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...
Solo Episode: Your Comfort Zone Is Crippling You
We lost power for 40 hours in 18 degree weather! On this week's solo episode, I muse on how losing power reinforced the fact that I will never like camping and why my version of being "outdoorsy" involves a screened-in porch and a temperature controlled room nearby. We dive into why your comfort zone is killing your potential, and why you shouldn't settle for what's familiar just because the unfamiliar gives you heebie jeebies. I dive into your voicemails on whether you might be mistaking drama
The art of taking life less seriously feat. Hayden Cohen
Our favorite influencer who makes us all feel better about sh*tting on influencers, Hayden Cohen (aka @hayderz), shares his journey on this week’s episode from handling social media for brands to becoming a social media sensation himself. Since 2020, Hayden has been known for his humorous and all-too-accurate impersonations of influencers, reminding us that it pays to take life a little less seriously sometimes.Hayden discusses his early days of content creation, the chaos of his days behind-the
Solo Episode: Embracing life's dualities and what you don't know about friendships
In this week's solo episode of 'Brutally Anna,' I'm spilling the tea (or at least, half spilling the tea) on the highs of strutting at Fashion Week to the lows of some unexpected personal drama. We're DIY-ing over in our house as I talk about everything I learned from teaching myself how to replace light fixtures and why you're probably more capable than you're giving yourself credit for. I dive into the unpredictability of life, the Philly Eagles' epic Super Bowl win, and why you don't have to
Love lessons and life hazards: Joey Zauzig on surviving and thriving
On this week's episode, I sit down with influencer and reality TV star Joey Zauzig, about navigating life’s toughest challenges and why sometimes, a six-pack is the best cure for heartbreak. Joey shares his journey from growing up in Fairfax, Virginia, to coming out in high school, facing and leaving an abusive relationship, and eventually establishing a successful career as an influencer and dating advice guru. Joey brings us into his current struggles after dealing with a traumatic home invasi
Solo Episode: Date yourself first and other lessons in independence
In this week's solo episode, I dive into the fundamental difference between wanting a man rather than feeling like you need one. From my early misconceptions about needing a man to teach me how to handle personal finances to being forced to learn how to handle my own sh*t, I outline the ways in which confidence is an active practice and not something you need to be born with. I answer your voicemails on how to deal with getting over a man who lied to you about his identity and differentiating be
When he wants to chase you, but he doesn’t want to be with you feat. Aurora Culpo
We’re joined by lifestyle influencer and podcast host, Aurora Culpo, this week as she discusses navigating her divorce and how she learned that you really can’t change a man, no matter how many hall passes you give him or how much you spend on lingerie. As always, we love a no-filter, brutally honest woman, and Aurora shows us that there is life after divorce and heartbreak, and there is freedom in the truth after living a lie.Aurora dishes on whether she believes “once a cheater, always a cheat
Solo Episode: Sometimes you were meant to fail so you could succeed elsewhere
On this week's solo episode, I'm diving into exposure therapy, how I got over my deep fear of flying, and why I'll always be an aisle seat biddie over a window seat biddie. I overshare about my EDM club days as an NYU college student, what the Avicii documentary can teach us all about why you're not untalented, you're just not in a space that appreciates your talent, and the endless saga to pick a new toilet for our master bathroom.I answer one of your voicemails on how to feel a sense of belong
Mel Robbins teaches us how to let go and feel worthy of the life and love we want
Podcast legend Mel Robbins joins me this week to discuss how to let go, let it be, and why her new book, “The Let Them Theory” will change your life.Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, marriage adviceA multiple New York Times bestseller, in-demand public speaker, and the host of the chart-topping Mel Robbins Podcast, Mel answers all of our most pressing questions in l
Solo Episode: Why you should show up, even if you don't show up pretty
