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Anna
Hi Anna, Please don't use my voice in your podcast, but you can transcribe my words and share it I want to talk to you about my best friend who has never had a boyfriend before and she's 32, dreaming of getting married and settling down and having kids. This first guy to give her attention she believes is the one. You know, like all of our first relationships, she's pretty much paying this guy to be with her in terms of she paid for her own engagement proposal, the flowers, the photo shoot, the hotel, the engagement ring. She gave him the money to do it and I'm having a hard time with it. He he asks her for money for his car, his designer clothes, his designer watch and she gives it. And he likes other girls pictures on Instagram, half naked single local girls and he barely posts her or claims her and he takes his social media very seriously. She's getting married to this guy and I'm genuinely concerned. I'm worried about her financially, emotionally. There's just a lot of red flags and I don't know if she'll listen to me. I've brought it up and she just ignores it. Dear Bitty, you can hold a mirror up to your best friend, but you can't force her to look into it. When I was in college, I watched my friend date a man who was definitively not in college. He was tall, good looking, what a press release called a rising star in his career, and despite being nearly two decades older than her, embodied the youth of a frat bro who could keep up with our 1am Fireball shots and late night pizza runs to the point that I nearly forgot he was in college when we were born. I nearly forgot, of course, until he asked her one day to lie to his friends about her age at a party he was hosting. It would be the first in a series of what he called harmless omissions that he would ask her to convince others of everything from how they met in a bar rather than on a dating app, why she wasn't currently working. She's taking time off of work to pursue her master's degree, of course. And the most harmless of all, removing her last name from her social media accounts so that no one in his inner circle could run a quick Google search on her. I thought pointing out the obvious to her would result in a coming to a messy breakup and eventually a new relationship where she didn't have to lie about her life. What I discovered instead was that holding a mirror up to her would ultimately result in her not only refusing to look in the mirror, but but running away from said proverbial mirror and our years long friendship. Instead of breaking up with her boyfriend, she broke up with me. It was only then that I realized that there are two kinds of people in the world. Those of us who choose to live waking up to the painful clarity of the truth, regardless of how disorienting it may be. And those of us who choose to stay sedated in a dream, furious at anyone who attempts to pull the plug. There's a line in the film Don't Worry Darling where the protagonist, Alice, starts to realize that she's been living in a simulation forced upon her by her husband. We're told what we remember, she proclaims at a dinner party, cracking the facade of a once perfect existence. Even more jarring to Alice is the fact that one of the other women in this simulation, Bunny, has chosen to live in the simulation rather than the real world. Because in the real world, her children are dead and in the simulation she can be with them, even if them is an illusion rather than a reality. We all have a choice, but this one is not yours to make. It is not your responsibility to run after her clutching the mirror in hopes that she'll stop and turn around to look at herself. Instead, put it down, walk away, and vow to live your life steeped in the beauty and horrors of reality. One day, either when she's ready or when she's forced to, she'll come back to pick up the mirror where you left it with love and aggression. Anna My unscripted thoughts are that, as the old adage goes, you can lead a horse to water, but you can't force it to drink. And your friend right now is the horse a Very thirsty horse. A horse that's about to collapse from dehydration. You are giving her the water. You're like, here, here's a gallon of water. Please drink up. And she's like, I'm not thirsty because my master told me I am not thirsty. And so therefore, is it your fault? And if the horse collapses and dies out of dehydration? No, you brought it water, you tried to save it. But if the horse doesn't drink, that is the horse's fault. Everybody is responsible for their own lives. And no matter how much it pains you to see your friend going through this, you are not responsible for her life. The best you can do is help her, and you've tried to do that. What I would really suggest is maybe have one more talk with her, sit her down in a non accusatory way and be like, why are you doing this? This man is taking advantage of you, from what I can see, and you are just allowing him. Because on some level I feel like you don't think you deserve a husband if you don't pay for a