Brutally Anna

This week, I’m closing the chapter on Brutally Anna by talking about mile 20—of the New York City Marathon, yes, but also of life. I ran that race back in 2017, and the thing about a marathon is you always know how far you have left. In life, you don’t. And this year felt like mile 23 for me: mentally brutal, spiritually draining, career-wise confusing, and laced with the kind of disappointment that makes quitting look like relief. But pushing through reminded me that the breakthrough always comes after the part where you think you can’t keep going. I get into the messy middle of my career, how I’m retraining my brain, why I’m stepping back from podcasting for now, and why giving up the right things is sometimes the smartest, bravest way to get to your own finish line. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In today’s episode, I’m talking about why I think the word “soulmate” is kind of bullshit—not because love isn’t real, but because we use that word to trap ourselves in relationships that aren’t actually right for us. I share how I once assigned the title “soulmate” to practically every man I dated in my twenties, what finally shifted when I met my husband, and why I now believe the strongest, healthiest relationships aren’t about fate or twin flames or being “meant to be”—they’re about two people choosing each other on purpose, every day, especially when life gets hard. I also get into how the soulmate label often keeps women stuck, why our culture rewards “pick me” behavior, and how the real work of love is not finding the missing half of your soul, but becoming whole yourself first. Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week’s episode is about how I think I accidentally found the cure for doom-scrolling: doing nothing—on purpose. Lately I’ve been trying to detach from my phone because I realized that constant productivity and comparison are killing my joy. Somewhere along the way, “rest” got rebranded as “laziness,” especially for women, and I’m done with that. So instead of polishing hardware or checking off my to-do list, I’ve been wandering around HomeGoods, calling it meditation. I talk about how the obsession with progress keeps us on the hamster wheel of capitalism, how my dad can go on a 14-hour flight with nothing but his thoughts, and how learning to simply exist—to be gentle, unproductive, and occasionally stupid in the best way, might actually be the most radical kind of self-care. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In this episode, I talk about what it’s really been like trying to get pregnant after spending my entire twenties doing everything in my power not to. I share how I went from never tracking my period to obsessing over ovulation sticks and smiley faces, and how coming off Zoloft for the first time in years forced me to actually face my hormones head-on. I get into my PMDD, the endless trial-and-error of antidepressants, the small lifestyle changes that finally helped me feel stable again, and the deeply unsexy logistics of “timed sex.” Mostly, I wanted to be honest about how no one prepares you for how hard this process can be—or how much it messes with your sense of control. It’s equal parts confessional, fertility crash course, and reminder that wanting a baby doesn’t automatically make it easy to have one. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Somewhere along the way, we started believing that if no one saw it, it didn’t happen — that joy requires an audience and meaning needs proof. In this episode, I talk about the psychological cost of living life through a camera roll: how documenting our memories actually weakens them, how performance has replaced presence, and why so many of our “best days” — including my wedding — end up feeling hollow when we live them for others. From weddings to friendships to social media validation, this is about reclaiming your life from the witnesses. Because the moment doesn’t become real when you post it — it becomes real when you let it belong only to you. Learn more about your ad choices. Visit podcastchoices.com/adchoices

I’ve ghosted more people this year than any other year of my life — and I don’t feel bad about it. The truth is, when you start building something of your own, people come crawling out of the woodwork. Old acquaintances suddenly want to “catch up,” but what they really want is a favor, a contact, a shortcut. For a long time, I said yes to everyone because I thought it made me kind. I thought giving without limits was the price of being a good person. But generosity without discernment isn’t kindness — it’s self-abandonment. In this episode, I talk about the difference between being needed and being wanted, and why it’s okay if people think you’re a “shitty person” for having boundaries. Because sometimes protecting your peace means disappointing everyone who only showed up to take a piece of you. Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week I’m talking about the art of dining alone, and why sometimes community is just you, your fork, and the courage to sit there unapologetically. Spoiler: I went out for sushi by myself, got seated in the middle of strangers’ dates, and somehow ended up in an accidental fake date with a man named Brad. We’ll also get into why friendships fade, why I don’t want a “big circle,” and why a Friday night on the couch with Dave, Sawyer, and Dateline might be the ultimate dinner party. Learn more about your ad choices. Visit podcastchoices.com/adchoices

