Session 120: Kylie Jenner

29:47And how did that go? And it was, I was really scared, but I knew I was really scared, but there was something just inside of me that knew that I wanted to do this. I had to make a decision for myself. Like, what do I really want? What can I handle? And even if I have to do this alone or however, like this is the choice that I'm going to make. And then I told my mom. Put on the wine. We're like crying. No, I was going to say I'm drunk. Yeah. now we're like crying yeah um no one was like angry at me no one it was just it was crazy crazy times stormy ever asked like what do you do of course and does she like understand she knows mommy makes makeup got it and she loves to go to ulta really she loves to go to ulta she loves to go to ulta shop for makeup and other products and she likes to buy my things and she likes my lip butter.

30:52She knows I make makeup. She knows I'm like always leaving for work. Right. I go to the office. I travel. So I explain to her, you know, why this is important, why I need to leave, and I try to keep her involved. I think it's important for her to know what her mom does and why I'm gone. A thousand percent. Yeah. Wow. And does she ever question cameras or is she just like, that's life? she actually loves it and I have to be the one to like set boundaries because she want we made a little tiktok last night and she begged me to do it and I could sometimes we make tiktoks and I'll just do it to because she thinks it's fun and then I will never post them but the the one that we made last night I did post but she loves to be on camera like did you see the paparazzi photos of us the other day going into the restaurant and she was smiling big she like when she sees a camera she's like she's you she loves it exactly how when's her birthday she's february 1st oh she's an aquarius or yeah aquarius right february 1st leo rising i'm a leo my son is february 2nd that's kind of crazy it's crazy i finished my glass okay i'll finish it oh no you have a lot to go of course you're drunk i know that's i am a lot less nervous you're very disarming thank you yeah i love that and i've noticed that from the moment that i met you at that charlie xcx show i was like oh she like makes you feel like you're her friend even if she i don't ever want to make I don't want to come off intimidating.

32:36Well, you do, but you don't, if that makes sense. You're like the really, really pretty girl in high school who would make everyone feel special. It really is genuine. I don't want to make people feel... Scared. Yes. What are you watching on TV? I'm watching The Testaments. The Testaments? It's called The Testaments, right? The Handmaids. Oh, is it a spinoff? Yes. Okay. I love The Handmaid's Tale. Uh-huh. Die for The Handmaid's Tale. Have you ever seen the show Industry? I haven't. You would love it. It's about stockbrokers in England. Okay. And they all, like, do drugs and party. Okay. And, like, fuck each other.

33:20And it's, like, am I describing it correctly? Yeah, but it's, like, really, it's kind of like succession. I'm going to write it down. It is the cuntiest show on television. Yes. The two main girls fight all the time. Okay. And like they fuck each other over and like are like low-key lovers. No. I'm always looking for a good new show. What else am I watching? Industry is great. Should we keep going? Yeah. Wait, so I just watched the Caterpillar documentary. Have you seen that? That the guy, he changes his eye color. What? That one's a little crazy. I started the second season of Beef. I haven't even seen the first.

33:56I'm into it. Okay. I'm really into it. I didn't finish the first season, but I'm into the second. what else? Movies? I just watched The Enemy again by Denis Villeneuve. Oh. Kind of cinephile? Do you have a letterbox? I do, but I downloaded it because my friends made me and then I just never opened the app again. The Enemy is kind of crazy. You should watch it. What's it about? You just have to watch it. Okay. It's about a guy who is watching movies and see someone in the movie that looks exactly like him. And then it goes from there. How old is it? 2013. 2013. Did you ever go to IPEC? Of course.

34:43You know, it just closed. I know. I'm so upset. It's so sad. It's so sad. That was my theater because they always had, like, we would always do little private things there all the time. Did you watch 90210 as a kid? I didn't. You would have loved 90210. I'm trying to think of what I watched. Gossip Girl? Yes, earlier seasons. Yeah. Like Vampire Diaries? Of course. I just rewatched everything. I got to like season six and then I stopped. Were you Team Damon or Team Stefan? Ugh, it goes back and forth. I was Team Damon. At first I'm Team Stefan and then I go hard left to Team Damon. Uh-huh. hard left to team Damon ah and then once like you know Damon's in the picture for a while I go back to Stefan yeah you're like it's too much I'm like wait but Stefan that is the best show of all time it is it really really is it is I stop because I'm like when it's over it's over I probably will take a few years off again did you watch have you ever seen scandal yes that's like my favorite show Yeah.

