
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

Jul 23, 2024 • 37min
206. Late Bloomer guide to releasing worry + finding love
Are you feeling like a “late bloomer” in your dating life? This week, 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: ✨RSVP for Lily’s Free Training - 3 Steps to Attract the Right Partner as a “Late Bloomer” ✨ Lily’s book: Thank You, More Please Show notes: http://datebrazen.com/blog/late-bloomer-guide-to-releasing-worry

Jul 16, 2024 • 33min
205. Healing after a hard breakup with Ginger Dean
Ever wondered how to heal from a toxic relationship and truly thrive? Lily is joined by licensed psychotherapist Ginger Dean, the genius behind the book, Loving Me, After We. They dive into the journey of healing from toxic relationships, highlight the importance of self-soothing, and chat about how to rebuild self-trust. Ginger shares her personal and professional experiences, drops some wisdom on emotional recovery, and introduces her latest book, 'Loving Me After We,' packed with practical steps to go from hurting to thriving. They also get into what it means to be the 'green flag' in relationships and the power of self-care practices like yoga, massages, and somatic work. You’ll hear about: The inner work needed to become the best version of yourself, focusing on baseline levels of emotional availability and self-awareness. Practices and shifts, in addition to therapy, to come home to yourself and create a self-care plan after a hard breakup. Self-care practices and ideas to take care of your well-being. Building or rebuilding self-trust after being in a toxic or the wrong relationship. Links: ✨ Get Lily's Free Training: Creating a Confident and Joyful-as-fuck Dating Life That Makes the Right Relationship Inevitable ✨ Ginger’s website Ginger’s book, Loving Me, After We Episode link: http://datebrazen.com/blog/healing-after-a-hard-breakup-ginger-dean

Jul 9, 2024 • 31min
204. How to ask your friend to be a co-conspirator for your dating life (and what to do if they're not supportive)
Why do we always feel awkward asking our friends for help with our love lives? Imagine the game-changing power of having a trusted squad of co-conspirators in your corner, ready to support you. This episode dives into how to ask your friends to be your co-conspirators in love—one of the top three ways to date IRL! Now, it's not that your friends are clueless about dating; they just need to learn how to help you in a way that matches your wants, needs, and desires. In this episode, Lily guides you through a co-conspirator invitation, so your friends can really be there for you. Here's what you'll learn in this juicy episode: Learn how to spot the friends who are perfect for this role and how to prepare for that all-important invitation Asking someone to be your love-life co-conspirator is an honor—here’s how to make sure you’re ready to have that convo. Not every friend will be a good fit as a co-conspirator, and that’s okay. Discover creative solutions to avoid dead-ends and establish boundaries. FAQ on Co-Conspirators: Everything from the best personality types for this role to how to figure out if your friends are mentally available, and overcoming the shame of asking for help. Tune in and transform your dating life with the help of your very own dream team! 🎙️✨ Links: You can pick up your copy of Thank You, More Please where all books are sold right now, and then sign up for Date Brazen Listening Guide at datebrazen.com/book! Friend Forward Podcast Fighting for Our Friendships, Danielle Bayard Jackson Show notes: http://datebrazen.com/blog/invite-friends-to-be-co-conspirators

Jul 2, 2024 • 41min
203. If you want to write a book, this is for you with Richelle Fredson
Ever dreamed of writing a book or want to share your story and ideas? If so, this episode is for you. Lily welcomes Richelle Fredson, her incredible book proposal coach, on the show. Without Richelle, Thank You, More Please would still be a dream! We're diving deep into main character energy and how to bring it to your writing and publishing journey. We're talking about what it takes to get published, the importance of sharing your story, and how to boldly step into the world with your unique voice. For nearly 20 years, Richelle has been a powerhouse in the book publishing industry. Known as the "six-figure book coach," she's worn many hats: publishing guide, guest teacher, and marketing strategist for bestselling authors. Now, she's here to help aspiring authors develop standout book concepts, killer book proposals, and vibrant online communities. Get ready to embrace your main character energy and share your story with the world, even if you don't think you're ready yet. We get into: Conquering the anxiety of "shooting your shot" Flipping the script on imposter syndrome: embracing bold, messy action Richelle's take: "Who gets to write a book and who gets published?" Diving in: "You can start before you think you’re ready" The real talk on getting a book published The book proposal: your golden ticket to traditional publishing and ultimate self-advocacy Overcoming comparison and self-doubt to start telling your story Links: Richelle’s website Richelle’s podcast Bound + Determined Lily on Richelle’s podcast You can pick up your copy of Thank You, More Please where all books are sold right now, and sign up for our book club at datebrazen.com/book! Show notes: http://datebrazen.com/blog/write-a-book-richelle-fredson