It’s been a couple months since I dropped into your ears, and I wanted to be honest about where I’ve been. I hit pause on podcasting to rethink my career, launch my Substack (maybe both), and figure out if this mic was really the best place for me to share. In that break, I realized two things: one, I hate editing video clips more than anything in the world, and two, I still love the freedom of just talking to you like this. So, I’m back for an eight-episode run—no promises beyond that, but I’ll be upfront with you when we get to the end. Today’s episode is about death and how losing people too soon has reshaped the way I live. I talk about stripping away the performance in friendships, birthdays, even social media, and focusing on the quiet, un-Instagrammable parts of life that actually make it worth living. If you’ve ever felt caught in the grind of “what’s next,” this one’s for you. Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week, I respond to a listener who knows her marriage is over—but can’t shake the guilt of being the one to end it. We talk about why women are taught to feel like the villain when they choose themselves, how shame is inherited, and what it really means to leave a life that was never built for you. If you’ve ever thought, “But he’s not that bad,” or “Who will I be if I walk away?”—this one’s for you. Also: why toilet paper holders are a metaphor for personal growth. Sort of. Just listen. ALL MY CHANNELS Newsletter: https://maybeboth.substack.com/ Instagram: https://www.instagram.com/maybeboth TikTok: https://tiktok.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week’s episode is brought to you by: the delusion that a man who lies to you repeatedly is still somehow “99% amazing.” In this episode, I unpack: Why 99% perfect still isn’t enough when the other 1% is gaslighting What it really means when you say “he’s so great, except…” Why “second chances” are often just “I’m scared to be alone” in a trench coat The emotional equivalent of playing a rigged slot machine with your self-worth And how to know when you’re not actually confused — you’re just stalling If you’re currently debating whether to leave a man who keeps texting other women — this episode is for you. Because you deserve more than 99%. You deserve 100%, or at the very least, a boyfriend who doesn’t flirt with married women behind your back. ALL MY CHANNELS Newsletter: https://brutalbanter.beehiiv.com/ Instagram: https://www.instagram.com/maybeboth TikTok: https://tiktok.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices

Let’s talk about thongs, grief, people-pleasing, and the radical act of not going to the damn party. In this episode, I unravel why I stopped molding myself into someone else’s ideal — whether it was for a man, a friend, or an aesthetic. I also talk about loss, what a photographer taught me about timing, and why your “no” doesn’t need an excuse (or a follow-up text). If you’ve ever contorted yourself to be chosen, approved of, or invited — this one's for you. Also, RIP to the thong I wore once in 2014. ALL MY CHANNELS Newsletter: https://brutalbanter.beehiiv.com/ Instagram: https://www.instagram.com/maybeboth TikTok: https://tiktok.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week, I’m talking about what it feels like to be unwanted—by men, by friendships, by jobs, by the popular girls with the trendy names who never wanted to sit with you at lunch. I share what growing up as the daughter of Chinese immigrants taught me about invisibility, advocacy, and watching my mom try to return a pot to Kmart in broken English while I stood there, 7 years old, already learning what it means to feel small. I talk about how I’ve slowly learned that just because someone doesn’t want you doesn’t mean you’re unworthy. It might just mean they’re not the right person, not the right door, not the right moment. I also get into rat metaphors, George Eliot, and why sometimes the bravest thing you can do is stop running and let what’s meant for you catch up. If you’ve ever felt like you had to shrink to be chosen—this one’s for you. Learn more about your ad choices. Visit podcastchoices.com/adchoices

She’s 32, never had a boyfriend, and just dropped thousands to fund her own proposal — hotel, flowers, the ring he gave her. Meanwhile, he’s out here liking thirst traps and asking her for money for designer watches. In this episode, I unpack the heartbreak of watching someone you love choose delusion over dignity — and why trying to save them might actually be a way of avoiding your own sh*t. Also in this episode: • The difference between generosity and desperation (and how thin the line can be) • The ex-boyfriend I tried to impress with an espresso machine I couldn’t afford • Why today — some random Tuesday in June — might be your new beginning • The illusion of arrival — what happens after you get the life you begged for This is Brutally Anna 2.0 — where it's us just now, and nothing's off limits. Learn more about your ad choices. Visit podcastchoices.com/adchoices

