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The Late Bloomer Show
The Late Bloomer Show
Author: Lily Womble
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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 Late Bloomer Show, 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 to the best relationship of your life.
After matching hundreds, Lily realized that with training, women can match themselves better than anyone else ever could. Now she helps thousands of women around the world build fulfilling, joyful and successful dating lives on their own terms. She's here to help you do the same.
If you're looking for unconventional, feminist leaning dating advice that works, this podcast is for you.
Along with her best kept secrets, Lily will share interviews with experts and live coaching sessions, so you can feel seen, heard and inspired.
Welcome to The Late Bloomer Show, 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 to the best relationship of your life.
After matching hundreds, Lily realized that with training, women can match themselves better than anyone else ever could. Now she helps thousands of women around the world build fulfilling, joyful and successful dating lives on their own terms. She's here to help you do the same.
If you're looking for unconventional, feminist leaning dating advice that works, this podcast is for you.
Along with her best kept secrets, Lily will share interviews with experts and live coaching sessions, so you can feel seen, heard and inspired.
302 Episodes
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Laura sat on her dream for years. She had already moved abroad, left her marriage, rewritten her book, built a whole new life in a new country… and yet the next thing she actually wanted to build — a business supporting women after divorce — stayed in a drawer. In this conversation, you'll hear exactly how she went from: • paralyzed by fear of judgment • hiding the work she'd been doing for years • waiting to feel "ready" • thinking she "should've figured it out by now" to owning her CEO energy, talking publicly about her work, pitching her idea in real life, and getting her first clients. We break down the exact moment things clicked, the messy middle, and the main character energy skills that helped her finally do the thing. If you've been circling a dream for months, years, or a decade… this episode is going to open something up for you. Work with Lily ✨ Main Character Life Mastermind — Applications open now.A 6-month container where you'll choose your main character project, release people-pleasing, build rock-solid self-trust, and take massive, messy action with a community that has your back. The 10-minute application will increase your main character energy on its own. Apply HERE 📚 Read my book: Thank You, More PleaseA feminist guide to breaking dumb dating rules and finding love. Order HERE Follow Lily everywhere: 📺 YouTube Channel 📸 Instagram 📲 Tiktok 🌐 Website
In this episode, Abby shares her late bloomer story with so much honesty and clarity. We talk about what it was like to be in her mid-30s, never having been in a serious relationship, carrying a loud "I'm behind" and "I'm weird" narrative, and feeling totally unsure how to talk about her dating history without spiraling. Abby opens up about moving to a new city, trying to date while feeling embarrassed about her experience, and struggling with the not good enough voice that made her avoid connection. She also shares what shifted for her as she started to process shame, build community, and trust herself enough to take up more space at work, in dating, and in her daily life. Inside this episode, you'll hear: how Abby learned to identify and quiet the "I'm weird" and "I'm behind" voice how belonging helped her stop self-isolating and start connecting what helped her ask for what she wanted (down to "I need 25% more texts") how she advocated for herself at work while doing two jobs how she built friendships, community, and eventually a healthy relationship what she wishes she could tell her past self, who felt so far behind This is a powerful example of what can happen when you stop avoiding your desires and start trusting yourself enough to move toward them. Work with Lily ✨ Join the live training: Stop People-Pleasing and Build a Stupidly Joyful Life live training-- December 3rd: Sign up HERE ✨ Apply to Main Character Life, my 6-month mastermind where Abby did this work — the space to release people-pleasing, build self-trust, advocate for what you want, and go after the life you've been circling for years. Apply HERE ✨ Get my Book — Thank You, More Please, Buy the book + grab your bonus HERE Follow Lily everywhere: 📺 YouTube Channel 📸 Instagram 📲 Tiktok 🌐 Website
