Brutally Anna

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 cheater” and how she realized that she wasn’t the exception, she was the rule. We navigate our experience with men who wanted to chase us, but didn’t want to be with us, why we think they do this, and how Aurora’s competitive upbringing affected her relationships as an adult.

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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 belonging when all you've grown up with is the feeling of being othered, and why it's important to go granular versus big picture when we're tackling the biggest challenges in our lives.

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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 advice

A 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 life from how to feel worthy, why we need to rebrand our relationship to anxiety, and why feeling “the spark” in a relationship is overrated. We dive into why it’s so difficult to leave a relationship, why women have been conditioned into being people pleasers, and why failure is often the impetus we need to change our lives.

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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.

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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 advice

The 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 relationship can ultimately strengthen it, and how she and her husband managed to take a struggling start-up to an internationally renowned skincare brand.

Mathilde shares why believing in yourself and your product, even if no one else does, can lead to great results, and why picking your life partner also determines your life's work.

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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 voicemails on how to mourn the loss of platonic friendships you thought would last forever, and where to start when you're trying to break the cycle of generational trauma.

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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 advice

On this week’s episode, we unpack the ways in which Taryn’s life worked out exactly the way it was supposed to, even when it wasn’t going according to her plans. From her days as an aspiring U.N. diplomat to competing in Miss America, Taryn unpacks all the reasons why it took her eight years of dating before marrying her husband and why she thinks that sometimes, the best advice to take is your own.

For anyone who has ever wondered when their life is going to begin, my conversation with Taryn shows us all that sometimes, the best things in life happen to us while we’re waiting to start living.

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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 impossibility. I answer your voicemails on why you're still feeling heartbroken after a breakup even when the rest of your life is getting better, and what to do when he says he still loves you, but just can't be with you.

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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 advice

Vivian's story shows us all how to stop letting other people write the narrative to your life and why you shouldn't avoid doing things just because they're hard. On this week's episode, we discuss harmful stereotypes and narratives about Asian women, why she left her first career on Wall Street and then her second career at BuzzFeed, and why she thinks everyone should get a prenup before getting married. We talk about that time she moved in with her boyfriend after one month of dating, whether she thinks money can actually make you happier, and why you can tell a lot about a person from the way they treat money.

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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 myself and why we should embrace and claim the bad days that lie ahead in the new year just as much as the good days. You asked, I answered - how do you handle retroactive jealousy when your partner is the most wonderful non-Chad ever, but you can't seem to get over your feelings about his ex?

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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 money

With 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 for everyone. 

What first started out as a hobby has now turned into a full-fledged business for Aleeza, who has focused on pairing marriage-minded individuals since 2007 first in the U.S. She offers her advice on how couples should handle conversations around money, religion, and how to handle awkward questions from family members at the holidays.

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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 zero and what it truly means to be a man when your definition of manhood doesn't fit everyone else's definition.

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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 money

This 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 family member, and finally, Dr. Z answers whether it’s possible to marry and live happily ever after with a narcissist.

For those struggling with depression, Dr. Z offers her practical and actionable advice on what you can do to start to feel good again and why healing has nothing to do with gratitude.

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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 advice

On 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 make me feel good in my twenties and how learning to be alone gave me everything I wanted in life.

You asked in your voicemails and I answered on how to get over heartbreak when you're doing everything right, but still feel devastated, and how to stop blaming yourself for the end of a relationship when it was everyone's fault and no one's fault all at the same time.

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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 money

We discuss everything from whether they believe if men and women can really be just friends, the awkward beginnings of both of their LTRs and how they found success by not taking themselves too seriously. Brandon reveals why he gave his girlfriend an ultimatum two weeks into their relationship, while Harrison shows us all that sometimes, you haven’t found love because you’re not looking in the right place.

We dive into where they believe all the good men have really gone (spoiler: some of them can be found at the UpDating after parties) and how they grew their live show from humble beginnings. For anyone who’s ever felt like they’ve been counted out, Brandon and Harrison want you to know that creating your own lane is always better than trying to compete in someone else’s.

