In short
Sydnee Washington (returning guest) and co-hosts discuss getting “life in order” as they age, health/insurance logistics, friendship boundaries and showing up (or not) without guilt, and shifting attitudes toward sex/intimacy and “coolness”/perception. They also share hope-in-recovery stories via animal rehab accounts (“Dodo”) and personal dating/communication preferences.
Guests
Sydnee Washington (comedian/performer; has ADHD/anxiety/depression; in a relationship; talks about past breakup and improving mental health; wants preventive doctor visits and WGA-based insurance). Caleb (co-host; solution-oriented; discusses phone habits/Android; comments on sex frequency and boundaries). Marie, Lisa, and others appear as friends referenced in stories (not guests).
Key claims
Preventively see a doctor when something feels off; don’t rely on solo phone calls—ask friends to help. Stop being “Old reliable” and set boundaries so people value your support. Silence and contentment can matter more than constant sexual performance; “cool” isn’t disinterest. Friendship is the real prize over status.
Notable examples
WGA insurance phone hold leading to naps; asking friends to sit with you. Missing a best friend’s wedding due to filming and compensating via honeymoon fund. “Dodo” rehab videos where injured animals recover. Dating follow-up via a 27-minute “meaning of life” video essay.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOSydnee's Life Updates
0:34 to 1:46
Sydnee shares her recent life changes and personal growth journey.
“Getting help from one of State Farm's 19 ,000 local agents when you choose to bundle home and auto.”
Health and Insurance Talk
1:46 to 4:28
Discussion on the importance of health check-ups and navigating insurance.
“First of all, you know there's always something with me.”
Mental Health and Friendships
4:28 to 8:06
Exploration of mental health support and the importance of friendships.
“I have ADHD, anxiety, depression, whatever.”
Travel and Vacation Dynamics
8:06 to 11:28
Discussing the complexities of group travel and personal preferences.
“I hooked up with a guy a couple weeks ago.”
Romantic Relationships and Expectations
11:28 to 14:01
Insights on romance, emotional connection, and relationship expectations.
“And by the way, I was never going on trips with gay guys.”
Casual Relationship Talks
14:01 to 15:40
Explore the dynamics of casual relationships, including sex frequency and personal preferences.
“Yeah, because that's what I do with my girlfriend.”
Shifting Perspectives on Sexuality
15:40 to 16:55
Discuss the evolution of sexual desire and the idea of asexuality in modern relationships.
“and someone cute is messaging me and willing to come over at the moment.”
The Beauty of Silence
16:55 to 17:45
Delve into the appreciation of silence in relationships and social settings.
“People are talking to you constantly You got to hear everybody's thoughts Yeah I mean, is your phone bricked up?”
Expectations in Friendships
17:45 to 19:10
Address the pressures and expectations of being a supportive friend in social circles.
“You ever, like, go to a restaurant and you're just sitting there eating and people are just eating and they're not.”
Finding Personal Boundaries
19:10 to 20:40
Explore the importance of setting boundaries and valuing personal time.
“She's just like classic mom who sends me like crazy articles like when she sees like even a single word that relates to my life.”
Show all 30 chapters
The Challenge of Showing Up
20:40 to 23:00
Investigate the difficulties of consistently showing up for friends and the need for balance.
“This is so on brand for me that I can't, like, I am the comedy.”
Remorse and Participation
23:00 to 24:25
Discuss alternative ways to show support when unable to attend events.
“And I don't want to have this thing where like we speak in such certainty.”
Family vs. Friendship Dynamics
24:25 to 26:00
Contrast family loyalty with the fluidity of friendships and the impact of upbringing.
“You know, I will say, you and Marie and Mateo and Liza, like, our whole little crew of buddies, y 'all are present.”
Navigating Changing Relationships
26:00 to 28:00
Reflect on the evolution of friendships and the importance of fighting for meaningful connections.
“and so unfortunately it means that someone that I barely know that I like well enough.”
The Nature of Friendship
28:00 to 29:26
Exploring the complexities and permanence of friendships compared to family ties.
“And I forget that friends could just cut you off at any moment.”
Value of Friendships Over Fame
32:21 to 34:20
Discussing the importance of meaningful relationships over celebrity status and fame.
“I rather have the friendship than the celebrity, the red carpets, all that stuff, because I've seen it, what it's done to people, they're miserable.”
Navigating Success and Authenticity
34:20 to 36:13
A conversation about maintaining authenticity while achieving success in a challenging industry.
“And I said, oh, yeah, no, I need to get more money.”
Personal Perceptions and Expectations
36:13 to 39:06
Exploring the misconceptions others have about personal identities and expectations.
“Have you seen that clip of him and Robin?”
Authenticity in Performance
39:06 to 42:00
Discussing the pressure of maintaining a persona versus being true to oneself in the public eye.
“And it's about like all the Barbies that I find on the internet reenacting stories that have happened in my life.”
The Nature of Coolness
42:00 to 43:56
Explore the concept of coolness and how it's misinterpreted by the younger generation.
“No, they don't want me to be Marie, but Marie is so freaking cool.”
Cool Encounters and Connections
43:56 to 45:32
A discussion about memorable people and the importance of genuine connections.
“And you just seem fucking boring and rude.”
Life Lessons from a Lesbian Cruise
45:32 to 47:31
Insights gained from attending a lesbian cruise and the experiences shared with older women.
“Like the characters, but then like you'll be in the green room somewhere and he's just like pouring his heart out and like showing you like, oh yeah, no, I'm cool online.”
Transformative Stories of Coming Out
47:31 to 49:48
Sharing impactful stories from women on the cruise about coming out later in life.
“I've been screaming about it from the mountaintops.”
Aging with Grace and Humor
49:48 to 52:43
Discussing the beauty of aging and the societal perceptions surrounding it.
“Like, die in terms of, like, tears coming.”
The Pressure of Appearance
52:43 to 56:00
Exploring the pressure to maintain appearances in the age of social media.
“It's okay to look like you're supposed to look.”
Aspiring to Be a Sex Symbol
56:00 to 58:30
Sydnee shares her desire to be recognized as a sex symbol like Queen Latifah and discusses the challenges of fame.
“For me, I think it's a little different because, you know, I do want to be a sex symbol.”
The Burden of Fame
58:30 to 1:02:56
The hosts discuss the challenges of being recognized and the impact on personal moments, emphasizing the need for personal space.
“If anybody listening to this gets the opportunity to do this for me.”
Queen Latifah's Influence
1:02:56 to 1:07:15
Sydnee expresses her admiration for Queen Latifah and discusses her impact on the LGBTQ community and representation in media.
“If I saw Queen Latifah walking towards a puddle and it was too big for her to walk around, I'm laying down on the puddle.”
Relationships Beyond Sex
1:07:15 to 1:10:03
The conversation shifts to the dynamics of relationships, emphasizing that intimacy is not solely about sex and the importance of emotional connection.
“But jokes aside, I need to find my own thing.”
Sydnee Washington's Upcoming Shows and Podcast
1:10:03 to 1:11:05
Sydnee Washington shares where to find her and details about her upcoming shows.
“Cut this up however you, I know I was like, you don't have ADHD, so I'm all over the place and I don't know what.”
Transcript
Automatic transcript. May contain errors.0:00Caleb Hearon:Apple Pay is the simple, secure, and fast way to pay. That's because your credit or debit card is right on your iPhone. Accepted at millions of places, from big box stores to boutiques, you can check out with your iPhone anywhere contactless payments are accepted. Apple Pay is more secure than a physical card because you authenticate your purchases with Face ID before you pay, and your actual card number is never shared with merchants. Add your debit or credit card to Apple Wallet to check out in seconds. Simple. Secure. Fast. That's Apple Pay. Terms apply. This episode is brought to you by State Farm.
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1:08Caleb Hearon:And for morning hikes up the mountain trail, good pace! To nighttime ghost stories from the camping chair. What a twist! Whatever level of active, Sierra loves it all. Head to Sierra or Sierra.com for the brands you want at the prices that let you do it all. From athletic to athletic-ish, Sierra's got it. Wave. I've had them done twice and I am obsessed with the idea of, you know, you want to upgrade yourself. You want to do a little... What'd you have done to them? Bigger both times? Yes. Okay. Yes. And I'm... I think if I get another gig, I'm going to get them done again. I don't know. I don't know.
1:52Caleb Hearon:First of all, you know there's always something with me. Yes. There's always something. I do know this. And so, I said when I come back on your podcast, I want to be well adjusted I want my life in order And we're not there yet We're not there yet What's going on? Well, the thing is that I'm in a relationship, things are good Comedy is going well But I feel like I want to move towards When I want to be an adult And I'm not I eat candy in the morning I'm smashing Red Bull Every other day I eat candy in the morning. I eat candy in the morning. You thought I was going to be like, I'm doing crack.
