Confidently Insecure

Latest Episodes:

The end of Confidently Insecure... Dec 29, 2025

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for now.

It's such a weird feeling to type this out because the confidantes have been a part of my life every week for the last 6 (!!!!!!!!) years!!! For now, Confidently Insecure is going on hiatus...the truth is that podcasting is REALLY hard as an independent podcaster. Most of the market is traditional celebs and huge companies producing amazing work and series and it's hard to keep up! The great podcast wave of 2021/2022 made it feel like EVERYONE you knew had a podcast and I am lucky to say that out of the 4.5 MILLION podcasts, I have been lucky enough to be in the .5% of the top listened to podcasts in the world. Crazy. I'll never forget seeing our pod on the top charts all the way back in 2019 when I first launched con pod. We've had the most INCREDIBLE guests including scientists, sex workers, activists, comedians, and friends. I've felt SO LUCKY to be the one holding that space for your ears every week and feel genuinely connected to each of you, confidantes. I read all the comments...I read all the messages...I feel so so so lucky to have had you all as an audience for the last 6 years. I am so grateful. I am so lucky. I feel so loved.

Stay tuned on this channel for more videos that aren't podcasts soon....and if you're not already following on IG & TT get more content there!!!!

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Help, My Feminism Is Falling Apart at the Thigh Gap 👩 Dec 01, 2025

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HAPPY WINTER YALL!! this episode has it all...including a brutally honest and absolutely unserious exploration of being a “bad feminist” in 2025. I confess all the little things I like — romantic tropes, protective behavior, fictional toxic men, and feminine indulgences — that technically shouldn’t align with feminist ideals but totally do because I contain multitude mmkay?!??!! Listener confessions join the party, and we talk about the real difference between desire and dependency, and why personal wants don’t cancel political beliefs. This one’s all about self-acceptance, laughing at ourselves, and remembering feminism has room for complexity (and a little trash taste).

✨ Chapter Timestamps

00:00 — Introduction + holiday updates + doc premiere panic

15:55 — Confessions of a “Bad Feminist” (the jar-opening discourse)

20:50 — The Allure of Fictional Men (Pedro Pascal, Joe Goldberg, help)

25:41 — The Pillow Princess Revelation (don’t @ me)

32:25 — Guilty Pleasures & Feminine Indulgences (yes, the Stanley Cup makes me feel safe)

37:07 — Listener Confessions: Feminism vs. Personal Desire (we’re all the same)

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How to Survive Your Conservative Family This Thanksgiving🔪 Nov 24, 2025

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Going home for Thanksgiving and already bracing for the political landmines your family is absolutely going to drop? Same.

This week’s episode is your official survival guide to dealing with conservative relatives, culture-war ambushes, and that one uncle who thinks Facebook memes count as primary sources.

I walk you through exactly what to say when someone at the table hits you with:

“Your generation ruined the family.”
“These elections are going to be rigged.”
“Drag queens shouldn’t be around kids.”

AND MORE!!!!!!

🎥 ALSO MY DOCUMENTARY IS ALMOST HERE

Be the first to see THE LIMITS OF FORGIVENESS, my new feature documentary about restorative justice and survivors rewriting what justice looks like.

Tickets are available NOW:

👉 www.moment.co/forgiveness

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Remember when we made a DOCUMENTARY?! THE ORGIN STORY Nov 17, 2025

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Thats right! YOU CONFIDANTS get to hear it here first - the early bird tickets are now on sale at moment.co/forgiveness for the next 7 days get your tickets to stream our documentary for only $10! sign up for our live premiere and join us for the q&a after! heres the episode that started it all....

www.moment.co/forgiveness

$10 streaming 12/17/2025

Live Q&A to follow ($10 add on!)

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🧠 mental health CHECK IN Nov 10, 2025

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THIS WEEK is an INTENSE QUICKIE...just the way we like it ;) hehehe we talk about migraines, addiction, and moving! Don't forget to mark your calendars for DEC17th! for the premiere of The Limits Of Forgiveness on moment.co !

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Calling out SH*TTY MEN ⚰️ Nov 03, 2025

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How do you hold people accountable without being labeled “toxic”? What if the person you need to call out… is your ex, your boss, or that one guy who still doesn’t know what emotional labor is?

In today’s episode, we’re diving into the deliciously complicated world of call out culture—and specifically how to do it with humor, honesty, and just the right amount of “how can we make men look dumb as f*ck.