35:56Scandal was amazing. Girls? No. I think you would like it. Kendall always talks about girls, but no. What's like the, like, what is your like prime differences between you two? There are many. There are many. She, well, first of all, she's like my favorite person on the planet. And I think as I get older, you just, do you have siblings? I have a younger brother. It's his birthday today. It's his birthday today. Happy birthday, Luke. Happy birthday, Luke. I think as you get older, too, you, like, she's just my best friend. She's my ride or die. We are, like, totally different people. It's really interesting.

36:40She's type A. I'm type B. Yeah. How are you type B? I'm go with the flow. Uh-huh. I don't really, like, make plans. my brain like I'm a little bit messy but I hate to say that you're messy like yeah kind of honestly but but not in like a I just am so disrespectful to my home and my like shits everywhere I think like the way that my brain works is not like right like I'm a little like I have piles of things, places, but I know where everything is. But I come from a family of type A's. They're really. Everybody is crazy. Is your mom type A as well? Yes. Oh my God. Right. Crazy. The most. Very organized.

37:34Very. And I'm just not, I don't have that in me. Yeah. I. Or, I'll cook. What do you like to cook? I like to cook tacos. I like to cook pastas. Steak. I'm really into making steak these days. How do you take your steak? I like it like medium well. You're like my friends. I'm going into medium. I'm slowly going into medium but I'm medium well. What is it about the well done that you like? I didn't say well done. I said medium well. And what do you like about it? So it's a little bit of pink. Like how much pink? Like a little bit of pink. Uh-huh. But like I said, I'm going into well, wait, medium.

38:18Medium. I'm going into medium. So you're going more pink. Sorry. Yes. I'm going to medium. What is your kid's favorite thing that you make? They, I mean, mommy potatoes. Mommy potatoes? They call it mommy potatoes, but it's my potatoes. That's really cute. And they have it for breakfast, lunch, dinner they love the potatoes that i make and pancakes my son really likes my banana pancakes yum so yummy yum he likes my banana pancakes i really like cooking um thanksgiving food honestly thanksgiving food has never done it for me oh it's the best like what what thanksgiving food do you like do you like candied yams i don't mind them why why are you saying it like that.

39:04I don't mind. Like, I don't like, like the cranberry shit that they have going on. Like everything. Let's go through the whole thing. Okay. Candidiums. Fine. But fine. I don't think you've had my candidiums. What is a yam? Is that like a potato? It's a potato. Yeah, it's fine. It's a fucking potato. Okay. Green bean casserole. What? Why not? I don't even know it like it scares me. Do you like ham? Love ham. Love ham. You know what? Do you like fried chicken? Love fried chicken. I think you should come over. I'm not kidding. Don't play with me. And I'll make you candied hams, green bean casserole and fried chicken.

39:45And I think you're going to love it. I'm shaking. I think you're going to love it. I'm going to take you up on this. Don't tempt me with die to do that okay I want to do it okay that's the we're gonna do it okay and it's okay if you don't like it I mean you're gonna love it I know I'm gonna love it but if you're like this just really isn't my steez you could just have the fried chicken I love fried chicken you know what I was gonna ask you about crumble cookies oh yeah do you really like crumble cookies I really did I did because I saw them everywhere and I don't really get out much these days really like you just spend your days in your home?

40:25Well, I travel a lot. But when I'm in LA, for some reason when I'm here, it's hard for me to leave the house. Why do you think that is? I think that's because