This week, it's the mini(est) of all solo episodes as we move into our forever home. I break down why it's important to show up, even when you're tired and feeling oogly moogly, and why we should all place a little less importance of milestone birthdays and start giving ourselves more milestone moments, regardless of what age we are. I'll be back next Thursday with a full solo episode where I answer your voicemails, so head on over to speakpipe.com/brutallyannapodcast to leave me a message. Lea
Why you should stop thinking and start doing with Mathilde Thomas, co-founder of Caudalie
If there's anything Mathilde Thomas' life can teach is, it's that we don't need to be ready in order to start.Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, love and money, marriage adviceThe co-founder of the viral French skincare brand, Caudalie, Mathilde joins me in the studio to discuss how she met her husband and his decidedly unconventional "pick-up line", why sometimes, taking a break from your relat
The LA Fires, my most humbling moment, and how to deal with friend breakups
This week, I'm discussing the LA fires, the devastation of losing your home and why insurance doesn't cover the most important parts of what made a house our home. And, since I'm just freezing in sub-zero Connecticut temperatures rather than experiencing the hellfire in LA, I decide my pride is fair game to take shots at in a feeble attempt to make you all chuckle a little by divulging way too much information about my most humbling experience ever (hint: diarrhea in a fridge). I answer your voi
Tough times are temporary and the power of female friendships with Taryn Delanie Smith
Former Miss New York, social media star and TV host Taryn Delanie Smith’s life could’ve gone in a very different direction if it wasn’t for the power of her single mother and the community of women who raised her.Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, marriage adviceOn this week’s episode, we unpack the ways in which Taryn’s life worked out exactly the way it was suppose
Introducing: Mantra with Jemma Sbeg
Ready to take a fresh path to self-discovery? Every Monday, Jemma brings you a new mantra, breaking it down to show you how you can apply it to your own life. Whether you’re facing a major transition or looking to evolve your everyday routine, Mantra is the podcast for you. Join Jemma every week for reflections, practical tips, and personal insights that’ll inspire you to live with intention and unlock your true potential. Follow “Mantra with Jemma Sbeg” wherever you get your podcasts. Learn mor
Solo Episode: When he loves you, but can't be with you, and why you should gaslight yourself
Don't do as Bernie Madoff did (ie. commit history's largest Ponzi scheme), but you can learn from why he was able to do what he did. This week, I'm discussing why sometimes, gaslighting yourself into believing you're capable of something well before you actually do it can be a self-fulfilling prophecy that snowballs into others believing in you, too. If you've ever written yourself off, tune into this episode and hear the stories that inspired me to create possibility where I once found impossib
Why you should get a prenup and how to be the main character feat. Vivian Tu aka YourRichBFF
We're joined this week with Vivian Tu as she doles out the advice we all need to hear on how to stop settling for less than what you deserve whether that's at work or in your love life.Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, prenups, marriage adviceVivian's story shows us all how to stop letting other people write the narrative to your life and why you shouldn't avoid doi
Solo Episode: When your year-in-review didn't live up to your expectations and my mantra for 2025
Happy New Year to all my biddies! This week, I'm breaking down how to appreciate your year-in-review, even if nothing profound or life-changing happened in 2024, and why you probably made more progress than you think you did. We're discussing how to handle those *weird* feelings you get when it feels like everyone around you cured cancer and went to the moon and you, on the other hand, managed to barely survive the year that just passed. I discuss how my faith and trust in God has helped me help
Date them until you hate them and why love isn’t enough with matchmaker Aleeza Ben Shalmon, the star of Netflix’s Jewish Matchmaking
If it’s not love at first sight…try again.Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and moneyWith decades of professional matchmaking wisdom, Netflix-star Aleeza Ben Shalom sits down and answers my questions on whether soulmates exist, why it doesn’t have to be love at first sight in order for it to be everlasting love, and whether there is someone out there fo
Luigi Mangione and why women fall in love with prisoners
