Take a Jill Pill – Details, episodes &amp; analysis

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Your First Jill Pill: Rants, Randomness, and Real Talk

Season 1 · Episode 1

Tuesday, February 10, 2026 • Duration 33:18

Welcome to Take a Jill Pill, the podcast where life is funny, messy, and sometimes a little embarrassing.

In this first episode, I introduce myself (an introvert’s nightmare), share an embarrassing story, rant about birthday cards and cashiers, answer a few listener questions, and even dip my toe into conspiracy theories…plus of course I have a discussion about Trader Joe’s snacks. (Oh, I leave ya with a little encouragement too.)

This episode is your first dose of the chaos, honesty, and relatable ranting you can expect every week. Consider it your very first Jill Pill!

*Here's the song I told you to listen to today: "Glitter" by Patrick Droney

Host: Jill Pickering

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TikTok

TakeAJillPill.com

YouTube

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Trailer: Introducing "Take a Jill Pill"

Season 1

Wednesday, January 28, 2026 • Duration 02:39

Welcome to Take a Jill Pill, a podcast for when life is lifing and you just need something that feels real, funny, and relatable. In this trailer, I’m sharing a little about me and what this show will actually sound like: honest conversations, random rants and observations, creativity, mental health, pop culture, cults, conspiracies…and whatever else comes up in the wild experience of being a human. I hope this can be your weekly dose of real talk, a few laughs, and something that makes your day feel a little lighter. New episodes coming soon. Trader Joe’s snacks highly encouraged!

Instagram: @jipimusic

TikTok: @jipimusic

Facebook: @jipicreative

YouTube: @jipicreative

www.jipicreative.com

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So…What Happened with Jill and Kate? with Kate Rapier

Season 1 · Episode 20

Tuesday, August 18, 2026 • Duration 01:35:13

Kate Rapier is finally on Take a Jill Pill, and we’re answering the question a lot of you have been asking: What happened with Jill and Kate?

After more than 20 years of friendship, music, touring, songwriting, podcasting, and basically growing up together, a lot has changed. In this episode, Kate and I look back at how we met, the beginning of Jill and Kate, our years in the music industry, some of our favorite (and funniest) memories, and why we ultimately decided to end Jill and Kate.

And yes, we talk about the harder stuff too. The friendship breakup. The five months we didn’t speak. Why I wasn’t at Kate’s wedding. And how two people who had been more like sisters than friends found their way back to each other and rebuilt a friendship that looks different, and healthier, today.

We also get into Kate’s life now, divorce, motherhood, life after music, old Jill and Kate songs, touring stories, conspiracy theories, Trader Joe’s snacks, unfortunate facial injuries, and plenty of things neither of us planned to talk about.

If you followed Jill and Kate, listened to Girls Just Pod to Have Fun, knew us from our years touring and singing with Kelly Clarkson, or have simply wondered what happened between us, this one is for you. Pull up a chair and a glass of wine, put on some comfy clothes…we have a lot to catch up on.

Host: Jill Pickering

Guest: Kate Rapier

https://www.instagram.com/katerapier

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Nobody Tells You This (But They Probably Should)

Season 1 · Episode 22

Tuesday, August 4, 2026 • Duration 31:21

I found myself thinking this week, I really wish someone had told me that.

Actually...I wish someone had told me a lot of things.

Things like the fact that almost everyone is making it up as they go. That your intuition deserves way more credit than you give it. That not every battle is worth fighting. And that some of the biggest disappointments in your life eventually become stories you tell without even thinking twice.

So this week, I'm sharing 5 things nobody really tells you, but maybe they should.

Plus, we end up talking about awkward Zoom goodbyes, Bryan Kohberger, New England accents, grammar, music, and a few listener questions along the way.

I hope one of these lessons meets you where you are today. And if nothing else, I hope you leave this episode feeling a little less alone in figuring life out.

Because remember…we're all kind of making it up as we go.

Thanks for listening to Take a Jill Pill!

Host: Jill Pickering

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Public Scandals & Revenge of the Ants

Season 1 · Episode 13

Tuesday, May 12, 2026 • Duration 44:54

This week on Take a Jill Pill, I survive a fire ant attack in Nashville, witness a chaotic e-bike accident at a preschool soccer practice, and officially declare that the ants are seeking revenge after I mocked them online. My feet may never recover.

We also get into my growing fear of cruise ships, why flying suddenly feels more stressful than it used to, and the emotional devastation of Southwest changing literally everything.