husband, essentially. And she's probably not going to react well to it. And then you have to make a decision whether you want to keep her in your life. The other thing I want to point out to you is that I think, especially as women, we take care of other people as a way to avoid taking care of ourselves. I'm not saying that's what's happening here, but I want to peek the question because you're clearly so bothered by the fact that she's about to marry this philandering loser. Do we know if he's philandering? I don't know. Maybe he's just a douchebag. Maybe he hasn't actually cheated on her. But honey, he is liking naked photos of other girls that he could possibly meet up with in real life. Okay, if he's not a philandering loser already, then he's going to be one. I'm going to call it, I'm going to minority report it and say that this man is not going to stay faithful to her. But what I want to say is, is that there's one thing to watch your friends go through something really shitty and feel responsible for helping them. And then there's another thing, to feel it so deeply on a personal level that we adopt that problem as our own problem. And I think sometimes we do this not just with men, but with friends, because we're trying to avoid something of our own. What in your life is a Little bit messed up right now. And instead of focusing on your life and how it's broken, you're focusing on the fact that your friend is so much more broken than you, that her life is so much more screwed up than yours. And I'm not saying that you're doing this in any sort of malicious way. It's just that sometimes we think that by saving other people, we can save ourselves. So maybe if you're going to save her in some way, that's going to replace your need to fix whatever's going on in your life that requires attention. For those of us who are broken, we find friends who are equally broken because they're a mirror onto ourselves. And then we see, okay, well, if I can fix them, that's like a project. And if I can fix their life, maybe that gives me a shot at fixing my own life. And what I want you to remember is that your friend is not a fixer upper. She's not some dilapidated house you bought on sale at a sheriff's auction. She's a human being that is going to choose whether or not she wants to fix her own life. If you're caught up in the lives of other people and the drama of your friend group, maybe take a step back from all that noise and realize what that noise is replacing. So many of us are afraid of silence that we fill our spaces and our minds and our lives with all this noise that doesn't need to be there, but it's there because instead of hearing our own voices, we get to hear everybody else's noise. You're only going to learn and grow if you listen to your own noise. So take a step back from hers. That's a party that you're not invited to right now. It's a party of two, and it's between her and her fiance. Ask yourself why it bothers you so much that she's about to marry the wrong man. And maybe realize that the answer lies more in your life than in hers. It's your job to make sure that if you watch her dig her own grave because you choose not to leave her, you're not also inadvertently digging your own grave next to her. If you relate more to the friend. If you listen to that story of the girl paying for her own engagement, paying for her own proposal, paying for her fiance's nice things, and you were like, huh, that sounds familiar. That is what I do. But what's wrong with wanting to treat your man? What's wrong with wanting to spoil him? Well, no, there's Nothing wrong with being kind and generous to your life partner. The problem is, is when you feel like you have to do it. And I'll tell you a little story. So when I was in my 20s, I dated a guy who made significantly more money than me at the time. And we never talked about finances, but it was very clear that we were not in the same socioeconomic bracket. And I felt very guilty about that. I was at the time a struggling aspiring actress and I held a series of odd jobs, but I by no means could afford to give him what he could give me. And he enjoyed nice things and I enjoy doing those nice things with him. He enjoyed going out to dinner to nice place that I would have never gone out to by myself. And he wanted to go on vacation every other month. And I didn't want to do that for a couple reasons. A cuz I was terrified of flying at the time and B, because I was a struggling aspiring actress. For those of you who don't know when auditions come up, they don't give you like two weeks in advance to prepare. They say, hey, tomorrow you have an audition for X, Y, Z role, be here at this time. And the answer is either yes, I'll be there or no, potentially I'll pass up the opportunity of a lifetime. So that makes it very difficult to plan any sort of vacation or any sort of plans that are immutable, fixed. And I remember always feeling bad about so many things. The fact that I didn't make as much money as him, the fact that I really couldn't go on as many vacations with him and I couldn't hold my own