2:33Caleb Hearon:You're like, no. Because I got to tell you, even when you were saying I'm not doing well, I'm like, Sid, you live in a beautiful apartment. I do. You have a lovely, admirable relationship. I do. You're getting up constantly. I have never seen you turn up to any function, the smallest function, an apartment hangout on my couch where the entire point is to get high and eat snacks. You have never not showed up full beat, hair, outfit. it so i don't when you say your life's not together i'm like keep in mind you're more together than i am and so i'm wondering what the hell you're talking about but then the candy in the morning obviously i'd like you off the red bull i'd like you off yes of course please it's just but lisa traeger you know we love her she's like you gotta have a vice you she's like you don't drink you don't smoke you're not committing crimes what is a little candy in the morning what is, you know, a Red Bull at 9 p.m.?
3:25Caleb Hearon:Yeah. And I said, Lisa's got a point. She kind of does. She's got a point. This is one of those moments where we got to hand it to Lisa. We got to give it to Lisa. You're like, you know what? You're making sense. Yeah. So, but I want to move towards, because, you know, I'm getting older, and you were just telling me about going to the doctor, and I'm like, I really need to take that seriously. My friend Kevin, Kevin Morby, who has been on the show, he gave me some of the best advice, and I really have taken it to heart. Okay. He said after 30, the first time something feels off, anytime something feels off, go to the doctor.
3:59Just immediately do it. And nothing feels off. I'm going just preventatively. Like I'm going just to get stuff run because I'm having a weird kind of re-flare up of my old hypochondria that I had kicked. But just anytime something feels off, just go. If you have, if you have, I know, and that's a privilege, if you have health insurance and stuff. I was like. But I'm saying if you have that option, and even if it's like it's going to cost you a little bit, but you technically could, do it. And, of course, if you're listening and you don't have health insurance, I send all my love and I feel bad that I said the thing, but this is for people who do have health insurance.
4:28Caleb Hearon:Okay. But look at this. This is what really messes me up. Right. So obviously I'm mentally ill. I have ADHD, anxiety, depression, whatever. And so I need to get my insurance through WGA. Yeah. Right. In order to do that, you got to get on the phone. Yeah. And I get on the phone. They got me on hold. They got me on hold. They said, I got to do this. I got to do that. by the time I get to the person who's actually going to start my insurance up, I'd already hung up and took a nap. Sid, here's what we're going to do. Yeah. And I'm sending this out to everybody. Everybody who's listening, I'm sending this out over the airwaves to you.
5:01Yes. We need to start leaning on our friends, even when we feel like it's not warranted. What you need to do is, if that's something that needs to get done, and you know I am not going to sit on that phone, you need to call me, you need to call Lisa, you need to call Marie, call somebody and be like, do you have two hours this week to come and sit with me and hold my hand while we do this? They do not. They do not. You do. I will make two hours.
5:22Caleb Hearon:Well, you got to take the D &D off. Text. Text. Don't play games with me. No, and don't you guys laugh at it either. No, you don't say it. You don't laugh at it. You got to name it. No, but I'll come over. I'll come over. Okay. We'll get it sorted. We're going to get it done. We'll get it done. We'll get it done. If this is the thing. It is the thing. We'll get it sorted. It is. And then after that, and then when I do get the insurance and I go to the doctor and everything is in order, I will still find a way to be like, you know what? It sucks. It sucks, yeah. It totally sucks. But you're doing, I think you're doing really well.
5:54I am. I feel like you're in a much better place than a couple years ago. Woo!
5:57Caleb Hearon:When I came the first time, just so true, I was fresh off a breakup. I just left LA. I was talking shit about everything and everybody. I was in a, I was like, bring back de Blasio. Like, I was saying anything. I was saying anything. and I want to apologize for a lot of the things that I said and now I'm in a good place. I am. Yeah. I am. I really like it. I am. The thing is that the world is on fire but I'm looking to the little light like you and my friends and, you know, the dodo. I go to the dodo when I just want to get in a better place. What's going on with the dodo? You don't know about the dodo?
6:35Caleb Hearon:What's up with the dodo? Come on, you know about the dodo. What are you going to the dodo for? Okay, so they do these videos, long-winded, rehabilitating animals. And so you'll see a little dog limping and missing an ear. And then all of a sudden, three minutes in, the ear is back. The dog is frolicking. It's got a Burberry scarf on it. They got a family. It's those things where you see this little thing that is doing bad. Dodo is like, no, there's light at the end of the tunnel. And it reminds me of like if that could happen, you know, for this beaver, then there's hope for me as well. Yeah. Yeah.
7:14Yeah. This is a channel of some sort?
7:17Caleb Hearon:Yes. Yes. It's on Instagram. It's on TikTok. It's on YouTube. Yeah. Get into it. I really might. Yeah. There's otters. There's capybara. Whatever you want. They got owls. There was an owl that was found in a train, and it was overheated, and it came out, and it looked a little wonky. Yeah. They were like, this owl should be gone. But it's still here. And they're like, he can't really hear or see. But he's alive. Oh, okay. And they got him with another owl that's like older and kind of out of it as well. And they're like besties. Yeah, of course. Yeah, and they'll try to talk to one of them. And they're just like, and I said, I relate to this.
8:00Caleb Hearon:It's just disassociating. You put these two fucked up owls together. Yes. They made a beautiful friendship. Yes. Yeah, that's us. Yes, that is us. That's me and you. No, you're way more there. That's me and you in a big way. Dude, that reminds me. I hooked up with a guy a couple weeks ago. Not the owls out of it. You're like, this reminds me of somebody I've had sex with. It's the video suggestions. It's the video suggestions. I hooked up with this guy. We had a fun date, and we went back to his place and hooked up. And he lives in L.A. You should have started with that. I know. And then yesterday, he sent me a link to a video, and he goes, this made me think of you.
8:36I should have sent it in the moment. This made me think of you the other day. I should have sent it in the moment, but sending it now. And I click on the link. It's like a 27-minute video essay that's like, what is the meaning of life? And I was thinking back on the date, and I'm like, what did we get into that this made you think of me? Because I'm like, I thought we had a nice time. But I was like, what did I put across that made you? And I was happy about getting the video. I liked it. That is the kind of stuff I'm into. I was like, a 27-minute video essay. That's the kind of follow-up I'm getting.
9:01Caleb Hearon:Well, because, you know, you're very heady. What is this? Cerebral? Okay. That's not the word you want. No, no, I'm just listening. I'm taking this in. I'm taking this in. I feel like you can have really good, deep conversations that it's about, you know, everything and anything. So I think maybe in the date, you kind of trailed off to that. Yeah. You're very funny, but you could get deep. Like, what else do we have to offer other than jokes? People like to tell me their problems. I know that happened on the date. He was telling me some of his problems. It's not a date if somebody's not trauma dumping over the breadsticks.
9:37You know, people are really apologetic when they do that, and I go, I far prefer this to stupid bullshit. Tell me your problems. Let's get into it. Because I've also, by the way, I've got solutions.
9:45Caleb Hearon:You are solution-oriented. We can fix this up. We can fix this up. You're a type A person, and I like that. Do you guys think I'm type A? I think you're type A. Okay. I think the way we were supposed to do, we were supposed to go on a trip. We were supposed to go to New Mexico or Mexico City or something like that. And you had You know The Airbnb The flights All that stuff You were on it The emails I trust myself Yes I trust myself To get things done right Yeah well you also were like Okay Sydney And Lisa's on the chat These bitches not doing nothing So that That was one thing You were like I have to come with a plan Because we can't Rely on them So that was that But also I wanted to say You said that you would never go On a girls trip Or something like that and then I saw you with girls on a trip.
10:31Caleb Hearon:What trip? Did you go to Ireland or Scotland? You know what? Dublin. I did. I was in the same city as some girls. I stayed separate. I stayed separate. I'm not doing the big house with girls anymore. I don't know. I'm not doing the big house with girls anymore, Sid. It's over. I love women. I have a lot of respect for women. I want to shout out all women. Right now I am shouting out all women. Shout out to you girls. thank you for everything that you do in the world you can't stay in the same house as me on vacation it's a mess why? there's attitude problems there's hair dryers everywhere there's clothes everywhere it's 45 minutes after we said we'd get out the door to get out the door just to go to lunch just to go to lunch we're coming back for a nap before we do the evening stuff I love women I have so much respect for women we're not staying in the same house on vacation anymore I'll be in my own hotel room I will see you at the plans you know I I hate when you're right.
