How do I find the right relationship when dating apps suck? How can I find better dates? How can I deal with that nagging anxiety that no one is out there for me? How can I navigate dating with more confidence and find that right relationship? Welcome to The Date Brazen Podcast, where we’ll answer ALL of these questions and so much more. Week after week, host, former top matchmaker and dating coach, Lily Womble brings you all the tools, strategies and coaching you need to build a clear path ...
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As a mentally ill hot girl who has struggled with unrealistic beauty standards since the womb and could use a (theoretical but maybe literal) lobotomy, therapist and author Alegra Kastens intertwines her clinical wisdom and lived experience to gab about books of all genres. Not a bookworm? Have no fear (or do because #anxiety): she has done the reading for you. All you have to do is tune in, Lobotomommies!
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The Neurobiology of OCD with Neuroscientist Uma Chatterjee
1:23:29
1:23:29
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1:23:29Neuroscientist Uma Chaterjee joins us to discuss OCD and the brain! If you are wanting to know more about your brain and body as they relate to mental health symptoms, this is the episode for you. This podcast is made possible by NOCD. NOCD offers effective, affordable, and convenient OCD therapy. Schedule a free 15-minute call today at https://le…
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236. How To Stop People Pleasing (And Build A Stupidly Joyful Life)
1:17:30
1:17:30
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1:17:30Are you tired of living for everyone else's expectations... and ready to step into your own dang spotlight? 🎬✨ In this behind-the-scenes episode, I’m sharing practical tools to stop people-pleasing for good — and start building the stupidly joyful, self-trusting, main-character life you’re meant for. Inside this episode: What people-pleasing really…
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Your Unconscious Is Showing with Dr. Courtney Tracy
50:23
50:23
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50:23Did you know that your unconscious accounts for 95% of your behaviors, thoughts, and emotions? That our consciousness accounts for 5%? In this groundbreaking book, Dr. Courtney Tracy teaches us how to better consciously manage the unconscious through her three-part unconscious model and 12 steps of consciousness. Every single human could benefit fr…
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235. You Deserve More Than “Fine”- Katie’s Story of Wanting More—and Getting It
56:25
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56:25RSVP for my new training- Stop People Pleasing & Build a Stupidly Joyful Life HERE Apply for Main Character Life Mastermind HERE Order my book, “Thank You, More Please”: https://www.datebrazen.com/book Follow me on ✨ Instagram ✨ Tiktok ✨ Youtube
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234. Go From Shrinking To Confident Main Character Energy
39:56
39:56
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39:56In this episode, we’re diving deep into Main Character Energy — what it is, why it matters, and how to start building it (even if you’re shy, introverted, or feeling wildly behind). You’ll learn: - Why Main Character Energy is even more important in unstable times - The three essential skills at the heart of a Main Character Life - The truth about …
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233. How Jackie Went From Burnt Out Background Character-- to a Magnetic, Joyful AF Life
54:17
54:17
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54:17She Moved Abroad, Quit Her Job & Took Her Life Back: Jackie’s Main Character Energy Story Burned out, stuck, and shrinking herself to stay safe—Jackie thought joy was out of reach. In this powerful episode, she shares how she went from emotional exhaustion to building a joy-filled life abroad with purpose, friendship, and bold-ass moves. If you're …
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The Right Relationship is Inevitable w/ Lily Womble
1:19:56
1:19:56
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1:19:56Lily Womble, an intersectional feminist dating coach and former top matchmaker, talks her revolutionary book Thank You, More Please: A Feminist Guide To Breaking Dumb Dating Rules and Finding Love. Lily addresses the impact of the patriarchy on dating while teaching you how to joyfully attract the relationship of your dreams. 10/10, no notes! This …
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Episode Spotlight: My Qualifying/Disqualifying Questions Strategy So You Never Go On A Bad Date Again
36:49
36:49
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36:49In this episode, Lily shares the ONE question that will revolutionize how you vet potential partners, ensuring you never waste time on lackluster dates and conversations again. Grab your notepad because this episode isn't just about strategy - it's a journey into reclaiming control of your dating narrative and steering towards the relationships you…
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Episode Spotlight: "How Can I Stop Being Lazy In My Dating Life?"
