
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

May 14, 2024 • 47min
196. How Julianne attracted a feminist man and is building an epic partnership
If you date men and have ever wondered if the feminist partner you want exists, this episode is for you! This week, we explore the Brazen Breakthrough tools, mindset shifts, and strategies that Client Julianne applied to attract a feminist man and is now building an epic partnership. Lily and returning guest Julianne dive into the evolution of Julianne's love life since her last podcast appearance. They discuss the importance of self-trust, essence-based preferences, and the empowering shift from muscling through dating to co-creating a fulfilling relationship. This is a must-listen episode for anyone wondering if their ideal partner exists. We get into: How Julianne used the Brazen Breakthrough tools to attract a proactive, feminist man her way How attraction is an essence-based preference Co-creating a relationship with someone can be fun! Links: Lily’s book, Thank You More Please, is available for preorder right now and you can grab it and the preorder bonuses with this link! The Brazen Breakthrough Show notes: http://datebrazen.com/blog/how-julianne-attracted-a-feminist-man

May 7, 2024 • 33min
195. How to date if you have social anxiety
How can you date with social anxiety? This week Lily gives us all a much-needed pep talk and lays out a roadmap for dealing with social anxiety while trying to find love. From her own experiences, she drops some wisdom on showing yourself self-compassion and bouncing back stronger, all to create a dating life full of joy! ✨ You’ll learn: Go S.O.F.T. Practice self-compassion, own your needs, feel your feelings, thoughts not facts. “Messy progress forward is okay.” “Feelings your emotions is reparenting yourself.” The goal is never to feel anxious again; it’s to increase your capacity for resiliency so that when you feel anxious, you know what to do about it. Even if you have anxiety, you can still make massive changes in your life. Links: Free Training With Lily Womble TODAY, May 7th! 3 Steps to Attract the Right Partner With a Joyful as Fuck Dating Life The Brazen Breakthrough Lily’s book, Thank You More Please, is available for preorder right now and you can grab it and the preorder bonuses with this link! Psychology Today Dr. Kristin Neff Burnout: The Secret to Unlocking the Stress Cycle, Emily Nagoski, Amelia Nagoski Show notes: http://datebrazen.com/blog/how-to-date-with-social-anxiety

Apr 30, 2024 • 51min
194. From attracting emotionally unavailable men to attracting the most proactive, loving partner with client Mishi
Is it possible to attract proactive, loving partners? Yes! Mishi joins Lily to share her story of how she went from attracting completely emotionally unavailable men to attracting the most proactive partner. They dive into Mishi’s journey - it's total empowerment vibes! From dealing with consecutive breakups to finding self-trust with the help of personal reflection and the Brazen Breakthrough program, Mishi's story is a roadmap to living your best life. They get into the nitty-gritty of self-growth and that ah-mazing moment when you start trusting your gut to attract the kind of connections you desire. We get into: How Mishi learned to rediscover herself after enduring two challenging breakups The most significant difference in Mishi’s dating life today The act of listening to your intuition and embracing self-trust Some of the Brazen Breakthrough strategies that Mishi found helpful, including Bless-Release and the Dating Feedback System What it’s like to be in a proactive and loving relationship Links: Free Training With Lily Womble on May 7th! 3 Steps to Attract the Right Partner With a Joyful as Fuck Dating Life Lily’s book, Thank You More Please, is available for preorder right now and you can grab it and the preorder bonuses with this link! Show notes: http://datebrazen.com/blog/attracting-proactive-loving-partner

Apr 23, 2024 • 24min
193. Owning your preferences is a feminist act
In this episode, we dive deep into the empowering world of Essence-Based Preferences (EBPs). EBPs aren't just preferences but a revolutionary act of self-ownership and empowerment. It's all about embracing what you want without any apologies or self-judgment. This episode is about defining your desires and creating a bold action plan that aligns with your deepest desires. Join us as we revolutionize the dating game and empower ourselves to attract nothing but the best. Let's do this! 🔥 You’ll learn: Let's get one thing straight - it's your absolute right to choose who you want to be with Owning your EBPs is a feminist act. It's about flipping the script and putting yourself at the center of your dating universe. Bye-bye, antiquated norms! EBPs are the answer to attracting the best partner in your life Under vs. Over-Functioning Preferences: It's all about finding that sweet spot. Too little? You're selling yourself short. Too much? You're losing sight of your true desires. Links: Lily’s book, Thank You More Please, is available for preorder right now and you can grab it and the preorder bonuses with this link! Free Training With Lily Womble on May 7th! 3 Steps to Attract the Right Partner With a Joyful as Fuck Dating Life Creating Your Essence-Based Preferences Comprehensive Guide Show notes: http://datebrazen.com/blog/owning-your-preferences

