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PODCAST

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

society & culture relationships

All Episodes

01:05:51

242. “I Want Love—But I’d Like to Skip Dating,...

The Late Bloomer Show ·

2025/06/17

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

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01:02:17

241. “I Stayed for a 4-Hour Date I Didn’t Want to Be...

The Late Bloomer Show ·

2025/06/10

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

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38:08

Episode Spotlight: How to Shoot Your Shot (Even If...

The Late Bloomer Show ·

2025/06/03

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

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13:04

240. Late Bloomer Series: Feeling undesirable? Here’s...

The Late Bloomer Show ·

2025/05/27

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

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24:44

239. Late Bloomer Series: How to Flirt

The Late Bloomer Show ·

2025/05/20

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

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34:11

238. Late Bloomer Series: How to Start Dating (If...

The Late Bloomer Show ·

2025/05/13

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

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27:06

237. Late Bloomer Series: How to Tell a Date You've...

The Late Bloomer Show ·

2025/05/06

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: https://datebrazen.com/book Get on the waitlist for Main Character

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01:17:30

236. How To Stop People Pleasing (And Build A...

The Late Bloomer Show ·

2025/04/29

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 people-pleasing really is (it’s deeper than being “too nice”) Why releasing people-pleasing is so damn hard (and why it’s not your fault) How to start rebuilding

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56:25

235. You Deserve More Than “Fine”- Katie’s Story of...

The Late Bloomer Show ·

2025/04/22

RSVP 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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39:56

234. Go From Shrinking To Confident Main Character...

The Late Bloomer Show ·

2025/04/15

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 isn’t just for you — it’s for your community, too - How to take

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54:17

233. How Jackie Went From Burnt Out Background ...

The Late Bloomer Show ·

2025/04/08

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. RSVP for my free training on April 23rd, 2025: https://www.datebrazen.com/joyful-life

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36:49

Episode Spotlight: My Qualifying/Disqualifying...

The Late Bloomer Show ·

2025/04/01

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.datebrazen.com/book ✨ Get our free, on-demand training: 3 Steps to

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17:34

Episode Spotlight: "How Can I Stop Being Lazy In My...

The Late Bloomer Show ·

2025/03/25

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 results in dating. ✨ How to do the most POWERFUL tiny steps in dating to get the biggest results. ✨ Why embracing self-care and giving

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32:29

Episode Spotlight: How to Bless and Release The Wrong...

The Late Bloomer Show ·

2025/03/18

In 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 mindset shift that will help you actually move on. ✨ Why setting boundaries is a radical act of self-love. ✨ How to embrace abundance instead of

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16:37

Episode Spotlight: Where Do I Even START With Dating?

The Late Bloomer Show ·

2025/03/11

In 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 pressure). ✨ Why your thoughts are not always facts—and how to shift them. ✨ The "Thank You More Please" challenge to clarify what you really want. ✨ How to

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23:48

Episode Spotlight: Owning Your Preferences is a...

The Late Bloomer Show ·

2025/03/04

If 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 Essence Based Preferences Guide" HERE ✨ Order my book, “Thank You, More Please”: https://www.datebrazen.com/book ✨ Get my FREE training, “3 Steps to Attract

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49:50

232. Sexual liberation, self-permission, and getting...

The Late Bloomer Show ·

2025/02/25

This 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 episode is your permission slip to do it your way. 🎧 Listen now and start reclaiming your power! Brandon Kyle Goodman (they/them) is a writer, actor, and

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18:11

231. How To Shoot Your Shot 100% of The Time

The Late Bloomer Show ·

2025/02/18

If 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 enjoy the process (yes, really). Here’s what you’ll learn: 💥 Why I DON'T believe in the advice "If he wanted to he would" 💥 Why "shooting your shot"

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23:04

230. How To Get Over The Fear Of Dating

The Late Bloomer Show ·

2025/02/11

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

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22:50

229. Flirting 101: My 3-Step Process to Flirt, Know...

The Late Bloomer Show ·

2025/02/04

In 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 human (not a dealbreaker). 💡 With 10 seconds of courage, you can change the course of your dating life. In this episode, we'll dive into: ✔ What IS

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