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17:34In this week’s episode of the Date Brazen Podcast-- Episode Spotlight: "How can I stop being lazy in my dating life?", I’m teaching you exactly what you need to do instead of falling for the productivity myth. (which will lead to better outcomes for your dating life!) What you’ll learn in the episode: ✨ How to ditch the idea that “doing more” will …
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OCD and Substance Use Disorders (w/ Dr. Patrick B. McGrath)
1:03:46
1:03:46
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1:03:46Dr. Patrick B. McGrath, a Licensed Clinical Psychologist with over 20 years of OCD treatment experience, joins Alegra to talk about the intersection of Obsessive Compulsive Disorder (OCD) and Substance Use Disorders (SUD). It’s an important conversation and one that is not had enough given the prevalence of these co-occurring conditions. Studies ha…
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Episode Spotlight: How to Bless and Release The Wrong People Without Mind Drama
32:29
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32:29In this episode, I walk you through my Blessing and Releasing strategy: a powerful step-by-step method to let go of the wrong people and make space for the right ones. Because holding on to what isn’t meant for you? That’s keeping you from what is. Here’s what you’ll learn: ✨ How to identify who to bless and release (and why it’s essential). ✨ The …
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Trigger warning: domestic violence Chelsea Bieker joins Books, Looks, and Lobotomies to discuss her national bestselling novel, Madwoman, a Book of the Month club pick the New York Times calls “brilliant in its depiction of the long shadows cast by domestic violence.” Chelsea talks the realities of domestic violence, motherhood, intergenerational t…
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Episode Spotlight: Where Do I Even START With Dating?
16:37
16:37
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16:37In this episode, I break down exactly how to start dating with confidence, self-care, and intention.-- especially if you've never dated before! You’ll get a step-by-step guide to move past fear, own your desires, and create a joyful dating life on your terms. Here’s what you’ll walk away with: ✨ How to start dating from a place of power (not pressu…
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Episode Spotlight: Owning Your Preferences is a Feminist Act
23:48
23:48
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23:48If you've ever been told you're too picky or need to be more open, this episode is for you. Your preferences aren’t the problem—they’re the key to dating with more joy and ease. I break down how to define your essence-based preferences so you can stop wasting time on the wrong people and start attracting the right ones. ✨ Get free "Create Your Esse…
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The Intersection of OCD and Eating Disorders
53:55
53:55
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53:55OCD can look a lot like an eating disorder, making it difficult for clinicians to make a differential diagnosis. In this episode, Alegra shares her lived and clinical experience with OCD and Eating Disorders to debunk myths, discuss the intersection of this co-morbidity, and more. This podcast is made possible by NOCD. NOCD offers effective, afford…
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232. Sexual liberation, self-permission, and getting messy with Brandon Kyle Goodman
49:50
49:50
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49:50This week, I’m joined by the brilliant Brandon Kyle Goodman—writer, actor, and sexual wellness advocate—to talk about breaking free from shame, embracing curiosity, and giving yourself radical permission to be messy in your self-discovery. If dating has ever made you feel like you need to “get it right” before putting yourself out there, this episo…
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231. How To Shoot Your Shot 100% of The Time
18:11
18:11
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18:11If you’ve ever hesitated to put yourself out there because what if they say no?, this episode of the Date Brazen Podcast is for you. We’re flipping the script on outdated dating rules that keep you passive and stuck. Instead of waiting, I’m teaching you how to co-create the dating life you want, how to shoot your shot like a boss, and actually en…
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Emma Noyes talks How To Hide In Plain Sight, the first mainstream fiction book to cover POCD (!!!), breaking Book Tok, self-publishing, and finding her real life Manuel who loves her not despite her OCD but because of her beautiful mind. Emma’s works have been published in over a dozen languages and include Guy’s Girl, How to Hide in Plain Sight, T…
