Explore every episode of the podcast Take a Jill Pill
| Title | Pub. Date | Duration | |
|---|---|---|---|
| New England, Winter Blues, & I'm Not Your Galentine. | 17 Feb 2026 | 00:51:58 | |
We’re talking Super Bowl thoughts, Olympic feelings, Nancy Guthrie (where is she?!), Valentine’s Day…and why I am absolutely not your Galentine. I’m ranking my Top 5 New England states (yes, I know there are only 6), answering listener questions, and sharing a brand new unreleased song exclusively here on the podcast. Basically, it’s winter blues mixed with hot takes and a few meaningful moments. When life is lifing, take a Jill Pill. 💊 To download the song I played today: takeajillpill.com/ready Listen to my Miss Indepodcast interview Host: Jill Pickering Follow me at: | |||
| Your First Jill Pill: Rants, Randomness, and Real Talk | 10 Feb 2026 | 00:33:18 | |
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 Find me here: | |||
| Trailer: Introducing "Take a Jill Pill" | 28 Jan 2026 | 00:02:39 | |
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 | |||
| So…What Happened with Jill and Kate? with Kate Rapier | 18 Aug 2026 | 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 Follow me at: instagram.com/takeajillpillpodcast Find Jill and Kate/Girls Just Pod to Have Fun at: https://open.spotify.com/artist/3nOFoJxsyWVGxnFQMqjeH0 https://podcasts.apple.com/us/podcast/girls-just-pod-to-have-fun/id1303203325 | |||
| Nobody Tells You This (But They Probably Should) | 04 Aug 2026 | 00:31:21 | |
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 Follow me at: | |||
| Public Scandals & Revenge of the Ants | 12 May 2026 | 00:44:54 | |
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:
As always, it’s chaotic, reflective, unhinged, and hopefully a little comforting too. Glad you’re here! Host: Jill Pickering Follow me at: | |||
| Dear Jill…Your Questions, My Advice | 05 May 2026 | 00:54:04 | |
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 Follow me at: | |||
| Faking Death, Speeding Cars, & The “Aunt” Hill I Will Die On | 28 Apr 2026 | 00:42:05 | |
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 Follow me at: | |||
| Songwriting: The Hits, The Misses, and The Awkward Moments | 21 Apr 2026 | 00:52:58 | |
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 Follow me at: | |||
| There's Something About "Mary" | 07 Apr 2026 | 00:32:33 | |
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 Follow me at: | |||
| Conspiracies, Chatbots, & Unpopular Opinions | 31 Mar 2026 | 00:31:17 | |
We’ve got a lot going on this week. First: the people have spoken and you want more cults, so don't worry, I’m working on it. But before that, let’s get into the Savannah Guthrie situation and why this story hit differently than expected, especially when it comes to advocating for someone you love and the vulnerability that comes with it. Also: could you fall in love with a chatbot? People are out here marrying themselves (no judgment, honestly relatable), and somewhere in all of this is a dating advice segment that I am maybe not the most qualified person to give. But, oh well. Plus: a conspiracy theory about what TV might actually be preparing us for, are we living in a simulation, this week's Trader Joe's find, Perez Hilton's spiritual awakening, Top 5 Unpopular Opinions, Listener Questions, and this week's Jill Pill: we’ve got a little bit of everything today! Host: Jill Pickering Follow me at: | |||
| Don't Let Me Join a Cult | 24 Mar 2026 | 00:41:41 | |
This week we’re talking about cults…a topic I’ve been intrigued by for a long time. I’ve had a few run-ins with them over the years and I’ve had to ask myself, “Am I an easy target?” I’ve wondered if I’m giving off “approachable for recruitment” energy. Just kidding, mostly. In all seriousness, I used to live in Brentwood, Tennessee and regularly drove past what I later found out was the Remnant Fellowship, aka the Gwen Shamblin/Way Down situation. At the time, I just thought it was a really beautiful church. Would’ve been a great place for a wedding. Turns out, there’s a lot more to it. So today we’re talking about “The Way Down: God, Greed, and the Cult of Gwen Shamblin” and getting into how a weight loss program turned into something much bigger, the stories and rumors I’ve heard just from living nearby, and how people may get involved in situations like these. Plus: some reality TV thoughts, hibachi mishaps, my Top 5 qualities in a person, listener questions, and this week’s Jill Pill: trusting your gut. Host: Jill Pickering Follow me at: | |||
| People Pleasing, Uber Rants & My First Very Tiny Guest | 17 Mar 2026 | 00:39:41 | |
This week I found myself trapped in a very warm Uber with a very talkative driver…which led to an unnerving realization: is this what I sound like on my podcast? Things get random today. Are you a people pleaser? How do you prefer your potatoes? Let’s talk about it. I also introduce a topic I’ve been curious about for years: cults…Consider this the preview, because next week we’re getting deep into one of the cults I find most intriguing. Plus, I welcome my first (and youngest) guest ever, my five-year-old goddaughter Gigi, who joins me for a very serious discussion. (Okay, it’s not that serious.) I also answer a listener question about the many jobs I’ve had over the years, from babysitting and flower delivery to music industry gigs and teaching songwriting. And of course, we wrap it all up with a Jill Pill dose of the week…this time with a little help from Gigi! Show Notes: Host: Jill Pickering Guests: Gigi Rapier Follow me at: | |||
