
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

Nov 26, 2024 • 23min
223. Stressed about your dating life (and nosy questions) during the holidays? This is for you.
Stressed about your dating life (and nosy questions) during the holidays? This episode is for you. Yes, it’s that time of year—when relatives turn the holiday dinner table into a Q&A about your dating life. Lily is sharing how to respond to every nosy question from relatives - that you don’t want to answer! This is your guide to handling intrusive questions with confidence while staying grounded and true to yourself. Tune in for the best strategies for setting boundaries, saying “pass the peas” to nosy questions, and finding joy in the season without letting holiday stress or stress about your dating life get in the way. You’ll learn: How to spot the self-judgment trap Why self-compassion is the antidote to self-judgement Boundaries that slay: “You don’t owe them your story” becomes your mantra for keeping nosy questions in check Active self-care strategies that keep you thriving How to build a joy plan that sticks Links: ✨ Register for The Late Bloomer's Guide to a Confident Holiday Season Dr. Kristin Neff - SelfCompassion.orgSelf-care Activities for Women, Dr. Cicely Horsham-Brathwaite

Nov 19, 2024 • 41min
222. Healing from co-dependency, people pleasing, and perfectionism in your dating life with Victoria Albina
Ready to stop emotional outsourcing and start owning your worth in dating and beyond? If you’ve ever struggled with perfectionism, people-pleasing, or the exhausting cycle of codependency, this episode will feel like a deep exhale. Lily invites her brilliant friend and colleague, Victoria Albina, to explore what it takes to recognize the patterns that no longer serve you and break free from them—so you can finally show up as the main character in your life. Through an intersectional feminist lens, Victoria redefines the trope of codependency as “emotional outsourcing,” helping us see how it impacts not just our relationships but how we exist in the world. Together, they explore how our nervous system shapes our sense of safety and belonging, offering practical tools for reconnecting with self-love and grounding in our voice and intentions. We get into: How emotional outsourcing holds you back from being your authentic self The three essential emotional needs: safety, belonging, and worth An in-depth look at the nervous system and its role in fight, flight, fawn, and freeze responses Grounding techniques to help you reconnect with self-love and intention How to expand your capacity for feeling good, seen, and safe Links: ✨ Register for The Late Bloomer's Guide to a Confident Holiday Season Victoria’s website Victoria on Instagram Feminist Wellness Free meditations from Victoria for Date Brazen Listeners: VictoriaAlbina.com/lily Show notes: http://datebrazen.com/blog/healing-from-codependency-with-victoria-albina

Nov 12, 2024 • 14min
221. SOFT practice for tough times
I’m diving into how to care for yourself when life feels heavy. If you’re feeling drained or disappointed post-election—or really, after any tough experience—I’m here with a simple but powerful framework to help you reclaim your energy. In this episode, I’ll guide you through the SOFT practice: Self-compassion, Owning your needs, Feeling your feelings, and Thoughts, not facts. I’ll share practical tools, like Dr. Kristin Neff’s self-compassion meditation, to help you navigate challenging times with more grace. Whether it’s political stress or personal struggles, this episode is for anyone who needs a reminder that you deserve care, kindness, and support. Links: Free 5-minute self-compassion medication from Dr. Kristin Neff: https://self-compassion.org/self-compassion-practices/ The Loveland Foundation: https://thelovelandfoundation.org/

Nov 5, 2024 • 27min
Episode Spotlight: How to create your essence-based preferences
We’re airing a popular episode about claiming your essence-based preferences. Lily takes you through what essence-based preferences are, how they can transform your dating life, how to know if you’re being too rigid, and how to create them for yourself. This is a juicy episode you’ll want to come back to again and again! Hot-takes and How-tos from this episode: How do you know if you're being too "rigid" Essence-based preferences can apply to everything that you want Figure out how to get to the root of what you want by crafting your personal love-life vocabulary Links: Main Character Dating (formerly Brazen Breakthrough)Episode 26: How to navigate money in your dating life Follow Date Brazen on TikTok

Oct 29, 2024 • 22min
220. Slow burn vs. "The Spark"
Is the slow burn vs. spark debate holding you back from meaningful connections? Discover why curiosity is your best ally in dating and how it can clarify your feelings without overwhelming you. Learn to navigate personal preferences, trust your instincts, and let go of guilt when interest isn’t there. Instead of stressing over instant chemistry, focus on what truly matters in your romantic life. It's all about reframing your approach to make dating lighter, more fun, and more aligned with your desires!

