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The Date Brazen Podcast

The Date Brazen Podcast

By: Lily Womble
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About this listen

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 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. Personal Development Personal Success Relationships Social Sciences
Episodes
  • 238. Late Bloomer Series: How to Start Dating (If You've Never Dated)
    May 13 2025

    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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    34 mins
  • 237. Late Bloomer Series: How to Tell a Date You've Never Been In A Relationship
    May 6 2025

    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 Dating: https://www.datebrazen.com/waitlist

    Learn how to work with me: https://www.datebrazen.com/

    Follow me on

    ✨ Instagram

    ✨ Tiktok

    ✨ Youtube

    🎧 Full show notes + transcript at: https://datebrazen.com/podcast

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    27 mins
  • 236. How To Stop People Pleasing (And Build A Stupidly Joyful Life)
    Apr 29 2025

    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 self-trust in small, powerful ways

    • Three practical steps you can take today to enter your Main Character Era

    If you’re feeling the heart pull to live bigger, braver, and more joyfully — the doors to Main Character Life are open right now.

    🎟 Apply for Main Character Life (closing May 2!): HERE

    This is my six-month small group mastermind where you'll learn to:

    • Release people-pleasing as your default

    • Build rock-solid self-trust

    • Take massive, messy action toward your dreams

    • Create a stupidly joyful life that finally feels like yours

    Work with Lily:

    Learn how to work with me: https://www.datebrazen.com/

    Order my book, “Thank You, More Please”: https://www.datebrazen.com/book

    Follow me on

    ✨ Instagram

    ✨ Tiktok

    ✨ Youtube

    Show More Show Less
    1 hr and 18 mins
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