Dare to Overshare

About Dare to Overshare

The conversations we avoid are the ones we need to have the most. Dare to Overshare is a safe space for the refreshingly human conversations we usually keep to ourselves. In each episode, Jackie sits down with artists, creators, entrepreneurs, and everyone in between to talk about the things most people are afraid to say out loud. We dive deep into topics like identity, healing, relationships, mental health, fame, failure, faith, self-worth, and more. It’s not about perfect interviews or polished answers. It’s about connection, honesty, and the kind of oversharing that makes you feel less alone. Because oversharing isn’t a problem, it’s a love language.

Publisher

Jackie Hollywood

Category

education · health & fitness · society & culture

Language

en

Explicit

Yes

First episode

25 Jun 2025

Latest episode

23 Sept 2026

Latest episodes

28 episodes in the feed.

1. 

   23 Sept 2026

   Why Smart Women Stay in Toxic Relationships | Relationship Coach Sabrina Bendory

   Why do smart, self-aware women stay in toxic relationships even when they know they deserve better? In this episode of Dare to Overshare, bestselling author and relationship coach Sabrina Bendory joins Jackie to break down the psychology behind toxic love, love bombing, narcissism, attachment styles, dating anxiety, self-worth, and why unhealthy relationships can feel so addictive. Sabrina opens up about losing herself in a relationship, trying harder to be chosen after being treated badly, and what finally helped her break the cycle. We also talk about how to tell the difference between butterflies and anxiety, why a healthy relationship can sometimes feel “boring,” whether “if he wanted to, he would” is actually true, and how dating apps may be changing the way we connect. We get into: • Love bombing vs. genuine interest • Narcissistic traits and early red flags • Why chaos can feel like chemistry • Anxious and avoidant attachment • Why emotionally unavailable people can feel so attractive • How to know if someone is boring—or if healthy love just feels unfamiliar • Dating apps, rejection, and the “buffet effect” • Why boundaries matter in healthy relationships • Why we keep trying to be chosen • What healthy love actually feels like • How to stop losing yourself in relationships Sabrina is the author of The Feminine Code and Detached and the host of the You Will Be OK podcast. If you’ve ever stayed too long, ignored a red flag, confused anxiety with chemistry, or wondered why you keep choosing the same type of person, this conversation is for you. Subscribe to Dare to Overshare for more honest conversations about relationships, dating, self-worth, healing, mindset, and the things we probably should be talking about more.

2. 

   9 Sept 2026

   Neville Goddard Manifestation Cheat Codes

   If you’ve heard of Neville Goddard but have no idea where to start, this episode is for you.I’m breaking down 8 of his most popular manifestation techniques — including Living in the End, SATS, Revision, I Remember When, Mental Diets, the Lullaby Method, and more — and explaining how to actually use them in real life.A lot of these techniques sound similar because they all fall under one main idea: stop experiencing what you want as something you’re still waiting for and start mentally experiencing it as already done.Think of them as different doors into the same room.Manifestation has completely shaped the way I think about belief, possibility and the stories I tell myself, and Neville Goddard’s work has been a huge part of that.In this episode:• Living in the End• SATS — State Akin to Sleep• Revision• I Remember When• Mental Diets• The Lullaby Method / Isn’t It Wonderful?• The Congratulations Technique• The Telephone TechniqueWhether you’re new to manifestation or you’ve been practicing for years, pick one technique that resonates with you, actually try it, and see what happens.Subscribe for more conversations about manifestation, mindset, human connection and becoming the version of yourself you actually want to be. Jackie’s socials: https://www.instagram.com/jackiehollywoodhttps://www.instagram.com/daretooversharehttps://www.tiktok.com/@itsjackiehollywoodhttps://www.youtube.com/daretoovershare

3. 

   24 Aug 2026

   Autism, Masking & What Reality TV Never Showed | Kyland Young

   You may know Kyland from Big Brother, The Challenge, and The Amazing Race, but in this episode, we get into the person behind the competitor. Kyland opens up about being diagnosed with autism as an adult, living with ADHD, masking in social situations, and looking back at some of his biggest reality TV moments with a completely different understanding of how his brain works. We also get into communication, accountability, toxic positivity, recovering from a serious injury, and of course… we talk competition. In this episode: • Being diagnosed with autism as an adult • Autism, ADHD & masking • What reality TV revealed about Kyland • Feeling “different” before having the language for it • Being misunderstood as fake or inauthentic • Neurodivergence in dating & relationships • Communication, conflict & accountability • Why intention doesn’t erase impact • The pressure to stay positive through hard times • His recovery from a serious back injury • What he would tell his younger self • Big Brother, The Challenge & The Amazing Race • Why Kyland believes he can win The Challenge If you’ve ever felt misunderstood, had to consciously think your way through social situations, or wondered what’s really happening behind the person you see on reality TV, this conversation is for you. Subscribe for more honest conversations, unexpected stories, and permission to overshare.

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

44,756

Score snapshot 15 Sept 2025

Apple Podcasts (US)

5.0 / 5

2 ratings

Podcast Authority Score: 74 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

85

Social presence

97

YouTube

76

Engagement

32

Contact Dare to Overshare

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.