wake up a little earlier in the morning to get one over on me, Taylor. No, it's not true. You are naturally gifted and you're also obsessed with craft, I think, and very, you've put in the work anyway, which is what makes you so good. And I know this is making you uncomfortable. But you do work so hard. And I do wonder, like, when are you going to take your foot off the gas? Do you feel like it's coming up soon? I mean, that's the thing is, like, before I started hosting after midnight, I was like, I'm going to take six months off because I need it. And then that job came up and I took that job and I said, okay, I guess not now. And then I had my special and like now I'm in a place where, well, I canceled the last two months of my tour, but it was because I got really sick. So that didn't really feel like a few months off. And I was like working on my book and editing my special.

So it wasn't like I was doing nothing. But that was a really big deal for me to even take like a few months off of touring. Like this is the first time I've been on a plane in a few months, which is like crazy for me. So that felt like a big step in the right direction. And then this year, I don't have any tour dates planned. Like I'll probably go do clubs to work on a new hour because I'm just always doing that because I love doing stand-up. But I'm not like making myself go on a big tour that I won't feel like I can get out of or anything. So this year is more about, you know, I think writing.

And that being said, I have to put out a book in like September. So I just, I know, I really, I keep, every year I keep going and next year, nothing and it doesn't quite ever happen. Well, nothing will probably never, yeah, I think nothing will probably never happen, but yeah, no, well, maybe I might get canceled. You might, maybe on this pod. You might, we can get there. We can get there, right? I can get you canceled. Yeah. I said, I set out on a plot to get you canceled so that you relax a little bit. And then, in like, in like four months when I feel like you've really rested, I retract everything. Yeah. I lied about that girl. Bring her back. That was actually, We AI'd her face to say all that.

It's like a really crude, like your lips being moved like paper machet or something. I do, I do think about that sometimes though. I go, oh man, what if I say the wrong thing and everyone's mad at me? And then I go, well, you could stop, you know? I know. And then you could run away and there'd be a reason. Well, that's how I conquered my fear of death. Same.

It's just starting to go like, well, it would solve a lot of problems. Yes. Oh, my God, yes. I think I tried that. I joke like that on stage at Larner where I was like, I go, I'm so scared. to die, but then I go, but then I'd be dead. Yeah. Then I get to be dead.

Sometimes if I'm doing like a college gig or something and I say something earnest and the, the audience is like nodding along or they go like, they go like, hmm, or something like that and it's not a laugh. I like, I feel cagey. Like I'm like, what are you doing to me? Well, are you doing a talk or are you doing a stand up? I do a lot of Q&A's at colleges now. All Q&A?

All Q&A. Oh, that's awesome. An hour of Q&A at colleges. I've been doing a lot of them. See, again, that's how you know you have a great personality, because when they hire me for colleges, they're like, you better bring material. You better be doing hard jokes that you've polished. No, they ask me to bring material and I say, no, I'm not doing that. Because I did a couple of, there was like a year there where I would say yes to doing stand-up at colleges.

And then it's horrible. I did a lot of colleges. It's horrible. They'll put you in a room with 200 feet ceilings. The lights are, it's lit for like a cafeteria setting. Yep. the students are somehow sitting at round tables. It's set for 3,000.

It's on the night of finals. Yeah. So 20 kids come in sweatpants. They're all getting extra credit to be there. It's free. They came for free pizza. They want the pizza. Like I just,

I did it and I was like never again. And now when they ask, I've turned down a lot of them because they're like, it has to be stand up. And I'm like, then no. Wow. I'm not,

I can't do it. Because it was soul destroying. Yeah. I was like, I can't. I mean, that's how I started doing standup full time as I was doing colleges when I was like 21. I was doing a lot of colleges. Which was so stupid. I was their age.

Yeah. And I and nobody was there on purpose. I mean, we were like tricking kids into a show. Like we were genuinely in the cafeteria while people were eating. And then they'd be like, and a comedian's here. And everyone's like, what? Like, who? Like, it was so weird. But it was a lot of like, it's a lot of crowd work like at that point because no one's listening. Or I would like show up thinking I was supposed to do stand-up, and they were like, you're going to host our Greek life talent show. No. Oh, yeah, which was mostly just me going out when there were technical difficulties or someone needed to, like, do a costume change. And they'd like send me out there. And everyone was screaming and yelling and like not listening.

And I remember I went back between acts at one point. And I go, you guys, I don't think they, I mean, they're not really listening. And the girl goes, well, if you do jokes, they'll listen. And I went, okay. And I went out the next time. And I tried to start a joke. And they just started chanting for the next guy who was coming on. So I'm like, anyway, so it's kind of weird when you're dating. And they're like, manny, manny, manny. And I was like, I am going to leave. And when they paid me for the gig, the people who paid me were like, we're really sorry.

So they knew. Yeah, they were like, hey, I'm so sorry we put you through that. Here's your $700. Yeah. And I was like, it's totally fine in five years on the tonight show backstage. They're going to ask me what was the worst time I bombed. And I now have an answer. So thank you.

Don't worry. You gave me a tonight show. show story. Don't worry about it. That is so fucking funny, dude. Yeah, it's not great. Yeah, I don't, I don't know how you do all the stuff you're doing and I do, I'm trying to get you to settle down. That's my big goal. I know. When we hung out, you were very much like, well, why, why don't you just stop? Like, why don't you just take a minute? And I'm like, you can do that. You're like, I just went to Europe for like three weeks by myself. And I was like, what? Like, that's what's so frustrating is because you say stuff and it just sounds so like,

it makes so much sense and you make it sound so easy, but then I go back to my life. And it's like you've been in space floating. And then you land back on Earth and you're like, oh, right, gravity. But I've been floating around with you where you're like, say no. Cancel. Who cares?

And then I'm back on the ground just like, oh my God, I'm so heavy again. Like I'm just weighed down by all these commitments I've made. What do you think the fear of saying no or like you're, I mean, you do just have an objectively, you have an objectively insane work ethic that I don't, by the way, I'm not, I'm not pro Taylor get rid of her work ethic. I think it's awesome. I'm like, we should probably meet in the middle. I probably need to be more like you and maybe you could be a little more like me in the regards of saying yes and no. I mean, you do a lot. I do plenty, but I'm not on your level. And I want to know, like, where do you think that comes from? What is that about? Probably from a place of inherent unworthiness. Let's go. I've been to therapy. Who out there feel unworthy? Jump, jump, get up, get up, get up. If you're feeling unworthy, makes it noise.

No, I think there's probably a deep, deep fear that I am probably not talented or special enough to get by on who I am as a person. so I need to at least be someone that everybody agrees like, well, she's trying really hard. You know, like we respect the fact that she's working really hard. So it's okay that we don't think she's that talented or something like that. Yeah. We need to find a medicine that will take this feeling from undeserving people like you and give it to the people who need to feel that way. Right.

Because this is the imbalance. Sort of an unworthiness transfusion. Yes, an unworthiness transfusion from the worthy yourself to this is the embassering. balance in our society is that a bunch of people like you who should not ever even have that feeling crossed their mind. The scent of that feeling shouldn't even waft in your direction. And then the people who are the absolute worst among us are literally waking up in the morning and being like, I'm the fucking best. I know. And that's what keeps you away from feeling worthy because you go, well, the second I feel worthy, I'm one of those people. Yeah.