On this week's solo episode, I'm breaking down my thoughts on our collective obsession with Luigi Mangione, the psychology behind why women fall in love with prisoners and how those theories apply to why you just can't seem to quit your situationship. I'm bringing it back to the only class I'll really ever remember from my days at NYU, the relativity of morality, and whether all is fair in love and war. On this week's voicemails, I answer your questions on how to rebuild your life from ground ze
How to stop being depressed and signs you’re dating a narcissist with Dr. Jaime Zuckerman
What’s the difference between a narcissistic person and a selfish person?Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and moneyThis week, I’m joined by Dr. Jaime Zuckerman, a licensed clinical psychologist and narcissistic abuse expert to discuss all the ways we can spot narcissistic personality disorder early on a relationship, how to deal with a narcissistic fam
Solo Episode: The art of being alone at the holidays and how long does it actually take to get over a breakup
Being alone (at the holidays or otherwise) doesn't mean you have to be lonely.Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, marriage adviceOn this week's solo episode, I discuss the choice to be alone at the holidays and why we all need to embrace aloneness, even if it completely and utterly sucks at first. I break down why I spent a lot of time with friends and men that didn't
Why you should go for the nerd and the power of creating your own lane with Brandon Berman and Harrison Forman, the creators of UpDating
This week, I sit down with Brandon Berman and Harrison Forman, the creators of the viral live dating show, UpDating, where contestants date blindfolded in front of a live audience. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and moneyWe discuss everything from whether they believe if men and women can really be just friends, the awkward beginnings of both of thei
Solo Episode: You can be married to a cheater, but don't date a cheater and how to get your power back after a break-up
This week, I'm breaking down my thoughts on Netflix's Ashley Madison documentary and the Laci Peterson story.Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, cheating, infidelity, narcissism, self-helpTune in for my thoughts on why (some) people cheat, why I think it's okay to be married to a cheater, but not to date a cheater, and how to spot signs of love bombing. We dive into t
What her boyfriend’s cancer diagnosis taught Kaitlin Reagan about forgiveness
Kaitlin Reagan knows a thing or two about letting go. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and moneyIn this week’s episode, I sit down with Kaitlin to talk about her journey as the daughter of a single mom in Brooklyn to TikTok stardom and losing her boyfriend, Francesco, to cancer along the way. Find out why Kaitlin doesn’t believe in long distance relati
Solo Episode: My emotional baggage around Christmas cards and dating advice on what to do when the chemistry is there, but the sex isn't
Emotional baggage comes in many forms and mine comes when it's time to make our Christmas card.Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and moneyThis week, I discuss the culture of Christmas cards and all the reasons why smiling photos of perfect families on a 5x7 make me feel some type of way and what to remember this holiday season if your life is looking a
How to laugh at death and finding love again after loss with Kelly Rizzo
Kelly Rizzo wants us all to know that it’s okay to laugh at death. She’s the creator of the award-winning production company, Eat Travel Rock Productions and recently competed on Fox’s Special Forces, but Kelly and I sit down today to talk more about how losing her husband, Bob Saget, forced her to learn that there is humor to be found, even in times of great loss. We tackle the topic of deciding not to have children, why it’s okay to choose the man over the life other people expect you to live,
Solo Episode: How a psychic led me to back to Zoloft
Happy Thanksgiving to all my American biddies and this Thanksgiving, I'm grateful for the psychic that made me realize that I needed to go back on Zoloft. This week, I'm discussing all things antidepressants, medication, and why a bad reading from a psychic led me to get back onto a good path with my mental health. I answer your questions about how to disentangle your life from a long-term partner and how to get over your first love when it feels like you'll never be loved again and, how to hand
The power of not belonging with Ava Lee
What’s it like to feel like an outsider your entire life? On this week’s episode, we sit down with beauty and skincare influencer, Ava Lee, on life before going viral for her “jelloskin” tips and the power of reinventing yourself. Ava dishes on growing up in Shanghai and her first time in America as a college student at Notre Dame. We unpack the nuances of the Asian-American experience, assimilation, and how sometimes, we have to be who we are not in order to discover who we are.Ava and I detail