Then we get into something a little deeper: public scandals, viral humiliation, and why the internet loves watching people fail. After listening to Oprah’s interview with Kristin Cabot from the infamous Coldplay kiss cam moment, I started thinking a lot about empathy, internet culture, and how easy it is to forget there’s a real human behind the meme.

Plus:

My Top 5 obscure holidays
Listener questions
What’s currently sitting on my kitchen table
The importance of celebrating small things

As always, it’s chaotic, reflective, unhinged, and hopefully a little comforting too. Glad you’re here!

Host: Jill Pickering

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Dear Jill…Your Questions, My Advice

Season 1 · Episode 12

Tuesday, May 5, 2026 • Duration 54:04

Welcome to my first ever Dear Jill episode. You sent in your questions (anonymously, don’t worry), and I’m giving you my honest, off-the-cuff advice. Am I qualified? Absolutely not. But I do have thoughts…a lot of them.

Before we get into that, I’m catching you up on a weekend in the New Hampshire mountains (where things get a little strange), a billboard that raised some serious questions about cremation pricing, and my strong opinions on “plogging” (why are we doing three activities at once??). Also, Effingham, NH. I mean, come on. My favorite town name.

Then we get into your questions. Everything from dealing with a family member no one likes, to friendship heartbreak, to being a chronic people-pleaser, to social awkwardness, to how to tell your girlfriend she’s not a great cook (gently). I’m answering it all in real time. No overthinking, just my best shot at being helpful.

For today’s Top Five, I’m sharing the top 5 pieces of advice I’ve ever received, then I answer a couple of listener questions, and wrap things up with this week’s Jill Pill, a reminder to stop riding everyone else’s emotional rollercoaster and start riding your own wave.

Take what works, leave what doesn’t, and let me know if I should ever do this again.

Host: Jill Pickering

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Faking Death, Speeding Cars, & The “Aunt” Hill I Will Die On

Season 1 · Episode 11

Tuesday, April 28, 2026 • Duration 42:05

I may need to reevaluate my driving and my sanity, but we’re pushing through anyway.

In this episode, I’m sharing a couple humbling “slow down” moments from strangers on the road, (apparently I’m the problem), along with a small but mighty personal growth win (SRG) and a few life updates, including an upcoming Trader Joe’s giveaway and my latest Love on the Spectrum obsession.

Then we get into more chaos, including the pronunciation debate I cannot let go of. “Aunt” vs. “ant” is officially the hill I will die on, and yes, it involves me almost losing it in a very inappropriate moment.

From there, we get into conspiracies around celebrities who may have faked their own deaths, Tupac, Elvis, Princess Diana, Michael Jackson…and what would actually drive someone to disappear and start over.

I also share the top 5 celebrity deaths that shook me, why those losses hit so hard, and the strange way we grieve people we’ve never met.

We wrap it up with listener questions and a Jill Pill that might be exactly what you need this week: take the risk.

Host: Jill Pickering

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Songwriting: The Hits, The Misses, and The Awkward Moments

Season 1 · Episode 10

Tuesday, April 21, 2026 • Duration 52:58

In this episode, I’m talking all things songwriting: the hits, the misses, and the really awkward moments in between...of which there are plenty.

I share how I got started writing songs, what it actually looks like to write in Nashville, and some behind-the-scenes stories from co-writing sessions including a few that were not exactly a natural fit. It’s a lot like dating if we’re being honest!

If you’ve ever wondered how songs come to life or what happens when they don’t, this one is for you.

I also answer your questions about the songwriting process, performing, and creativity, break down my top 5 songs of all time, and play an unreleased song I’ve never shared before.

I wrap it up with a Jill Pill that is simple but powerful: tell people what you see in them.

Glad you're here for another fun episode!

Host: Jill Pickering

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There's Something About "Mary"

Season 1 · Episode 9

Tuesday, April 7, 2026 • Duration 32:33

This one starts with decaf coffee and Starbucks anxiety…and somehow ends with me in a feud with a 90-year-old woman.

Her name’s Mary (not her real name), and yes…she does not like me. And yes, I care a little more than I should. Thumbs down, major glare energy. We talk about why we get hung up on people not liking us, why it’s uncomfortable when we can’t fix it, and when it’s time to just shrug and keep walking.

Also: I ran into my junior high “Boyz II Men” ex (of course I brought up the story), reflections on playing live again after the Hunter Hayes and Blü Eyes show, and a very serious, highly debated Top 5: Ice Cream Flavors. Yes, I’m an ice cream snob.

Take your daily dose of the Jill Pill. Side effects may include laughing at yourself, realizing some people just aren’t your people, and maybe caring a little less (in a good way).

Host: Jill Pickering

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