Who doesn't know. And everyone's walking around going, this piece of shit. I think you've, yeah, I think you've paid your penance though towards that idea like I feel like at a certain point you go like all right I think I did enough years of doubting my worthiness and stuff that right now I can go now I can go self-obsessed mode and I think it'll all even out self-obsessed mode let's go self-obsessed mode you're self-obsessed mode um am I self-obsessed mode who's doing it right doing it right is well self-obsessed is probably not the right word is the issue yeah like I probably didn't use the right term for that. But I actually would support you being self-obsessed for a little bit.

I think that people call it delusional. Well, no, but it's not delusional because I want you to be obsessed with the things about yourself that are just true and present and great. And so I don't need you to be delusional. I would give delusion to my untalented friends. I don't need you to have delusion. Well, you know what the problem is? I can see myself from every angle and some of them are bad. So that's, I mean, I think when you're somebody who's like, I think sees your self correctly. I mean, it's the same thing with like dating. Like you're not the right person for every single person you're going to go out with. But for someone, you're perfect or their soulmate. You're their dream. But for somebody else, you're like a nightmare and just a bouquet of red flags.

So that's kind of where I'm always operating from is a place of like, okay, well, you're really great, but you also suck a lot. And it just depends on who's interacting with you. And everyone's opinion of you is correct probably to some degree, which is exhausting to feel that way. Because I really also when I figured out that I needed mood stabilizers, it was like, oh, all the times that I felt great about myself, I was hypomanic. So that really fucked with me for a little while where I was like, oh shit. Like was that like not real or something? But now I miss it.

Now I'm like, oh man, I could use a little hypomania. I'm missing my mania. Yeah, I'm missing a little bit. Bring back my mania. I know because I really, that was self-obsessed mode. I was like, it's all happening for me. And look, I have four specials on Netflix, so it didn't not work.

I'm saying, bring back the mania. I know, I know. No, don't bring back the mania. I know actually. No, I think. The closest I've gotten recently is a Sudafed P.E. And I was like, whoa. I want to see you on the Sudafed.

It was great. I want to be with you off the Sudafed. Get her out. Get her outside. We need to get her to the karaoke bar now. And I'm like, I'm one of the greats. And they're like, what happened? I'm like, I took two.

Yeah, Taylor's cool. except when she gets on suit-of-fed, she gets really cocky. It's interesting the thing you say about everyone's, everyone has an opinion about me on the right. Yeah. I operate, I think, from the opposite of like, everyone has an opinion about me and either they're wrong or it doesn't matter. Like, I'm like, I know everyone has an opinion about me.

And I think, I think mostly I go with the wrong just because I'm like, they don't know, like, most people don't know me. You know what I mean? Like most people that have an opinion about me don't actually know me, regardless of what they think they know. And so when it's positive or negative, I go, if it's positive, I go, that's sweet, but you can't really know.

And if it's negative, I go, well, you're fucked in the head and you also don't really know. You know what I mean? And I think that is a difference, that I'm noticing. But it's similar in that I give everybody credit for their opinion.

And I go, everybody's right. And you go, everybody's wrong. Like, I accept not the super positive or the super negative. That's, that's what I'm saying is, I think that's interesting, is that neither of us is taking that in. Yeah.

I'm also not really internalizing the praise. My self-worth comes from my own praise, but I try not to engage. How do you do that? I just like myself. And I'm not turning shit around. I'm asking for me. I like myself.

I don't know. I just, it's fun. I go, I talk to myself and I go, you're all right. That's how you talk to yourself? I go, well, sometimes it's bad, but most of the time. I genuinely, most of the time I go,

I go, hey, you need to work on that, and that's okay. You're good at working on things. You're good. Or you go, I notice a problem in myself and I go, ooh, we should work on that. But it's not as big as a lot of people's problems. Don't stress out too much about it. You're good.

And then I do work on stuff. But you know what I'm saying? I just try to frame everything as positively as I can. When I was younger, I definitely did not. And I just think I, yeah, I just kind of, I tried to get to a place where I'm just like, it's okay. You're good. Okay.

I talk to myself, I talk to myself really gently now these days. Yeah. You're like gentle parenting yourself. These days, it's embarrassing. If you heard the way I talk out loud to myself alone in my apartment. You're out loud talking to yourself? Oh my God, it's humiliating, Taylor. No, that's good.

You're supposed to do that. If anyone ever heard this, my neighbors might actually know how sick I am. Like, I will walk around my apartment and be like, this place is a mess. That's okay. That's like the jinx shit. Like, hey, sometimes we have messy apartments, buddy.

I'm literally, I'll call myself buddy. Hey, buddy, sometimes the apartment's messy. We'll just clean it up. That's so nice. Shit like that. Crazy. Oh, the only time I speak out loud alone is, and I've just started doing this, and it does weirdly help is when I'm, I get really depressed.

I just go out loud. I'm really sad. I thought that was going to hit differently in this room. I thought everyone was going to go, good job. But no, that was not a joke at all. No, it's sweet in a way. But you just say, I'm really sad out loud. I go, I'm really sad.

What does it do for you? You know, I think because when I was younger, I was, every time I got depressed, I would get mad at myself because it meant that I wasn't doing enough. I was like, well, you should have run more today or you should have eaten more spinach or you should have lifted weights this morning. You should have gotten up earlier. You should have been outside. You're like, I go through the laundry list of like all the things I didn't do because when I was a kid, it was like, oh, if you're depressed, you're not praying hard enough. You're not working out. You're not eating right.

and so that was where my brain usually went and now being older and being like sometimes you're going to be sad a lot of the time you're going to be sad and it's fine and acknowledging it and sitting with it is like that's the growth for me is I just go okay I'm really sad right now and I guess that's sort of my way of saying and it's okay you're okay buddy yeah yeah I think that's totally lovely and I think I do the same thing when I have a bad day where I'm like feeling so negative sad or upset or whatever. I will, when I find my,

when I catch myself in it, I will be like, is today a wash or can we fix this? And the answer is sometimes we can fix this. And I go, no, you need to take a shower, go on a walk,

come home, put on some clean clothes, read a book, do your laundry. Like there are days when I'm like, you can fix this and you need to. And then there are days where I'm like, it's a wash.

Today we're going to feel bad. Today we're feeling bad. Today you can do whatever you want. you can cancel plans you can get totally stoned you can do whatever the fuck you want today's a wash but then tomorrow we got to get back to it that's really nice yeah that's something that i've tried to get better about not so much with like depression but i'm better about that with my health now because i'm like okay if you get sick you need to like shut it all down because otherwise you're not going to get better and you can't really do that to yourself anymore we did that for years

and years and years and i think you've run out of grace yeah physically i feel that too yeah yeah It's that starting out and like busting your ass to make a career thing where you're just like whatever it takes. I'll sleep three hours a night. And then you get to a place where you're like, hey, this has got to stop probably. Yeah. Where I'm like, oh, I can't take red eyes every week anymore. Because for years you just do that on the road. You're like, well, that's the cheapest flight.