40:41honestly, paparazzi or in LA, it's just easier to be spotted, I think. so the thought of like trying to find an outfit and like getting ready and present and then I go back and forth because that's a silly way to think about it but it's honestly the truth but do they just wait by your house for your car to leave no because I don't really leave got it so they don't really wait for me anymore do you remember the height of it like did it used to be way worse it used to be so insane you i don't even know how i'm like a normal person right now like what would it what was it like the things that they would say to me and how they would treat me as a child oh no is diabolical like inappropriate i would be coming out of a thing and they'd be like you fucking slut what when i was 16 you're lying i'm not lying the things that they would say to me i would never try to give them a photo so i would just jump in the car and then there would be like six of them and they would stand in front of my car as i was like 16 like turning my car on whatever and they would all stand out because i would just be like you know hiding and they would just be like oh I'm like you know mock me what they wanted to just make more money off a scandalous photo they wanted you to be like this crazy and I was an underage girl by herself I didn't have security I didn't have security till after I had my daughter because I really didn't want to be I really wanted to not have security I wanted to be normal I wanted to be with my friends I wanted to be on my own in the world like I did not want and so you were just completely alone yes and That must have been so scary.

42:34It was scary at times.

42:39When is it not gifting season? That I don't know. But I do know that once again, it is coming up. We have Mother's Day and Father's Day. And you will need to start using that Venmo balance that's sitting pretty in your account with the Venmo MasterCard. It makes it so easy to use that balance. The Venmo debit card, I just feel like is a genius invention because every single person I know uses Venmo. And it's just so simple. You can also add it to your digital wallet so you can tap to pay. It's also graduation season. If you have a sibling, if you need to get a graduation gift, it really is just so easy.

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43:48Best time ever. And I'm just so grateful that I'm able to see the behind the scenes. Of this? Yeah, because I've watched some episodes and I see it on TikTok and whatever. but to see the behind the scenes is so special. Do you feel comfortable? Yeah. I'm so happy it was at a house. I know. You were like, I thought I was walking into a studio. Yeah, and I feel like studios kind of make you feel not comfortable. Right. This is perfect. Okay, I'm so glad. Well, are you ready to do the Tell Me What's Wrongs? Yes. Okay. I cannot figure out my own style and fashion for the life of me. I hate everything I wear and it's so hard to feel confident.

44:25I'm a creative person too and follow random fashion accounts, etc. But anytime I'm in a changing room, it's tears. I get overwhelmed and end up picking up only the safe options and then hate myself for it later. How do I break the cycle? First of all, me too. I feel like I get into that cycle too. Do you? Or is it easy for you? No, it's, I'm like, for the longest time would only wear like the same, like I hate trying on jeans. I hate trying on, like trying on pants is like my worst nightmare. Why? So you have like a few. I have like three or four pairs of pants that I wear. Okay. But I love that.

45:01Yeah. I just got rid of so many things. Cause I'm like, I only want things that just make me feel good. Like I want 10 pairs of jeans, two leather pants. Like I don't need, I think it's, I think that actually helps. I would say that's my advice. Like go through your closet, really try on everything and see what fits you the best down size. And also, So what would be my advice for that? You have such a creative and like individual style. I feel like that's why people loved you so much from the start. Like you had your own thing going on. How did you like find that on like how were you like how did you find confidence to like own your own style?

45:45When I was dressing, I mean back then I really wasn't looking. I feel like when you start to look at other people and maybe what works for them might not always work for you. What makes me feel good? What kind of colors make me feel good? Like I was really experimenting back then. Now I'm a little more, I do get in my head about it though. It's hard, I will say. But then when I have moments, when I'm like freaking out about an outfit too much and I've spent over like 40 minutes trying to pick an outfit, I'm just like, you know what? I'm going to put on my favorite pair of jeans and a fucking white top.

46:24And I'm going to enjoy the night. I mean, you know what changed my life was when you went to Coachella in a leather jacket and jeans. And I talk about it. I actually talk about it. I pretty much spoken about it on this podcast as like my Mecca for Coachella outfits. Oh, my God. I love that. Because I was like, she just didn't care. Yeah. She just went in leather jacket and jeans. And sometimes it has to be like that. Sometimes it has to be like that. and you pick your moments because trying to pick an outfit, it will make me spiral. It will make me overthink. And then I get there and I'm like in the worst mood.

46:57When I start to feel myself get in that mood, I'm like I'm putting on the most simple outfit and I'm getting a cute bag or whatever and I'm just going to enjoy the night. Sometimes it's about the accessories. Sometimes it's about the accessories. I agree. Absolutely. Like sometimes it's about a ring or a necklace or a bracelet that will make you feel like you're not just wearing something simple. Absolutely. That's good advice. Thanks. Every time I encounter a situation with a guy and he starts showing interest in me, I pull away. I've done this since I was younger and now I'm in my mid-20s. I think I'm defensive because I'm scared of rejection.