Apr 16, 2024 • 50min
192. From hard breakups to a joyful AF dating life with client Danielle
Ever wondered how to bounce back after a significant breakup? This week, Danielle, one of our Brazen Breakthrough clients, opens up about her journey through healing and self-discovery. She reflects on her past relationships and how she redefined her intentions and boundaries to rediscover herself. This episode is a testament to self-compassion, offering dating insights and profound thoughts on personal growth and finding joy. We get into: How Danielle realized she wasn’t getting what she truly wanted in dating Breaking patterns of complacency and shrinking away from what you want Shifting from second-guessing yourself to trusting your intuition The lessons and takeaways from Brazen Breakthrough that help Danielle show up and support others (and herself) The impact on Danielle’s dating life, including creating stronger boundaries and dating with intention The act of reclaiming your sense of Self Links: Free Training With Lily Womble on May 7th! 3 Steps to Attract the Right Partner With a Joyful as Fuck Dating Life The Brazen Breakthrough Waitlist Show notes: http://datebrazen.com/blog/hard-breakups-to-joyful-af-dating-life

Apr 9, 2024 • 52min
191. Big Dating Energy with Therapy Jeff
Did you know you’re most attractive when you are authentically you? Well, that’s precisely what this week’s guest, Therapy Jeff, says! Jeff Guenther, known as Therapy Jeff, joins Lily for a conversation about the intricacies of modern dating, the evolution of therapy in the age of social media, and authentic self-expression. Therapy Jeff's insights on modern dating and mental health are a breath of fresh air. In a world saturated with dating advice and unrealistic expectations, his book, 'Big Dating Energy,' offers a refreshing perspective: that lasting love stems from embracing one's authentic self. In an era of self-doubt and comparison, Jeff reminds us that we are inherently lovable and deserving of genuine connection. We get into: What dating advice/problems/framing Jeff’s book, Big Dating Energy, aims to solve Addressing beliefs like “It’s my fault, or I’m not good enough.” The idea of feminine and masculine energy and the notion of “not being in your feminine enough.” Cognitive overload and how to get in touch with your intention when using social media or dating apps Links: Lily’s book, Thank You More Please, is available for preorder right now and you can grab it and the preorder bonuses with this link! Jeff’s book, Big Dating EnergyTherapy Jeff’s websiteTherapy Jeff on TikTokTherapy Jeff on Instagram Show notes: http://datebrazen.com/blog/big-dating-energy-with-therapy-jeff

Apr 2, 2024 • 22min
190. Shooting your shot challenge
Nervous about sending a DM to a cutie or asking somebody on a date? If you answered yes, then this week’s episode is for you. Lily explores the mindset shifts and practical steps needed to step out of your comfort zone and shoot your shot! Whether it's sliding into those DMs or asking someone out face-to-face, this episode is your guide to overcoming the nerves and getting what you want. Grab your pen and paper, and get ready to take notes. By the end of this episode, you'll be ready to revolutionize your approach to dating. Asking for more of what you want leads to more of what you desire. This episode is part strategy and part hype. You’ve got this and Lily’s got your back! You’ll learn: “The only thing separating you from getting what you want is your willingness to ask for it out loud.” Shooting your shot is about giving your permission to be the main character of your story How to get over the paralyzing fear of asking for what you want The role permission, self-trust, and courageous action play when shooting your shot It’s not about doing it perfectly. It’s about doing the thing. Your job is to pursue what you want, trust your desire, and take messy, courageous action toward those desires. Links: Pre-order Lily’s upcoming book, Thank You, More Please! Show notes: http://datebrazen.com/blog/shooting-your-shot-challenge