11:27Caleb Hearon:Because you're right. You're fucking right. You really are. And we're too grown. We're too grown. And by the way, I was never going on trips with gay guys. That was so far out of the realm of possibility. I was never going to go. The gay guy vacations where it's like, we're going to Cockstock Island and we're going to. Fire Island, you mean? Yeah, well, whatever they call it. Yeah, we're going to Cockstock Island and we're all going to stay in a 25-person house and everyone's bringing K. Yes. I was never involved in that. So I was willing to trust women due to my massive respect for them. And then I lived with some of them on trips, and I said, it's a different situation.
12:04Caleb Hearon:It's the thing is when we all come together, right, that's where it becomes a mess. If you do one-on-one, if me and you went on a trip, you could deal with one mess. Yes. Six messes, that's too much. Me and my friend Allie can go on trips together. We can stay in the same place, one woman at a time. I'm a one-woman-at-a-time guy. I'm very conservative. You would be amazing as a straight guy. Oh, God. Amazing. I know it. Why don't you do it? I know it because I, you know, there's varying responses when I say this kind of stuff, but I'm not attracted to women and that upsets people. They get really upset.
12:35I don't want to have sex with women. Why? Do I not want to have sex with women? Yeah. I can't get hard about it.
12:45Yeah, it just doesn't make me hard at all. That's an amazing answer.
12:48Caleb Hearon:Okay. It doesn't make me hard at all. Which I have in common with a lot of straight guys I've learned. to hear my girls tell it i'm not the only guy feeling that way i mean the thing is i mean what is hard you know what is wet say that you know i feel like we're so in a in a time where everything is like so sexual like we gotta fuck fuck fuck fuck we gotta be with all these people and it's just like i'm done i've did all that i'm i'm i've juiced that out and so it's no longer about the, oh, fuck, thank, fuck. It's like, what do we have together? I'm trying to get to where you are. If we can't have sex, then what?
13:25Yeah.
13:26Caleb Hearon:How do you satisfy me? Not even just like mentally, just like existence. How do we be together and I'm content? You and I, I've actually come to your house, and if I could just be in a corner on the couch, scrolling, and you somewhere, you know, doing what you do on the phone, you know, your meetings and whatnot, I could do that all day. I could literally do that and feel like we had a solid day. I have that with all my friends. It's the romance part of it that becomes troublesome. That's why you got to look in and say, that could be romantic. Yeah. Yeah, because that's what I do with my girlfriend.
14:03Caleb Hearon:That's what I do. She'll be on the phone working or whatever, and I'll be scrolling. I'm like, damn, this is, whew, I love this relationship. Yeah. You know, and then occasionally, you know, we have sex and I'm like, this is nice as well. Occasionally. But if we don't occasionally, yes. Yes. Hey, you guys talking about you got to have sex three times a week. You're not working enough. You got a lot of time on your hands. You're having sex three times a week. Somebody's unemployed. Somebody's got a lot of free time. Somebody's not doing enough Sudoku. Yeah. Are you having sex three times a week?
14:37Caleb Hearon:Yeah. Having sex five times in one night, bitch, you are not dehydrated. I am. I'm not doing five times. First of all, I'm doing one time. We're good. Sydney can't be having sex five times a night. She has candy to eat in the morning. Exactly. She's got to get up and go to the candy store. Yo, you never just like finish having sex and then there's just like some sour powers right now. You're like something to take the edge off. Come on. Come on. Yes. Some of those little rips, sour candies. Oh, I love the rips. Straight to the dome. Listen, I just got my teeth in order. You know, a lot of cavities have been filled.
15:11Caleb Hearon:I have Invisalign. I shouldn't even be fucking with candy. But I'm like, again, I need something. I need advice. Yeah, I don't care about sex. So it's like, I need the candy. I need the red pill. Don't care about sex. This is crazy to say on such a wide platform. Yeah. But can you get to the point where you've exhausted all of the sexual things you could possibly do that you're at a place where like, yeah, I did that. I'm trying desperately. I do think I'm getting close. I will say there's been a shift in the last three years. where there are times that I'm kind of horny and someone cute is messaging me and willing to come over at the moment.
15:47And in the past, I would have dropped everything. I'd stayed up until three in the morning even though I had to be up at five. I'd do anything. And now I'm just like, there's something that has shifted, but I'm not fully where I want to be. I'd like to get to complete asexuality. That's where you want to get to. That would be ideal. Don't you think life would be amazing? I think you'd take it too far.
16:03Caleb Hearon:But no shade to the asexuals out there. Hey, I love the A. But no, I... A. Shout out to the A. But, I mean, being intimate, there's something about that that is also beautiful. But the way that they've ran through this, like, sexual talk to talk you through it. Oh, let me spit in your mouth. Like, all of this saying out loud. Yeah. It's kind of giving me the ick. Like, I don't even really do dirty talk no more. Really? I like silence. Oh, nothing? Hearing nothing? Oh, I'm wet. I am Slip off the bed Okay, okay Nothingness is amazing Yeah Just like Because sometimes somebody will talk too much And you're like Actually, let me call the car Let me get up out of here See, I can't do no talking But you talk for a living, Caleb Yeah Aren't you exhausted?
16:56Caleb Hearon:People are talking to you constantly You got to hear everybody's thoughts Yeah I mean, is your phone bricked up? No, I got the Android Okay, you got the Android I got the Android Well, you're close to brick It changed everything. It changed everything. The green bubbles. Android is great. The green bubbles. People are not texting me. People are emailing me and saying, I think your number changed. I wanted to ask you about this. And I go, that's perfect. Keep it in the email. I love that. Do not be texting me unless you're a very dear friend. Yeah. I think that because I hear all these opinions and I'm seeing all the content and everybody's got a show, everything's great.
17:34Caleb Hearon:It literally has taken, you know, all the fun out of things that just hearing nothing is actually exciting. Yeah. To sit in silence. You ever, like, go to a restaurant and you're just sitting there eating and people are just eating and they're not. So how was the day? They're talking about work. Like, just not hearing that. Yeah. You're like, the food tastes better. Yeah. The bartender is actually, you could just hear the jigger and the shaking. You're like, oh, that's music to my ears. Yeah. But I don't know. Maybe it's just me. Maybe my antidepressants is just too damn high. I think I might have to go down.
18:10Caleb Hearon:I'm really happy with the weight. I might have to go down on it. The things you're saying are making me very happy. Really? Yeah, I'm happy for you. Do you know what I can't shake in my mind right now? What? Earlier when you asked if I was type A, the only person that didn't shake their head yes was Michelle. And that's completely fine except for Michelle texted me yesterday. Okay. Michelle texted me yesterday, sent me a link to an article. Okay. Hold on. The article was headlined. She sent me a link to a New York Times article. The article was headlined, Celebrity assistants exist to indulge their bosses, but when does duty cross a line?
18:47And really, really sent that to me. Is that passive-aggressive? People don't respect me. I mean, you know, it's really, really interesting. Yeah, Michelle? Yeah.
19:02Caleb Hearon:So what you been telling your mom? Yes! Yes! That's what I said! I wasn't going to bring mom into it because I don't know the comfort level. That's a great question. Mom loves Caleb, like huge fan. Oh, the moms love you. Down. She's just like classic mom who sends me like crazy articles like when she sees like even a single word that relates to my life. So she saw Assistant and she was like, perfect, perfect article. Celebrity and Assistant, she said this has to pertain to Michelle. When does duty cross the line? When does duty cross the line sent me? Hold on, Caleb. I just want, we do respect you, right?
19:34Caleb Hearon:But there's something about your aura that just gets us too comfortable. Yeah. Where it's like, I could see you in an authoritative manner, but I'm also like, but he's got his knees out. Like, you can't tell me what to do when I can see your calves. That's what's happening with all of these guys over here. I don't know. I will wear anything to start getting some respect. It's really crazy. Slacks I want to see some I want some business slacks I will wear a fucking Three piece suit If that's what it takes You know And also I'm glad that you brought this up About not being taken seriously Me too What's going on?
20:09Caleb Hearon:Okay So I'm here for the pivot Because I People say that they like Everybody likes me Oh you're everybody's friend You're so nice It's true I want to shut it down Why? I'm ready to Just do I want to be a I want to be a Bic Not bitch But Bic I want to be the B-I-C in bitch. Why is that? Oh wait, did I spell it right? No, it's B-I-T. The T comes first, but you don't want to be the Bic. You don't want to be the Bic. Because then what are you? Once again, a joke. Let's be the Bic. Let's be the Bic. The lighter brand. I want to get things going. This is so on brand for me that I can't, like, I am the comedy.