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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-help

Tune 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 the reasons why it's dangerous to commit to a relationship or a marriage before you've committed to what you want in life and how to spot the difference between someone who loves you and someone who loves what you do for them. I answer your voicemails on why a long-distance relationship turned cold once it was no longer long distance, and how to get your power back after getting your heart broken and watching your ex move on before you.

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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 money

In 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 relationships, how she overcame her family history of drug addiction, and why she’s done trying to fit into anyone else’s life but her own.

For anyone who has ever been angry at the cards they were dealt, Kaitlin’s story shows us all that it’s not about what happens to us, but what we do with what happens to us that determines our fate. We muse on whether it’s really possible to find everything you want in a man, why she still wears a promise ring from Francesco, and how she knew she was finally able to move on after his passing.

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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 money

This 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 little less than picture perfect. I dish on what my "honest" Christmas card would say if I had carte blanche to write what I wanted on the back of our card and why sometimes, you're not behind, you're just on a different path. Tune in as I answer voicemails on whether you should choose love or money and just how important sex is in a relationship.

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Kelly Rizzo wants us all to know that it’s okay to laugh at death.

Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money

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, and how she’s managed to start over after having the rug pulled out from underneath her.

For anyone who’s grappling with the loss of a spouse, Kelly wants us all to know that it’s possible to move forward and find love again without negating the love you once had. We discuss whether she would ever go on Special Forces again, her journey from atheism to Christianity and why she believes finding peace is more important than finding closure.

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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.

Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money

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 handle Thanksgiving when you have nothing to be grateful for.

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What’s it like to feel like an outsider your entire life?

Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money

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 our early days in social media and how we got over the cringe of being “that girl who thinks she’s an influencer”, how serving sizes are a uniquely American concept, and how she healed herself by going back to her eastern gastronomic roots. For all the biddies who believe in second chances, tune in to find out why it was not love at first sight for Ava and her husband Ben, and who her favorite ex was.

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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.

Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money

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 rut, and what to do when you're tired of dating, but not tired of hoping to find love. I answer your voicemails about how to stop being fetishized as an Asian-American woman on dates, and how to cope with your ex moving on and getting engaged to someone else.

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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.

Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money

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 opinions for how couples should approach money in relationships. If you’ve ever felt limited by the social constructs of gender, sexuality, and identity, this episode is here to remind you that the only right identity is the one that frees you instead of limits you.

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On this week's solo episode, I discuss why sometimes, losing everything you have is the key to getting everything you want.

Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money

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 what a man's intentions are on a date, when you should or shouldn't meet his parents, and how to move on from a man who fell out of love with you.

Leave me a voicemail at https://www.speakpipe.com/brutallyannapodcast for me to answer on upcoming episodes.

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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.

Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money

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, Serena reminds us all that no one knows what they’re doing, but that the ones who are successful are the ones who dare to try.

My conversation with Serena sheds light on how the scarcity mentality implemented by the patriarchy forces women to settle and why you should never be confused in relationships. For anyone who has ever felt like they’ve taken the wrong turn in life, this week’s episode shows us all that sometimes, the wrong turn can lead you to the right destination in the end.

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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.

Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money

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 choosing between two men and why we should all look for the squatty potty of a man versus the cheeseboard of a man.

You can now leave me voicemails to answer on future episodes here: https://www.speakpipe.com/brutallyannapodcast

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Vanderpump Rules star and entrepreneur Katie Maloney shows us why the path not taken is often the path we’re meant to take.

Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money

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 anyone’s drama, even if it means being alone.

For anyone who has felt like their life has, metaphorically, ended, Katie’s story of overcoming a traumatic brain injury and her divorce shows us that there’s no limit, in her words, to the amount of software updates you can have in life. 

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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.

Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money

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 thinks cheaters should marry. We unpack her PCOS diagnosis and her fertility journey and how Lindsey navigates her career and her newfound motherhood.

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We’re kicking things off with Violet Benson, host of the podcast Almost Adulting and the brain behind the viral Instagram account @daddyissues_.

Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money

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 broke her heart, and the active practice of letting go of who you were so you can become who you’re meant to be.

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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.

Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money

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 for the premiere of Brutally Anna on October 28th with new episodes 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.

Follow Anna: 

https://www.instagram.com/maybeboth/

https://www.tiktok.com/@maybeboth

https://www.youtube.com/@maybeboth

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