Brutally Anna

Brutally Anna

Welcome to Brutally Anna, a podcast about finding love, losing love, and all the things we think about a lot, but don’t talk about enough. I’m your host, Anna Kai aka @maybeboth across social media, here to remind you that life can be beautiful, even when it’s freaking brutal. On this brand new podcast, I’m joined by some of your favorite creators and experts on how they navigate dating, how to stay hopeful when you’ve kissed one-too-many frogs or Chads, and most importantly, how to love yourself when you haven’t yet found someone else to love you. Each week, we tackle everything from dating after divorce, how to ask for what you want from a relationship, and what death can teach us about love and life. If you’ve ever wondered how to begin again when life as you know it has ended, this podcast is here to remind you that the best thing to come out of rejection is often our reinvention. Join me on Mondays as I sit down and get you the brutal truth so that you can find your truth. Don’t forget to follow me @maybeboth across social media and subscribe to Brutally Anna wherever you get your podcasts.

Episodes

June 19, 2025 24 mins
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 differenc...
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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: htt...
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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://w...
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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 ...
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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 ...
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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 al...
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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. Pl...
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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 st...
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Picture this: I'm chilling (or warming really) in a swanky Utah hotel room, staring at a scenic snowy mountain while my outdoor gas fireplace blazes away because I couldn't figure out how to turn it off. I'm here on a brand trip, but before this, I was in LA for a memorial. Some heavy stuff has been on my mind: the sudden loss of loved ones, the meaning of life, and what's truly important. Spoiler: It's not meeting work deadlines. ...
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March 31, 2025 73 mins
Jenny Yang has tried to save the world in many ways, but for now, she's saving us all with a little bit of humor. Named as one of Variety's top 10 comics to watch. Jenny talks about her transition from her slam poetry days and a high-stress career in politics to comedy. She shares how her upbringing as an Asian American immigrant shaped her path and her passion for representation in Hollywood. Jenny opens up about personal struggle...
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I'm scared of K-12 kids, having kids, and having kids who might get bullied. Unpacking all of the above on this week's solo episode after an encounter with Girl Scouts selling cookies and why I think I'd be capable of murder (under the right circumstances! It's a joke - don't come after me FBI!). I tackle listener voicemails about toxic friendships (not all friends are forever) and family dramas. Stick around for my reflections on ...
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On this week's episode, podcaster and wellness coach Ashley Lemieux opens up about the heartbreaking loss of her unborn son to sepsis in 2020 and how she turned her grief into a mission to help others. Ashley talks about her hit podcast 'Healing Her,' her social media channels, and her bestselling books, all aimed at supporting people navigating some of the most heartbreaking moments of their lives. She also shares personal stories...
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March 20, 2025 31 mins
We're talking DIY pest control, why owning a home is (kind of) a scam (that I willingly participate in and have a love/hate relationship with), and why it's a privilege to be able to try at all, even if you fail. I discuss why we need to make it more socially acceptable for women not to be motivated by some higher "purpose" other than making a living, and I answer a listener's question about what to do when you're tired of dating a...
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This week, I'm joined by founder and self-proclaimed candle snob, Lindsay Silberman. From her ambitious beginnings as a magazine editor to pivoting into the world of social media influencing and entrepreneurship. Lindsay reflects on her career in the evolving magazine industry and how being hit by a car in 2018 gave her a new lease on life. She takes us through the highs and lows of launching her candle brand, Hotel Lobby Candle, d...
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On this week's solo episode, I'd like to remind that you that for every time I thought my life was ending in my twenties, it didn't. And so, if my dramatic ass can recover from every breakup, career failure, and cringeworthy moment I've lived through, so can you. I welcome you into the chaos of my inner world because even your queen biddie can get caught up in what's next versus what is now. I read some juicy secrets from you guys ...
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On this week's episode, we dive into the life of powerhouse entrepreneur and NYT bestselling author, Loren Ridinger, who shares her story of building a global business empire with Market America and Shop.com alongside her late husband, JR. The conversation explores 'Life After Rejection,' as Lauren recounts their early years, falling for JR despite his initial disinterest, and their shared vision that transformed into a legacy. L...
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It turns out I didn't need a higher dosage of my Zoloft, I just needed eight hours of sleep. Speaking to you from Florida, I'm sharing all my thoughts this week on prioritizing yourself and why taking a step back can sometimes be the only way forward. We're taking a deep dive into the awkward realm of friendship breakups, why it's important to know the difference between someone who wants to be friends with you and someone who want...
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This week, I sit down with Radhi Devlukia, a New York Times bestselling author, wellness influencer, and entrepreneur, about her journey from being a dietitian to becoming a holistic wellness advocate. Radhi delves into her upbringing in the UK, her career transition from aspiring pediatrician to dietitian following her mother’s advice, and her subsequent interest in Ayurveda. She highlights the importance of making small, sustaina...
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It's a mini solo this week because I not only left a coffee curdling in my closet for four days, I'm also losing my voice. We're diving into the madness of weddings this week - from extortionate bachelorette parties to bridezilla friends and how to handle those years when you feel like you're blowing all your free time and life savings on wedding-related events. I talk about the importance of setting boundaries and the liberating j...
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On this week's guest episode, I'm joined by Joanne Lee Molinaro, aka The Korean Vegan, who reveals her journey from courtroom drama to cooking fame. With nearly 5 million followers, she's not just whipping up vegan delights but also running marathons, publishing NYT bestsellers and winning awards (ahem, hello James Beard). Joanne gets real about growing up as a child of North Korean immigrants in suburban Illinois, feeling like an ...
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