

The Date Brazen Podcast
Lily Womble
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.
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.
Episodes
Mentioned books

Nov 28, 2023 • 28min
172. How to thrive during the holidays as a single badass
This week, Lily addresses questions she's gathered from her TikTok community, centered around navigating the holidays while single. She delves into the complexities of solo celebrations, sharing her hottest takes, fiercest encouragement, and spiciest support. Whether you're wondering how to handle prying relatives, seeking advice on thriving as a solo adventurer during the holidays, or craving solidarity, Lily's got you covered. Tune in for a dose of wisdom, a dash of humor, and a sprinkle of festive cheer as Lily guides you on thriving this holiday season as a single badass. Register HERE for the upcoming live training- Dec 7th, "How to thrive during the holidays as a single badass" Download the Free "Guide to Essence-Based Preferences" HERE.

Nov 21, 2023 • 37min
171. Money and your dating life: A conversation with financial therapist Aja Evans
Financial therapist Aja Evans joins Lily this week to discuss money and your dating life. The conversation is meant to inspire you to take up space in your financial life, challenge limiting beliefs, and prioritize relationships that align with your values and aspirations. Aja is a Licensed Mental Health Counselor who specializes in financial therapy. In this episode, she helps us understand the connection between emotions and money and explores the varying dynamics of partnerships and money. Episode Topics and Hot-takes: You don’t need to make yourself smaller to accommodate a potential partner's ego. Aja helps us understand how to move through financial shame. How to talk about money and finances on a date Links: Aja’s websiteAja on Instagram Show notes: http://datebrazen.com/blog/money-and-your-dating-life-with-aja-evans

Nov 14, 2023 • 40min
170. Decolonizing coaching and building self-trust with Shirin Eskandani
This week, Lily welcomes Shirin Eskandani to the podcast! Shirin is a former opera singer turned coach who, in this episode, opens up about her quest for fulfillment beyond external achievements. From navigating the challenges of dating to discovering the unexpected depth of inner work in coaching, Shirin shares the transformative power that led her to pursue coaching with a commitment to inclusivity and decolonized perspectives. Shirin shares her mission to diversify the coaching world, highlighting the need for more inclusive certifications. Lily and Shirin also dive into the concept of being "wholehearted," exploring themes of empowerment and the profound impact of coaching on personal and professional aspects of life. Listen in to hear this fantastic conversation that empowers self-discovery and self-trust. Hot-takes from this episode: Nothing outside of you will ever make me feel fulfilled or enough. That is something you have to be working on yourself. “It isn't just about my dating life. It isn't just about my work. How we do one thing is usually how we do all or most things.” Decolonizing is about questioning and getting curious about what you value and believe and whether those values and beliefs were handed to you from society or family. Then, decide that you get to choose what you value and believe and how you want to move forward. Links: One-on-One Coaching with LilyWholehearted Coaching: The PodcastWhole Hearted Coaching Certification Shirin on Instagram @wholeheartedcoaching Wholehearted Coaching Certification Program on Instagram @wholeheartedcertification Show notes: http://datebrazen.com/blog/decolonizing-coaching-and-building-self-trust-shirin-eskandani

Nov 7, 2023 • 47min
169. Harnessing your fears to step into your power with Farnoosh Torabi
Farnoosh Torabi joins Lily on the podcast this week! Farnoosh is a leading financial expert, host of the So Money podcast, and author of So Money, Psych Yourself Rich, and When She Makes More. In this episode, she discusses the teachings and insights from her new book A Healthy State Of Panic, Follow Your Fears To Build Wealth, Crush Your Career, And Win At Life. The book (and this episode) illustrates how fear can be your superpower in this heartfelt and clever guide to maximizing your success to live richer and happier. Lily also parallels the topics in Farnoosh’s book (related to fear) and how they can apply to the dating world. This is a fun, thoughtful, and heartfelt episode! Featured Conversation Topics: The difference between harnessing fear and indulging it? How to build a healthy relationship with fear The fear of rejection, loneliness, and exposure in dating As you listen, think about one action step you can take to move with your fear in a more healthy manner. Links: One-on-One Coaching with LilySo Money with Farnoosh TorabiA Healthy State of Panic, Farnoosh Torabi Show Notes: http://datebrazen.com/blog/harnessing-your-fears-with-farnoosh-torabi

Oct 31, 2023 • 48min
168. Healing, Hilarity, and Main Character Energy with author and TikToker Devrie Brynn Donalson
Get ready for a healing and hilarious episode! Lily introduces a special guest who radiates "Main Character Energy" in every aspect of her life. Devrie Brynn Donalson, the creative force behind the book, "You're Gonna Die Alone (& Other Excellent News)," unpacks her life-altering choices and journey. Devrie reflects on her inspiring journey to Scotland, her struggles with body image, and her pursuit of self-discovery. Lily and Devrie also delve into the compelling dialogue on personal growth and societal pressures. This episode is a rollercoaster of emotions, filled with humor, wit, and authentic storytelling. Don't miss this captivating conversation on the Date Brazen podcast! Featured Conversation Topics: Devrie shares the story of her bold decision to move to Scotland, a journey sparked by friendship breakups and a quest for self-discovery. Discover how Devrie makes life-altering decisions by imagining herself as the main character in her story, ultimately guiding her choices. The challenges of growing up in a culture fixated on body size and appearances and the impact it can have. Devrie's thoughts on the fear of being unlovable and how it influenced her choices and relationships. Links: One-on-One Coaching with LilyDevrie on Instagram & TikTok @devriebrynn You’re Gonna Die Alone (& Other Excellent News) Show link: http://datebrazen.com/blog/healing-hilarity-and-mce-with-devrie-donalson