If you're stuck in a spiral of overthinking — replaying conversations, asking 15 friends what to do, imagining every worst-case scenario — this episode will feel like a deep exhale. Overthinking isn't you being "careful." It's a self-trust deficit. And that is a skill gap, not a character flaw. In this episode, I break down: • Why anxious rumination feels so real and so urgent • How patriarchy, people-pleasing, and fear of rejection trained you not to trust yourself • The difference between careful planning and dress rehearsing tragedy • Why outsourcing decisions to friends keeps you stuck • What self-trust actually is (and why it's messy, imperfect, and learnable) • Tiny, doable steps to rebuild your self-trust today • How this plays out in dating, boundaries, and big life decisions • A framework to stop overthinking and start acting from your gut If you've been doubting yourself for years — in your dating life, your friendships, your career, your boundaries — this episode will teach you how to finally have your own back. Self-trust is a skill. And you're about to learn it. Work with Lily ✨ Main Character Life Mastermind — Applications Opening soon!Sign up for my free training-- Stop People Pleasing and Build a Stupidly Joyful Life-- on Dec 3rd to be the first to apply. RSVP HERE 📚 Read my book — Thank You, More PleaseA feminist guide to breaking dumb dating rules and finding love Order here: https://datebrazen.com/book Follow Lily everywhere: 📺 YouTube Channel 📸 Instagram 📲 Tiktok 🌐 Website
Feeling like the supporting character in your own story? This episode is your plot twist. We unpack Main Character Energy (MCE) as a buildable skill set—not a personality type—and show how tending to your needs heals burnout and expands your capacity to show up for the people and causes you care about. In this episode, you'll learn: The 3-part MCE framework: Permission → Self-Trust → Massive, Messy Action Why MCE isn't selfish—it's the power source that fuels your impact (both/and) The tiny tool that changes everything: 10 Seconds of Courage Five rapid-fire ideas to practice 10 seconds of courage today (self-care, belonging, shoot-your-shot) How to stop "best-friend energy" (people-pleasing, perfectionism, over-functioning) and step center stage Work with Lily Free Live Training (Dec 3): Stop People-Pleasing & Build a Stupidly Joyful Life —RSVP HERE Main Character Life Mastermind — Get details + apply (when open) or join the waitlist HERE Main Character Dating — My signature program to build a joyful, self-trust-filled dating life and attract an aligned partnership. Learn more: https://datebrazen.com/dating Get my Book — Thank You, More Please Buy the book + grab your bonus: https://datebrazen.com/book Follow Lily everywhere: 📸 Instagram 📲 Tiktok 📺 YouTube Channel Subscribe so you never miss an episode. You've got this—and I've got your back.
If you've ever found yourself doing everything right and still feeling exhausted, this conversation is for you. In this episode, Lily sits down with Maureen, a writer, educator, and book coach who transformed her life from chronic burnout and perfectionism to joyful, sustainable main character energy. They dive into: ✨ How perfectionism becomes emotional armor (and how to take it off safely). ✨ Why joy—not hustle—is the most powerful growth strategy. ✨ The role of self-celebration and community in creating a life that feels like your own. Maureen's story is a reminder that you don't have to blow up your life to change it. You just need new tools for how you treat yourself while you grow. Connect with Maureen: 🔗 narrative-drive.com 📝 narrativedriven.substack.com/ Work with Lily: 🌸 Main Character Life Mastermind — A 6-month small-group experience starting in January to release people-pleasing, build rock-solid self-trust, and become the main character of your life in 6 months or less. Get early access + bonuses: https://datebrazen.com/life Free Live Training: Stop People Pleasing and Build a Stupidly Joyful Life — December 3rd: https://datebrazen.com/joyful-life/ Get Lily's Book: Thank You, More Please HERE Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel
Ever catch yourself thinking: "Am I doing enough to find love?" That question sounds productive—but it's usually fear in disguise. Fear that time's running out. Fear that what you want might never happen. In this week's episode of The Late Bloomer Show, I walk you through the 10-step "Am I Doing Enough?" checklist—the one I give my clients when they start to spiral. You'll learn how to: 💗 Practice self-compassion (so you stop hustling for worthiness) 🎯 Create your Essence-Based Preferences 💎 Bring in community and support 🎉 Celebrate yourself like it's part of the plan—because it is You don't need to "just try harder" in your dating life. You need an effective plan that prioritizes your self-trust along the way. Work with Lily: → Free Essence-Based Preferences workbook: datebrazen.com/workbook → Read Thank You More Please: datebrazen.com/book → Learn more about Main Character Dating: datebrazen.com/dating → Learn how to work with Lily: datebrazen.com Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel
Should you wait for the slow burn? Or chase the spark? This question keeps so many late bloomers stuck in overthinking, second-guessing, and dating people who aren't right for them. In this episode of The Late Bloomer Show, Lily breaks down the real truth about attraction and connection, including: The pros + cons of both the spark and the slow burn Why both approaches can lead to wasted time What to focus on instead (hint: curiosity > rules) How to ground yourself with Lily's Date Feedback Compass If you've ever stressed about whether you "knew" soon enough or felt enough chemistry, this episode will give you clarity and freedom. 🎧 Listen now and find out why curiosity—not binaries—is the most powerful dating tool. Work with Lily: → Free Essence-Based Preferences workbook: datebrazen.com/workbook → Read Thank You More Please: datebrazen.com/book → Learn more about Main Character Dating: datebrazen.com/dating → Learn how to work with Lily: datebrazen.com Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel
Dating while struggling with body image fears can feel like an impossible task. In this episode, Lily is joined by Bri Campos, LPC, and body image coach, to explore the idea of body grief—the distress and loss we feel when our bodies change—and how it impacts dating. Together they cover: → The 4 aspects of body image you need to know → Why rushing to "body love" skips over the real healing work → How fatphobia and privilege show up in dating dynamics → Practical tools to move through body grief with compassion so you can put yourself out there and find love in exactly the body you're in If you're a late bloomer who's avoided dating because of how you feel in your body, this conversation will give you the validation, tools, and hope to take your next steps. Learn about Bri's work here→ https://www.bodyimagewithbri.com/ 💥 Want more support? Start here: → Free Essence-Based Preferences workbook: datebrazen.com/workbook → Read Thank You More Please: datebrazen.com/book → Learn how to work with Lily: datebrazen.com Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel
In this powerful live coaching session, Lily sits down with Veronica for a live coaching session—a listener and Main Character Dating client—to explore what it really looks like to start dating again after a painful breakup…while also navigating chronic pain, a disability, and a world that often is deeply ableist. They explore: ✨ How to know if you're really ready to date again after a breakup ✨ Navigating dating apps with a disability ✨ Setting boundaries that honor your body and your bandwidth ✨ Why self-compassion is a dating strategy This episode is full permission to do dating your way. 💥 Want more support? Start here: → Main Character Dating-- closing 10/17/25: datebrazen.com/dating → Free Essence-Based Preferences workbook: datebrazen.com/workbook → Read Thank You More Please: datebrazen.com/book Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel
What do late bloomers most want to know about sex? In this episode, Lily sits down with Dr. Juliana Hauser—sex therapist, TEDx speaker, and author of A New Position on Sex—to answer the top 10 questions late bloomers have about sexuality, intimacy, and pleasure. They cover everything from starting with little or no experience, to disclosing your sexual history (or lack thereof), to navigating body image, chemistry, pain, and more. Whether you're 20, 30, 40, 50+ and wondering where to start, this conversation is a must-listen. 🎧 Listen in now and discover the tools, confidence, and compassion you deserve in your sexual journey. 📖 Grab Dr. Juliana's new book A New Position on Sex: A Guide to Greater Sexual Confidence, Pleasure and Authenticity available now right HERE 💥 Work with Lily: → Main Character Dating: datebrazen.com/dating → Free Essence-Based Preferences workbook: datebrazen.com/workbook → Read Thank You More Please: datebrazen.com/book Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel
If you've ever felt behind in love or life, this episode is for you. On pub day for her new book, End Emotional Outsourcing: A Guide to Overcoming Codependent, Perfectionist and People Pleasing Habits, Beatriz Victoria Albina joins me to talk about how to stop centering everyone else's needs at the expense of your own—and start dating with self-worth. We unpack: 💎 What "emotional outsourcing" is and why it keeps you stuck in people-pleasing, perfectionism, and codependency 💎 How to reclaim your agency and desire without guilt 💎 The BRAVE framework for building self-loyalty, step by step 💎 Why being a late bloomer is often an act of brilliance—not failure Her book is out today! Go grab "End Emotional Outsourcing" wherever books are sold and start building the love life (and LIFE) that puts you back at the center. Order your copy → https://beatrizalbina.com/book/ 💥 Work with Lily: → Main Character Dating: datebrazen.com/waitlist → Free Essence-Based Preferences workbook: datebrazen.com/workbook → Read Thank You More Please: datebrazen.com/book Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel
Taylor hasn't been in a relationship since she was 19. Now, at 31, after eight ghostings and countless near misses, she's wondering: "Why not me?" In her words: "Hope is scary." Because every time she's let herself hope, she's been let down—and she's started to believe maybe she's just not worth the effort. In this raw and powerful live coaching session, we unpack what's really underneath that fear—and build a brand new belief: ✨ "Massive change happens when I trust myself and advocate for myself." In this episode, you'll learn: 💎 How to move from "I know the tools" to actually feeling them work 💎 What to do when self-compassion feels completely out of reach 💎 The thought error that keeps so many late bloomers stuck in shame 💎 Why practicing hope (even when scared) is the bravest dating move you can make If you've ever felt behind, broken, or like dating is a hopeless slog—this one's for you. 💥 Work with Lily: → Main Character Dating: datebrazen.com/waitlist → Free Essence-Based Preferences workbook: datebrazen.com/workbook → Read Thank You More Please: datebrazen.com/book Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel
Becca came into this coaching session feeling stuck, frustrated, and deeply alone in her experience: "I'm 37. I've never had a relationship. It feels like I'm missing something that everyone else figured out." This episode is for the late bloomer who's never really seen their story reflected in dating advice—and is tired of wondering, "What's wrong with me?" Together, we worked through: – The fear that it's too late to have what you want – How to shift from self-blame to self-trust (without pretending it doesn't still hurt) – The exact first step to start dating from your real power Becca left with a new plan—and a very different energy. If you've ever thought "Maybe it's never going to happen," I want you to listen to this one. 🎧 The Late Bloomer Show, episode 250. Available now wherever you get your podcasts. 💥 Want more support? Start here: → Main Character Dating: datebrazen.com/waitlist → Free Essence-Based Preferences workbook: datebrazen.com/workbook → Read Thank You More Please: datebrazen.com/book Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel
Today on The Late Bloomer Show, I'm coaching Dana. Dana is a badass who's never been in a relationship—and she came to our session asking the question so many late bloomers carry: "Are men going to see that as a red flag?" In this episode, we go deep and get tactical. 💎 We create her Essence-Based Preferences in real time (including the exact words she'll use to vet potential dates) 💎 Build a clear vetting plan so she never has to waste a weekend on a "blah" date again 💎 Make over her dating profile so it reflects who she actually is: adventure traveler, joyful weirdo, emotionally aware, deeply feminist We also talk through how to show up confidently when you feel behind, how to stop apologizing for your inexperience, and how to date like you're not dead yet. 💥 Work with Lily: → Main Character Dating: datebrazen.com/waitlist → Free Essence-Based Preferences workbook: datebrazen.com/workbook → Read Thank You More Please: datebrazen.com/book Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel
"I've never had a relationship last a year. It feels like I missed my window." That's what Jennifer told me at the start of this session. She felt behind. Like it was too late to have the love story she wants. Like she had somehow run out of time. And if you've ever looked around and thought, Everyone else got the memo on how to do this. I didn't, this episode is going to speak directly to you. Together, we work through: – The fear that your best love story is already off the table – The weight of "Nobody picks me" – What happens when old thoughts make new dating hope feel impossible – How to use the SOFT method to feel your feelings and rewire your beliefs, without bypassing the hard stuff By the end, Jennifer says: "It's not over. I'm worth it." And she means it. 🎧 If you're a late bloomer who's still hoping it's not too late, press play now. 💥 Ready for more support? Start here: → Main Character Dating: datebrazen.com/waitlist → Free Essence-Based Preferences workbook: datebrazen.com/workbook → Read Thank You More Please: datebrazen.com/book Follow Lily everywhere: 📲 Tiktok 📸 Instagram 📺 YouTube Channel