On this week's episode, former director of Betches Media turned content creator Nicole Pellegrino shares her journey as we delve into her candid and often humorous takes on marriage, millennial life, and her rescue doLouie. She opens up about the impact of her mom's passing, her parents' divorce, and why she strives never to take life too seriously, because, in her words, "we're all just floating on this rock." Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Nicole: https://www.instagram.com/nicolepellegrin0 https://www.tiktok.com/@nicolepellegrin0 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Fashion and beauty influencer, Kristina Zias, dives into her 13-year journey from being called 'cringe' to becoming a body positivity queen featured on The Drew Barrymore Show and People Magazine. We discuss juggling motherhood, cross-country move, and running her own business and why her delusional confidence has led her to achieving (and running!) races and experiences she never thought she once could. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Kristina https://www.instagram.com/kristinazias/ https://www.tiktok.com/@kristinazias Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week, I'm joined by comedy powerhouse Zarna Garg as she recounts her transition from practicing law (where her clients mostly ended up in jail) to becoming one of Variety’s '10 Comics to Watch.' Known for her razor-sharp wit, cultural insights, and brutally honest takes on life as an immigrant mom, Zarna dishes on her zig-zag journey. Imagine litigating to realizing you’re better at telling jokes about your mother-in-law than getting people out of jail. Add 16 years as a stay-at-home mom in NYC (three kids and a soul-crushing shoe-box apartment), and you have the perfect recipe for a comedy. Listen as Zarna talks about her stumble into a comedy club, where she hilariously tore into her mother-in-law and had an epiphany: 'Hey, I’m good at this!' She also doles out practical advice: dreams can change (now she’s got someone else getting her cilantro), persistence beats proof, and even gives a shout-out to her 'world-class ego destroyer' mother-in-law. Zarna's story is as inspiring as it is hilarious, packed with eye-openers on motherhood, chasing dreams, and making audiences—and mother-in-laws—laugh out loud. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Zarna https://www.instagram.com/zarnagarg/ https://www.tiktok.com/@zarnagarg Learn more about your ad choices. Visit podcastchoices.com/adchoices

From his humble beginnings playing with Barbies, dealing with bullies, and rocking TJ Maxx instead of Abercrombie, Bran shares how he went from the "fat, poor, gay kid" to our internet gay bestie. Bran recounts his first Grindr hookup (complete with crabs) and dishes on his modern-day love life: think more situational-ships than relationships. We get real about his epic mental health breakdown, panic disorders, and how therapy and meds turned things around. Now, he's all about self-love, spreading good vibes, and focusing on making bank before worrying about love. My guest this week, Noelle Downing, shares her journey of finding joy and purpose after experiencing significant loss at a young age. Despite the loss of her mother to cancer at age seven and her father to a heart attack at age sixteen, Noelle has cultivated a life filled with optimism and creativity. She talks about her early beginnings as a content creator, her side hustles, and the perseverance that led to her success. Noelle also discusses her spiritual beliefs, the impact of her parents' deaths on her life, and the importance of rejection and resilience in shaping her path. Throughout the conversation, her optimism and self-love shine through, offering inspiration and a reminder that joy can be found even in the darkest times. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Bran: https://www.instagram.com/bran_flakezz https://www.tiktok.com/@bran_flakezz Learn more about your ad choices. Visit podcastchoices.com/adchoices

My guest this week, Noelle Downing, shares her journey of finding joy and purpose after experiencing significant loss at a young age. Despite the loss of her mother to cancer at age seven and her father to a heart attack at age sixteen, Noelle has cultivated a life filled with optimism and creativity. She talks about her early beginnings as a content creator, her side hustles, and the perseverance that led to her success. Noelle also discusses her spiritual beliefs, the impact of her parents' deaths on her life, and the importance of rejection and resilience in shaping her path. Throughout the conversation, her optimism and self-love shine through, offering inspiration and a reminder that joy can be found even in the darkest times. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Noelle: https://www.instagram.com/noelledowning/ https://www.tiktok.com/@noelledowning Learn more about your ad choices. Visit podcastchoices.com/adchoices

Comedian, social media sensation, and bestselling author Anna Akana joins me this week as she discusses her journey from dealing with the tragic loss of her sister to suicide to becoming a comedian where she found solace in making others laugh. We dive deep into the challenges of dating in LA, dealing with grief, the quirks of menstrual products, and the importance of allowing yourself to be bad at something before you get good. Plus, you'll laugh at some truly unexpected places, like when we discuss leaving a menstrual disc in for three months (yes, really). It's about turning your pain into your power and remembering to enjoy the process—even when life’s a bit of a mess. Follow Anna Kai: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Anna Akana: https://www.instagram.com/annaakana https://www.youtube.com/user/AnnaAkana https://www.tiktok.com/@annaakana Learn more about your ad choices. Visit podcastchoices.com/adchoices

Creator of Pilates Body Hotties and former Love Is Blind cast member Raven Ross joins me this week to talk about her transformative journey from a self-described shitshow to the wellness maven she is today. Raven reflects on life in her early twenties working three jobs, the impulsive decision to join 'Love is Blind,' and navigating public scrutiny while staying true to herself. She delves into her early passion for pilates, her struggles with body image and eating disorders from her dance career, and the profound impact of losing her father suddenly last year. Follow Anna: https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Raven: https://www.instagram.com/pilatesbodyraven https://www.youtube.com/@pilatesbodyraven https://www.tiktok.com/@pilatesbodyraven Learn more about your ad choices. Visit podcastchoices.com/adchoices