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Dating can feel like a rollercoaster of emotions—excitement, hope, fear, and sometimes, pure panic. In this episode, we’re tackling the fear that keeps so many incredible people stuck on the sidelines. If you’ve ever thought, What if I get rejected? What if I say the wrong thing? What if I’m not enough?—this one’s for you. I’ll walk you through how…
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Intentional Weight Loss After ED Recovery - My Journey
1:39:04
1:39:04
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1:39:04I am joined by my very own dietician Gabby Barreto to talk about my journey with intentional weight loss after eating disorder recovery. For so long, I felt trapped by both diet culture and anti-diet culture. I thought I had two choices: extreme restriction and an ED or staying in a body I didn’t feel good in because I’ve had an ED in the past. Fin…
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229. Flirting 101: My 3-Step Process to Flirt, Know If Someone’s Into You, and Ask Them Out with Ease
22:50
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22:50In this week’s Date Brazen Podcast episode, Flirting 101: My 3-Step Process to Flirt, Know If Someone’s Into You, and Ask Them Out with Ease, I’m breaking down my 3 step process to exactly how to flirt, know if someone’s into you, and ask them out with ease. Here’s the deal: 💡 Flirting is a learnable skill. 💡 Awkwardness? It’s just a sign you’re hu…
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228. How to build confidence and agency in your dating life with Julie and Yue of the Dateable Podcast
54:37
54:37
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54:37Today on The Date Brazen Podcast, I'm talking to Julie Krafchick and Yue Xu-- dating and relationship experts and co-hosts of Dateable, one of the top podcasts on modern relationships, featured by The New York Times, HuffPost, and Oprah Daily. Tune into this episode to hear- Understanding your dating archetype can help you navigate relationships be…
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227. You can't say the wrong thing to the right person, here's why
17:15
17:15
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17:15In this episode of the Date Brazen podcast, Lily unpacks her favorite piece of dating advice: You can't say the wrong thing to the right person. This 15 minute episode will free you from so much anxiety and worry in your dating life, so you have more time and energy to shoot your shot with confidence. Takeaways Dating is a microcosm of your hopes a…
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Episode Spotlight: The complete dating detox guide
22:29
22:29
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22:29Enjoy this ep spotlight! This episode is brought to you by my free, live SHOOT YOUR SHOT CHALLENGE: From "late bloomer" to confident dater in 5 days ✨ Links: Get Lily’s Book, Thank You More Please HERE. Follow Lily on Instagram and Tiktok. Subscribe to Lily’s Youtube channel HERE.
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226. Creating your pleasure goals for 2025 with Susan Hyatt
43:53
43:53
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43:53In this episode of the Date Brazen podcast, Lily engages with Susan Hyatt, a master certified life coach, bestselling author, and TEDx speaker. They discuss Susan's mission to empower women through her Bear process, which emphasizes self-care, body wisdom, and breaking free from diet culture. The conversation explores the importance of creating a t…
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Corrected Episode Spotlight: Late Bloomer guide to releasing worry + finding love
36:49
36:49
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36:49We're taking a break for the holidays (coming back Jan 7th, 2025) so enjoy this ep spotlight! This episode is brought to you by my free, on-demand training: 3 Steps to Attract the Right Partner as a “Late Bloomer" - RSVP HERE ✨ Are you feeling like a “late bloomer” in your dating life? In this Episode Spotlight of the Date Brazen Podcast, Lily bust…
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225. Your Complete 2025 Dating Plan: How to go from "late bloomer" to finding the right partner with confidence
35:07
35:07
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35:07In this episode of the Date Brazen podcast, Lily outlines a comprehensive seven-step dating plan for 2025, aimed at helping listeners create a joyful and fulfilling dating life. The plan emphasizes the importance of claiming desires, understanding essence-based preferences, and utilizing qualifying questions to find the right partner. Lily also dis…
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In this episode, Lily addresses the feelings of loneliness that can arise during the holiday season, especially for singles. She provides a three-step framework to help listeners navigate their emotions, emphasizing the importance of recognizing and acknowledging feelings, finding comfort and belonging, and choosing accessible positive thoughts. Th…
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223. Stressed about your dating life (and nosy questions) during the holidays? This is for you.