And I'm trying to save as much money as I can when I'm on the road. And then I realized you're on the road four or five days a week. That's most of your life. You need to spend a little bit of that money on a hotel that's safe. and a flight that's not at four in the morning. Yeah. Like that was a big difference for me and has made a big difference as far as like my quality of life and just prioritizing sleep as well.

Because like the fact that I wasn't sleeping was most of the reason I was so unwell mentally and physically for so much of my 20s. Of course. It's like the most important thing we can do. Yeah. It's like sleeping and drinking water. They have to happen. Yeah, which is why when you do press in New York and you're like on West Coast time

and they're like, no one should ever put a comedian on live TV on a hundred, 120 minutes of sleep. No. Like first thing in the morning and I'm always like, what am I doing here? Like this is crazy and it fucks me up for a few days. And it's just like, yeah, it's just kind of not worth it anymore to not sleep for a night. You know? So, but I do say no to a lot more than I used to.

And that was what was kind of fun about getting your DM about the fundraiser. It was the first time in a long time that something had come in where I went, well, I'm doing that. Like, no matter what. Like, I'll have to go do that for sure. because I don't really have that anymore. When you're younger coming up in comedy, like every opportunity is, well, I have to do that.

Like, I just have to make it work. I have to do that. Yeah. And it was nice to feel that feeling on like a personal level where I was like, well, I have to go do that. I have to go meet Caleb. Yeah. And we had a good time.

We had a great time. It was really like an amazing, beautiful, inspiring night. Like, I was really happy to be a part of it. Yeah. You came, you killed, you made a very, very kind donation to the 1080. I did not kill. I will say that. I bombed kind of hard.

At my show? Yeah, yeah, yeah. I had a break. Girl, we are going to have to do something. We did. I had a rough set. You in reality are in a fight. You in reality are in a fight to the death. And at the moment, you're winning somehow. Well, you know what's so funny is I had to follow you, which I was like, okay, this is not going to go great. And then I went out, and I don't know why I thought this would be funny, but I went out and you had been talking about Devil Wars Prada too. And I said, thinking everyone would know it was a joke, I went so crazy.

I'm also in the Devil Wars prodded too, but then people just clapped. Because I forgot I'm successful now. Sounds good. And I thought everyone would be like, ha, ha, ha, they would never put you in that. But no,

everyone just clapped. And then I had to go, oh no, I'm so sorry. I was just nervous about following Caleb. And then everyone was like, what? So that was...

We were proud of you? Yeah, yeah. It felt like missing a step on the stairs to like start the set off. You and the battle against reality. The idea that you bombed at this show is crazy. Well, you guys, I don't know if anyone

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For ones you don't want anymore, Rocket Money can help you cancel them in just a few clicks. Canceled in just a few clicks. This is a celebrity in the 2010s? They have tools that automatically create transaction categorization across accounts plus customizable categories and tags to reveal spending patterns and add context wanting to start saving for that big family vacation this summer these tools are here to help let rocket money help you reach your financial goals faster join at rocketmoney.com slash show true that's rocket money.com slash show true rocket money.com slash so true what is going on with dating? Oh my gosh. I want to get the update. I want to hear about yours too and this is not defleck.

It's not deflecting. It's not deflecting because I also I'm just this is me just treating you like a life coach for an hour quite frankly because we we talked a little bit. bit about it at coffee and again you were just like well just do this and I'm like I can't just do this like that's insane um I am that is one thing that I this year I'm like you need to take some serious time off from touring so that you can date because when I was hosting a show three days a week and then on the road four days a week and I'm like why can't I meet anybody because you're always on stage under lights and there's no one up there yeah so like and I part of me when I took the after midnight job,

I was like, maybe I'll meet someone on set and I don't have to stop working. And I can kind of double up. And then it was just like the nicest, most platonic set you've ever seen in your life. Everyone's like wonderful, lovely friends. I think our PAs started dating and I was like, fuck.

Like, God damn it. Rick, I wanted to fuck the PAs. God damn it. No, I was like, so someone found love here. I just making sure someone calls a meeting. Everyone's fucking each other and no one's fucking me. Just kidding. I actually didn't think you were allowed to date people at work.

And then I had HR. I have the joke about it in the special, but I had HR training. And they were like, no, you can if you tell us. And I was like, every show I've ever seen is like the big issue is like, we can't date because we work together. And that's just fiction. Yeah. It's crazy. Well, and the funny thing is the HR, the policy is just like, what HR gets to know about it.

Exactly. It's like, if you tell us. Yeah, as long as you let us know, like, how do it go? Like, how is it? Yeah, you guys can do it as long as you fill us in, girl. What are you looking for? What are you looking for? Tell me now.

You know, there are probably 10, anywhere between 10 to 100 people that listen to this show. And some of them might be eligible for you. What are you looking for? Maybe it'll find you. Oh my gosh. You know what? I mean, what's really devastating that I've realized recently is I do unfortunately think I want someone funny. Taylor, I know.

Doesn't that suck? Doesn't that make you sick? It makes me sick. Because now it just got more impossible. It got so hard. Like I have a friend who wants to date like a millionaire and I'm like, that is easier to do, I think. Yeah. Than finding someone really funny.

There's more of them. There's more of them. There's more millionaires than funny people. There really is. Genuinely funny people. No, I'm sick to hear this from you because saying. Yeah. Because for years, I don't know if you do this.

But for years, I would kind of go back and forth because I would like date a comedian and then it would fall apart. And I would go, well, I can't date comedians. And then I would date a normal. person and then I would go, that doesn't work either. And so then I'd go back to like someone in this business or a comedian. And so I'd kind of flip flop. But the last couple people I've dated have been more like normal people. And I have, and they were great. And but I still like, I don't know. I just am like, when did I stop thinking I was worthy of that requirement, I guess? Because I just, when I was younger, I was like, that's number one. They have to be fun.

And then I got older and I was like, that's a big ask, I guess. And everyone around us is funny. Like all our friends are so funny. So you go, okay, well, you don't get everything from your partner, but I can get funny from all my friends. And then you're like, but the person I'm going to hang out with forever the most is not funny. I don't know. Because there's lots of people who can hang. There's like a lot of people who have good senses of humor and will laugh and can like, you know, banter a little bit. But there's a difference between banter and being funny. Yeah. It's tough. I need someone funny and I'm realizing it and it's making me sick. It's so hard. Because now I'm going on dates with these gay men and boy, some things I used to let slide are not working anymore. Really? Like what? You know, a lot of gay guys, I love gay guys. Okay. Gay guys are like a totally foundational part of my chosen, like my found family, my community. I would do anything for gay guys. Gay guys, I love you. That having been said, a lot of times I'll go on dates with these gay guys and look, we have a problem.

Something happened when we got accepted. Maybe it was the legalization of gay marriage. I don't want them to get rid of it. But something happened where a lot of gay guys lost their touch. And now there are a sizable amount of gay guys who think that quoting real housewives and drag race exclusively is them being funny. And that is, of course, not true. And it's not funny really at all. Yeah.