SAVE THE DATE: DECEMBER 17 2025!!!!!!!!! IF YOU KNOW, YOU LISTENED TO THE EPISODE!!!!!!!!!!

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🎀Millennials vs Gen Z: 🎀The Great Generational Feud Oct 27, 2025

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The war over skinny jeans, side parts, and the 😂 emoji rages on — but what’s really behind the Millennial vs. Gen Z feud?

In this episode we break down the cultural clash between two generations raised on Wi-Fi, caffeine, and emotional damage. From the evolution of humor to the rise of ironic detachment, we hilariously dissects why Gen Z thinks Millennials are “cringe,” why Millennials can’t stop oversharing, and how social media keeps us pitted against each other.

But beneath the memes and middle parts lies a deeper truth: both generations are just trying to survive late-stage capitalism, mental health crises, and the algorithm — in their own weird ways.

🧠 Chapters:

00:00 – Intro: The Generational Feud Nobody Asked For

02:02 – Millennials: The Analog-to-Digital Transition

05:07 – Gen Z: Digital Natives & Social Awareness

07:38 – Cultural Cringe: The Divide Gets Petty

10:17 – Social Media: The Algorithm Loves Drama

13:16 – The Evolution of Humor Online

15:51 – Finding Common Ground & Collaboration

18:28 – Why We Actually Need Each Other

20:55 – Conclusion: Embrace the Cringe

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She Killed, Conquered, and Claimed the Throne #HtH WU ZETIAN Oct 20, 2025

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In this episode of Hoes Throughout History, we dive deep into the unhinged, unstoppable, and undeniably iconic life of Empress Wu Zetian — the first and only female emperor of China. From concubine to supreme ruler of the Tang dynasty, Wu played the political game like a damn chess master while rewriting what it meant to be a woman in power...and the brutal rumors spread by salty men who couldn’t handle her crown. Was she ruthless? Sure. Revolutionary? Absolutely.

🎧 Chapters:

00:00 — Introduction to Empress Wu Zetian

03:08 — The Rise of Wu Zhao: From Concubine to Empress

11:55 — Wu Zetian’s Reign: Power, Politics, and Reform

15:59 — The Fall of Wu Zetian: Abdication and Legacy

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my EX is still in the GROUPCHAT 👻 Oct 13, 2025

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Breakups used to end when you gave back the hoodie and blocked their AIM screen name. But now? Your ex is still in your group chat, haunting your Spotify playlists, and popping up in your “On This Day” memories like a digital poltergeist. 💀

In this episode of Confidently Insecure, I’m unpacking the new hellscape of digital breakups — from the psychology of why we hold onto those tiny online connections, to the emotional chaos of navigating shared group chats, and the art of a full-on digital exorcism (delete, block, cleanse, repeat).

We’ll talk about what it actually takes to move on in the age of social media, how to reclaim your digital space, and why closure isn’t something they give you — it’s something you create.

If you’ve ever said “I’m totally over them” while still checking their Venmo feed... this one’s for you

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burnout to 💫 PSYCHEDELICS 💫 w/ BOBBY LENNOX Oct 06, 2025

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What happens when you go from corporate burnout to facilitating psychedelic healing in a church? Bobby Lennox, founder of Jaguar House Ministries, joins me to talk about his wild transformation — from miserable suit-and-tie life to deep spiritual work through Bufo (aka the mystical toad medicine 🐸).

We get real about:

💫 The power of psychedelics for mental health and trauma healing

🌀 What actually happens during a Bufo ceremony

💬 The crucial role of integration (because tripping is the easy part)

🏛️ How Bobby legally created a psychedelic church to help others heal

🌿 And why community + compassion matter more than “perfect enlightenment”

This one’s part therapy session, part cosmic sermon, and fully life-changing. Whether you’ve done plant medicine before or are just curious what all the “toad talk” is about — this episode will open your mind and maybe even your heart.

🧘‍♀️ Listen wherever you get your podcasts

📱 Follow Bobby & Jaguar House Ministries:

https://jaguarhouse.org/

https://www.instagram.com/_bobbylennox_/

https://www.instagram.com/jaguarhousechurch/

💌 Connect with me on IG/TikTok: @kelseydarragh

If you love deep convos about healing, spirituality, and what it means to actually grow — subscribe and join the Confidant fam 💖

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