22:30
22:30
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22:30Stressed about your dating life (and nosy questions) during the holidays? This episode is for you. Yes, it’s that time of year—when relatives turn the holiday dinner table into a Q&A about your dating life. Lily is sharing how to respond to every nosy question from relatives - that you don’t want to answer! This is your guide to handling intrusive …
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222. Healing from co-dependency, people pleasing, and perfectionism in your dating life with Victoria Albina
41:10
41:10
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41:10Ready to stop emotional outsourcing and start owning your worth in dating and beyond? If you’ve ever struggled with perfectionism, people-pleasing, or the exhausting cycle of codependency, this episode will feel like a deep exhale. Lily invites her brilliant friend and colleague, Victoria Albina, to explore what it takes to recognize the patterns t…
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I’m diving into how to care for yourself when life feels heavy. If you’re feeling drained or disappointed post-election—or really, after any tough experience—I’m here with a simple but powerful framework to help you reclaim your energy. In this episode, I’ll guide you through the SOFT practice: Self-compassion, Owning your needs, Feeling your feeli…
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Episode Spotlight: How to create your essence-based preferences
27:08
27:08
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27:08We’re airing a popular episode about claiming your essence-based preferences. Lily takes you through what essence-based preferences are, how they can transform your dating life, how to know if you’re being too rigid, and how to create them for yourself. This is a juicy episode you’ll want to come back to again and again! Hot-takes and How-tos from …
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“Should I give them another chance, or should I ‘just know’ if they’re right?” Hot take: The whole slow burn vs. spark debate might be keeping you from finding a meaningful connection. This episode challenges the idea that a romantic connection needs to fit neatly into a “slow burn” or “spark” to be worth pursuing. In this episode, you’ll learn: ✨ …
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How do you date with intention and authenticity during an election season? You’re in luck! Lily is back with a special episode all about dating during the election. She explores how to navigate the heightened political climate with a boundaried, agency-filled plan to attract people who truly align with your values. Lily also shares tips on crafting…
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218. How to build main character identity (and stop being the "best friend")
30:31
30:31
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30:31Playing the sidekick in your own life? Not it. Step into your power, claim your main character identity and start making bold moves today. Why not you? Lily is dishing all about main character energy—what it is, what happens when you're not living in it, and how to level up and claim your spotlight. We’ve all been there—shrinking our desires becaus…
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BONUS: From paralyzed to launching her dream business with Mastermind client, Laura
41:13
41:13
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41:13Ready to crush it and take your dreams to the next level? This episode is ALL about that! We’re diving into Laura’s epic journey of leveling up her life, how she tapped into her MCE (yep, Major Character Energy), and broke down her big dreams into totally doable, bite-sized steps. And guess what? It worked! You’ll walk away feeling fired up, knowin…
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217. From comfort zone to a joyful, main character life with Mastermind client, Katie
54:44
54:44
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54:44Ready to stop playing small and start living big? This week, Mastermind client Katie shares how she embraced main character energy, stepped out of her comfort zone, and began living a joyful AF life! From ditching self-doubt to creating a social life that lights her up, Katie talks about the bold moves she made—like taking a sabbatical and going on…
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Bonus: From burnout and overworking to setting boundaries with work and creating more space for joy and connections with Mastermind client, Juliet
34:12
34:12
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34:12Do you feel like you're burning the candle at both ends with nothing left for yourself? In this bonus episode, Lily chats with Juliet, a client from the Main Character Energy Mastermind, about how she transformed her life by setting boundaries at work and making room for joy and meaningful connections. Juliet’s story is all about taking back contro…
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216. Stop overthinking your love life decisions (and how to actually trust yourself)
48:51
48:51
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48:51Are you stuck in a cycle of overthinking and self-doubt? Lily tackles exactly how you can break free from that mental loop. We dive into the real cost of overthinking—how it's draining your energy, wasting your time, and slowing down your life’s momentum. Lily shares methods to help you stop doubting yourself and start building a rock-solid foundat…
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215. How to ask for exactly what you want, nurture big dreams, and overcome your fear
47:11
47:11
