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

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.

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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

Margarita's socials:

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

https://www.instagram.com/edgeofparadise

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

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.

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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

Tara socials:

https://www.instagram.com/tarakatchur

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

In this episode, one of my favorite artists, Lew, sits down with me to chat about the messy truths of dating and the real struggle behind the artistry. This conversation is raw, reflective, and painfully relatable—especially if you've ever ignored red flags just to feel loved.

We overshare about:

Taking back a cheating ex and gender double standards

Trusting your gut and spotting red flags early

The pressure to define “exclusive” in today’s dating world

How heartbreak can harden you—and how to soften again

Moving to LA with no job, no money, and no backup plan

The emotional rollercoaster of working in entertainment

Drake being the GOAT of storytelling

Lew’s story is a reminder that rock bottom builds character—but courage is what makes you stay.

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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

Lew's socials:

https://www.instagram.com/lewintherain

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

In this episode, we dive into what it feels like to wear all the hats: being a mom, a creator, and a woman rediscovering herself while holding it down for everyone else. From breaking generational cycles and snapping out of people-pleasing, to navigating identity beyond motherhood and embracing the alter ego we all lean on sometimes.

We talk:

Early midlife crises and the “stuck” feeling no one warns you about

The mask we wear vs. the healing we need

How becoming a mom fast-tracks your evolution

Breaking generational traumas and raising emotionally aware kids

The mental load women carry and why self-care isn’t selfish

The reality of “snapback” culture, identity loss, and reclaiming your body

Calling out toxic masculinity and why men need safe spaces too

This one’s for the mom who feels like she’s losing herself, the creative stuck in a loop, the woman learning to say no, and the human just trying to make sense of it all.Tyler said it best: "I'm a mom and still a baddie."

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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

Tyler's socials:

https://www.instagram.com/tylertherapy

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

Artist and Director Phenix Red joins me for a raw, unfiltered convo about what it means to be a woman in a world that’s constantly telling you to be better, prettier, thinner, calmer. We talk body dysmorphia, emotional sensitivity, and the very real struggle of trying to “heal” while still being pissed off at the systems that broke us.

We get into everything from WebMD spirals to chasing beauty trends to looking for meaning in a culture obsessed with productivity and perfection. Phenix opens up about growing up with a father who didn’t like women, why she’s been hesitant to speak on feminism, and the fine line between fighting for equality and just... hating men.

We also touch on imposter syndrome (she doesn’t believe in it), human design, and why playing like a child might actually be the secret to success.

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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

Phenix's socials:

https://www.instagram.com/phenixredmusic

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

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

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_