Brutally Anna

Anna Kai

  • 1 hour 1 minute
    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 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.


    Leave me a voicemail: speakpipe.com/brutallyannapodcast


    Follow Anna: 

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

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

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

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    19 December 2024, 10:00 am
  • 1 hour 26 minutes
    Why you should go for the nerd 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 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.


    Follow Anna: 

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

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

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

    Follow Brandon & Harrison: @updatingshow @bermmy16 @htforman

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    16 December 2024, 10:00 am
  • 54 minutes
    Solo Episode: You can be married to a cheater, but don't date a cheater and why some long distance relationships fail

    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.


    Leave me a voicemail: speakpipe.com/brutallyannapodcast


    Follow Anna: 

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

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

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

    Learn more about your ad choices. Visit podcastchoices.com/adchoices

    12 December 2024, 10:00 am
  • 1 hour 16 minutes
    What cancer 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 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.


    Follow Anna: 

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

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

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

    Follow Kaitlin @kaitlin_reagan

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    9 December 2024, 10:00 am
  • 1 hour 5 minutes
    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 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.

    Leave me a voicemail: speakpipe.com/brutallyannapodcast

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    5 December 2024, 10:00 am
  • 1 hour 18 minutes
    How to laugh at death with Kelly Rizzo

    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.


    Follow Anna: 

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

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

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

    Follow Kelly @kellyrizzo

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    2 December 2024, 10:00 am
  • 47 minutes 5 seconds
    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.


    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.


    Leave me a voice at speakpipe.com/brutallyannapodcast


    Follow Anna: 

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

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

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

    Learn more about your ad choices. Visit podcastchoices.com/adchoices

    28 November 2024, 10:00 am
  • 1 hour 6 minutes
    The power of not belonging with Ava Lee

    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.


    Follow Anna: 

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

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

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

    Follow Ava @glowwithava @byava

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    25 November 2024, 10:00 am
  • 49 minutes 26 seconds
    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.


    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.


    Leave me a voicemail: speakpipe.com/brutallyannapodcast


    Follow Anna: 

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

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

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

    Learn more about your ad choices. Visit podcastchoices.com/adchoices

    21 November 2024, 10:00 am
  • 1 hour 25 minutes
    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.


    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.


    Follow Anna: 

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

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

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

    Follow Cyrus @cyrusveyssi

    Learn more about your ad choices. Visit podcastchoices.com/adchoices

    18 November 2024, 10:00 am
  • 52 minutes 35 seconds
    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.


    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.


    Follow Anna: 

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

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

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

    Learn more about your ad choices. Visit podcastchoices.com/adchoices

    14 November 2024, 10:00 am
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