| Boy Bands, Reality TV, & Ambiguous Grief | 10 Mar 2026 | 00:47:11 | |
In this episode, I’m getting a little more serious than normal and talking about the strange, complicated reality of ambiguous grief and what it’s like navigating life with aging parents, from preventing scams and thinking about medical decisions to those unexpected moments when you still feel the urge to call your mom, no matter your age. I also lighten things up a bit with a rant about overly bright headlights, the Jeopardy and Wheel of Fortune contestant anecdotes, and then I rank my Top 5 boy bands of all time (a very serious discussion). Plus: the random things that make you feel like a kid again, my favorite song I’ve ever written, a guilty pleasure iPhone app, and this week’s Jill Pill: the simple thing that helped me process a lot this week. Host: Jill Pickering Follow me at: | |||
| Hard Pass: Things I’m Never Doing Again | 03 Mar 2026 | 00:54:58 | |
This week on Take a Jill Pill, I spiral casually through the very suspicious number of conspiracy theories showing up in my feed. Am I just noticing it more, or are our phones actually reading our minds? I have questions. I’m also sharing my official Top 5 Things I’m Never Doing Again (some of these were character-building experiences and I’m actually glad I did them all….I think), answering listener questions about things I still want to try, and weighing in on the best airports to be stranded in, because apparently we’re planning for that now. I also reflect on the oddly specific things people know me for and why I might need a small rebrand before it’s too late. Plus, a quiet but important reminder about something many people are still chasing: enough. If you would like to get unhinged with me, I’d love for you to join me! Host: Jill Pickering Follow me at: | |||
| Jimothy, Deviled Eggs & Other Things I Can't Explain | 28 Jul 2026 | 00:56:16 | |
This episode is exactly what happens when my brain is left unsupervised. We're talking about Jimothy the raccoon, a restaurant that only sells deviled eggs (yes, really), a pedicure that turned into a full-blown character assessment, and the stranger who decided to perform karaoke directly into my ear. Along the way, we also get into what caring for my mom with dementia has taught me about human connection, why age-gap friendships matter more than we realize, and the uncomfortable question I asked AI that completely called me out on my BS. Plus: I’m glad you’re here! Host: Jill Pickering Follow me at: | |||
| The Pink Dunkin’ Glove, Aliens, and Why I’m Easily Influenced | 24 Feb 2026 | 00:47:31 | |
In this episode of Take a Jill Pill...shocker...I get a little unhinged. I confess how I absolutely got sucked into Dunkin’s latest marketing ploy…yes, the pink iced coffee glove. And then we end up in a rabbit hole about aliens, angels, the supernatural, why Katy Perry went to space, and what I actually think aliens might be like. Spoiler: I think they’re like totally dope, dude. I also drop a new Top 5 that mashes up two of my favorite things, music and marketing. I’m not giving it away, but I think you’re gonna hear some familiar sounds. To wrap it up, I answer listener questions about AI’s role in music creation, beige flags, the food I could realistically eat for a month straight, and plenty of other random nonsense. It’s a vibe today, my friends. Host: Jill Pickering Follow me at: | |||
| Behind the Scenes: Music Industry (Part 1) | 14 Jul 2026 | 01:04:59 | |
You voted, and this one won by a landslide. This week I'm taking you behind the scenes of my twenty-ish years in the music industry…from touring the country in a silver minivan and playing biker bars to touring arenas with Kelly Clarkson and other artists. I'm sharing what life on the road was really like, the parts nobody sees, how one unexpected opportunity changed everything, and why touring wasn't necessarily always as glamorous as I imagined. Plus: Backstage celebrity encounters, my top 5 venues I've ever played (#1 might surprise you), listener questions, and enough stories that this had to become Part 1. Whether you've always been curious about the music industry or just want to hear how I once ended up wearing a "Fresh Meat" hat at a butcher shop on stage, this one's for you. Host: Jill Pickering Follow me at: | |||
| Trader Joe's Wants to Know My Plans. CERN Wants to Change Time. | 07 Jul 2026 | 00:42:09 | |
This week on Take a Jill Pill, I'm back after a week off and catching you up on everything: the guy who climbed the Empire State Building to propose (and got arrested for it), my Dunkin summer haul, and why the algorithm knowing my grocery store guy is getting way too close for comfort. We also get into the marketing strategy behind Trader Joe's cashiers (yes, it's real, no, it doesn't change how I feel about the hummus), a very current conspiracy theory about CERN shutting down, and a Fourth of July story I wasn't planning on telling but somehow did. Then it's the Top 5 things I used to care about and genuinely don't anymore, plus your questions on Taylor and Travis's wedding, Trader Joe's marketing, why I don't love soccer, and my family history. And of course, today's Jill Pill: a question about what you might be avoiding and whether it's really worse than what's on the other side of it. Host: Jill Pickering Follow me at: | |||
| The Most Important Question You're Not Asking Yourself with Dr. Lee Long | 23 Jun 2026 | 00:59:29 | |