because I thought that if I didn't make an equal amount of money to the guy that I was dating, I was not an equal person. So I made it up to him in really weird ways. I went above and beyond in planning maybe not quite as expensive things for him, but in very thoughtful gestures for him. Threw him this massive surprise party where I cooked dinner for 30 people, which was insane given that we lived in New York City at the time. And I was in his tiny kitchen. And I remember with whatever savings I had at the time, I was like, I'm going to save my money so I can buy him an espresso machine. And so then I bought him an espresso machine. And I think I thought that having that in his apartment would be a reminder that I did enough, that I wasn't freeloading off of him, that I was enough. But the reality is, is that he was never with me. Because he thought that I was making a ton of money. He knew I was a struggling actress, and he was with me because I assume he liked me. And when what really happened was that I did not feel good enough for him. And so I ended up doing all of these things for him in order to try and convince myself that I was worthy of him. And ultimately, we broke up because I needed to learn how to be alone in order to figure out that my value wasn't tied to my job. My value wasn't tied to how much money I made. Now, look, I was lucky in the sense that the guy that I was with, my ex, was not trying to take advantage of me. But I say this to tell you that I relate to her because I think where she's coming from is she thinks she doesn't deserve the husband and the life that she wants because she's never had it. It's been a long 32 years. I mean, make no mistake, I'm not going to sugarcoat it. 32 years to go without a relationship is a long time. It's almost long enough to start to believe that maybe you don't deserve a relationship. And so that's where your friend is right now. And she's thinking, well, I have this and I can't screw it up, so how do I not screw it up? Let me see if I can keep him by buying him into staying with me. And that's where she is. And I hate to break it to you, but everybody is on their own journey, and there's almost no way she's going to learn this without doing it the hard way. So your job is either to figure out whether you want to sit there and watch her do this or whether you just can't be friends with her right now and you need to step away and work on yourself. Either way, you're going to make the right decision. And if she chooses to marry this guy, she's also making the right decision for herself. Because all of us need to pay tuition for an education. Some of us with our money, some of us with her time. And in this case, she's paying it with her money and her time. If you're listening to this episode, you are either one of two people. You've either, A, never heard of me before and you stumbled upon this because you are in the same predicament and you have a friend who's about to make the baby biggest mistake of her life, or B, you are a devoted follower of my podcast and you've been wondering where the I've been the last month. Well, the truth is, I am starting over. And I hope that you can take this day to start over with me, because I have recorded about 30 some episodes of my podcast and I just realized this isn't working for me. It felt like I was doing what everybody else was doing. And so, against the wisdom of conventional knowledge that you're supposed to interview guests who help you promote your show, I have decided to turn this into a solo episode show. So welcome to brutally Anna 2.0. If you've never been here before, I'm so happy you're here. And if you are joining me again, I'm so happy you've decided to stay. We're gonna do things much more differently around here. As you can tell, I started the episode of with one of your questions. You can submit your questions, as always, via a voice memo or an email or a dm. I will read it if you don't want me to use your voice, or you can leave me a voicemail and I'll use it in the next episode. I still want to answer your questions. I still want to talk to you guys. And I don't know what you're dealing with right now, but I just have to say that no matter how perfect everyone else's life seems on social media, no one has it figured out. And I know everybody says that, but truly, let me just tell you about the fact that I thought that having a million followers on Instagram and TikTok would mean I would never have a bad day again. I was so naive to think that I would just arrive at this place of utopia, of sheer bliss, of I don't know what it is, and I would just be okay. But here's the thing about climbing the peak of one mountain is that you're there and you're like, what's next? And you can see the other peaks in the horizon. But, you know, in order to get to those other peaks, you have to climb down the mountain, and then you're in the valley again, and the valley feels kind of sad because it's not as sunny and no one's applauding for you when you're in the valley. But in order to get to the next peak, we have to go down the first