Dare to Overshare
Dare to Overshare
Podcast Description
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.
Podcast Insights
Content Themes
The podcast explores themes of vulnerability, mental health, and personal connection, featuring episodes that delve into topics like loneliness, emotional growth, and the struggles of modern relationships. For example, the episode with Calvin Cobb covers fears surrounding panic attacks and the search for authentic connections, creating a welcoming space for guests to express their true selves.
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.
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.
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
Lew’s socials:
https://www.instagram.com/lewintherain
https://www.tiktok.com/@lewintherain
Disclaimer
This podcast’s information is provided for general reference and was obtained from publicly accessible sources. The Podcast Collaborative neither produces nor verifies the content, accuracy, or suitability of this podcast. Views and opinions belong solely to the podcast creators and guests.
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