And so I'm going on these dates and I'm going, God, he's cute. He's got a good job. He seems to have a lot of friends and love in his life. like all these green flags. And then the only time he really says something even in the cadence of a joke is him repeating something that some horrible woman said on TV. Yeah. And I just can't deal with it.

I'm sorry, those women are horrible. And I just can't deal with it. And so I have come to a place where I'm like, no, I think I actually, I'm going to need to find someone who has a sense of humor. Yeah, I know. Like an actual point of view. No, but I look around at who's a good example? Oh, I have a great example.

So like my friend Kelsey Cook, one of my best friends, I don't know if you know if you know, she's so funny. She is engaged to Chad Daniels, who is also an incredible comedian. And that's really fucked my shit up the last few years. They shouldn't do that. Yes, because I was like, it's fine. And by the way, her ex was also a comedian. So she's just been dating. She's been in long-term relationships with really funny guys.

And I'm like, fuck me, man. Like, I thought we were all going to settle. I thought we were all just going to find people who thought we were great. and, you know, would sort of bask in our light and, like, bring other things to the table. When did everyone decide we're not settling? Yeah, it's like, what? I just got comfortable with the idea.

And now everybody's, like, finding their true love. It's bullshit. So the two of them, and they have, like, a podcast and I'll see clips of them, and I'm like, that looks amazing. Like, I want to do bits with somebody at home. Yeah. That looks great. Every time I do bits with somebody, I'm not at home,

and it sucks. What is at work or on camera? And I'm like, I want to do it at home in bed. Yeah. I want that for you. This is good to hear. I know. I'm putting it out there. I also wanted, I would love ideally another bisexual person. Yeah. I also want to, ideally, another very funny bisexual person. Now, why do they need to be bisexual? They don't need to be anything. This is a dream vision board list, Caleb. Yeah. Well, I'm sorry, let me rephrase the question. Because I would also like another bisexual person for you. Yeah, thank you. But I'm curious what is the wanting them to be bisexual? of it all. Are you guys going to swing together? I just, no. Or is it just so that they understand, so you can both be like, oh my God, that girl and that guy?

Yeah, I just, I don't know. I just kind of want someone who like, I just want my best friend who like gets every part of me. Yeah. You know, I just want somebody who like grew up with religious trauma and is also bisexual and is really funny. Yeah. And now that I've said it, the universe has to give it to me. And it will.

Because that's how it works with manifesting. You're looking for a queer person with religious trauma. I got great news. The pool is big. I know. And I know most of them. And actually most of them listen to this show. That's why I'm saying it on this podcast.

That's why I came here today. You wouldn't respond to a DM, would you? I have. Yeah? I mean, from like a stranger, it depends. It depends if they, because it's hard when people DM you and then you look at their page and there's nothing there. Yeah.

And you're like, did you really think that I was going to say, sure? Yeah. to going to drinks in Chicago where I do not live. Yeah. With someone who has no hard posts and their profile picture is of a motorcycle. Like, did you really think that I was just going to be like, oh, sure. Like, that doesn't make any sense to me. I've had some people flirt with me in the DMs.

Well, a lot of people flirt with me in the DMs. Most of them are. Civilians? Yes. Yes. Yes. Not comedians. And they, most of them are just like, it's really crazy.

Like I'm like, they're so age. inappropriate or they're so, it just makes no sense. But then sometimes there'll be someone that like, they message me something cute that seems like, I'm like, oh, this person seems normal and funny. And I go to click on the profile. The profile picture is like a group photo from 300 feet away. And then the profile itself is locked. It's a private profile.

And I'm like, well, you know I'm not going to accept that message. Like I can't even give you the chance, even though the message was cute, it's fucked up. It's so weird. And if you are going to DM someone you don't know at all. send a photo or something. Well, Instagram won't let people send photos to, like, I don't know if your accounts like this. Mine can't get photos. What?

They can't send me photos. I thought you just had to accept the message to see the photo. Oh, see, but I can't. I'm not accepting the message until I know what's up. I'm not going to accept the message on the whim because the photo could be something crazy. Yeah, but then you've just seen a crazy photo. There's a lot of fucked up shit on the internet. But then they see that I've seen it.

Well, then they've seen that you've seen it. And, you know, if I'm on Grindrinder. You know what I got to get off grinder, actually. I have no experience. It's like at a point where it's like I should not be on Grindr, full face on Maine. My grinder is me smiling and my name Caleb. Like it's just me.

I know I talked to you about doing dating apps because you told me you were on Hinge and I was like, you're on Hinge? You're too famous for that. I'm on Hinge. Really? Oh, I'm on Hinge. But don't you go on a lot of dates

that are just meat and greets? I'm gotten really good at sorting that out. You have. You never end up on a date with someone who like lied about not seeing of your stuff or not knowing who you are and then you're on the date and then it's clear that they have and they did and they lied. Maybe twice. Not that that's ever happened to me. No, that maybe twice, but it was sweet both times that they were like, hey, I obviously have like

seen your stuff, but I didn't want to make you uncomfortable. Which is great. That's nice. I've never had anyone like Trojan horse show up to the date just because they're a fan. Yeah. Usually they will message me and be like, like sometimes guys will try to be like, hey, I'm a huge fan. I'd love to take you for a drink, but it's not romantic just so you know if you'd be into that. And I'm like, well, of course not. I have no desire. I don't need to make a friend. I'm not like 12 at a new school. Yeah. I'm sorry. I'm like a grown adult with plenty of friends. Like, no, I don't need to make a new friend. Unless, I will say the only time I'm receptive to that is when I'm solo traveling abroad. Oh, then you'll then you'll then I'll be like, I'll be like, fuck yeah, let's go get a

drink platonically. Really? Yeah, because then I'm like, that's fine. Now I have no friends over here. I'm bored. I'm trying to see the city. You live here. Then I accept it. Yeah. But if I'm in New York And a guy messages me on Grindr and I was like, do you want to be friends? I'm like, well, no, no, no shade, but absolutely not. Yeah, you're like, I'm very busy. I am extremely busy and I don't see my actual friends. Actually, my friends are pretty upset with me. Right, yeah.

I asked you to hang out and I was like, by the way, you can cancel on me. And I didn't want to. You did. That was sweet, though. Well, I've, you know, that's again, probably low self-worth. But also I'm like, Caleb's so busy. If he needs to cancel, that's fine. And anybody really busy gets it.

I'm never really canceling big due to busy. I'm always canceling due to some sort of spiritual message I've downloaded from the universe. Oh, that's saying you need to just be sad today? No, not usually sad. It's more like I'm supposed to have three meetings in the afternoon, but they're a little spread out. And the universe speaks to me via several different messages and carriers and says to me, you should take the afternoon off and go to the park. Oh.