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20:46Caleb Hearon:It just comes out. And I don't even try. But no, I'm actually tired of being taken for granted or people just know that I'm going to show up and I'm going to be supportive and I'm going to repost and comment. I gotta stop all that. I gotta shut it down. I gotta start creating boundaries and I gotta make people miss me and be like, oh, maybe she won't. Maybe she got something else to do. I need to do that. Why? What consequences are you facing? You know, you do know that we have a lot of mutual friends, a lot of people in the industry and I do think that when people think that you're always going to show it, they just, they don't, they're not as appreciative of your support.
21:27Caleb Hearon:They're like, well, you know, you always here. You know, you always going to swing by. Old reliable Sydney. Yeah. And I want to, I actually, no, I can't make it to your birthday, bitch. No, I can't make it to your wedding. I won't be there. I just won't. No, I can't. Yeah. But there is a wedding I got in my, I am going to go. I just, I'm type B and I haven't responded yet, but I'm going to RSVP. Yeah. Yeah. But I want someone to wonder what else could I possibly be doing? Yeah. To not show up to your shit. I like that. Yeah, I need that. I like this era for you. Yeah, because... Don't do it to me.
21:58Caleb Hearon:No, no, no. I would never. Thank you. I would never. But I do think because we always have our phones and the particles and everybody is just like have all this access, we have lost the wonder of like, are they coming? Like, will I see them? Yeah. You know? That feeling of, I wonder if Caleb is coming to my birthday. Like, you came. You showed up. I was like genuinely so happy to see you. And I think that's lost in the, oh, I know these people are coming, you know? Let me ask these random friend of a friend to come and then be more excited to see. You don't even know this bitch's middle name. Like, why are you so, ah, so happy to see, you know?
22:41Caleb Hearon:I want to feel that when I see a friend that, yeah, I just saw you yesterday, but I'm here. I'm here for your taping. I'm not talking about Marie, but I'm just talking about in general. Not Marie. Okay, yeah. Marie, show me love all the time. This is why I'm telling everybody all the time. Maybe. I'll try. I'll try to be there. I'm hoping to come by. Because that's the thing is I don't really know. And I don't want to have this thing where like we speak in such certainty. Yes. They're like, I will be there. I wouldn't miss it for the world. And then that's the shit that causes these like you get 10 texts right before the event being like, I know I said I would come, but I got hit by a bicycle.
23:14And then it's pictures of the injury so that you know they're not making it up. I'm like, I don't want to participate in that. I don't need to know. I trust. If you are in the mood to be at the thing you said you would be at and you said you would come, that's cool. But if not, you really don't need to, like, provide evidence and, like, a court filing to me. It's all good.
23:32Caleb Hearon:Do your thing. I think that we also need to be okay with people saying, I'm not coming. Yeah. I'm not. I don't need a reason. I'm not coming. I'm just not coming. I can't make it. Yeah. But people are scared to say that. people are upset to hear it and I just want to get in a better place where I'm not feeling bad for like actually I just don't want to fucking go. Do you know how many times I've dragged myself to things where like my eye is kind of pink and my wig is flipped and my toe is dead and my belly button is falling out and I'm there. I'm there in the audience hearing somebody say the same jokes that I done heard but they need me there.
24:11Caleb Hearon:They need my support because I am a cheerleader and I'm like well I need to be in bed. Yeah. Yeah, my friend Amina, Amina Amani, she always is like, Sydney, it is okay to say no. It's okay for you not to be there. They will live. And I said, you know what? I want to get more into that. You know, I will say, you and Marie and Mateo and Liza, like, our whole little crew of buddies, y 'all are present. We show up. Y 'all show up. Yeah. I'm very, I'm like, I really am impressed by you guys and trying to, I'm trying all the time to be on the level and be as good of a friend to y 'all as y 'all are to everybody?
24:47Because I'm like, y 'all really show up in a way that's crazy.
24:51Caleb Hearon:Well, I'm not cool with my family. First of all, say that. Because if I had family, oh, y 'all bitches wouldn't see me. If I had family that I fucked with, oh, babe. I wouldn't be at anything. I would, the partiful, blocked. Like, I would not be going to nothing. But because my friends are my village and everything, I want people to know that this love is real. If I could give you a kidney, I would. I don't suggest you have it, but I would give it up because that is what it's about. I think we're so also lost in the internet of everything and commodifying everything that you don't know what's real, what's fake, what's endearing.
25:35Caleb Hearon:and so when I see my friends, I'm like, hey, I might not post a picture of you, but you know we locked in. That's why I'm trying to get better. When I say I'm not coming and I don't want to give you the reasons, I'm talking about people that, I'm talking about fringe people that I'm like, I'm trying to make more space for the people I really need to show up for. I need to show up for the people who have showed up for me, my good, good, dear friends and loved ones. I need to make more space for those people and so unfortunately it means that someone that I barely know that I like well enough. No, I can't come to your, I don't know, like trivia for your cousin's work party or whatever.
26:11And I envy people who can make time for that, but I'm not going to be the guy. That used to be me. Because I got to show up for my people.
26:17Caleb Hearon:That used to be me. Yeah? But I want to know what are ways that people can show up that is not just like physical. Because maybe we need to give people other options. Yeah. Like if you can't make it, you know, Venmo me$50. A hundred times. You know, I bought snacks thinking you were going to, I got all this food thinking y 'all were coming. Send me some money. Yeah, I did. I had to, because of Trash Mountain and the filming schedule last year, I had to miss one of my best friend from childhood's wedding. Like just no way around it. Because I'm the lead of the movie and we can't reschedule the shooting schedule because we have no money.
26:52And I was just like, girl, I love you, but there's simply nothing I can do. And I dropped a fat fucking check on the honeymoon fund. like a stack. Wow. Because I was like, that to me doesn't replace my missing the wedding. I feel horrible about it, but... When she got that... This is what I can do.
27:14Caleb Hearon:She was like, you know what, baby? This is what I can do. You can't make it to the baby shower. That's okay. I'm good with that too. Yeah. So I do think there's ways to show remorse and participation for when you can't be there the way you want to be, but it doesn't replace. It's like, of course, we would have both rather I just be there. Yeah. I mean, getting back into like my family stuff, it's just like, you know, I grew up in a very like, not a nuclear home. I grew up with my great aunt and uncles. And so already I'm not with like my mom, my dad, my sister, my brother. And the way that they raised me, it's just like family is everything.
27:55Caleb Hearon:Family is everything. And so to be the opposite of where I am, like friends are everything. My mind totally flipped. And I forget that friends could just cut you off at any moment. If they don't want to be your friend anymore, that's done. Family is forever. Like my brother, my sister, they text me and I'm like, we are related. I guess I do need to respond or call you back. Also, we don't do friendship in that way. None of our inner friends would just drop us at any moment. You think Marie, Mateo, Lisa, me, Amina, you think any of us would just be like, nah, we're done with Sydney? No, no, no.
28:34Caleb Hearon:I wouldn't let them. Oh, I'm supposed to know, baby. What? None of us would do that. That's crazy. But I do have some relationships that kind of just drifted off. And I'm like, I'm surprised they didn't fight for it. You know? But like, what is this all about? Was it just something that you were like, oh, I guess this was different season, different reason, you know? Because I would fight for our friendship. I would fight for, oh, Marie, I'll lay on the train tracks for her. I know you would. You know, I would, because that is so important. We made a joke when you did our podcast about like, you know, we don't have to make all money doing our podcast.
29:13Caleb Hearon:I'd rather us just be friends. And she was like, you wouldn't want to make a million dollars? You would rather us just be friends, you know?
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32:21Caleb Hearon:I rather have the friendship than the celebrity, the red carpets, all that stuff, because I've seen it, what it's done to people, they're miserable. Not you. Not you. I like to think I'm a little more invested in the friendship, personally. I like to think that's why it's not affecting me that way, the way that we've seen it. I mean, we've seen it ruin so many nice, good people. Ruin. Just destroy them. Bad. They're so lonely and sad. The brain fried. But it's because they forgot, and I don't blame anybody. It's a really insidious thing. It's really, really hard to stop it from destroying you.
32:56But they let themselves forget that, like, the biggest gift of all of this is the people. The biggest gift of all of this is the friendships, that we get to be around the coolest, nicest, funniest people. We get to work with the best people who just want to laugh and have fun and make good shit. That is the best part of all this. It's not the fucking parties with people more famous than you. It's not the luxuries of, like, traveling well. Those things are certainly nice. But, like, you really can't forget that the people are the best part and forsake everything for more money and more status because that's when it fucking ruins you.
33:30The people are the best part.