Oct 24, 2023 • 43min
167. How to go from dead-end dating to only great dates with Brazen Breakthrough Client Michelle
This week, we're breaking down the journey to creating a dating life that's joyful, boundary-filled, and confidently your own. Michelle, a Brazen Breakthrough client, joins Lily for a fantastic conversation about how she went from dead-end dating to only great dates. Plus, hear how she learned to stop compromising her desires and find joy in all areas of her life. 🔥 Hot-Takes Alert! 🔥 Ever wondered, "What if I do this thing and it doesn't work for my love life?" We're diving into that fear and breaking it down. It's time to stop compromising your desires. Learn how to permit yourself to want what you want without apology. The "shoulds" – we all know them, but how do we escape their grasp when it comes to dating, life, and love? 🗨️ Michelle reminds us, "Dating feels less like a 'life or death thing' when you are having fun in other areas of your life." Links: ✨Join The Brazen Breakthrough Now! ✨ The doors to Brazen Breakthrough close on Oct 27th at 11:59 pm EST

Oct 19, 2023 • 2h 15min
Bonus: Create a Confident and Joyful AF Dating Life
Lily is bringing you a bonus episode! If you missed her free live training, Create a Confident and Joyful-as-Fuck Dating Life, or want to hear it again - you’re in luck! Today, Lily is sharing the entire training on the podcast. This training will help you build confidence, practice self-compassion and self-trust, and ease in your dating life. In this episode, you’ll learn: How to create a fiercely confident as-hell dating life (without the overwhelm, anxiety, and burnout). How to be completely dating-app optional and find juicy dates in person The anxiety-relieving plan of action that will make the right relationship inevitable. You’ll also get a special invite to join us in my signature program, The Brazen Breakthrough. This bonus replay is jam-packed with Q&As that cover many dating questions and questions about what it's like being a part of The Brazen Breakthrough. There is so much good stuff - this is such an informative (and fun) episode! Links: ✨Join The Brazen Breakthrough Now! ✨ The doors to Brazen Breakthrough close on Oct 27th at 11:59 pm EST

Oct 17, 2023 • 52min
166. How to stop panic dating with Brazen Breakthrough client Anna
Anna joins Lily to share her experience in the Brazen Breakthrough (Lily’s proven feminist as fuck group coaching program). In this episode, Anna shares what led her to join the Brazen Breakthrough and how it helped her feel supported, get unstuck, and stop panic dating. This episode is going to be so freaking good! We’re excited for you to listen to Anna's story. If it resonates and you are listening on the day it airs - October 17th - join Lily for a live free training. In this live free training, Lily will teach you how to be dating app optional, how to create a dating life with more ease, joy, and power, and how to make the right relationship inevitable. You’ll also learn about the Brazen Breakthrough. It’s going to be an amazing time. Find all the links below; we hope to see you there! Hot-takes from this episode: How to approach finding a partner in a way that is sustainable for your mental health and move away from panic dating “You’re for the few and not for the many.” When you learn the skill of self-advocacy and step deeper into agency in your love life, what you believe is possible is inevitable. Anna shares how understanding what she wanted in her dating life led to her going on a great date! Links: Join Us TONIGHT, October 17th, for the Free Live Training → ✨ Creating a Confident and Joyful-as-fuck Dating Life That Makes the Right Relationship Inevitable ✨ The Brazen Breakthrough Show link: http://datebrazen.com/blog/stop-panic-dating

Oct 10, 2023 • 24min
165. How to start dating as a "late bloomer"
If you think you are “behind” in your dating life, this episode is for you. Lily is going to teach you how to start dating with confidence. Your “lack of romantic experience” is not a dealbreaker for finding love. If you’ve never been in a relationship… If you’ve never been kissed… If you’ve never had sex… There’s ZERO wrong with where you’ve been. There’s only the invitation waiting in front of you to build what you want NOW and move forward. Don’t NOT go to the party because you’re afraid you’re too late. The best stuff happens at a party once it’s started, anyway. Hot-takes from this episode: “If you believe that your lack of experience is embarrassing, then that is holding you back from finding love on your terms.” “The idea of being a late bloomer rushed me into dating to “fix it.” “Your assumed late-bloomer status does not have to be your identity.” Neutralize your dating history with self-compassion. History does not mean anything about what is possible. Build a strategy that honors your power Bring on a community that supports the hell out of you Links: Join Us on October 17th for Free Live Training → ✨ Creating a Confident and Joyful-as-fuck Dating Life That Makes the Right Relationship Inevitable ✨ Show Link: http://http/datebrazen.com/blog/start-dating-as-a-late-bloomer

Oct 3, 2023 • 21min
164. How to create an in-person dating life if you're scared to start
This week’s episode is all about in-person dating! Lily is sharing step-by-step how to build confidence and become the version of yourself who approaches people in person with empowered action. This in-person dating lesson isn't meant to make you micromanage; it's to help you SHOW UP for your desires. The advice inside this episode will help you approach somebody in person in the next 30 days. You’ve got this, and Lily and the entire Date Brazen community have your back. Episode Hot-takes: Permit yourself to be in progress, and stop self-blaming for being “bad” at dating. “How do you get out of self-blame? By practicing self-compassion.” “Commit to getting messy and practicing. You are not good at in-person dating because you haven’t practiced yet.” What if you just took one action step today? Celebrate yourself! “Self-celebration is an in-person dating strategy. Celebrate every time you practice in-person dating!” Links: SAVE YOUR SPOT for Creating a Confident and Joyful-as-fuck Dating as a Burnout Feminist Badass Show notes:http://datebrazen.com/blog/approach-in-person-dating-even-if-youre-scared