Oct 22, 2024 • 23min
219. Election Dating Survival Guide
How do you date with intention and authenticity during an election season? You’re in luck! Lily is back with a special episode all about dating during the election. She explores how to navigate the heightened political climate with a boundaried, agency-filled plan to attract people who truly align with your values. Lily also shares tips on crafting a profile that reflects your values, managing tough discussions on dates, and knowing when to "bless and release." Get ready to learn how to vet dates based on political beliefs, set firm boundaries, and confidently steer conversations. You’ll learn: Understanding your boundaries and using essence-based preferences to define how you want to feel in a relationship How to incorporate your political values into your essence-based framework Best practices for bringing up politics in dating, including a reminder that “You cannot say the wrong thing to the right person.” Guidelines for dating during an election year, focusing on asking questions and prioritizing your emotional well-being Tips for including your political preferences in your dating profile Navigating heated political discussions during a date with grace Links: Pick up your copy of Thank You, More Please where all books are sold! 121. Dating Apps, AMA 135. How to create your essence-based preferences 162. The complete dating detox guide Show notes: http://datebrazen.com/blog/dating-during-an-election

Oct 15, 2024 • 31min
218. How to build main character identity (and stop being the "best friend")
Tired of playing the sidekick in your own life? Discover how to step into your power and claim your main character identity. Uncover the essence of main character energy and learn to take up space without fear of rejection. Explore the three essential skills of self-trust, permission, and messy action. Get inspired by the concept of taking bold steps with just 10 seconds of courage. It's time to embrace your imperfections and own your story—because you deserve to shine!

Oct 10, 2024 • 41min
BONUS: From paralyzed to launching her dream business with Mastermind client, Laura
Ready to crush it and take your dreams to the next level? This episode is ALL about that! We’re diving into Laura’s epic journey of leveling up her life, how she tapped into her MCE (yep, Major Character Energy), and broke down her big dreams into totally doable, bite-sized steps. And guess what? It worked! You’ll walk away feeling fired up, knowing that what you want is not only possible—it’s practically calling your name. This is your sign. Time to hit play, step into your power and go after what you want. We get into: Why action without community = dead-end vibes Laura’s raw, real talk on going through Main Character Life Mastermind during a tough time of grief How deep personal growth impacts everything, including your relationships The badass move from inaction to taking bold steps toward your biggest dreams Real talk: Confidence is EVERYTHING, and asking for what you want is the key to getting it How to create the support system you need to step onto that bigger stage in your life Links: Applications are open for the Main Character Life Mastermind!Laura’s websiteLaura on Instagram: @cheekylamiki @dispatcheddivorcee Show notes: http://datebrazen.com/blog/from-paralyzed-to-launching-her-dream-business-with-laura

Oct 8, 2024 • 55min
217. From comfort zone to a joyful, main character life with Mastermind client, Katie
Ready to stop playing small and start living big? This week, Mastermind client Katie shares how she embraced main character energy, stepped out of her comfort zone, and began living a joyful AF life! From ditching self-doubt to creating a social life that lights her up, Katie talks about the bold moves she made—like taking a sabbatical and going on solo adventures. It wasn’t easy, but she trusted herself enough to push past fear and take massive, rewarding actions. We get into: Breaking out of your comfort zone and going after what you want Building joy and meaningful social connections The power of self-trust and why it’s okay to invest in yourself Katie’s breakthrough journey and how she stopped playing small Don’t miss out on the chance to take control of your own story! Tune in and step into your main character energy. Links: RSVP for Take That Risk with Confident Main Character Energy Show notes: http://datebrazen.com/blog/comfort-zone-to-mce-with-katie

Oct 3, 2024 • 34min
Bonus: From burnout and overworking to setting boundaries with work and creating more space for joy and connections with Mastermind client, Juliet
Do you feel like you're burning the candle at both ends with nothing left for yourself? In this bonus episode, Lily chats with Juliet, a client from the Main Character Energy Mastermind, about how she transformed her life by setting boundaries at work and making room for joy and meaningful connections. Juliet’s story is all about taking back control and living fully to share how stepping into her power completely flipped her life around. From feeling burned out and isolated to creating deep friendships and a fulfilling love life, Juliet’s transformation is nothing short of inspiring. We get into: Truly believing in what you need and want unlocks the power to make aligned choices Identifying the key components and values of your ideal life is the first step toward living it How Juliet nurtured deeper connections with friends Finding more space for joy within all facets of Juliet’s life Overcoming internal criticism shifts your mindset from self-doubt to self-compassion Turning “dating sucks” into “I can make dating fun!” Links: RSVP for Take That Risk with Confident Main Character Energy Show notes: http://datebrazen.com/blog/from-burnout-to-boundaries-with-client-juliet