Mar 26, 2024 • 41min
189. Body liberation, Dating, and Black Joy with Jessica Wilson, MS. RD.
We're diving into the intersection of body liberation, white supremacy, and dating with the incredible Jessica Wilson, MS. RD. As the author of "It's Always Been Ours: Rewriting the Story of Black Women's Bodies," Jessica brings her expertise as a dietitian, storyteller, and community organizer to the forefront. Together, Lily and Jessica explore the interplay between shrinking our bodies in response to white supremacy and shrinking our desires, unpacking how Black and Brown women can reclaim their body liberation and prioritize care in the dating world. We get into: The interplay between shrinking our bodies in response to white supremacy and shrinking our desires Jessica’s view on how Black and Brown women can reclaim their body liberation and prioritize care in the process of putting themselves out there in dating “Your body is not the problem,” Spaces to seek out body liberation support and community How do we set boundaries for those, not on the same page or path with body liberation? Jessica’s favorite moment of Black Joy since writing her book Links: Pre-order Lily’s upcoming book, Thank You, More Please! Jessica’s website Jessica’s book, It’s Always Been Ours Show notes: http://datebrazen.com/blog/body-liberation-dating-and-black-joy-with-jessica-wilson

Mar 19, 2024 • 47min
188. How to glow in the f*cking dark with Tara Schuster
Trigger warning: This episode contains mentions of suicide. You are worthy. If you need more convincing, this week’s episode is not to miss. Tara Schuster, author of Glow in the F*cking Dark: Simple Practices to Heal Your Soul from Someone Who Learned the Hard Way, joins Lily on the show! In the book and throughout this conversation, Tara shares practical steps to liberate yourself from emotional suffering, heal your past, and own your future. Tara served as Vice President of Talent and Development at Comedy Central, where she was the executive in charge of critically acclaimed shows such as the Emmy and Peabody Award–winning Key & Peele, the Emmy® Award winning @Midnight (now After Midnight on CBS) amongst many others. Over the last twelve years, Tara has spent her “10,000 hours” on the other side of the couch studying philosophy, therapies, religions, and even memoirs of the adults she admired so that she could find emotional freedom from a neglectful and psychologically abusive childhood. Lily and Tara get into: “It’s not magic having a different life. You can’t sit back and wait for it to happen; you have to work for it.” What inspired Tara to write Glow in the F*cking Dark and its mission: the practice of finding your essential self. Thoughts and advice for overcoming lack of self-trust and self-criticism Tara shares her self-compassion party trick! How Tara got to a place to make decisions rooted in her own best interest, especially in dating Links: Pre-order Lily’s upcoming book, Thank You, More Please! Get Instant Access to Creating a Confident and Joyful-as-fuck Dating Life That Makes the Right Relationship Inevitable Glow in the F*cking Dark, Tara Schuster Tara’s website Tara on Instagram The Loveland Foundation Show notes: http://datebrazen.com/blog/glow-in-the-dark-with-tara-schuster

Mar 12, 2024 • 32min
187. All about speed dating with Maxine Simone Williams, founder of We Met IRL
Are you tired of swiping left and right, endlessly scrolling through dating apps, hoping to find a genuine connection? In this episode, Lily welcomes Maxine Simone Williams, the creative powerhouse behind a New York City-based initiative, We Met IRL, reshaping how people meet and mingle, diving deep into the world of speed dating and real-life encounters. Maxine shares her journey of building We Met IRL and why her speed dating events make dating fun again. Plus, Lily and Maxine tackle common dating concerns like handling rejection at speed dating events or overcoming social barriers for the shy and introverted. Tune into this episode as Lily and Maxine journey beyond the screens, where in-person connections thrive. They get into: Dating assumptions that these events challenge - making dating fun again! Are dating apps the only way people are meeting people? Instagram vs Phone Number: what to give out when meeting IRL What if nobody chooses me at speed dating How to go about meeting people in real life or speed-dating if you are shy or introverted Links: Pre-order Lily’s upcoming book, Thank You, More Please! Get Instant Access to Creating a Confident and Joyful-as-fuck Dating Life That Makes the Right Relationship Inevitable We Met IRL on TikTok @wemetirl We Met IRL on Instagram @wemetirl Show notes: http://datebrazen.com/blog/speed-dating-with-maxine-simone-williams