
The Date Brazen Podcast
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.
Latest episodes

Feb 18, 2025 • 18min
231. How To Shoot Your Shot 100% of The Time
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 We’re flipping the script on outdated dating rules that keep you passive and stuck.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" is a dating superpower 💥 The confidence shift that makes asking for what you want feel good This episode is all about bold moves and big results. Listen now and start shaping your love life on your terms. ✨ Main Character Dating is now open for enrollment. Join now. ✨ Links: Get Lily’s Book, Thank You More Please HERE. Follow Lily on Instagram and Tiktok. Subscribe to Lily’s Youtube channel HERE.

Feb 11, 2025 • 23min
230. How To Get Over The Fear Of Dating
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. This episode is brought to you by my free, live SHOOT YOUR SHOT CHALLENGE: From "late bloomer" to confident dater in 5 days ✨ Links: Get Lily’s Book, Thank You More Please HERE. Follow Lily on Instagram and Tiktok. Subscribe to Lily’s Youtube channel HERE.

Feb 4, 2025 • 23min
229. Flirting 101: My 3-Step Process to Flirt, Know If Someone’s Into You, and Ask Them Out with Ease
Flirting isn’t just for the naturally charming; it’s a skill anyone can learn! Discover how awkwardness is merely a sign of being human, not a dealbreaker. With just 10 seconds of courage, you can transform your dating life. Explore a simple three-step process that makes flirting feel effortless and natural. Plus, learn how to become rejection-proof and practice strategies to boost your confidence in tricky situations. Get ready to stop overthinking and start making connections!

Jan 28, 2025 • 55min
228. How to build confidence and agency in your dating life with Julie and Yue of the Dateable Podcast
Today on The Date Brazen Podcast, I'm talking to Julie Krafchick and Yue Xu-- dating and relationship experts and co-hosts of Dateable, one of the top podcasts on modern relationships, featured by The New York Times, HuffPost, and Oprah Daily. Tune into this episode to hear- Understanding your dating archetype can help you navigate relationships better. How to use their quiz in the Dateable book helps identify strengths and weaknesses in dating. How to use the "Sunday test" helps assess compatibility with a partner. What to expect with sexual chemistry in early dating-- can it develop over time, or do you need to expect "The Spark". And more! Julie Krafchick & Yue Xu are active daters turned dating insiders, and top influential voices of modern dating, relationships, and connection in the digital world. They’re the authors of How To Be Dateable and the co-hosts of the podcast Dateable, which has been named one of the top podcasts about modern dating and relationships by the New York Times, The Huffington Post, Oprah Daily, and more. They’re also the hosts and executive producers of the dating experiment show Exit Interview. Julie brings her background in human-centered design and qualitative research, while Yue shares her experience as a dating coach. Together you can find them at https://www.dateablepodcast.com/ and @dateablepodcast. Their book How to be datable comes out January 28th, 2025- TODAY! Get Julie and Yue's book at howtobedateable.com And learn about their work at https://www.dateablepodcast.com/ This episode is brought to you by my free, live SHOOT YOUR SHOT CHALLENGE: From "late bloomer" to confident dater in 5 days ✨ Links: Get Lily’s Book, Thank You More Please HERE. Follow Lily on Instagram and Tiktok. Subscribe to Lily’s Youtube channel HERE.

Jan 21, 2025 • 17min
227. You can't say the wrong thing to the right person, here's why
In this episode of the Date Brazen podcast, Lily unpacks her favorite piece of dating advice: You can't say the wrong thing to the right person. This 15 minute episode will free you from so much anxiety and worry in your dating life, so you have more time and energy to shoot your shot with confidence. Takeaways Dating is a microcosm of your hopes and fears. Self-care in dating enhances your quality of life. You cannot say the wrong thing to the right person. The right person will ask for clarification. Focus on a minimum viable audience in dating. You are for the few, not the many. Embrace the messiness of human connection. Your desires matter and are achievable. This episode is brought to you by my free, live SHOOT YOUR SHOT CHALLENGE: From "late bloomer" to confident dater in 5 days ✨ Links: Get Lily’s Book, Thank You More Please HERE. Follow Lily on Instagram and Tiktok. Subscribe to Lily’s Youtube channel HERE.

Jan 14, 2025 • 22min
Episode Spotlight: The complete dating detox guide
Enjoy this ep spotlight! This episode is brought to you by my free, live SHOOT YOUR SHOT CHALLENGE: From "late bloomer" to confident dater in 5 days ✨ Links: Get Lily’s Book, Thank You More Please HERE. Follow Lily on Instagram and Tiktok. Subscribe to Lily’s Youtube channel HERE.

Jan 7, 2025 • 44min
226. Creating your pleasure goals for 2025 with Susan Hyatt
In this episode of the Date Brazen podcast, Lily engages with Susan Hyatt, a master certified life coach, bestselling author, and TEDx speaker. They discuss Susan's mission to empower women through her Bear process, which emphasizes self-care, body wisdom, and breaking free from diet culture. The conversation explores the importance of creating a thriving environment, embracing pleasure, setting boundaries, and taking bold actions in midlife. As they approach the New Year, Susan shares insights on goal-setting and the significance of living a pleasure-centered life, encouraging listeners to overcome obstacles and embrace their potential. You'll learn: Susan Hyatt is a master certified life coach and bestselling author. The Bear process focuses on self-care and body wisdom. Environmental detox is crucial for creating a thriving space. Mindset work helps break free from diet culture. Pleasure is essential for healing and well-being. Setting boundaries is key to listening to your body. Embracing bold actions can lead to personal growth in midlife. New Year energy can be harnessed for goal-setting. Creating a pleasure-centered life enhances overall happiness. Obstacles are not greater than one's potential. This episode is brought to you by my free, on-demand training: 3 Steps to Attract the Right Partner as a “Late Bloomer" - RSVP HERE ✨ Links: Get Lily’s Book, Thank You More Please HERE. Follow Lily on Instagram and Tiktok. Subscribe to Lily’s Youtube channel HERE.

