Brutally Anna

Brutally Anna

By Anna KaiSociety & Culture
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Brutally Anna episodes

  • 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 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.


    Follow Anna: 

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

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

    Follow Aleeza: @aleezabenshalom

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    59 min
  • Solo Episode: 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 zero and what it truly means to be a man when your definition of manhood doesn't fit everyone else's definition.


    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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    47 min
  • 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 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.


    Follow Anna: 

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

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

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

    Follow Dr. Z @dr.z_psychologist

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    1 hr 2 min
  • 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

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

    1 hr
  • 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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    1 hr 25 min
  • 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

    52 min
  • 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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    1 hr 15 min
  • 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

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

    1 hr 4 min
  • 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

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

    1 hr 17 min
  • 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

    48 min

About Brutally Anna

From the publisher's feed

Welcome to Brutally Anna — the podcast where we stop pretending we’re fine and start telling the f*cking truth.

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