And then I received that message from the universe and I put it into action. Do you ever get scared that you're going to cancel something? Go out in public? someone's going to see you and then it's going to get back to the people you canceled on that you were just in the park? I don't lie. Oh, you don't. You go, I need to be in the park today. I don't want. I'll say I need to be in the park today or I'll say, hey, I can't do this anymore. And then if I see 100%. And then if I saw them in the park, I'd be like, hey, this is why I couldn't do it. Had to be in the park. I'm a human being. I deserve to go to the park. I'm obsessed with you. It's fun to go to the park. That's incredible. I would never, I'm always

coming up with a reason. Really? Yes. Of course. I rarely, if it was something the, really inappropriate to cancel, like a huge work obligation, then I guess maybe I would come up with a reason. But for the most part, especially with friends, I tried to just be like, hey, I'm not feeling this anymore the way I thought I would be when we planned it. So I'd need to- If you had said that to me, I would have been devastated. If you had been, there's no nice way to say, hey, I'm just not feeling seeing you today. No, no, no, no, no. It wouldn't be just not, this isn't hitting for me, the idea of your company. It's just, I really thought I would get to Tuesday and I'd go, I would love to catch up with them and I got here and guess what?

You're crazy girl. It wouldn't be just sitting and talking with a friend. It'd be like, oh, I agreed to go to paintball with seven lesbians or something. Have you done that? And then of course, you don't have, you have no idea the kind of things I can get into with lesbians. These lesbians are, they're planning activities that you can't even imagine. Oh yeah, no, paintball with seven lesbians is.

Tracks. Yeah, that's, you got to be in the right headspace for that. They always want to do something kooky and sometimes the day will come around and I'll go, I'm not the guy who said yes to this anymore. Right. I'm a different guy. I'm not the guy who said yes to this. The guy who said yes to this, he's smiling down on us right now.

He wants you guys to have so much fun. But the guy who's in me right now cannot get on a party bus. That's true. I do make some plans. And then when those plans come up, if I were being honest when I cancel, I would say, I thought I would be different by Wednesday. But I'm not. I release a dove for him.

Yeah. I release a dove for the Caleb who said yes to this. And I say, and I said, ah-wa. I send him off. into the universe and I say, God, I love that he thought we would do this. Yeah. But the me, who is me today cannot show up to game night. Yeah, but I want to, I want to want to. I want to want to. And that being said, I am going to start hosting a game night. And if any of my friends try to cancel prison, you guys have to come. Are you easy to cancel on? Uh, I don't think so.

No, you're, you're, you, right? You hold it against people? Not hold it against, but I'm definitely, I'm a pusher. You are. You're like, come on. I'm like, come on. We're young. We're going to die someday. Oh, wow. I go, we only live once. That's so interesting. Because one thing I really appreciated about you at that fundraiser is there was like, oh, we're all going to the bar for the after party. And you came up to me and you were like, we're all going to the bar. Are you coming to hang out? And I went, well, I took like half a breath in and you saw my hesitation. And you went, hey, you can go, you can walk over with me right now. As soon as you want to leave, I'll take you home. You don't have to stay that long. And by the way, if you don't want to go, no one's going to

care and you're not going to make anyone upset. And I went, See, but to me that's pushing. To me, that's, to me, that's being, to me, that's my push. And you know what? It fucking worked. Because that was the only thing you could have said to me that would have gotten me there. He's like, you said the perfect thing. And I was like, oh my, again, that's why I walked around for the next week going,

do you have to do you like him as an entity? I met that guy. And he's just as good as you think. Like, I was really just like, so. I mean, you obviously have a gift for like knowing what the person in front of. of you needs to hear in order to get them to do what you want. But it's, bring it back.

But it's really impressive. I mean, I also want to ask you, what is it like just having chemistry with every single person you meet? Does that make dating hard? That is not the case. It is the case. Taylor,

do you know what? I am working on, by the way, speaking of me not letting people off the hook easy, I am on a journey. I'm on a lightheartedness journey right now. Oh. And I am working.

And you can ask Holmes, because Holmes is the biggest victim of my pushing. I am working on. And I got, I got, I got positive praise from Holmes recently that I am getting better about letting people do their own thing. Okay. And Holmes, Holmes recently canceled something on me or said they couldn't do something that we were maybe going to do.

And I said, and where I would normally say like, you evil bitch, you hate me. This cannot, this will not stand. I'll see you in court. Right, right, right. Instead of doing my normal thing, which is half a joke and half me really wanting them to do something, I said, I love you. have a great day. I totally understand. And they got scared that I was sick or something. And they said, or something wrong with you? And I said, no, I'm on a journey. I'm a journey of self-improvement in

this area. And they said, well, I've noticed. And thank you. I appreciate it. So in case you're wondering, even even guys like me, evil, evil guys like me can change. Can make change. So inspiring. Yeah. My friends and I love canceling on each other. And I think it brings us closer every time someone goes, hey I'm so sorry I just can't and the other person goes that's okay I barely wanted to go and we go oh my god I love you so much oh we're so much and oh we're so healthy and I love you and you're the best yeah I can't do stuff like that because I have abandonment issues so do I yeah well doesn't that hurt you when someone cancels you're an extrovert with abandonment issues and I'm an introvert with abandonment issues yeah and if I if I did see them I would get closer to them and that would make it even more

painful if they ever left me so it's actually for the best that we don't get close that you stay in tonight. Yeah, yeah, yeah. Yeah. I understand that. No, I do. I'm becoming increasingly avoidant. Are you?

I think so, yeah. Why is that? I don't know. It just, it's, I have too much control over my life, I think now. Yeah, right? Yeah. And then you're kind of like, ooh, that sounds like an opportunity for my peace to be disturbed rather than like an opportunity for connection and fun.

Yeah. And now we're circling back to dating and why it's so hard. Yeah. Because going on dates, even if they're a good. date if they're not your person, it's still disappointing. Yeah. Even if like it was a nice time and you both had fun and maybe neither of you were feeling it romantically.

Like that's the best a date can go other than it's my soulmate. And it's still like, oh, I left for nothing. Yeah. I got ready. I didn't hang out with my friends tonight. Yeah. I didn't relax tonight. Yep.

I didn't do any of the things I'm supposed to be making more time for except for dating. Yep. And it didn't go well. And now I've spent the night on that. That's why you have to have, I think it has to have rules. A 45 minute first date. Yes. Coffee.

Afterwards. Coffee. One drink. Yeah. You got to. And you got to also get comfortable being like after one drink, after one, like one singular drink, if you're not feeling it, being like, hey, this was so much fun. It was nice to meet you. Where are you headed?

Yeah. I think if you know somebody a little bit through mutuals or whatever else, you can do more than coffee for the first date. But if you are going in blind date, you know, set up, app date, whatever, it's a 45 minute coffee. Yeah. I think every dating app profile needs to have a voice note. I think I need to hear your voice before I meet up with you. Yeah. I do voice note early in the text because I've met up with people who look exactly like their photo. Yeah. They have hidden nothing from me. Yeah. They have accurately represented themselves. Yeah. Appearance wise. And I hear their voice and I go absolutely not. Yeah. Can't do it. The voice is a lot. The voice is a lot. It's how you carry yourself.

It's your voice. Yeah, you got to do the voice. You got to do the voice. The voice can be a problem. Not for guys like me and you though. No, voice prompt is good. Hinge. A lot of voice prompts on there. A lot of voice prompts on Hinge was fun. And a lot of, and by the way, a lot of the gay guys that were mask fishing, the voice prompt will bring the truth to light. We'll bring the truth to life. There's a lot of backwards ball caps until that voice prompt comes around.