47:33Oh, me too. How do I allow myself to become vulnerable without my brain convincing me there is something wrong with the guy? What do you have to say about that? I'm the same way. I'm terrified of rejection. I'm like terrified of it And I get it all the time and it's horrible So what's your advice for that? My advice is like It's like jumping into cold water Like you just have to do it That one's hard Dating's hard nowadays I think I might be genuinely stupid I did fine in school But like I literally don't understand the subtext Or whatever of anything I watch or listen to or read I'm always just like I liked that Or that was weird I've been hanging out with these people who are more creative and it feels like they're running laps around me after we watch a show or a movie.

48:17Is this a valid insecurity? It's definitely valid and I feel like that in different ways too. I'm in situations where people run laps around me all the time. But then we'll be in a different situation and I can run laps around them all the time. You know, I think it's just, you're not going to be super educated in every single, or maybe you are. Right. But I don't think you're going to be like, Like, yeah, but I've been in situations like that, too, where I'm like, I have no, my, my, like, art friends and stuff, like, I'm just kind of diving into it and learning, but they're like, you know, this art and da-da-da and this year, da-da-da, and I'm like, I have no idea what you guys are saying.

48:51No, no, no idea. Yeah. But then if they're like, they want to talk to you about clothes, you'll know. Yes, clothes, movies, children. Yeah.

49:02Like, what? Makeup.

49:09Okay. Podcasts, you know. You do. You are kind of an expert in podcasts now. I'm not. You kind of are. You think so? I kind of think so. You're in your podcast era. Oh, my God. You're either going to leave this podcast being like, I'm never doing a podcast again, or that was fun. I would come back here every day. No, you wouldn't. Yes, I would. This is so much fun. I'm having a really fun time with you. Me too. I think I need a podcast. Kylie, don't fucking play with me right now. If you had a podcast, I would be sat weekly. Weekly sat. That's kind of cute, too, if I were, like, really sat. Like, what if we just, like, sat on the floor on my podcast and we just, like.

49:47I called it Sat with Kylie. Yes. Anyway. But, yeah, I would say the advice is that you are smarter in areas that you're not allowing yourself to feel. It's okay if you're not educated in movies or whatever she said. I'm barely educated in movies. Bye, who cares? Let them educate you. Yeah, you can always Google it. Sure. Chat TPT. Chat. Hello, chat. You know, and then, you know, the things that you are educated on. Yes. Yes. By the way, the worst advice. Okay. No, but it is good advice. Like, you are educated in stuff that they're not educated in. Yeah. So who cares? So wait your turn. Wait your turn.

50:29Wait your turn. Wait your turn. You just fucking wait. Yeah. Cheers. How many times have we cheers? Like a million. Cheers after every question. We do. My best friend's an extrovert who doesn't know how to spend time alone. Well, I'm an introvert who needs alone time after being with anyone for too long. She always wants me to be with her. On runs, on calls, study dates. I love her, but it's really annoying. I'm with her six out of the seven days a week, and it's draining my energy and making me resent her. She can't take a hint and will pester me until I agree to be with her. I'm that friend.

51:07Well, she wants to have sex with you.

51:13I'm just kidding. Wait, so you're the friend that pesters until they be with you? I need to be with people at all times. I can't be alone. I used to be like that. I think I grew out of it, but I definitely used to. I can understand that feeling until you're like, you know what it was? It was like me forced to be alone when I was pregnant for the first time. Oh, because. And that changed everything for me. I've never had so much alone time in my life. And now I'm a different person because of it. What did you do with that alone time? Nothing. Well, I would make a schedule for myself in my head.

51:49Yeah. I had to make schedules so I didn't go crazy. Right. But yeah. Anyway, what the fuck was the question?

