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

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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

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

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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_

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

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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

In this episode, I sit down with Zamaria Thompson, who is a health and wellness coach and creator and we get into the real tea on gut health — how mindfulness while eating matters and doing less is often more helpful than doing more. We also dive into the mindset side of wellness: how the universe is never on a budget (so yes, you can ask for more when manifesting) and why even the most positive, uplifting people still need to fully feel the “hard” emotions. Plus, a little detour into relationship talk — the art of soft vs. hard launching your partner.

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

https://www.daretoovershare.com

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Jackie's socials:

https://www.instagram.com/jackiehollywood

https://www.instagram.com/daretoovershare

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

https://www.youtube.com/daretoovershare

Zamaria's socials:

https://www.instagram.com/happyfitzam

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

In this episode of Dare to Overshare, I sit down with the multifaceted Kimmy Tan — YouTuber, musician, tattoo artist, and all-around creative force. We dive deep into her journey of evolving beyond cannabis content and embracing her full, authentic self online. Kimmy opens up about what it really means to break out of toxic relationships and how your brain isn't fully developed before 25. We also discuss the fear of our significant others passing away amongst other fears we have. This episode is raw, real, and full of wisdom and laughs.

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

https://www.daretoovershare.com

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Jackie's socials:

https://www.instagram.com/jackiehollywood

https://www.instagram.com/daretoovershare

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

https://www.youtube.com/daretoovershare

Kimmy's socials:

https://www.instagram.com/kimmytanofficial

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

https://www.youtube.com/@kimmytan420

https://www.youtube.com/@kimmytan2.0

In this episode of Dare to Overshare, Jackie Hollywood sits down with astrologer Chad the Maverick to explore how astrology can be a grounding tool in everyday life—without letting it dictate every decision. Chad shares his experience navigating the world as a Black male astrologer in a field often dominated by white women, and how his presence is helping shift the culture of modern spirituality.

They talk about using astrology as a way to deepen self-awareness rather than control relationships or obsess over cosmic timing. Chad opens up about why he doesn’t read his partner’s birth chart unless asked, and why we shouldn't let things like Mercury in retrograde run our lives. This episode is all about reclaiming your intuition, tuning out the noise, and aligning with your passions.

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

https://www.daretoovershare.com

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Jackie's socials:

https://www.instagram.com/jackiehollywood

https://www.instagram.com/daretoovershare

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

Chad's socials:

https://www.instagram.com/chadthemaverick

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

In this thought-provoking episode, Jackie is joined by V The Plug for a raw, reflective, and hilarious deep-dive into modern dating, gender roles, and the hustle behind OnlyFans / Sugar Baby culture. Vanessa opens up about signing up on a sugar baby site, seriously considering selling feet pics, and the internal moral tug-of-war that followed. This is a deep conversation about self-worth, boundaries, and what truly aligns with one's values.

In this raw and inspiring episode, CEO / Founder of Exist, Alicia Waldner, shares how she turned bold choices into big business. From launching her tech startup with half a million dollars earned on OnlyFans to navigating the tech world as an unapologetically 'sexy' female founder, Alicia holds nothing back.

We dive deep into her personal journey—what drove her to take risks, how she handled judgment, and what it really takes to build an empire on your own terms. Alicia also opens up about surviving a toxic relationship that nearly derailed her path, and how she found the strength to leave, heal, and rebuild stronger than ever.

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

https://www.daretoovershare.com

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Jackie's socials:

https://www.instagram.com/jackiehollywood

https://www.instagram.com/daretoovershare

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

Alicia Waldner's socials:

https://www.instagram.com/aliciawaldner

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

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

https://www.instagram.com/theexistapp