Yeah. But it's like, it's something they can't change. It's like, you might not like my voice. Like, you know, if you project on, it's easy to project a bunch of stuff onto a photo of a person. Yeah. And then if you meet up with them and it doesn't fit the picture in your head of what they were going to be like. It's like, well, you know, I'd like as much information as possible.

I would like to hear your voice. I would like to see your whole face and body. And I would like you to write down all of the products you use that include fragrance. Yeah. To get an idea. Oh, fragrance is a big one. Yeah. But you know what?

Here's what I'll say. I don't need to see nudes before we hook up. That's my, that's one thing about me. Right. And I know that might be a gay guy specific thing. Yeah. I was like I don't think I've ever asked for that. Gay guys are sinned in that album ASAP Rocky.

That album is coming through. It's like, hey, how's it going? I'm Craig, album. And it's like, whoa. And sometimes it's hot. You know, if you're like particularly horny, you're like, okay, we did get to the bottom of things quickly. But I would far prefer, I've said this on here before, boring old news, but I would far

prefer to figure out about your body in person in real time. Right. Old school. I think it's more fun. Yeah, it's like unwrapping a gift. Yeah. Well, I also, I need to get to know somebody. She hits, is not having it with me today.

He keeps like shaking his head and laughing at me. He's not liking my energy. on this episode? That's the problem with having people that work with you that you've known for a really long time. Like that's why I hired my sibling because I can't get away with Jack shit.

Oh, he won't be here for long. Yeah. No, it's good because you can't get away with anything because there's always someone there going. That's the problem. Chance his time with the company is almost up. He knows too much. He's going to have break issues on a road trip.

Me and the fine folks the Clinton Foundation are going to find a solution to the chance question very soon. soon. Well, because you can't just fire him. The internet will cancel you for that. Oh, they'd be so mad if I fired a chance because they don't know what happens behind the scenes. But yeah, we're going to, we're going to find a, he's going to take a small plane trip that doesn't quite make it to the destination. Who's going to look up all the true or false facts? Oh, anybody. A robot could do it.

Chat, chat, GBT, can you come up with a true or false segment for so true? We're going to replace chance with chat. I go chat Look this up Oh I had another question about Okay so you don't think you have chemistry with everybody But I'm sure everybody feels like they have chemistry with you Right?

That's sweet I hope that's true I mean do you hope that's true? Do I hope that everyone feels like they have chemistry with me? Yeah that'd be amazing Really? Oh I hope everyone thinks I'm the Oh I hope everyone thinks I'm a delight But like romantically do you find yourself going on a lot of dates

Where afterward they're like I had a great time and you're like, I was playing record ball with my own personality. Oh, you weren't bringing much. Yeah, there is a gap. There's a gap between sometimes, uh, I will say a guy thinks the date went way better than it did just because I was at work.

Yeah. Because you were doing crowd work with one person. Yeah. I was, I was, I was making shit happen. Mm-hmm. I was turning things on and off.

I was, I was keeping the server engaged. I was, I paid the bill. I, I made the date a beautiful experience for them. Yeah. It's like,

you know how that there's like that, that thing happening now where people are like, growing up is just realizing the magic of Christmas was all the work your mom did behind the scenes. That's me on an okay date. You know what I mean? I'm like, you thought it was magic, buddy, because I put the stockings up, you know?

Yeah, yeah, yeah, yeah. And then, yeah, they'll be like, oh my God, I can't wait to see you again. And I'm like, really? I feel like we could go a while. Oh, no. Yeah, that's tough. That's hard.

And sometimes I'm, I think I'm much better on a date when I know they're not, I'm not going to see them again because then I do just go into like crowd work mode where I'm just like, like interviewing them. Yeah.

Because I'm like, well, I can have an interesting conversation with anybody for three hours, you know, and certainly for 45 minutes over coffee. Yeah. So then I probably seem more interested than I am. Yeah, you're running out the clock. Oh, when I was like on dates with straight guys, I was like, oh my God, I really get into it. And then they're like, whoa, like, because they're not used to being asked like very deep

questions. Yeah. And so when you're like, what's the worst thing that's ever happened to you? They're like, whoa. Like they're really. Oh my God. This girl's like intellectual. Yeah, exactly.

They're like, well, she's really into me. And you're like, no, I just, you know, need to. I'm away with a joke. I need to get something. I'm leaving here with something. I need to get some material out of this. Yeah. Have you seen that Denzel Washington clip?

No. With Jamie Fox? No, what is it? I think about it all the time. What is it? It's Denzel and Jamie, two of our greatest minds,

talking about, is it the Oscars? Like an actors on actors? Something like that. But of course, Denzel's wearing like sweatpants and a T-shirt. I love,

I'm obsessed with Denzel's like, over it era. He's in interviews now just being like, don't fucking ask me that. Next question. That's awesome. And he should. But he, yeah, he said he was talking about an award show where he didn't win an award and he goes,

I'm leaving here with something. And then he talks about like stealing. He took, he took something. He took like some, like a meal or a code or something. But it's just very, the way him and Jamie and Jamie is laughing so fucking hard, it's up there for me. That's awesome. I think about it a lot. I need to look at that up.

Yeah, that's great. And Jamie, Jamie Fox does a Denzel impression for Denzel. That's incredible. Of course. Oh, God. I love Jamie Fox. Jamie Fox is very talented. He's one of our greatest.

He's one of our greatest. And I don't think it gets talked about enough. And here we are saying it. And here I am saying it. Everyone spread the word. People don't talk about how great Jamie Fox is? Look, he's not lauded enough for everything he does well. He's genuinely funny.

He's a great actor. He is a great singer. We just don't have a lot of people doing it on that level. Jamie Fox, come on the pod. Jamie Fox, I don't know. I don't want him to come on the pod. We have to know each other first. Oh, okay.

Oh, yeah, you don't really have anyone on that you haven't met, which is like really another thing I really admire about you. I just think Jamie and I, we should be friends first. I want to meet Jamie in the world some way, some way that isn't orchestrated. You know, I want to maybe,

maybe we bump into each other at a restaurant. And I say, Jamie, you don't know me, of course, but I'm a huge fan, Jamie. And then he says, you know what,

let's go for a walk. We go for a walk. We get lunch, we cut up, we have some fun, we chit chat, we get to know each other. And then after several months

or years of, friendship and getting to know each other, hanging out, checking in on birthdays. I'm actually, I'm really bad at birthdays, so I shouldn't say that. I'm so bad at birthdays. I'm bad. Nobody's none of my friends hear from me on their birthday. Yeah. And I just can't, I can't, there's too many. Everyone's being born all the time. I know. I forget my best friend's birthday every single year. We've been best friends for 22 years. Every year, I talk to her on her birthday most years. I know. Don't, don't even, doesn't occur to me. And then two weeks later, I'm in the middle of the country somewhere doing a show and I went, oh my God. And I text her and I go, I'm really sorry. And

She's like, I don't care. This is why I don't get bent out of shape if people don't remember to say happy birthday to me. I'm like totally fair game. The only person in the world whose birthday I remember is my mom's. That's it. And that's the only one you need to remember. That's it. It's for mom.