33:31Caleb Hearon:How did you get to where you are, Caleb? How are you doing it? Like, I just, you're still a nice person. You still look out. How do you not get sidetracked and be like, yeah I'm about to go to Beyonce's party like how do you not be that person? I think it's the same I guess this isn't true for everybody who experiences this but it's just growing up so fucking poor just growing up so poor and I just never really forget like yeah this is all crazy it's a gift to be able to pay my bills and take nice flights and to have freedom at all to have freedom really is such a privilege and gift But yeah, I just feel like it feels impossible to me.
34:13It's not impossible, actually. We've seen it happen. I just can't imagine how I would lose myself in it. I can't imagine it.
34:19Caleb Hearon:Me and Marie went to Soho yesterday, and we went to Margiela. And I said, oh, yeah, no, I need to get more money. Because the way it felt so good to walk up in that bitch and know that your car was not getting declined. And then I was looking at these crazy prices. I was like, yeah, I got that. Like I said Oh now I see why people embezzle Now I see why people Rob, steal, and kill Because I know when we walked in They was like You know we bouncing off the wall They're like they ain't buying nothing They just here wasting time And then Because you know We are indecisive We trying on this shoe I'm like oh my ankles are zashy Marie's like oh my feet are Feet too dry Like we were being really silly And then the sales associate realized I was like no no no We're about to Spend some coin in here.
35:09Caleb Hearon:And I said, that's what I want to do. I want to do this with my friends. I want to take a trip and us just not think about money. Because I grew up poor. And shit, last year I was poor. So I like, I know how. Let's not forget. Yeah, let's not forget. But it just feels so good when you could treat the people that you're with good. And get the things that you want. Who knows how many times I'm going to wear these shoes. I go to Union Hall. I'm not wearing my Marshallas at Union. I'm not wearing my Marshallas at Bell House or, you know, on the side of Bushwick. Like, I'm not doing that. But I want to get the nice things and I want to do – I want the success like you have, but I don't think I'm ready for everything that comes with it.
35:56Caleb Hearon:That's what it is. What do you mean? What do you think you're not ready for? I think that I come in with my heart first and some people are like business or like they're just going to be funny. I can't do that Like we even having this deep serious conversation No laugh happening That's me most of the time I know You know And so I feel like a lot of people have to be on Like they have to mask And I don't I can't do that I'm telling you I mean I ran up on Daniel Kalua yesterday Because I didn't think it was him And I If I was him I would be like You're crazy Like I would have just yelled at like What's wrong with you But he was just so kind And I'm like I don't know if I could be professional all the time.
36:41Yeah. I'd run up on Daniel Kluha too. Have you seen that clip of him and Robin? No. That clip? She, ooh. The ooh, I'm gonna ooh. There is a clip of him doing Robin, oh, what is her last name? She's so wonderful. Look it up, look it up. Robin. Robin Daniel flirting. Robin Daniel flirting. Google chants. It's Robin Roberts. Robin Roberts. Who's Robin Roberts? She is so fabulous. Robin Roberts. There's this clip of him. Robin Roberts? She has like a show. There's a clip of him. Let me see Robin Roberts. Yes, play this clip. Play this clip.
37:15Caleb Hearon:Oh wait, yes! He is - Oh wait, she's fab. I'm buttering you up because can you tell us anything about Black Panther? Can you tell us in a little something? No, you know, you gotta give me more butter, man. That's not enough butter, man. You gotta come back. You better be glad we're not doing the same thing. I'm right back at you. What do you do? What do you do? You are too much. You are right on time. Oh. The gay is slipping. The gay is slipping. Keeping it real. The way he's looking at her. And I'll bring it up. You have to, man. You gotta make it your tallest hat. You gotta make it come on your tallest hat.
37:54Caleb Hearon:That's right. I'll bring more butter. I'll bring the butter next. I need him. First of all, both things. I need to hang out with her and I need to hang out with him in a different way. I need. Oh, yeah. You can. Thank you. Oh, my God. That's the shit I'm talking about. Can you do a class? That's the reason to be alive. Me? Yes. Daniel Kaluuya needs to do the class, and I'm going to enroll. No, you're good at it, too. I see you in the interviews, and you're very, like, you're not coy, but it's something you got. You have something with you that it's, like, I don't know if you would really have sex with them, but I'm sure somebody in the interview would be, like, is he coming on to me?
38:33Caleb Hearon:Sydney. Is it me? It might be me and you. Sydney, I feel like we have that connection. We do. We do. But you know what? You let me be goofy and weird and strange. And that's because people don't know that about me. Like, they see the outside and they're like, she's put together, all that ass. Teeth poppin'. Hello. Teeth shining. Yeah. And then I'll be like, you have nice nail beds. They're like, what? Like, who's looking at your nail beds? Do you think that people have a perception issue with you? Do people want you to be something that you're not? Yes. Yeah. Yes. Like right now I am doing my show called My Black Barbie Story.
39:10Caleb Hearon:And it's about like all the Barbies that I find on the internet reenacting stories that have happened in my life. It's so goofy and odd and strange. It's like why would you tell these stories? It's like because that's who I really am. I don't, I want to look good but I'm a mess. Things have happened to me that I'm like, I should be ashamed of, but they're not. Why am I ashamed? They happen and that's who makes me who I am today. Apple Pay is the simple, secure, and fast way to pay. That's because your credit or debit card is right on your iPhone. Accepted at millions of places, from big box stores to boutiques, you can check out with your iPhone anywhere contactless payments are accepted.
39:53Caleb Hearon:Apple Pay is more secure than a physical card because you authenticate your purchases with Face ID before you pay. and your actual card number is never shared with merchants. Add your debit or credit card to Apple Wallet to check out in seconds. Simple. Secure. Fast. That's Apple Pay. Terms apply. This episode is brought to you by State Farm. Listening to this podcast instead of doom scrolling? Smart move. Another smart move? Getting help from one of State Farm's 19 ,000 local agents when you choose to bundle home and auto. Bundling. Just another way to save with the personal price plan. Prices are based on rating plans that vary by state.
40:29Coverage options are selected by the customer. Availability, amount of discounts and savings, and eligibility vary by state.
40:36Caleb Hearon:Sierra has all the best active and outdoor brands for the super athletic stuff, like running gear for cruising up the trail. Woo! And the super athletic-ish stuff, like fishing gear for chilling by the creek. Nice cast. Fitness apparel to push for higher reps. You got this. And golf balls priced so you can afford to lose one. Or a few. Head to Sierra or Sierra.com for the brands you want at the prices that let you do it all. From athletic to athletic-ish, Sierra's got it. So I wouldn't be so interesting or an amazing storyteller if I didn't allow those things to happen. And I just want to release myself of like posting and making sure everything looks right or getting online and making sure that, oh, my lace is not showing.
41:23Caleb Hearon:It's like I can't. I'm actually exhausted. I literally have no strength. I want to show up in a bonnet and talk shit and be like free. Like the people on TikTok in Missouri. Like I want to be like them. But because I've set myself up where like I'm always wearing a heel. I'm always beat. I got my lashes on. People see that and they're like, oh, you're going to come and be cool and collect. No, I'm sweating. I'm sweating right now. My coochie is damp. And it's not because you're making me feel sexy. I'm just, I'm nervous. Yeah. The anxiety is running through me right now. So what do you think the perception problem is?
41:59People want you to be X, but you are Y. What are the X and Y?
42:02Caleb Hearon:The X is, okay, here's the X, Marie. They want you to be Marie? No, they don't want me to be Marie, but Marie is so freaking cool. She's so funny. She's like, yeah, I'm not worried about that. She'll show up late. She's not going to say sorry. She's like, hey, y 'all, what's up? Like, let's start. Like, she's not worried about, like, if you're mad or not. She's like, well, I know that I'm a deliverer, you know? That's not me. I'm saying sorry. Like, I'm sweating. I'm stressed I'm fumbling I'm I have a lisp I'm saying words wrong like I want to come off so together but I'm gonna show every time that I'm not but people like you like her you just got it you just you know Marie though there's something really funny that I think about often with both of you actually where I think there are a lot of there are a lot of particularly like 20 somethings in Brooklyn that they're trying to do cool by being aloof and uninterested they're not asking anybody any questions they're not interested in anybody else they're trying to do cool through like disinterest and like nose in the air behavior but they're doing that to try and impress or be like people like you and Marie and nobody actually cool is like that y 'all aren't like that y 'all care about people y 'all ask questions y 'all like no Marie's not going to apologize for being late but she doesn't need to because you know it's not coming from a place of malice and it is really like marie's like getting her energy together she's showing up great energy every time it's not like she shows up late and then she's a huge bitch she shows up late and she's the life of every room she's in it's like there's something about coolness that i think a lot of particularly young people like younger people are really not understanding that they think being cool is being the the person who cares the least in the room and the actual coolest people the ones that they actually look up to are not like that and i'm like Like, y 'all got to get that figured out because it's really not cool.