peak we ascended and conquered, learn when we're in the valley and climb back up the next peak. So do it with me. Okay? This is one giant experiment in what the next phase of Brutally Anna can be. And today is June 18, and it is not a special day unless it's your birthday. In which case, happy fucking birthday. But if it's not your birthday and it's not an anniversary, today is not a day that anybody's like, yeah, I'm going to start over today. But today can be the day you start over. Just because it's not the New Year's doesn't mean that today can't be a special day. What if I challenge you today to just take June 18th and make it a special day? Maybe today is the day you finally start working on that business plan you've been dreaming of forever. Or you finally join the running club that all the Gen Z people are joining so that they can find their husbands. Honestly, why is Gen Z just crushing life? Because millennials, we just drank ourselves into oblivion and went to bars and hoped find our partners in bars and on dating apps. And Gen zers are like, no, I'm going to run and pick up a hobby that not only improves my physical health, but possibly could net me the love of my life. So maybe today is the day you sign up for the running club that you say you're going to, but you're afraid to because you haven't run since high school and you're afraid that you're going to be slow. What if you are slow in the beginning and it's a little embarrassing, but then you find that other guy who's also a little bit slow, and he's like, dude, I haven't done anything ever but lift weights. And my mile time is 20 minutes a mile, which is basically walking, so will you just walk this with me? And you're like, cool. And then that guy turns out to be your husband? Or, what if you don't? What if you join this running club and you find everybody grotesque and you say to yourself, that's okay, even if I don't like the people around me, I have discovered that I can do the things I told myself I was going to do. And so you do the running club for a few weeks and you realize everyone pisses you off and you decide, okay, I don't like the people at this running club, but I'm gonna keep running. And you keep running. And then you start getting into really great shape. And then one morning you're running and you happen to get into your elevator of your building, and there's a guy that also got home from his morning run, and you start chatting and that ends up being your husband. I don't know how you're gonna meet your husband. I assume you wanna meet a husband I'm just saying that these are all the possibilities that I just thought of in the last 60 seconds, of the myriad of ways in which you finally doing the thing that you said you were going to do could net you the life that you wanted, and it might not happen in the way that you thought it would. Like you think, I'm gonna sign up for the running club. I'm gonna meet my husband. And in fact, you hate everybody at the running club, but you continue running and then you meet your husband, because you go for runs in the morning now. And you would have never met him if you hadn't started that habit. That's what they call the butterfly effect, my friends. So allow yourself to be a butterfly. So the premise of this podcast is that it's going to be a little scripted, a little unscripted, and ultimately, it's supposed to make you feel better. So the question I answered earlier in response to the woman who asked about what she should do about her friend who's about to marry this guy who's taking advantage of her. You can lead the horse to water, but you can't make it drink. I have been given this viral gratitude journal so many times. I've been gifted it by so many brands on so many trips. I have given it away every single time because I've never journaled in my life. And I've been struggling lately. I mean, if you've been following me on my socials, I have been talking openly about how depression has been kicking my ass and upping the Zoloft helped. And staying consistent on the Zoloft helps because it turns out that if you don't take antidepressants consistently, your moods will also be inconsistent. Shocking, I know. So I'm on a consistent antidepressant regimen. But I just realized, too, I was like, I need a practice. I need an active practice. That's not chemical. I need something physical in my life. And I just decided that instead of waking up every morning and telling myself everything that was wrong with my life, because even though I'm living a life way beyond my wildest dreams, I was waking up and thinking about, well, this didn't happen. Happened for me, and this video didn't perform well, and what am I going to do now? And here's how I'm deficient. I was like, I'm going to wake up and tell myself three things that I'm really grateful for. And I made myself cringe the first morning because I was like, God, I feel stupid. And then guess what happened. I felt a little bit better because I woke up and I was like, great. There are three things I have right now. And here's where I can start my day. I can start