The Late Bloomer Show
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.
Episodes
“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 desir...
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 dangero...
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...
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)
→ H...
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...
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 (e...
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:
- Read more
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 f...
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...
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...
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 ...
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?
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 S...
In this kickoff to the Late Bloomer Series, Lily gets real about how to tell a date you’ve never been in a relationship—without spiraling, oversharing, or self-abandoning. If you’ve ever felt behind in love, this episode will help you embrace your story, communicate with confidence, and stop making your dating history mean something it doesn’t.
✨ Grab Lily’s book Thank You, More Please + get the bonus Podcast Listening Guide: htt...
Are 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...
In 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 people-pleasing, perfectionism, and "best friend identity"
- Why healing burnout is...
She 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 craving your own main character energy moment, this one's for you.
In 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 truly desire.
Links:
✨ Order Lily's book, “Thank You, More Please”: https://www....
In 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 get you better r...
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