43:57And you just seem fucking boring and rude. Do you know what I mean? It really bothers me.
44:02Caleb Hearon:Who's the coolest person you've met? The coolest person I've met? Yeah. As of late. The coolest person I've met as of late. Damn, I don't know. This is tough. Who is the coolest person I've met lately? Or somebody that you went back, you're like, damn, that was such a good time. Like, I need to see more of them. So many people like that. I mean, I'm trying to think the coolest person I've met lately. I really, it's a funny time to ask me because I've been really in my, like, trying to support my friends bag right now. Like, I'm taking trips just to see friends' concerts. Like, I'm really trying to, like, do that whole thing.
44:35But who's the coolest person I've met lately? You know what? Oh, oh. There's this guy called Kochi May who plays in Kevin Morby's band. Okay. And I've been seeing Kevin a lot right now. And it's not that I've just met him, but we got to really have a conversation for the first time after the show in L.A. and just a cool guy. Just a really nice guy, down to earth, really fucking good at what he does. He has a fucking, in Kevin's show right now, he has a saxophone solo that brings the fucking house down. He also plays the flute. He plays all kinds of cool shit. Plays the bongos. Come to me. But he's somebody...
45:11Come to me. That I was like... Okay, I'm gonna get into him. He's cool. He's cool as fuck. I'm gonna get... He used to play with Sharon Jones and the Dab Kings. You ever listen to them? No. They're great. I'll show you some of their stuff. They're great. Or maybe he still does play with them. Sorry, Coachy May, if I'm getting that wrong. Do you have a picture of him? I'm a visual person. I'll show you one later. Yeah, okay. But that was a person who I was like, oh, he's so fucking cool. I'm really glad we got to chit-chat.
45:34Caleb Hearon:You know who's really cool? Who I truly enjoy hanging out with? Richard Perez. Richard Perez is so... We're supposed to have him on the show. He is so goddamn funny. You have to. He's so funny. DNA funny. Like the characters, but then like you'll be in the green room somewhere and he's just like pouring his heart out and like showing you like, oh yeah, no, I'm cool online. But I do worry. I am thinking about this. I do stress. And I'm like, I love these moments. Because online, I'm like, I see this perception. And I, well, no, I see this thing that he's putting out. And I'm like, oh, he's great at branding and marketing.
46:12Caleb Hearon:But then I also get to see the real him behind the curtain. and that's what makes me want to hang out with him more even though I only see him at the shows. But I think he's so cool. And Marley. Marley is out of her mind. But very fun and just being themselves. Richard, yeah. Marley's so funny. Richard's so funny. Richard's in a camp of people in specifically New York comedy that I'm like, we've run into each other a couple times. I have so much respect for him. I would like to spend more time with him. And I actually need to make a better effort about that. That's something I'm trying to do right now is like, make a better effort.
46:48It's very easy at this point in my life to curate every single minute of my day with only people and things I like. Like, I could really go every day and never be in an uncomfortable situation. Really? Oh, yeah. Yeah, because at this point, I don't have to be anywhere. I don't report to anybody. This is my job.
47:01Caleb Hearon:Okay, talk your shit. Do you know what I mean? I hired them. These are my buddies. Like, I have whoever I want on. Nobody tells me who to have on my show. I don't have to... There is no place I have to be that I don't want to be, which is mostly great, but I'm trying to make sure that I'm forcing, not forcing, but creating opportunities to meet new people and be a little out of my comfort zone. Yes, and I'm glad you mentioned that because I was recently on a lesbian cruise. This Alaska cruise kind of changed your life, no? I've been screaming about it from the mountaintops. Tell me about it. I went to, well, I was hired.
47:37Caleb Hearon:It's called Olivia Travels. And so at first I've been dragging cruises for a whole year because I saw the poop cruise and I said, you can't pay me. You can't get me to be on no damn cruise. I don't want to be stuck underwater. I can't swim. The food's going to be bad. The people are going to be in bad shirts. And then Olivia Travels hit me up like, hey, here's this money. And then I looked at - They said, here's the number. Here's the number. I looked at my bank account. I said, yeah, no, no, no. I could do a cruise. No, for real. And it's all gays? Yeah, let's go. And so the thing is, is that you see the gay cruise for the men and then you see the lesbian cruise and you're like, it's not the same.
48:12Caleb Hearon:It's not the same. And which is good because, you know, I'm not a party animal. I don't do drugs. I'm sober. You know, I'm good with a sweater on. I love a nice little turtleneck. I don't need to have my tits out and oiled up, you know. So I don't want to be on an all gay men cruise. So I was like, lesbian, let's go. But the thing about this cruise is like everybody's a lot older. And they're not like teeny boppers. They're not in their 20s. A lot of people are like 40 and up, 65, 70. and these are people who, listen, they pretty much paved the way for, you know, a gay like me. So I'm on a cruise, 2 ,000 people plus Alaska.
48:52Caleb Hearon:I don't want to be, I'm not paying to be cold. Like that's just, I don't understand white people when they're like, I'm going to go to Mount Everest. Like I don't get it. Why are you paying money to be on ice? That's, that's insane. Like just open your fridge, go in your refrigerator, go in the basement. I don't know, but I just, I couldn't pay money to want to be around snow. and to be freezing because I have anemia. So I say yes. I go on and I'm with my girlfriend. So already I have my security blanket. But I go in and I'm like, I have to be open. I can't be closed off just because these people are older than me or white and just from places that I've never even heard of.
49:32Caleb Hearon:It's okay. You got to be open. And then I got on there. It was so transformative because these women were telling me their stories. They're like, I'm a late in life lesbian. I married a man. I had kids. And I didn't feel this free until I came out. And I came out when I was 55. And I wanted to die. Like, die in terms of, like, tears coming. I just wanted to melt into the floor. Yeah. Because to be somebody else for 55 years, to have this life for somebody else, and now you're like, oh, my God, I feel like I'm twirling in a field of just, like, dandelions. I'm like, oh, my God. And this is why I'm like, I need to be more out and proud and existing because of people like this.
50:16Caleb Hearon:And then I got on stage and I did my 45 minutes. I made my, you know, my little jokes. I was like, Frankie and Grace is in the building. You know, the golden girls. Betty White, where you at? Like, you know, I was doing that. But for the whole thing, I was basically doing some of the stories that I do on my Black Barbie show. And then from my How to Start a Fire. And they were like, you are so authentically you. and even when there's moments where you're like oh that didn't go over what you're being yourself and that is so important to be seen and to be doing your type of comedy they need this and so they all these women came up to me who I thought I had nothing in common with other than that we're like lesbians were just pouring out their love and explaining to me how I think that I'm so different it's like we're all trying to figure it out we're not that much different and it was I want to go back on their cruise again for sure.
51:09Caleb Hearon:I thought I was going to have a threesome or an orgy. That didn't happen, but you know, it was great. Was there a man on the ship? They working. They doing the work. There's trans, there's non-binary. You don't have to necessarily be gender. It's like, are you a lesbian? There wouldn't really be room for me. I could bring you. I could bring you I honestly think you would take over and it would become a cult on the cruise and I'm scared like I think somebody like you should do this but I'm scared I'm definitely scared I think you would have those ladies going insane those are my girls oh oh and you know I just want to talk a little bit about ageism you know everybody's so scared or their first thing oh you old bitch you old like it's like I'm living Yeah, I'm alive.
52:04Caleb Hearon:I'm a living woman, first of all. I'm alive, you fucking idiot. You want me to be dead? You want me to be a dead, young, hot hoe? Is that what you want? And the documentaries say that the men like when the hoes are dead and young. But, I mean, I think that getting older is beautiful. It's beautiful. What? The men like when the hoes are dead and young. Yes, it's true. I watch the documentary. Yeah, they're killing these young women. Yeah, but I went there and I was like, It's all about aging with grace. When everybody is getting under eye bluffs and cutting their eyelids off and getting all this filler and shit, I do need to just lean into it.
52:42It's okay to age gracefully.
52:45Caleb Hearon:It's okay to look like you're supposed to look. To me, ageism is only funny when you're not actually scared of aging. I think ageism is hilarious, but I'm playing. I'm so excited to age. I'm not getting anything done. I am very excited to age because I want to play those roles. That's one thing with these actors. I'm like, y 'all are destroying your instrument. Yes. Why are you doing this? Yes. Stop. You don't look like anybody who's ever lived before. I hate this. People look bad. You don't look like anyone has ever lived before. It's crazy to say. You look like a new species. Like, stop yanking your shit.
