Claim OwnershipThe Late Bloomer Show
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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.
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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
Ever catch yourself thinking: “Why would they like me? What’s wrong with them for wanting me?” This sneaky belief keeps so many late bloomers stuck in self-doubt, playing small, and avoiding the very love they crave. In this episode, Lily gets personal about how this thought showed up in her own love life—even when she met her now-husband—and shares the powerful mindset shifts and tools you need to bust through this myth for good. Inside: ✨ Why this belief is so common for late bloomers ✨ How it blocks you from trusting healthy connection ✨ The ACK tool to start rewiring your brain for worthiness ✨ Real-life reframes to help you believe, “Of course they like me!” Listen now and start stepping into your main character energy—for love, dating, and beyond. Work with Lily: 🔗 Learn about her signature program, Main Character Dating: datebrazen.com/waitlist 🔗 Book: Thank You More Please 🔗 YouTube Channel 🔗 Tiktok 🔗 Instagram
Think dating apps are the only way to find love—but secretly hate them? Same, friend. In this episode of the Date Brazen Podcast, I’m sharing my complete, no-BS guide to using dating apps in a way that protects your sanity and increases your chances of finding the right relationship. Inside, you’ll learn: → Why deleting and re-downloading apps keeps you stuck → The exact rules for stress-free swiping (hint: 20 minutes a day) → How to write a profile that qualifies the right people—and filters out the wrong ones → Why you should never, ever try to be “chill” in your dating bio Plus, I’m revealing my personal photo rubric and conversation starters that actually spark connection. Dating apps are flawed—but with this episode, you’ll know how to make them work for you. Work with Lily: 🔗 Learn about her signature program, Main Character Dating: datebrazen.com/waitlist 🔗 Book: Thank You More Please 🔗 YouTube Channel 🔗 Tiktok 🔗 Instagram
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 to move through dating fear with self-compassion, community, and a whole lot of self-trust. Because here’s the truth: fear is normal, and it doesn’t have to be in the driver’s seat. You don’t have to be fearless to find love—you just have to be willing to take messy, brave action toward what you want. Hit play, and let’s reframe your fear into power. Takeaways: ✨ Self-compassion isn’t just nice; it literally helps your body handle stress better. ✨ Feeling afraid to date? That’s human. You’re not alone. ✨ Messy action beats overthinking every time. ✨ The right person won’t need you to perform or say the perfect thing. ✨ If you desire more, it’s because it’s possible for you. Let’s go get you what you want. 💫 Get your free Essence Based Preferences Guide here. Work with Lily: Get Lily’s Book, Thank You More Please HERE. Follow Lily on Instagram and Tiktok. Subscribe to Lily’s Youtube channel HERE.
This episode is your mid-year reset, late bloomer style. Whether you've been dating with no luck, stuck in swipe fatigue, or haven't dated in 15 years, this seven-step feminist dating plan is your guide to attracting the best relationship of your life. In this replay of one of our most popular trainings, you’ll learn: ✨ How to create your Essence-Based Preferences to vet potential dates ✨ The IRL dating plan that actually works (even if you're socially anxious) ✨ What to say on dating apps and how to write a profile that’s magnetic AF ✨ And why what you want isn’t too much—it’s the key to finding the right match 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 You've got this—and I’ve got your back.
In this vulnerable and wisdom-packed episode, Lily sits down with Liz, a former Main Character Dating client, to talk about what it really takes to come back to yourself after a heartbreaking, sudden breakup—and how that healing work can lead to the most aligned love of your life. Together, they discuss: Why we feel “behind” in dating (especially as queer late bloomers) The emotional labor we carry as single people and how to release it How to trust yourself again after a breakup or identity shift The shame-desire cycle and how to break it Liz’s journey coming out later in life and finding queer love with deep emotional resonance What self-trust really looks like after pain Whether you’re newly single, starting to date again, or exploring your sexuality later in life—this conversation will meet you with compassion, truth, and the reminder: you’re not too late, and you don’t have to settle. Work with Lily: 3 Steps to Attract the Right Partner as a Late Bloomer If you’ve felt behind in dating, this free training is for you. Learn how to: Release embarrassment and claim what you really want Attract dates without overthinking or scarcity Build a joyful, unbothered dating strategy rooted in feminist self-trust RSVP here- https://www.datebrazen.com/training 🔗 Learn about Main Character Dating: datebrazen.com/waitlist 🔗 Book: Thank You More Please 🔗 YouTube Channel 🔗 TikTok 🔗 Instagram
