Dare to Overshare cover art

Dare to Overshare

Dare to Overshare

By: Jackie Hollywood
Listen for free

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 2025 Jackie Hollywood Economics Leadership Management & Leadership Personal Development Personal Success Relationships Social Sciences
Episodes
  • Amanda Butler: "I Have 93 Italian Husbands” - Navigating Life After Breast Cancer
    Sep 3 2025

    Amanda Butler joins me for one of the most raw, vulnerable, and empowering conversations we’ve had yet. Diagnosed with stage 2 breast cancer in her early 30s, Amanda walks us through what it really looks like to navigate womanhood, dating, and identity when your body and life are completely redefined — seemingly overnight.

    We get into:

    – Life post-cancer and what doctors don’t prepare you for

    – Dating while in medical menopause

    – Brain fog, no libido, and the silent mental toll it takes

    – Comparing dating in the US vs Internationally

    – What cancer clarified about love, friendship, and her future

    – The unexpected wisdom we gain from our parents

    and so much more!

    This is for anyone who's ever felt like their body betrayed them, or like they’re grieving the life they thought they’d have. You are not alone.

    Wanna overshare? Apply to be a guest on the show!

    https://www.daretoovershare.com

    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


    Amanda socials:

    https://www.instagram.com/hiamandabutler

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

    https://www.instagram.com/cancerbaddies

    Show More Show Less
    39 mins
  • Kaitlyn Herman: "Reality TV Is Darker & Crazier Than You Think" - The Truth Behind The Cameras
    Aug 27 2025

    I sat down with Kaitlyn Herman — former Big Brother contestant turned Life Coach — and we're talking reality TV trauma to cancel culture. We chat about what people don’t see when they're watching reality shows, and how the version of someone you meet on screen is not always the same as the energy you’d get in real life. Kaitlyn shares what it’s really like being judged by millions and how that experience shaped who she is and what she does for a livng today. We also get into the chaos of separating the art from the artist and why sometimes it's okay to be a hypocrite. This episode is part tea, part therapy — and we hope you’ll leave with a new level of compassion for the people you see on TV.

    Wanna overshare? Apply to be a guest on the show!

    https://www.daretoovershare.com

    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


    Kaitlyn's socials:

    https://www.instagram.com/kaitlyn_herman

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

    Show More Show Less
    48 mins
  • Flo Tapia: "I Used To Bed Rot For Weeks" - Rewiring Your Brain and Finding Your Purpose
    Aug 20 2025

    In this episode, I’m joined by content creator Flo Tapia for a deep, unfiltered convo about the highs and the lows of being your own worst enemy. We get into struggling with laziness, toxic relationships with weed, bed rotting, and the constant challenge of building structure when you work for yourself. We discuss rewiring your brain and the power of shifting your mindset in real-time using the 5 second rule. From psychedelics and spiritual awakenings to the dark side of concerts, this episode is full of moments that’ll make you feel seen.

    Wanna overshare? Apply to be a guest on the show!

    https://www.daretoovershare.com

    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


    Flo's socials:

    https://www.instagram.com/highitsflo

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

    Show More Show Less
    49 mins
No reviews yet
In the spirit of reconciliation, Audible acknowledges the Traditional Custodians of country throughout Australia and their connections to land, sea and community. We pay our respect to their elders past and present and extend that respect to all Aboriginal and Torres Strait Islander peoples today.