53:17And I'm not saying don't get anything done. It's not my business. I know it's different for women. Whatever. Everybody do your thing. Whatever. But I just mean in general, I wish everyone would stop yanking and plumping and teasing their shit until they looked completely inhuman. Men as well. male actors are fucking destroying their faces. And I'm like, for what? You don't look better. It's really driving me crazy. Now, there are people who have had some very tasteful work done. I'm pro - Very tasteful.
53:41Caleb Hearon:I was like, okay, name the doctor. But then there's other people that's like, name the doctor so they can go to jail. Okay, we must arrest them immediately. Put the doctor in prison. In prison underneath. Yes. You know? But I will say that, you know, I've had my breasts done. and you can't tell because they're very demure right here. And I've had them done twice and I am obsessed with the idea of, you know, you want to upgrade yourself. You want to do a little... What'd you have done to them? Bigger both times? Yes. Yes. And I think if I get another gig, I'm going to get them done again. I don't know.
54:20Caleb Hearon:This is 12 years ago. You know what I mean? Oh, I'm pro boob job. Yeah. You know, 12 years of D-Cup. Now I'm like, What else can I do? I might go smaller. Who knows? But I think obviously it's amazing to have the money or the access if you want to do a little something. But I think it's the cameras. That 4K has fucked us up. The things that we weren't looking at before, now we are. I was never like, oh, my eyelids are drooping. Now in that 4K camera of the clips that we got to post to make sure that we have people in the seats, Now I'm like, why does it look like it's, do I have a lazy eye or like, did I have a stroke?
55:01Caleb Hearon:Like that's the stuff that I'm looking at now. And that wouldn't happen if we had like a pixelated camera where from afar it looks good. You can't even zoom in. I'm planning to look bad. Yeah. When I am in my 50s, 60s beyond, I am planning to look bad. I'm planning to be 62 and people going, is he 95? I'm planning to have, I'm planning to be in the sun. I'm planning to laugh so much that my shit's all wrinkly and fucked up and weird I am planning to when I scrunch my forehead it's already kind of happening when I scrunch my forehead I'm planning for the lines to go crazy like waves I am planning to look straight up bad I'm gonna bald in a crazy way I'm already starting in the back it's good to just be who you are supposed to be I'm planning to look the hoes are gonna come and even if you're not about hoes people are gonna want you they're gonna want you see this is the thing I'm like you really yeah it's an energy thing now you're not gonna get everybody with energy, but you can get a lot of people with energy.
55:57Caleb Hearon:Yes, you can. I'm planning to look bad. I mean, you got it, man. You got it. For me, I think it's a little different because, you know, I do want to be a sex symbol. I do want to get out there. I want to be on Out 100 one day, you know. I just want to be there like, yeah, I am that girl, you know, that lesbian woman that's out here who's older, who's, damn, you want to take her out. You know who I'm thinking of? You want to go take a nap with her, you know. You know who I'm thinking of? Queen Latifah Yes Oh my god Queen Dana
56:34Caleb Hearon:And classy And I've ruined that for myself Because I've been on podcasts and I've told all my business But the mystery behind this one And it's not even mystery It's just like you're gonna know what you're supposed to know And the people who know what they're supposed to know Those people are close to me some random bitch on her toilet is not going to hear my business you know what I mean if I could go back I would do it like Queen I would do it like she is everything that people should aspire to be I do she is everything to me I saw a video of her recently one of these annoying fucking paparazzi people if you are paparazzi we should be allowed and I do not want this cut to legally give you I'm sorry or if you're one of the people that waits everywhere for the autographs legally give you This is a disgusting business.
57:21You are the scum of the earth. You're bothering Queen Latifah outside of a Starbucks? Yeah. I should be allowed to... Well, yes, you should be allowed to get hurt.
57:33Caleb Hearon:I also want to put this out here for you. No shade. Please don't cut this. But I've been out with my friend, and you're literally just trying to be at a concert. You're just trying to be out here. You're with your friends. You're trying to get some coffee. You're just trying to exist with your people. And then there'll be that.
57:55Caleb Hearon:I know. I know. I know your friend is crying. I know their mom just died. But can I, I just love your pod. Can I take a photo with you? Like, y 'all got to read the room. I love them down. Now, I want y 'all to, you know, follow me or whatever. But when I'm with you and I see the. I. I, I, I'm sorry. That kills me every time because it's like we see you. We see you in the peripheral. You know what I will say? Like waiting. Here's the only thing. I've been thinking about whether or not I would say this or not because I am really grateful. Okay. No, we are. I'm a, thank you. You need fans. You need people who love.
58:34Caleb Hearon:Yes, I want that. And I mean it. I really am so grateful for my life. This is the one thing I would say. If anybody listening to this gets the opportunity to do this for me. When I'm on a dance floor, just leave me alone. Yeah. That's just dancing. That's it. coffee, dinner, lunch, bike ride I've made peace with all of it I get it, it's part of my job I'm so lucky I just really, really, really for my mental health, genuinely need people to leave me alone on the dance floor like in a very serious way I tried to go dancing the other night and it was 12 people lining up to do meet and greet and selfies all I wanted was to let loose and dance with my friend and I literally almost started sobbing I was so sad it just makes me feel really inhuman actually No, I see you.
59:17But I don't complain about this. No, you don't. I really, really don't.
59:19Caleb Hearon:You never say anything about it. Every time I've been with you, you've been like, you know, this is what it is. But in the back of my head, I'm like, hey, I know they saw that we were deep in the conversation. Like literally. That's the other thing. If someone's crying, leave us be. Well, there have been a number of times that me or the person I'm with is crying and someone's like, I know I shouldn't. And I'm like, okay. Well, then just don't this time. But most of the time I'm happy. I'm happy. I want to be a part of people's day. I want to make people happy. You do make people happy. I love my job, but just dancing and crying, I think those are the moments I'd say, let it be.
59:50Dancing and crying. Also, doctor's office is the one I'm having to say now.
59:53Caleb Hearon:Whoa. I've had medical providers stop me. I'm strep throat, sickest I've ever been a couple months ago, leaning on the counter at urgent care, just like, please give me amoxicillin, please give me amoxicillin. And the girl working the desk goes, I know I shouldn't do this, but I'm such a big fan. I was like, girl, I am dying in your medical office. Yes. I literally can barely stand up. there are times but what were we even talking about Queen Latifah Queen Latifah someone cornered her someone cornered her one of these while she's getting in her car and they're asking about Tupac and she goes so classy which would be so fucked up she's so classy she goes you know I miss my friend and we had we had a lot of fun in the 90s sweet I'm gonna cry sweet I'm gonna cry sweet as can be like I literally love her I want the world for her Queen Latifah if you can hear me I just think she deserves everything and I want whatever she wants I don't know that I want her to keep doing TV shows I think I like her back in movies Stop it I just I want her so much Equalizer bring it back Bring it back Is it over?
1:00:51Caleb Hearon:Yes Oh okay You don't know? That's for the best And no shade And I Listen Law and Order SVU We gotta shut it down We gotta shut it down Mariska Hargitay I love you Olivia Benson Like I'll get the tattoo Yeah But we don't have the equalizer Yeah We have Law and Order SVU Literally it's only about sex crimes Yeah We're doing that for a hundred more years Yeah We don't want to see Queen Latifah's stunt double do a backflip back into Queen Latifah having perfect hair. You don't want to see that. Now that's fucked up. Yeah. That's homophobic. I think Hollywood, the least that Hollywood could do for us, they've taken so much from us.
1:01:31Caleb Hearon:They have. The least they can do is once a year holiday film with Queen Latifah and LL Cool J. Oh, man. $200 million budget. Yes. Whatever they need. Can they do it? Once a year. By the way, it doesn't have to be Christmas every time. St. Patrick's Day. Fourth of July Whatever they want to do She makes people so happy I've heard so many people have like Incredible Experiences with her And the fact that she protects Her family and her personal business But she still values her work Where is that at? I'm gonna cry I'm gonna cry She had an interview with Angie Martinez And watching her in the whole interview I was like, this is a master class of one, letting an interviewer be an interviewer and not being defensive, but also just being genuine in like what you want and need as an artist.
1:02:25Caleb Hearon:You can do that without being an asshole or being, you know, violent to the people who pay your bills. Yeah. You know? Oh, I love her. Yes. Can you get her on here? Queen. I would never. I would never subject her to this. I wouldn't let her come on here. Why? she has no business doing this. What? She deserves the world. Come on. She should never have to step into this den of this den of gay bullshit nonsense. I barely even think you should have to do it. I mean, Queen Latifah, you are never allowed in this studio. I would do anything. If I saw Queen Latifah walking towards a puddle and it was too big for her to walk around, I'm laying down on the puddle.