Today's podcast episode is a coaching session with Michelle. She's in her 50s, divorced after a 24-year marriage, and getting back into dating after being with one person her whole adult life. In this raw and powerful coaching session, we unpack the overwhelm of dating apps, the anxiety of being “naive,” and the pressure late bloomers feel to already know how dating is supposed to work. Michelle shares how: → Dating apps make her feel panicked in 3 minutes or less → She’s afraid she missed the memo on how to flirt or date → All she really wants is a partner to laugh with at a family campsite, but dating feels like an IMPOSSIBLE way to get there. We talk about self-compassion, letting go of judgment, and what it means to stop settling—not just for the wrong relationship, but for a miserable dating life. 📺 Or watch the video version on YouTube! (@datebrazen) Work with Lily: 🔗 Free Live Training on June 17th: datebrazen.com/lets-go 🔗 Learn about Main Character Dating: datebrazen.com/waitlist 🔗 Book: Thank You More Please 🔗 YouTube Channel 🔗 TikTok 🔗 Instagram
In this very first live coaching session on The Date Brazen podcast, you’ll meet Ellie—an amazing, big-hearted late bloomer who's never had a romantic relationship, and who thought dating was something she missed the memo on. Sound familiar? Together in this episode we explore: Why Ellie stayed on multiple 4-hour dates she didn’t even want to be on How to process feeling behind in your dating life The surprising strategy shift that gave Ellie permission to want what she wants How to practice self-compassion and build dating resilience in real time so you can put yourself out there and attract the right people If you’ve ever felt behind, unchosen, or like you’re "too late" to find what you want—this episode is for you. 🎉 And don’t miss Lily’s free live training: ✨ 3 Steps to Attract the Right Partner as a "Late Bloomer" ✨ on June 17, 2025. Sign up at datebrazen.com/lets-go Work with Lily: 🔗 Learn about her signature program, Main Character Dating: datebrazen.com/waitlist 🔗 Book: Thank You More Please 🔗 YouTube Channel 🔗 TikTok 🔗 Instagram
Does the idea of making the first move in dating make you feel awkward AF? You’re not alone. In this episode, I’m breaking down exactly how to shoot your shot as a late bloomer—without spiraling into self-doubt or waiting for someone else to make the first move. You’ll learn: ✅ The mindset shifts that make it easier to take bold action in dating ✅ Why making the first move 100% of the time is a game-changer for attracting the right relationship ✅ How to bounce back from rejection (without losing your confidence) Work with Lily: 🔗 Free Live Training on June 17th: datebrazen.com/lets-go 🔗 Learn about Main Character Dating: datebrazen.com/waitlist 🔗 Book: Thank You More Please 🔗 YouTube Channel 🔗 TikTok 🔗 Instagram
If you’ve ever feared that you're not attractive or desirable because it’s never happened before, this episode is a must-listen. Lily breaks down the internalized fears many late bloomers carry—and how to reframe those thoughts with compassion, context, and confidence using her signature ACK mindset tool (Acknowledge, Compassion, Kind Reframe). You’ll also get a powerful challenge to reconnect with your body and spark self-trust this week. 🎧 Prefer to watch? Head to YouTube for the full episode. 📆 And don’t miss Lily’s free live training on June 17th: 3 Steps to Attract the Right Partner as a Late Bloomer – save your seat now: datebrazen.com/lets-go Links + Resources: 📚 Buy Lily’s book Thank You More Please: datebrazen.com/book 💖 Work with Lily: datebrazen.com 🎥 YouTube Channel 📱 TikTok 📸 Instagram
If flirting feels awkward, forced, or like a foreign language—especially because you feel “behind” in dating—this episode is your new playbook. Lily breaks down her step-by-step approach to flirting IRL with courage and ease. You’ll learn how to strike up a conversation, gauge interest, and shoot your shot—without spiraling or second-guessing yourself. 📺 Want the visual breakdown? Watch it on YouTube: https://www.youtube.com/@datebrazen Don’t miss Lily’s FREE June 17th, 2025 training: ✨ 3 Steps to Attract the Right Partner as a Late Bloomer ✨ You’ll learn how to: ✔️ Release shame about being a late bloomer ✔️ Build rock-solid confidence in what you want ✔️ Start dating successfully this summer RSVP here: https://datebrazen.com/lets-go 📚 Grab Lily’s book Thank You More Please: https://www.datebrazen.com/book Follow Lily on: ✨ Instagram ✨ Tiktok Learn how to work with Lily: https://www.datebrazen.com
Are you a late bloomer wondering, “How the hell do I even start dating?” In this episode, Lily breaks down the exact 6-step roadmap to go from anxious and avoidant to confident and aligned in your love life. You’ll learn how to drop shame, claim your essence-based preferences, use dating apps with boundaries, and build your IRL dating strategy—messy and awkward and powerful. Here’s how to work with Lily: ✨ On Demand Training: 3 Steps to Attract the Right Partner as a Late Bloomer ✨ Buy her book: Thank You More Please: https://datebrazen.com/book ✨ Download the free "Create Your Essence-Based Preferences" Guide HERE Follow Lily on: ✨ Instagram ✨ Tiktok ✨ Youtube
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