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Dare to Overshare

Dare to Overshare

Written by: Jackie Hollywood
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About this listen

Dare to Overshare is your new favorite safe space where vulnerability meets vibe. Each week, Jackie invites artists, creators, dreamers, and doers to her cozy studio for the kind of deep, unfiltered conversations you wish more people were having. It’s not about interviews—it’s about connection. Every conversation is raw, real, and refreshingly human. From laugh-out-loud moments to jaw-dropping confessions, our guests go there—sharing personal stories, bold opinions, and the kinds of truths you usually only tell your best friend after a glass of wine.Copyright 2026 Jackie Hollywood Economics Leadership Management & Leadership Relationships Self-Help Social Sciences Success
Episodes
  • EMoney: "I Don't Cry When My Friends Die": Repressed Feelings, Reality TV Lies & Growing Up Weird
    Jan 21 2026

    This week, artist EMoney is in the building and we get very real, very fast.

    EMoney was on Season 6 of MTV's Are You The One so he knows what goes on behind the cameras. We’re unpacking the absolute chaos of reality TV — from the psychological high of morally questionable people to the behind-the-scenes manipulation that happens with executive producers and cast members. Is it entertainment... or emotional warfare?

    We also dive into the heavier stuff: why some of us can cry during movies but not in real life situations like death, the quiet day-to-day sadness we avoid with dopamine scrolls, and living with Trichotillomania since childhood. Plus: the Taylor Swift discourse that might get some of y’all mad (you’ve been warned), cancel culture fatigue, and why Gen Z is basically shutting the bar scene down. It’s unfiltered, a little unhinged, and full of the kind of honesty you’re not supposed to say out loud.

    Follow us! Jackie's socials:

    https://www.instagram.com/jackiehollywood

    https://www.instagram.com/daretoovershare

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

    https://www.youtube.com/daretoovershare

    Emoney's socials:

    https://www.instagram.com/emoneydoesit

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

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

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    49 mins
  • Margarita Monet: "You Don't Need Trauma To Be Interesting": From Band Breakups to Self Love
    Jan 7 2026

    Margarita Monet, lead singer of Edge of Paradise, joins me to talk about the pressure to have “trauma” to make good art, the truth about being in a rock band, and why healing doesn't have to be performative. From band breakups and anxiety to cultural expectations around aging, marriage, and motherhood—we cover it all.

    In this episode, we get into what it really means to be honest, how to let go of people without losing yourself, and how Margarita built confidence without conforming to the “tortured artist” stereotype. She shares how being a frontwoman in a rock band shaped her, the guilt of not having a traumatic past, and why she’s unlearning people-pleasing for good.

    If you’ve ever felt like you needed to struggle to be taken seriously—or felt pressure to stay in relationships (creative or personal) that no longer align—this one’s for you.

    Follow us!

    Jackie's socials:

    https://www.instagram.com/jackiehollywood

    https://www.instagram.com/daretoovershare

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

    https://www.youtube.com/daretoovershare

    Margarita's socials:

    https://www.instagram.com/margarita.monet

    https://www.instagram.com/edgeofparadise

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

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    53 mins
  • Tara Katchur: "I Was Ghosted By My Bridesmaids" - Wedding Drama, Addiction, and Colonoscopies
    Dec 10 2025

    In this episode, Reality TV Casting Producer Tara Katchur gets honest in a way she never has before. She talks about the childhood friends who ghosted her on her wedding day, what it felt like to keep showing up for people who didn’t show up for her, and the moment she finally learned to listen when someone shows you who they are.

    Tara also opens up about growing up with a dual-diagnosed mom and the years she spent being the “parent” in her family. She shares the ultimatum that changed everything and the exhaustion of always keeping it together.

    She even tells the story of the colonoscopy she had at 24—how gaining twenty pounds led her to a doctor’s office, and how finding polyps early ended up saving her life.

    We wrap with a conversation about beauty pressures coming from shows like Love Island, and what she’s learned about putting herself out there online. As Tara says, it costs nothing to support someone’s work… even though the internet can be a strange place.

    Follow us!

    Jackie's socials:

    https://www.instagram.com/jackiehollywood

    https://www.instagram.com/daretoovershare

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

    https://www.youtube.com/daretoovershare

    Tara socials:

    https://www.instagram.com/tarakatchur

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

    Show More Show Less
    49 mins
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