When I renamed the podcast The Late Bloomer Show, some of you may have wondered: "What if I don't feel like a late bloomer — is this still for me?" I recorded a mini podcast episode talking about exactly that:) Listen here. Here are my hot takes: 🌱 "Late bloomer" to me means feeling "behind" in any way. To me, late bloomer isn't about the amount of experience or inexperience— it's about the feeling of being behind where you thought you "should" be. That feeling is so real, and this community, podcast, and movement is here to remind you: you are right on time. 🌱 If you do identify as a late bloomer, I'm right there with you, I did, too. I'm so excited to usher in this new era of the podcast. 🌱 And if the phrase "late bloomer" doesn't resonate with you, that's okay too. Because if you've ever felt pressure, shame, or that nagging sense of being "too late, too much, or not enough" — then this space was built for you, too. ✨ This mini episode dives into exactly what The Late Bloomer Show is for — and why it's for you, whether or not you use that label. 💜
Are you afraid that raising your standards means you'll be alone forever? Today on The Late Bloomer Show, I'm coaching Marissa, who stayed long after she knew her relationships were over—because she thought starting from scratch would be worse than settling. In this episode, we dig into: ✨ Why we shrink our needs to keep relationships ✨ The guilt that keeps us stuck for years ✨ How to believe what you want in love actually exists ✨ The exact shifts helping Marissa trust herself and ask for more If you've ever worried you're "asking for too much," this conversation will help you see your love life—and your worth—in a whole new way. Work with Lily: 🔗 Learn about her signature program, Main Character Dating: datebrazen.com/waitlist Get the book, "Thank You More Please": datebrazen.com/book 💻 Learn how to work with Lily: datebrazen.com Let's connect: 📲 Tiktok 📸 Instagram 📺 YouTube Channel
"More is possible than you currently realize." ✨ Big news ✨ The Date Brazen Podcast is now The Late Bloomer Show 💜 This change is for every late bloomer who's ever felt behind, too much, or too late. For anyone who's been told to shrink or settle. For everyone who needs to hear: 🌱 You are not alone. 🌱 You are not too late. 🌱 What you want is possible. In this vulnerable episode of The Late Bloomer Show, Lily opens up about the rebranding of her podcast and what it truly means to embrace the late bloomer identity. This conversation is more than just a name change, it's about creating a space where late bloomers can feel seen, supported, and empowered. Lily shares why community matters so deeply, how self-compassion changes the journey, and why feminist perspectives are essential in reframing what it means to be "behind." Work with Lily: Download the free Essence-Based Preferences Creation Guide: datebrazen.com/workbook Get the book, "Thank You More Please": datebrazen.com/book 💻 Learn how to work with Lily: datebrazen.com Let's connect: 📲 Tiktok 📸 Instagram 📺 YouTube Channel
"Why do I have to do all this work just to be given a chance?" In this deeply moving live coaching session, Lily talks with Caleigh—a brilliant late bloomer feeling burned out and heartbroken after years on dating apps. On the surface, it's dating fatigue. But underneath, they uncover how internalized misogyny shows up in dating: feeling like you have to be less intense, less emotional, or hide your anger just to be seen as desirable. In this episode, you'll hear: ✨ Why dating can feel like Groundhog Day, especially for late bloomers ✨ How grief and shame linger around never having had a serious relationship ✨ The truth about anger—and why feeling it might change everything in your love life ✨ How perfectionism sneaks into dating and keeps you stuck ✨ Concrete tools to raise your standards without giving up hope If you've ever wondered why dating feels like so much work, or worried that your big feelings make you "the problem," this episode will make you feel seen—and give you practical ways to keep going without losing yourself. Work with Lily: Download the free Essence-Based Preferences Creation Guide: datebrazen.com/workbook Get the book, "Thank You More Please": datebrazen.com/book 💻 Learn how to work with Lily: datebrazen.com Let's connect: 📲 Tiktok 📸 Instagram 📺 YouTube Channel
If rejection makes you want to hide under the covers and never date again—this episode is your roadmap back to brave action. Lily shares one of her most painful rejections from her dating life, how it nearly derailed her belief in love, and the five-step Rejection Resilience Side Quest she created to help late bloomers build the skill of shooting their shot without spiraling. Inside this episode: ⚡️ Why rejection feels so dangerous (and why that makes total sense) ⚡️ A 5-step framework to depersonalize "no" and take bold action anyway ⚡️ A rejection aftercare protocol that actually helps you recover faster ⚡️ How building resilience leads to getting more of what you want in love and life This is the most essential skill in dating that no one teaches—until now. 💥 Want more support? Work with Lily: 🔗 Learn about her signature program, Main Character Dating: datebrazen.com/waitlist 🔗 Book: Thank You More Please 🔗 YouTube Channel 🔗 Tiktok 🔗 Instagram