52:05That was funny. Oh, I need those jeans is what I was planning on asking you. The Kai jeans. I need them. But you said you don't like trying on jeans. I know, but I said to Louise, show them off. They're a little like, you know what I'm saying, but they're the best. And the Kai on the ass is just everything. They're the best, like, baggy low rise. this is like a style we did off of like our best selling style. Now I'm like, what is it? When you're like selling things. Oh, CVC, QVC. Buy now. No, these are, these are the best. I really want those jeans. I said to Louise, I was like, I need those fucking jeans.

52:47What size do you think you'd be though? They're not actually, I don't know about that. I'll send you like three. Yeah. Just send me multiple sizes. Send you three. But what was the question? Yeah. Right. Wait, she's... Oh, she can't be... This friend can't be alone. Okay, okay. So... Okay, my advice, my only advice to that is clear communication. Okay. She has to sit her down and say, I actually... This is how I'm actually feeling. I think communication and being honest in any relationship is very important. And you need to just have a conversation with your friend. Are you confrontational? Yes.

53:30I, I get that. I think I am. I think you are. I'm confrontational. Sorry, this is such a pivot, but did you ever have like any college experience at all? Like, did you ever like go to a college party? Like, did you ever like... College I might have missed a little bit. I went to a lot of high school parties. Lots of high school parties. College was, you're 20, I'm like... Were you ever worried about people like filming you drinking? When you were underage? Um, yeah. But was the phone, like, less present then than it was now? Because I feel like everyone's out now. The phone was way less present, and I think we would hide it.

54:10We would put it in, like, a drink, or, like, Stoss would be there and, like, pass me, like, a little sip of something, or, like, you know, if we're, like, smoking a cigarette, she'd, like, under, and I'm, like, you know? Yeah, yeah, yeah, yeah. But cigarettes are kind of back. Cigarettes are so back. Thank God I've been, like, hiding for so many years. They're back. I'm only a drunk. I'm really only a drunk cigarette. There's very few times where I'm like, I need a cigarette. I'm in Europe in the summer. Always. Like midday. I'll wake up and smoke a cigarette in Europe. Exactly. Like, bye. There are no rules.

54:40Yeah, there are no rules. Out on the terrace of my hotel room, cigarette. Because they burn so fast in Europe. They're perfect. They're perfect. Oh, my God. I want to go to Europe right now. I want to go to Europe, too. I want to go. Take me to Europe. I want to go now. I'm having a Europe summer. Are you really? No plans, but I'm going to be there. Okay, I'm going to go to, I'm in France all of June. France all of June. Okay. Oh, she's saying no? All of June? Manifest, babe. Yeah, I'm manifesting. You are in France all of June. I'm going to be in France all of June. And I'm going to smoke cigarettes all of June with my hot French boyfriend.

55:15I want a cigarette right now. Should we smoke after this? Yes. I have, I will smoke after this. Okay. Because we had our wine. Yeah. And we deserve that. Of course we deserve that. It's the least we can do for ourselves. You want to know who's the best person? Who? Kris Jenner. Yeah. I think you've met her on that carpet. Is that the only time? Yes. No. Yes. That is the only time. When I tell you she's the best person on the planet, like she really is. The way that she lives life is so inspiring. And her energy, like when we go on vacation together, when we're out together, like she, her vibration is so on another level.

55:51And like, she just enjoys life. She enjoys people. She's like, you know, wants everyone to feel good. She's, she's, she's da, da, da, da. She's just living her best life. No, this generation, we don't drink anymore. We don't drink anymore. We don't do anything. We don't like cook and invite people over for fried chicken. Well, it's because of COVID. It's because of COVID. It's because of TikTok. It's because of like, everyone just wants to lay in bed and just be on the internet. I feel numb to my surroundings and life right now. I'm right out of college and even just ended my four-year relationship.

56:28And I really don't feel sad or nostalgic about anything. Just like I wake up and do my thing and that's it. I'm worried that I'm like a psychopath or something. And if I stay this way and that I'll stay this way. If it's just a phase, what can I do to get out of it? You know, when you're a kid, time moves really slow. Yes, very slow. Time moves very slow. Years are like centuries. And I read something recently that says the reason that you felt like that as a child is because you were experiencing so many new things at once. So as an adult, instead of getting into routine where time moves really fast, do new things.