Therapist, author, and friend Dr. Lee Long joins me for a conversation that has genuinely changed the way I think about relationships, conflict, anxiety, and even everyday frustrations. We start with Trader Joe's, conspiracy theories, and why humans are wired to search for meaning. Then we get into the powerful question at the center of Dr. Lee's book, WAIT, Where Am I in This? Why do we spend so much energy trying to change other people? Why do certain situations trigger such strong reactions in us? Why do we spiral over unanswered texts, feel stuck in the same relationship patterns, or find ourselves getting way too angry at strangers on the road? Dr. Lee explains how one simple question can help us stop looking outward for answers and start understanding what's happening inside. We talk about self-awareness, people-pleasing, mind-reading, control, emotional triggers, and the difference between focusing on yourself and being selfish. He even walks me through my own road rage in real time, which was both enlightening and slightly humbling. If you've ever found yourself thinking, "If they would just change, everything would be better," this episode might give you a completely different perspective. Because the most important question you're probably not asking yourself is: Wait... where am I in this? You can find Dr. Lee Long here: Get his book on Amazon or Audible: WAIT, Where Am I in This? Podcast: Wait, Let’s Talk About That Website: www.drleelong.com Instagram: @dr.leelong Host: Jill Pickering Guest: Dr. Lee Long Follow me at: instagram.com/takeajillpillpodcast Disclaimer: We talk about a lot of therapy-related topics in this episode, but this is a podcast conversation, not a therapy session. Dr. Lee Long is not my therapist, and nothing discussed here should be considered mental health treatment or individualized professional advice. If you're looking for support with your own situation, please connect with a licensed mental health professional. | |||
| I'm Literally Just Sending You a Really Long Audio Message | 16 Jun 2026 | 00:45:21 | |
This week, we're doing something just a little different. I have a lot of random thoughts and so you're getting a really long audio message from IDK your BFF Jill, and I hope you're going to be okay with that. We're catching up on a few ongoing sagas (still no Nancy Guthrie, still no bear spray), I scored the Dunkin' Pineapple Cup, and then I just…start talking. About everything. The random thoughts that live rent-free in my brain, the questions I have that I don't actually need answered, and a few things I learned this week that genuinely rocked my world. We've also got top 5 karaoke songs, listener questions, and a Jill Pill about the freedom of just saying no. It's a bit of a random episode, and very much an audio message I might send to my friends. So, here goes nothing! Host: Jill Pickering Follow me at: instagram.com/takeajillpillpodcast | |||
| It's a No From Me, Dawg | 09 Jun 2026 | 00:38:13 | |
This week, I have some thoughts about the NXIVM cult. What started as a self-help and leadership program somehow turned into a secret society, branding ceremonies, and a lot of red flags. I’m talking about how ordinary, intelligent people can get pulled into groups like this, and why it's not always as obvious as you'd think. Plus, I'm sharing my Top 5 true crime and real-life drama podcasts, including some absolute favorites that will completely consume your life. (Links to them are below) I’m also answering some listener questions about:
And for this week's Jill Pill, a reminder to be careful what you normalize…because the things we accept over time have a way of shaping our lives. Grab your coffee, watch out for bears, and let's get into it. Host: Jill Pickering Follow me at: instagram.com/takeajillpillpodcast Links: Read The Goodpasture Chronicles | |||
| The 3 Emotions Quietly Draining Your Energy | 02 Jun 2026 | 00:54:46 | |
This week we’re talking about: yard sale anxiety, a disastrous run of Chipotle mobile orders, Dunkin’ freebies, emotional overwhelm…and somehow it all makes sense. (I think?) I'm doing my first listener chat with Meghan…loyal Dunkin’ lover & fellow New Englander, to talk about the cult-like world of Dunkin’ giveaways, then I get into the three emotions that may be quietly sucking the life out of you: guilt, worry, and chronic overwhelm. Plus, my top five kitchen staples, listener questions, celebrity crushes, and a reminder that sometimes it's okay to stop trying so hard and just start fresh tomorrow. Take a Jill Pill and come hang out. Host: Jill Pickering Guests: Meghan - Fellow Dunkin’ Fan! Follow me at: | |||
| This One’s For the Birds…(if they’re real…) | 19 May 2026 | 00:35:53 | |
This week on Take a Jill Pill, we’re covering Gerald the dolphin and his underwater cities, government bird drones, talking animals, dirty sodas, Gracie Abrams, and why I may officially be becoming a Bird Lady. The episode starts with summer arriving in New Hampshire and me getting territorial over my beach walks…and somehow ends with me questioning whether pigeons are spying on us. (Have you ever SEEN a baby pigeon??) I also share my top 5 birds (yes, really), answer listener questions about social media, starseeds, and life’s surreal “wow” moments, and talk about why nature might be trying to tell us more than we realize. It’s fun, chaotic, a bit thoughtful, and definitely one of those episodes where we just keep following the rabbit trail wherever it goes. Host: Jill Pickering Follow me at: | |||