Dec 20, 2024 • 37min
Corrected Episode Spotlight: Late Bloomer guide to releasing worry + finding love
We're taking a break for the holidays (coming back Jan 7th, 2025) so enjoy this ep spotlight! This episode is brought to you by my free, on-demand training: 3 Steps to Attract the Right Partner as a “Late Bloomer" - RSVP HERE ✨ Are you feeling like a “late bloomer” in your dating life? In this Episode Spotlight of the Date Brazen Podcast, Lily busts nine myths commonly believed by “late bloomers” and shares practical steps to overcome them. With a focus on self-compassion, Main Character Energy, and the idea that dating is a learnable skill, Lily’s insights will shift your perspective and boost your confidence for joyful AF dating experiences. Feelings of shame and isolation often accompany those who feel behind in their love lives. This episode aims to help you shed the "late bloomer" identity, provide you with a sense of relief, and galvanize you to take action toward your deepest desires. You’ll learn how to: Embrace self-compassion and connection Distinguish between thoughts vs. facts Break free from societal (and patriarchal) dating norms and define your dating journey Heal and neutralize "late bloomer" conditioning Let go of those who aren't right for you with grace (bless and release!) Embrace your current stage in life and recognize that you’re whole as you are Redefine what “blooming” means to you Links: Get Lily’s Book, Thank You More Please HERE. Follow Lily on Instagram and Tiktok. Subscribe to Lily’s Youtube channel HERE.

Dec 10, 2024 • 35min
225. Your Complete 2025 Dating Plan: How to go from "late bloomer" to finding the right partner with confidence
In this episode of the Date Brazen podcast, Lily outlines a comprehensive seven-step dating plan for 2025, aimed at helping listeners create a joyful and fulfilling dating life. The plan emphasizes the importance of claiming desires, understanding essence-based preferences, and utilizing qualifying questions to find the right partner. Lily also discusses the significance of in-person dating, building a unique dating profile, and fostering community support to enhance the dating experience. The episode encourages listeners to take control of their dating lives and believe in the possibility of finding the right relationship. You’ll learn: Create a 2025 dating plan to make the right relationship inevitable. Claim what you want unapologetically in your dating life. Essence-based preferences help you define how you want to feel in a relationship. Qualifying and disqualifying questions are essential for vetting potential partners. In-person dating is still alive and can reduce reliance on dating apps. Build a dating profile that reflects your true self and essence-based preferences. The Thank You More Please challenge helps you recognize evidence of what you want in your love life. Community and support are crucial for a joyful dating experience. You are worthy of care and support in your dating journey. What you desire in love is possible, no matter your past experiences. This episode is brought to you by my free training: The Late Bloomer's Guide to a Confident Holiday Season. If you feel behind in your dating life in ANY way, my live, free training - The Late Bloomer's Guide to a Confident Holiday Season - will help you build a boundary plan for nosy relative's questions AND create a 2025 dating plan so you can BLOOM in your love life and attract the right partner with ease next year. Links: ✨ Register for The Late Bloomer's Guide to a Confident Holiday Season Get Lily’s Book, Thank You More Please HERE. Follow Lily on Instagram and Tiktok. Subscribe to Lily’s Youtube channel HERE.

Dec 3, 2024 • 20min
224. The Loneliness Fix
In this episode, Lily addresses the feelings of loneliness that can arise during the holiday season, especially for singles. She provides a three-step framework to help listeners navigate their emotions, emphasizing the importance of recognizing and acknowledging feelings, finding comfort and belonging, and choosing accessible positive thoughts. The conversation encourages self-compassion and resilience, offering practical advice for managing loneliness and fostering emotional well-being. You’ll learn: Recognize that loneliness is a hard moment and allow yourself to feel it. Emotional granularity helps in understanding and processing feelings. Self-soothing is essential for immediate comfort during loneliness. Reaching out to friends for support is crucial, even if they can't always respond. Creating a joy-building plan can help combat feelings of loneliness. Choosing accessible positive thoughts can shift your mindset. It's normal to feel lonely, especially during the holidays. Building resilience helps in managing future feelings of loneliness. You are worthy of love and support, regardless of your current situation. Your desire for connection is valid and can guide you towards it. This episode is brought to you by my free training: The Late Bloomer's Guide to a Confident Holiday Season. If you feel behind in your dating life in ANY way, my live, free training - The Late Bloomer's Guide to a Confident Holiday Season - will help you build a boundary plan for nosy relative's questions AND create a 2025 dating plan so you can BLOOM in your love life and attract the right partner with ease next year. Links: ✨ Register for The Late Bloomer's Guide to a Confident Holiday Season Get Lily’s Book, Thank You More Please HERE. Follow Lily on Instagram and Tiktok. Subscribe to Lily’s Youtube channel HERE.