57:06Go to Kylie's house and eat fried chicken. You know, take a pottery class. So I started doing things to help time move a little bit slower. You've opened my third eye. Yes. You've literally opened my third eye. Like literally book a pottery class. Do things. Just do random shit. Go to Disneyland. Oh, I love Disneyland. You know, but we've done that. We've done that a bunch of times too. I mean, I have. But like do something. Do something new. Don't have a Euro summer. Go to Australia. No, but we're having a Euro summer. I'm just kidding. We're having a Euro summer. I'm so sorry I said anything.

57:42We're having a Euro summer. No, but yeah. Jake, an amazing guest. I've been thinking about breaking up with my therapist for a while. I'm just so scared of starting over. Like, she knows everything about me, but she also agrees with me all the time and gives me the most basic ass quotes. I'm just paying her to rant at this point, but at the same time, I kind of need that to help. She needs to move on. She needs to move on. I'm breaking up with my therapist right now. Break up with your therapist. And who cares if she knows everything? It's not like she's going to say anything. Was that ever a concern for you, talking to a therapist?

58:14like no but a little bit yeah I'm still a little guarded and I've had two therapist experiences now I don't have one I don't know were they like spoke to people no no no no but when I'm just saying I've only had experience with two therapists and not for a long time like I'm not in therapy right now. Wow. I didn't know that about you. Yeah. And you're just able to kind of like raw dog life. Exactly. I have totally raw dog life and I'm fine. You seem fine. Thank you. I think what I need to do and what I do often, which I think is really healthy is like delete the apps. Like what? Like TikTok and Instagram?

59:03Like I'll take a week every now and then, sometimes too and just like delete the apps you're just like it becomes loud yes delete the apps um live life because i don't know oh my last question for you okay like ever wait no not ever are you having fun i'm having the best time but i feel like i'm trapping you oh i need to ask you yeah bora bora is it as beautiful as it seems i didn't love bora bora

59:36you did it go to Turks and Caicos babe okay did you have you been to Turks Caicos before best place ever what's it like oh my god let me tell you everything tell me tell me the mornings the weather the sunrises the sunsets the way that the air feels the fucking sand the crystal blue water is the water warm warm oh the water's warm I need it every day I'm mourning not being there which probably isn't healthy but I'm like it's the warm water the sand the gorgeousness the food you should go for your birthday I know where were you just vacationing I was just vacationing in the Bahamas. I mean. Cheers.

1:00:24Well, Kylie, what did we learn today? I learned. This has been one of the most, I feel so locked in with you right now. I feel so locked in. I want a cigarette. Now. Now. Do we have some at the house? My security always has some. Can we please smoke? Security, emergency cigarette. But your security is so lovely. The best. When they came over to like check out the surroundings, like they, they just spoke so highly of you. And it made me so much more excited for this. Like I was like, I was like, I'm so nervous. And they were like, she's so good at it. They were like, she's the best. Yeah. And then Manny out there was like, they're the best.

1:01:07And I was like, Manny's like my, like, he literally like, will like take my daughter somewhere. Like I trust him. With, yeah. Yeah, my kids. But what did we learn today? We learned that. First of all, this is my kid. Who's calling? Hello? Hello?

1:01:28Hi, Angel. Okay. Bye, I love you. That's really cute. Oh, what are we going to do? Do you want babies? I think I do want babies, but, like, I think I want to do it the Andy Cohen way. What's the end you call it away? 40, adopt two, call it a day. I like that. Yeah. Theo and Annabelle. Theo and Annabelle. Cheek, right? I love Theo and Annabelle. I love Annabelle. Right? Yes. Yeah. And that's what I want to name my two babies. I want to adopt them and call it a day. Even if I'm not with someone, that's what I want. Well, Kylie, this has been a dream. Thank you for doing this. I'm so happy. I couldn't be happier to be here, really.

1:02:17I love you. I love you. I love you. I love you. I think you're the best. You are the best. You are the best. You're the best. You're the best. And I had so much fun with you. And I didn't even, for the first time, didn't even notice everything else. Sorry. Let's have a cigarette. Let's have a cigarette. Bye, pussies. I love you.

1:03:15We'll see you next time. Free samples. Zero pressure. Right now, get up to 45 % off with minimum purchase. Plus, get a free professional measure at Blinds.com. Rules and restrictions apply.