Solo Episode: Your struggle is your superpower and other unfiltered thoughts from my hotel room in LA
On this week's solo episode, I'm coming to you, kind of live, from my hotel room in LA with a mixture of gratitude and Wellbutrin. We're reminding ourselves that our mental state is not always an accurate reflection of what the reality is around us, and that having sad moments doesn't make us sad people, it just makes us people. For those of you who find yourselves in struggle city this time of year, tune in for my advice on how to light the fire under you to get yourself going when you're in a
How to be yourself in a world that wants you to be like everyone else with Cyrus Veyssi
Beauty influencer and TV host Cyrus Veyssi wants us all to know that if a space wasn’t made for you, you can make a space for yourself. On this week’s episode, Cyrus discusses their experience as a non-binary child of immigrants in suburban Boston, why it’s important to understand the difference between someone’s intent versus their impact, and how they use beauty as an act of forgiveness to themselves.We discuss queer dating, why Cyrus prefers to set up straight men and women, and their opinion
Solo Episode: What to do when everything is falling apart
On this week's solo episode, I discuss why sometimes, losing everything you have is the key to getting everything you want. If you're wondering how to keep your life together when it appears to insist on falling apart, tune into this episode as we chat about how your "all is lost" moment is not your demise, but your redemption. I dive into the "all is lost" moment in my life that led me to my TikTok career, and why everyone should learn to dine alone. I answer your voicemails on how to determine
You’re not delusional you just need to learn to ask for and work for what you want with Serena Kerrigan
The queen of confidence, Serena F*cking Kerrigan, wants us all to know that you’re not delulu (*delusional in non-TikTok speak), you just haven’t been taught how to ask for what you want. This week, we discuss the importance of listening to your intuition, why Serena believes that we need to emphasize the importance of a woman being confident over a woman being palatable, and why she would never go back to an ex (spoiler: it’s like trying to un-spoil spoiled milk). Using her life as her muse, Se
Solo Episode: The safe man is leading you into dangerous territory
On this bonus solo episode, we're diving into why dating apps are the gift wrapping of men and why I'm the not-so-proud owner of no less than a dozen cheese boards. Tune in as I unpack the psychology about why gift wrapping influences how much we like the gift itself, how it relates to dating, as well as why sometimes, the safe choice and the safe man isn't actually safe at all. I answer a listener's question about how to handle dealing with the fallout of choosing the wrong man when she was cho
What divorce can teach you about the power of being alone and the rebirthday of Katie Maloney
Vanderpump Rules star and entrepreneur Katie Maloney shows us why the path not taken is often the path we’re meant to take. On this week’s episode Katie details her life as a college dropout, her days before reality TV and VPR, and how she decided that she could only find her best life if she found the courage to end her marriage. We discuss whether she would ever get married again, how she’s found peace as a single thirty-something in L.A., and how she’s no longer willing to be dragged into any
The blessing of getting dumped on your birthday with Lindsey Metselaar
Lindsey Metselaar, host of the hit dating podcast, We Met At Acme, proves that getting dumped on your birthday can sometimes lead to great things. On this week’s episode, find out why women should listen to what men actually say, why Lindsey believes women are less likely to fall in love at first sight than men, and how the most heartbreaking relationships are sometimes the shortest ones.Lindsey talks about that time she was the other woman, quitting drinking (and other things), and who she thin
Why you’re attracting all the wrong men and getting over your daddy issues with Violet Benson
We’re kicking things off with Violet Benson, host of the podcast Almost Adulting and the brain behind the viral Instagram account @daddyissues_. On this episode, we dive into how Violet managed to break the intergenerational trauma of her upbringing, why she thinks you keep attracting all the wrong men (aka Chads), and whether she really believes that you can meet the right person at the wrong time.Violet dives into her childhood as the daughter of Russian immigrants, the first boy that ever bro
Brutally Anna Trailer
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