Yeah. But Jamie and I have a couple years of beautiful friendship. Wow. And then he says, oh, I got this movie coming out. And I go, well, if you want to come on the show and talk about it. And he goes, yeah, I'll be in New York. I'll pop by. And then we do a beautiful, so true episode.

Crazy that you think your connection with Jamie Fox is going to be forged during an imprompt to walk rather than some sort of project or party you go to or any sort of like, you know, his team reaches out about doing the pod. You think you're going to run into him and he's going to go, want to go for a walk? If his team reached out about doing the pod, I would say no. You would? Yes. Would you really?

Yes. Ask them if I don't say no to everybody. A lot of people ask to come on the show that I say no to. We have to walk. What? Damien, I need to go on a walk first because I feel. that we, it would be revealed, everything that would need, everything that needs to be revealed would be revealed on the walk. And then the episode is just, you know, then it's gravy.

But I mean, if, if Jamie's team reached out to me and said, Jamie wants to go on a walk, well, then we're talking. Put me on the email. Yeah, I remember when I, because I think, I started seeing clips of you on TikTok and I was like, who is this? This is like the funniest person I've ever seen. And then that's how I figured out you had a podcast. And I remember, uh, I was, I was talking to, oh, my social media manager at one point. I was like, I think Caleb Heron's like the funniest person on the internet. She goes, we should do his podcast. They go, I can't do his podcast.

I don't know him. That's not how that podcast works. And she goes, oh my God, you get on that podcast. I go, no, he has friends on. And that's what's so great about that podcast. I'm like, I'm just like, I'm like, I'm a real. I was like, I'm a real fan and I have respect for that project. And I go, the reason that podcast is so great is because he only has his friends on.

And so they have a rapport. And he could interview a stranger and be. great, but he doesn't want to. And that's what I love about Caleb Heron. This was back when I only said your whole name full first and last name because I didn't know you. Do you know what's interesting to me, Taylor? What? You are, you are so good at making this interview not about you. I will say, and it's always a back and forth. We talk about each other, you know, but a lot of people try to, and I know what you're doing, because this is what I do. Well, you're doing what I do. I go on other people's podcast and I go, this is my show now.

And you are one of the only people who has succeeded at it on so true. And I'm, I'm, I'm, I'm oscillating in my head between being impressed and being so angry with you. But it's genuine. It's not, it's not a plan I came in with. Like, Caleb's not going to get anything over on me. Like, I, look, I'm, you can edit this however you want. You can ruin my life.

I'm genuinely, I am genuinely a huge fan. I had a lot I wanted to say to you. I put it out on the siblings group chat because we're all big fans. I said, does anyone have anything they want? want me to ask Caleb because I'm going on the pod today. I came in with questions from other people. That's how big of fans we are over here at Camp Taylor. But even this, but even this moment.

I'm sorry. You just, it's, it's, it really is impressive. Well, it's hard. This is a meet and greet for me. So I'm, I can't just sit back. That is so silly. It's not silly.

That is silly and ridiculous. It's not silly. We've gone on a walk. We've had our walk. And it was great. We've had our walk. Yeah, it's so interesting to me. I really am, I'm fascinated by you.

Well, I find myself fascinated by you. What did you think? You think I was going to come in here and be like, what have you got? Ask me things. No, but I would love that. I, no, I'm not, I'm, I'm, I'm just interested in it. What do you want? What is the goal for you? Here right now? No, not here right now. In life. Like, what do you, what do you want out of life? What is the point of all this? Oh, man. Why are you doing all this? Oh my God. Is this punishment for me asking you questions? Yeah, you're in trouble now. Here's a hard ball question. Yeah. I mean, I really do, I think for a while when I had no time for a personal life and I was working really hard. which I'm look still in that season but we're coming out of it I was like you're fine on your own you don't need anybody it's all good and it's probably better this way and I really do I really do want

to like fall in love again and it's been like a while now and it's been even longer since I've I think like my last couple relationships I was I think making a lot of compromises where I was like you don't need all the things you want. And it's okay if the person you're dating, you know, let's just, it doesn't have a job or, you know, wants to be open or is like way hotter than you, which is not something I want ever again. I do not ever want to date someone who's hotter than me again. I want someone who is as hot as me exactly with the same level of attractiveness. I do not want to feel uncomfortable in my own home. and I want, I don't.

I want to eat as much popcorn as I want and I don't want to be doing, like I just, I want to eat normally in front of a person. I don't want to see a 12 at the breakfast table. No, I want to eat nachos. The way I eat them alone in front of another person, that to me is true love. I don't want anyone super hot again. My last two relationships, they were so hot and I hated it. I hated every fucking second of it. I'm just eating like the tiniest pieces of tofu in front of them, like just chewing like a fucking

American girl doll. Like not even really I was so uncomfortable The whole time I hated it So I don't want that again But anyway, sorry I got lost for a minute But I

Opposite by the way I love dating hot people You do? Oh yeah, I go look at him I don't I don't look at him Oh my gosh But you can't

But you don't want it You don't want it Well I want someone funny I don't want someone crazy hot Yeah Like they're not gonna be hilarious It's true

It's just not gonna happen It's not their fault So we want someone Equally as hot as you Exactly And I'm not saying I'm not saying I'm hot. I think I'm cute and I want that. That's what I want.

All right. The same amount of attraction. Exactly. And I want someone who's cute in the same way I'm cute too. I want the same genre. Yeah. Of cute. I've been on a journey with what you've been saying where at first I was like,

exactly. You don't, I was so on your side. It's like you don't need everything you want or you don't, whatever. It's like you need everything you want. You deserve it. You should get everything. And then you're like they have to be cute in the exact way I.

am and I'm like, maybe the sacrificing was good. I know. Maybe actually. I only go between the two extremes where I'm like, I'll do whatever you want and that's fine. And like I have very specific specifications now that I want. So, because, you know, I grew up in church and I was like, make your list of all the things you want in a spouse and then God will give them to you.

And what they don't tell you is when you stop believing in God and you make that list, that list isn't going to anyone. Yeah. You know, there's no one to, no one to deliver on that list. So it really is just you. writing things down that you want. And then every day you look at that list and go, wow, it hasn't happened yet. And then you go, maybe I'm not good enough for that. Kelsey told me to,

again, my friend Kelsey Cook, she told me, she goes, you need to make a list of all the things that you bring to the table as a partner. She goes, because you need confidence when you're dating. So she goes, make a list of all the things you bring to the table. And I think it'll make you feel better. She goes, that's what I did when I was single. It really helped. And I said, okay. And she goes, I'm going to call you tomorrow and you better have done it. And so the next day, she calls me. She goes, did you make your list? And I said, yes. She goes, how to go. I said, I didn't get very far. And she said, what did you write? And I said, I wrote funny, fast reader. Okay. And that's it. That's as far as I got. Funny and fast reader. Funny and fast

because you don't want to write down like cute enough. And that's what I felt like. And then I was like, I think that's as far as I got with it. And she goes, that's the saddest thing I've ever heard. I'm going to break down these walls of yours. I know. We're going to get through there. But then sometimes I'm like, I'm great. I think, look, I think I'm a catch. And I also think, If you're not into it, I fully get that. I get that completely. Yeah. So I'm, look, I'm, I'm very easy to reject, cancel on anything. And I'm like, I understand that. But also, there's people that I'm like, you should be in love with me probably. There we go. Yeah. That I like to hear. Now that I like to hear. Yeah. But then there's other people where I'm like, of course. And you should, and you have lots of options.