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47:11Want to know how to ask for exactly what you want, nurture your biggest dreams, and crush your fears along the way? You’re in luck! Lily and her guest break down how to tap into your main character energy and own every aspect of your life. In this episode, you'll learn how to reclaim the parts of yourself you’ve left behind, nurture your inner ligh…
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214. From an exhausting job, to taking a huge leap and confidently prioritizing herself with main character energy with client Erica
44:16
44:16
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44:16Ever thought about making a big leap from your current job to your dream career? Discover how Erica ditched an exhausting job and became a full-time romance novelist with main character energy! Lily welcomes Erica a former Main Character Energy Mastermind client who made the leap from feeling stuck in her career to living her dream as a full-time r…
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213. How Jackie went from burnt out to taking a huge risk (that paid off) with confident main character energy
53:09
53:09
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53:09What happens when you stop playing it safe and start betting on yourself? In this episode, Jackie spills on how she shifted from burnout to bold moves, and what it takes to embrace that Main Character Energy. Jackie, a former Main Character Energy Mastermind member, joins Lily for a convo about how she went from frozen in fear and burnt out to maki…
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212. Knowing if something is right, long-term relationship questions, and dating as an independent badass with Ali & Erica of Finding Mr. Height
50:23
50:23
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50:23Is it possible to stay true to yourself while navigating the world of dating? Absolutely! We’re pulling back the curtain with special guests Ali and Erica from Finding Mr. Height. Lily sits down with the duo to discuss how they decided to start their dating podcast and offers a glimpse into the clues, details, and breadcrumbs that help you figure o…
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211. Why you need to brag more to find love (and how to do it)
26:28
26:28
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26:28Hot-take: Bragging is key to attracting more in your dating life. That’s right! We’re diving into Lily's favorite chapter from her book, Thank You More Please: A Feminist Guide to Breaking Dumb Dating Rules and Finding Love. It's all about the Brazen Bragging Revolution! 🚀 Lily breaks down why bragging isn’t just a power move but the key to attract…
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210. From feeling "behind" in dating to confidently shooting her shot 100% of the time with client Allyson
32:52
32:52
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32:52What does it take to go from feeling "behind" in dating to confidently making your move every single time? This week, Lily welcomes client Allyson, who shares her journey from feeling behind in dating to embracing self-compassion and taking control of her love life. They chat about the game-changing power of self-love, shaking off society's BS stan…
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OCD Is An Earthquake In The Brain with Stephen Smith
57:15
57:15
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57:15Stephen Smith, co-founder of the teletherapy platform NOCD, joins us to share his lived experience with OCD (sexual obsessions, relationship obsessions, and more) that fueled him to create a a virtual therapy platform specializing in the treatment of OCD. Like many, Stephen did months of general talk therapy with a therapist who didn’t understand O…
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209. From paralyzing dating fear to confidently Blessing and Releasing with client Miriam
40:21
40:21
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40:21What if the key to transforming your dating life is all about owning your worth? Listen in to find out how Miriam went from dating fear to confidently choosing people who were aligned with what they truly wanted. Join Lily and client Miriam as they dive deep into the thoughts that so many of us have about dating, worthiness, and settling, and how t…
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Stephanie Foo, author of the New York Times bestseller What My Bones Know: A Memoir of Healing from Complex Trauma, brought CPTSD to the forefront of mental health care. She joins us to talk about her healing journey, what CPTSD recovery means to her, emotional flashbacks, the painstaking search for a therapist, “the dread”, and more.This podcast i…
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208. Why I want you to make the first move 100% of the time (and how to do it successfully)
38:54
38:54
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38:54Hot-take: You should make the first move 100% of the time. If you read that and feel a sense of fear, that’s okay! In this episode, Lily breaks down everything from rocking a proactive mindset to embracing those awkward moments and showing yourself some self-compassion so you can confidently make the first move every time. This is the most passiona…
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207. Coming out, trusting yourself after a breakup, and finding love with my client, Liz
42:29
42:29
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42:29Are you wondering, “How do I pick up the pieces after this horrible breakup?” This week, Lily dives straight into an inspiring conversation with Liz, a former client who turned the heartbreak of a broken engagement into a powerful journey of healing and finding new love. Liz keeps it real, sharing her experiences of embracing pain, seeking support,…
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