my day from a place of positivity. And I think I was hesitant for a while to talk about how I was feeling shitty about my life, because I was looking around at my life. I was like, look at all these beautiful things I have. I got everything I asked for. I got the husband that's supportive and kind and great, and I have a fucking dog. And I have a house in the suburbs. And I look like I live in some version of the Stepford Wives that was actually filmed in my town. And I'm still not happy. And I had such a hard time admitting that publicly, because if you get everything you ask for in life and you're still unhappy, doesn't that mean you're just some ungrateful asshole? And so I didn't talk about it, and it just sort of ate away at me. And then I realized that this is why people who have everything kill themselves. And I don't mean to say that to be morbid, it just is morbid. I never understood why. Way back, I think it was in 2018, Anthony Bourdain killed himself. I was like, how could he do that? He has everything. He's Anthony Bourdain. He had everything that anybody could ask for. He had a job that took him to all these places. Everybody knew who he was. I don't think money was a problem. And yet he ended his life prematurely. Yeah, sure, he wasn't a spring chicken, but, like, he could have lived another 30 years. I mean, old Italian, actually, I don't know if he was Italian. Bourdain, that's French. Okay, old French guys, whatever. He just looked like one of those guys that could have lived to be 110 years old, still making fucking souffle from scratch with tomatoes that he grew in his own backyard. I don't think tomatoes are in souffle. It's like, how does somebody like that take their own lives? The same with Avicii. I don't know if you've seen the Avicii documentary. It's on Netflix, and it's absolutely heartbreaking, and it's beautiful. And it's such a reminder that you really can be at the top of your game. You can be Avicii. He was, and I think still is, maybe the greatest DJ of our generation. He totally changed the genre. You wanna talk about being the best DJ in the world. I mean, he was the dj. He was commanding insane rates. He could have any woman he ever wanted and he took his own life. He ended it at a very young age. And so when I look at that, I'm reminded, oh, it's not about what I have. It's about the fact that I need to say, stop delaying my happiness. I think we all do this. We say, oh, I'll be happy when I get this. I'll be happy when I get a boyfriend. I'll be happy when I get married. I'll be happy when I get a house. And then we get all those things and then we're not happy and we wonder why. So I want to leave you with this quote today and I remember exactly where I was when I saw it. I was sitting in Keen Steakhouse in midtown Manhattan. This was New Year's Eve 2017 into 2018 with my now ex boyfriend, then current boyfriend. And this was on a box bottle of Malbec. The Malbec is called El Enamigo and here's what it said on the bottle. At the end of the journey, we remember only one battle. The one we fought against ourselves. The original enemy, the one that defined us. That's all for this week. Thank you so much for listening. Please like subscribe Share show me all the love we're doing brutally Anna 2.0 and I am so happy to have you here with me.
Brutally Anna: Episode Summary – "My Best Friend Paid For Her Own Engagement Ring"
Release Date: June 19, 2025
In this poignant episode of Brutally Anna, host Anna Kai delves into the complexities of friendship, boundaries, and the painful realities of watching a loved one make questionable life choices. The episode centers around a listener's heartfelt concern for her best friend, who is about to marry a man exhibiting numerous red flags.
Anna opens the conversation by addressing a listener's distressing situation:
Anna Kai ([00:55]): “My best friend who has never had a boyfriend before and she's 32, dreaming of getting married and settling down and having kids... she's pretty much paying this guy to be with her.”
The listener describes how her friend is financing every aspect of the relationship—from the engagement ring to the proposal—while the fiancé continues to seek financial support for personal luxuries and displays questionable online behavior, such as liking suggestive photos of other women.
Anna empathetically responds, using a powerful analogy to illustrate the limits of one's ability to help a struggling friend:
Anna Kai ([03:20]): “You can lead the horse to water, but you can't make it drink... She's like a very thirsty horse... you are giving her the water.”
She emphasizes that ultimately, each individual is responsible for their own choices and well-being, no matter how much others care or try to intervene.
Anna shares her own experiences to shed light on the dilemma of trying to save a friend. She recounts a past relationship where she felt inadequate due to financial disparities, leading her to overcompensate in the relationship. This personal story underscores the importance of self-worth and the dangers of seeking validation through others.