And you should go explore that. That part I don't like to hear. Yeah, yeah, yeah. So, Taylor, what is so true to you? What's so true to me. Yeah. Every hotel room. needs to have a plunger in the bathroom. Yes. By default. I've been on the road a long time. They never have a plunger in the bathroom. Yes.

You always have to ask for one. I have actually gone out and purchased one when I was in a hotel room for the weekend. What are you doing in there? Well, you have no idea how many times I've had to ask. Well, here's what happened because I was in New York for 10 days. And on night two, I plug the twig, I clog the Twitter. Okay, whatever.

That's okay. It's fine. And I call down to the front desk and I say, hey, I'm really sorry. I know it's midnight. Can you just bring up a plunger and leave it outside the door? And I'm going to take care of what's going on in here. We understand each other. And she goes, totally.

We can do that. They call back two minutes later and they go, hey, so we actually need to send somebody up to do it. And I said, that's not necessary. I can handle it. I'm 32. I've done this. I've been on this plan in a long time. Yeah.

I can plunge a toilet. And she goes, all right. Then they call back again, different guy. And he goes, hey, so we don't have any plungers here. I go, in the building? What? He goes, we don't have any plungers here. only have a snake. So we have to send somebody up with the snake to unclog the toilet.

And I'm like, okay. And they're like, we're really sorry. And I go, I'm really sorry. And so they send a guy up at midnight, brand my sibling and I opens the door. And this guy, it comes and he goes, first thing he says before we even say hello, he goes, hey, it happens to everybody. It's okay. He goes, I do this every night. I do this every night. He goes, look at this. He pulls the snake into the doorframe so we can see it. He goes, look at this. He's a tall guy. It's taller than him. He goes, look at this. Let me do my job. I do this every day. Don't worry about it. This is so sweet. It was amazing. He comes in. He does the thing. It sounds horrible. It's the noises coming from the bathroom. Oh my God. It sounded like someone being

strangled with a shower curtain. It was horrible. He comes out and he goes, he goes, it's done. See, it's easy. He goes, and by the way, I didn't see anything. I go, well, that's not true. But he goes, it's fine. He goes, I didn't see anything. And he goes, and I'm so glad I saw you guys. All right? This was fine.

And he goes, and I love you guys. He goes, and I love you guys. And we're like, thank you so much. That was really nice. He goes, yeah, don't worry about it. He goes, how long you stay in? I go like another week. And he goes, well, if I see you again, I'll come do it again.

It's fine. It was the nicest thing. We were like, he left. We were like, we were like, we didn't learn his name. Like, we were, he's amazing. He's like, he's like, he's like, He's gonna, hey, that nasty shit you did in there? Don't worry about the nasty shit you did.

I don't see anything. I'll come back. I hope you do it again. And I love you guys. I love you guys. I love you guys. I know. Isn't that nice? I know.

And I wouldn't have had that experience if they put a plunger in the bathroom, but they need to do that. Especially in New York, okay? The plumbing here is not great. All right. California could have handled what I did in there. Yeah. Yeah. Yeah.

Yeah. Yeah. Yeah. The shit I'm doing needs to happen in a newer state. these old states can't handle what I'm putting down. That is so funny, dude. Wow, what a beautiful experience. Yeah.

That, by the way, is the whole reason to be alive. Yeah. Interactions like that are the whole reason to be alive. That's so true. Talking to that guy is the reason to be alive. Yeah. There's no other point point. There's no purpose of being alive if you're not talking to that guy.

Yeah. Oh, I love him. You want to play a game? Yeah. How do you think you're going to do? I think I'm going to do bad, but I'm excited. Okay. That's beautiful.

And I'm going to go fast because I know you hate it when people go slow. But I'm so nervous. Okay. Don't be nervous. I'm going to read you 15 statements. You're going to tell me as quickly as you can if what I just said was true or false. If you get 10 or more correct, I think you know.

Yeah. We're going to give you 50 U.S. dollars. Are you ready? Yes. All right. Elijah Wood was born in Toronto. False. Cedar Rapids, Iowa.

The letter Q does not appear in any U.S. state name. False. True. What? Oh, fuck. Sorry. I went Albuquerque. That's a city.

A group of lemurs is called a conspiracy. Oh, I hope that's true. True. True. The tallest person ever recorded was 8 foot 11 inches. False. True. Temecula Valley High School opened in 1963.

I know I went there, but I don't care. I do not claim Temecula. True. False, 1985. Yeah. Platapuses don't have stomachs. True. True.

And is it platypuses or platy pie? Plata pie. Nice. It is true. Friday Night Lights, the series ran for 10 seasons. False. False. Five.

Hinge was released in 2000. 2013. False. True. Singing in the rain won the best, the Oscar for Best Adapted Screenplay. Oh, I should know that. That's my favorite movie. False. Don't look at me like that. It is false. Okay, I thought so. Carmel never, Carmel never spoils.

Caramel, however you say it. No, I wasn't, that's not. However you say it. That's not what I meant. Never spoils. True. That is false. The Houston Texans are the third oldest NFL franchise. False. False. They're the newest. Okay. Palamar College's mascot is the asteroids.

Yeah, that's true. False. It's the comments. What? Oh, fuck, all. Fuck you. Fuck this show.

That I should have, that's the same. What's the difference between an asteroid and a comet? Do you know? An AI chat bot could never do that chance. What do you know?

What's the difference between an asteroid and a comet? Do you know? Um, um, oh, let me guess one doesn't have a tail. Well, is that it? Well,

I bet they look different. God, Johnny Appleseed was a real person. True. True. There are no Walmarts in Alaska. True. True. False. York peppermint patties are older than Joe Biden. True. It is true. How'd she do? Eight. Oh, Taylor. You know what? I deserve that asteroid one. That was crazy. The mascot of a place, didn't you go there? I did go there for a year and a half. And that's why I was like, I know this. But asteroid and comet, that's like if you were trying to think of the word for comet, I know.

And you said asteroid. Everyone would know what you were talking about. Chance is a sick fuck. Oh my God. Bad guy. I really don't. I enjoy this segment when I'm listening, but not when I'm here participating. It's not fun that we do it to be, but we should stop.

That sucks. The fans would riot. They love that segment. Taylor, I really, I think the world of you, I think you're so great. I mean, I'm obsessed with you. Tell us, tell people where they can find you and where they can watch your special. You can watch all my specials on Netflix. The new one's prodigal daughter, but watch whatever you want.

and yeah that's that's it mostly nice thanks for coming on dude thanks for having me