1:03:03Yes. You understand? This woman means so much to me. Yeah. She can't come in the so true studio.
1:03:07Caleb Hearon:Listen, there is not a bad living single episode ever. Ever Dana Dana And we need I want more people Like that I need more people Out here in the streets Just Like you could tell She's just She smells good Yeah She takes care of everybody Yeah She was hanging out with She's friends with Meg the Stallion So she knows You know she knows how to have fun Yeah Okay Yeah And that's That's what I want for myself Like she is existing In LGBTQ Without being like I'm gay I'm gay I'm gay Like I'm a lesbian man. I'm like, everything's gay. Like, she's just being herself. And I'm like, that's what, that is what it's about.
1:03:47Yeah.
1:03:47Caleb Hearon:That, you know, but I, you know, for pride, I do want to be on out 100. Like, I'm sorry. I'm sorry. I want to be in one of those. We need to. Sydney, what's so true to you? So true to me. It looks so true to me. So true to me. You, you don't have to have sex all the time in a relationship. You don't. I know, but you're big on this right now. I'm big on it because, I feel like a lot of people are putting a lot of weight on that. They're like, oh, if this sex is not good, if we're not doing it enough. It's like, why aren't you focused on the actual experiences you're having outside of the bedroom?
1:04:23Caleb Hearon:Yeah. That's like, at the end of the day, what if I can't have sex? What if my vagina falls out or closes up or all my holes are done? Like, what if I lose my legs? What if I lose my ass? Like, what if I'm just a nugget? Yeah. And you can't do anything to me? Yeah. Would you leave me? Oh, I can't put my stuff in you. I can't finger you. No. Like, what about me? Yeah. As just a person, wouldn't you want to spend that time with me and be in a relationship with you? We could kiss. Yeah. I could put your finger in my mouth. Yeah. But we don't have to have sex. I'll put your finger in my mouth. Yeah.
1:04:57Hey, I love hanging out with you and we don't have sex at all.
1:04:59Caleb Hearon:I know. So I understand the connection. Sometimes I do feel like I'm dating you. That's really beautiful. Yeah, because when we go, we fight over the bill and then you run around and you sneak and you do it. And then I catch you and then I sneak. And you're like, no, you can't do that. And I'm like, well, he should pay. But I just want to let you know that I don't want you to pay. I have pretty Republican views on men in the bill. I get pretty Republican about men in the bill. It's not cute, but so many people benefit from it in my life. They're not pushing back at all. Yeah. I get real conservative about being a man and paying the bill.
1:05:30Caleb Hearon:And somebody with legs like that, with legs like those, you should. Sydney walked in the studio today and immediately started rubbing on my legs. I know. I've never seen Like they are Oof These guys right here They're juicy These are special to me But like it Oh I like these boys Solid They're kind of dripping in sweat right now This dude is a little humid It is a little humid But again So true You don't have to have sex all the time In a relationship Yeah I support It should be Maybe 30 % of your relationship Okay It should not You said okay I said okay I just 30 % The number surprised me 30 % I don't know what number But the thing is I don't know what number I think.
1:06:09I just, 30 was like, whoa, to hear a number two, it's kind of, okay, yeah.
1:06:11Caleb Hearon:People think that if they stop having sex, the relationship is over and that is just not true. Yeah. Sometimes, I'm not thinking of it. Some people just don't want to have it, but I still want to be with you. I still want to hold hands. I still want to do this life with you. Yeah. But then you're like, well, we're just friends. It's like, that's not true. I think one of the biggest relationship mixes, the hardest thing, there's so many different types, but I think one of the biggest, hardest ones is the but high sex drive, low sex drive relationship. I think this is the hardest thing to overcome.
1:06:41Yes. And yeah, it's tough when someone doesn't want to have sex.
1:06:45Caleb Hearon:I want to say this on camera. My girlfriend is getting it, okay? I don't want y 'all to think that I'm depriving this woman. It's good you said that because I was wondering. I know, I know. I was wondering. Because she's going to go out there and be like, wait. Do they know you be throwing it back? I do. I do. I'm saying all this, but I'm also, you know, in the bedroom. It's a little different. But I'm just saying that it should be an option. Yeah. Yeah. And you guys have a beautiful relationship. We do. I envy what you guys have. You guys have a very beautiful connection. We're looking for a third.
1:07:14I know, I know, I know. But jokes aside, I need to find my own thing. I'm working on it.
1:07:19Caleb Hearon:You got it. I'm working on it. He's not going to be in New York. How about that? You think? Yeah. That's really bad news. It's okay. I moved here kind of thinking that he might only be in New York. That's a fucked up reason to be in New York. No, I moved here to date. Isn't that crazy? People say it's horrible, but I love it. And then I immediately met my ex, who I love to death. New York dating has been very good to me. Hey, I just want to let you know, there's people who actually, you know, zip code, they've been here. They born on, you know, New York City soil. And you think your ass just going to come in, gentrify and get love?
1:07:52Caleb Hearon:Hey, it's not happening. You can't do that. My two big plans are to gentrify and find love. I'm planning on taking over in every sense of the word. You know me. That's what I'm after. That's what I'm after. So you want to play a game? Yes. Okay, Sid, I'm going to ask you, I'm going to read you 15 statements. You're going to tell me as quickly as you can if they're true or false. And if you get 10 or more correct, we're going to give you 50 US dollars. You ready? Yeah. All right. Scorpions are arachnids. True. True. The first airplane flight lasted two minutes. False. False. 12 seconds. The capital of South Dakota is Bismarck.
1:08:24False. False. Pierre. Neptune has 16 moons. True. True. Clark University's mascot is Jonas the Cougar. False I went to Clark University
1:08:41Caleb Hearon:But I wasn't looking at no damn mascot I was trying to survive It's true Pears originated in Central America True False, China Moon Knight is a Marvel Comics character True Condors have the largest wingspan of all flying birds False. False. It's albatross. Microwaves have longer wavelengths than radio waves. Say that again? Yeah. Microwaves have longer wavelengths than radio waves. True. False. The New York Liberty played their first season in 2002. False. False. 1997. Exactly. Hot air balloons are older than cars.
1:09:25True. True. The skull is the strongest bone in the human body. true false it's the femur every square is also a rectangle
1:09:37Caleb Hearon:i should know this i should know this because this was this was on the pod true it is true okay yeah the vietnam war ended in 1975 i'm not answering that well i'm not no next next question The Soho Grand Hotel. No. One of the realest answers I've ever seen on this show. The Soho Grand Hotel has 17 floors. False. It's true. How'd she do, Chance? Nine. Oh, damn. Give me that one. You know what? The Vietnam War, let's give it to her. Yeah. Oh, shit. I'm dead. Sid. Oh, my gosh. I'm not answering that. No. Listen. No. Cut this up however you, I know I was like, you don't have ADHD, so I'm all over the place and I don't know what.
1:10:30You did great. I'm sorry. Sid, tell the people where they can find you and how they can support.
1:10:34Caleb Hearon:I thought we were done. No, baby. No, they got to know where they can find you. Oh my God. You can find me on Instagram. Just Sid B-W-J-U-S-T-S-Y-D-B-W. Don't go over on TikTok. Nobody cares about that. I have a podcast called Mess with Marie Faustin. Please subscribe to that. And I will be in Edinburgh in August from the 5th to the 16th. I'll be doing my show, My Black Barbie Story. Please come through if you're in Scotland because I need y 'all in the seats. Love you. Love you more. Apple Pay is the simple, secure, and fast way to pay. That's because your credit or debit card is right on your iPhone.
1:11:12Caleb Hearon:Accepted at millions of places from big box stores to boutiques, you can check out with your iPhone anywhere contactless payments are accepted. Apple Pay is more secure than a physical card because you authenticate your purchases with Face ID before you pay and your actual card number is never shared with merchants. Add your debit or credit card to Apple Wallet to check out in seconds. Simple, secure, fast. That's Apple Pay. Terms apply. I don't think I can be your friend, Isabella said. Rebecca's stomach flipped. This is the love story of real hinge couple Isabella and Rebecca, written and read by me, Temi Denton-Hurst.
1:11:48Caleb Hearon:Listen to the free audiobook now.
1:12:18featuring fall's best dressed. Make your move. Order on the Sweetgreen app.
From the publisher
Welcome! This week’s guest is the hilarious Sydnee Washington! Sydnee and Caleb talk about cruise ships, the need for more Queen Latifah in the universe, flirting, and much more!
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