Anna Kai ([06:45]): “I ended up doing all of these things for him in order to try and convince myself that I was worthy of him.”
Anna delves deeper into the emotional struggles her friend's actions may stem from, suggesting that long periods without relationships can lead to feelings of unworthiness. This segment explores the psychological underpinnings of why someone might go to great lengths to secure a relationship, even at their own expense.
Anna Kai ([12:10]): “She's thinking, well, I have this and I can't screw it up, so how do I not screw it up? Let me see if I can keep him by buying him into staying with me.”
Transitioning from the friend's situation, Anna advises the listener on the importance of setting healthy boundaries. She highlights the need to prioritize one's own mental health and not become overly entangled in another's struggles.
Anna Kai ([18:30]): “Your job is either to figure out whether you want to sit there and watch her do this or whether you just can't be friends with her right now and you need to step away and work on yourself.”
In an introspective turn, Anna announces a significant shift in her podcast format, revealing her decision to move towards solo episodes. This change is motivated by her personal journey of self-discovery and the realization that she needs to focus more on her own well-being.
Anna Kai ([25:50]): “I have decided to turn this into a solo episode show. So welcome to Brutally Anna 2.0.”
Anna bravely shares her own mental health battles, discussing her struggle with depression despite outward successes and happiness. She talks about adopting a gratitude practice to foster positivity and combat negative thoughts.
Anna Kai ([32:15]): “I just decided that instead of waking up every morning and telling myself everything that was wrong with my life... I'm going to wake up and tell myself three things that I'm really grateful for.”
Anna reflects on the misconception that external achievements and possessions lead to lasting happiness. She cites the tragic deaths of public figures like Anthony Bourdain and Avicii to illustrate that success does not immunize one against internal struggles.
Anna Kai ([38:45]): “When I look at that, I'm reminded, oh, it's not about what I have. It's about the fact that I need to say, stop delaying my happiness.”
Encouraging listeners to take proactive steps towards their own happiness, Anna challenges the notion of waiting for external milestones to feel content. She emphasizes the importance of personal agency in cultivating a fulfilling life.
Anna Kai ([44:00]): “We all say, I'll be happy when I get this... Then we get all those things and then we're not happy and we wonder why.”
In her closing remarks, Anna shares a meaningful quote that encapsulates the episode's themes of self-reflection and personal battles.
Anna Kai ([50:30]): “At the end of the journey, we remember only one battle. The one we fought against ourselves. The original enemy, the one that defined us.”
Boundaries in Friendships: It's crucial to recognize the limits of how much one can help a friend without compromising their own well-being.
Self-Worth and Validation: Personal value should not be tied to external achievements or the ability to support others financially or emotionally.
Mental Health Awareness: Even those who appear to have it all can struggle internally, highlighting the importance of addressing mental health issues openly.
Personal Growth and Happiness: Happiness is an ongoing personal journey that doesn't solely depend on external milestones or societal expectations.
Anna Kai ([00:55]): “She's pretty much paying this guy to be with her... he asks her for money for his car, his designer clothes...”
Anna Kai ([03:20]): “You can lead the horse to water, but you can't make it drink.”
Anna Kai ([18:30]): “Put it down, walk away, and vow to live your life steeped in the beauty and horrors of reality.”
Anna Kai ([38:45]): “It's not about what I have. It's about the fact that I need to say, stop delaying my happiness.”
Anna Kai ([50:30]): “At the end of the journey, we remember only one battle. The one we fought against ourselves. The original enemy, the one that defined us.”
Brutally Anna continues to offer raw, honest discussions about love, friendship, and personal growth, encouraging listeners to confront harsh truths and embrace their authentic selves. Whether you're seeking advice on navigating romantic relationships or striving to improve your mental well-being, Anna's candid approach provides valuable insights and heartfelt support.