Jun 25, 2024 • 50min
202. Releasing toxic positivity and negative self-talk with Katie Horwitch
Struggling with self-doubt or negative self-talk? This week's episode is a game-changer! Lily's got Katie Horwitch as her guest, and they're diving deep into how inner dialogue shapes our lives. Katie's not just any guest—she's a rockstar author, speaker, and self-talk activist with over a decade of experience flipping the script on negative self-talk. In this episode, you'll get the lowdown on how to recognize and shift negative thoughts and discover the hidden issues behind them. Katie's the founder of WANT: Women Against Negative Talk and the voice behind The WANTcast. Plus, her debut book, "WANT YOUR SELF: Shift Your Self-Talk and Unearth The Strength in Who You Were All Along," is out now and ready to inspire. Don't miss out—tune in and start transforming your inner dialogue to reshape your life! We get into: How our self-talk shapes our view of ourselves and the world. Recognizing when self-talk negatively impacts your life and how to change it. Building the skill to confidently accept your answers when facing tough questions about what you truly want. Figuring out the underlying beliefs behind your self-talk, such as "I’m not allowed to want this"—what’s driving that thought? Exploring, understanding, and shifting not just your self-talk, but your whole self. Hot-take: "Be as fully you wherever you go. That’s how you learn, grow, and become the truest version of yourself." Links: Katie’s website Katie’s book: WANT YOUR SELF: Shift Your Self-Talk and Unearth The Strength In Who You Were All Along Lily on Katie’s podcast: 178: Revamp Your DATING LIFE + FIND LOVE For Real with Lily Womble of Date Brazen Show notes: http://datebrazen.com/blog/negative-self-talk-with-katie-horwitch

Jun 18, 2024 • 39min
201. How to make self-care a habit with Dr. Cicely Horsham-Brathwaite
Ever wondered why you often overlook the self-care you desperately need? This week, Lily chats with the amazing Dr. Cicely Horsham-Brathwaite who drops some serious knowledge on managing stress, building habits that stick, and incorporating practical self-care into our everyday lives. Get ready for some game-changing insights straight from her awesome books! We get into: The three must-have types of self-care for ultimate well-being How to spot the red flags that scream you're neglecting self-care Handling high-stakes pressure in dating and staying grounded Why stress isn't all bad—it’s all about balance and self-compassion How inequality affects self-care for Women of Color and how everyone can be co-conspirators in making a change Fun and easy activities to seamlessly weave self-care into your daily routine Links: Dr. Cicely Horsham-Brathwaite’s website You can pick up your copy of Thank You, More Please where all books are sold right now and sign up for our book club at datebrazen.com/book!

Jun 11, 2024 • 37min
200. It's publish day! Surprising things I've never shared about the book process
My first book, Thank You, More Please: A Feminist Guide to Breaking Dumb Dating Rules and Finding Love, is out in the world right now. I'm SO EXCITED! My business manager Jayla Rae joins me to reveal the little-known, lesser-discussed pieces of my book-writing journey. She’s leading me through questions about what I learned while writing the book, what I am most looking forward to, and thought-provoking questions about the book from Date Brazen clients! Join us on this behind-the-scenes book journey! We get into: Getting real and raw while writing the book and the juicy stories within The feels and the fun of sharing my book with friends and family for the first time. Answering burning questions from the Date Brazen community about the book, future plans, and beyond! Links: You can pick up your copy of Thank You, More Please where all books are sold right now and sign up for our book club at datebrazen.com/book! Show notes: http://datebrazen.com/blog/book-pub-day-qa

Jun 4, 2024 • 35min
199. Main character energy and taking up space with my publisher, Krishan Trotman
How can embracing your main character energy and taking up space transform your journey? In this episode, Lily sits down with Krishan Trotman, VP and Publisher of Legacy Lit Books, to discuss the exciting journey of co-creating Lily's new book 'Thank You, More Please,' which hits shelves next week, June 11th. 📚✨ Tune in to hear Krishan’s own main character energy story, behind-the-scenes details about Lily’s book, and a deep dive into the world of publishing diverse voices. Don't forget to pre-order 'Thank You, More Please,' coming out June 11th. Your pre-orders mean the world and help ensure the book gets the recognition it deserves. 🌟 Your support is immensely appreciated! We get into: Krishan’s main character energy story and her role as VP and Publisher at Legacy Lit The co-creation of Thank You More Please Advice for aspiring authors on writing, getting published, and maintaining the motivation needed for long-term projects 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! Krishan on InstagramLegacy Lit Books Show notes: http://datebrazen.com/blog/mce-taking-up-space-with-krishan-trotman

May 28, 2024 • 48min
198. Shedding stressful dating myths and attracting more with Damona Hoffman
Do you ever feel trapped by outdated dating rules and wonder if there's a better way to attract more? The amazing Damona Hoffman joins Lily to dismantle the four big dating myths and introduces the four pillars of lasting love for healthier, more fulfilling relationships. Damona helps to outline these myths and paves a clear path with actionable next steps, making the dating process easier and helping you find what you desire. Damona says, “You have more control over what happens in your life than what you allow yourself to believe. How deep are you willing to dig?” Damona Hoffman is a regular contributor to The Drew Barrymore Show, NPR, and The Washington Post. She was also featured in Season 11 of The Real Housewives of Beverly Hills. Damona has created content and collaborated with most major dating apps, including Bumble and Match, and she was named the Official U.S. Dating Coach of OkCupid in 2021. Her podcast, Dates & Mates, was named Best Podcast of the Year by The Black Podcasting Awards. Damona’s first book F the Fairy Tale, was released January 2, 2024. We get into: Using dating apps with intention + why Damona says to take notifications off your dating apps and track what is going on in your dating life. The three C’s when designing your profile: Color, Context, Character. The four BIG dating myths and how to ditch them! Including the preferences list myth, the chemistry myth, and the soulmate myth. Links: F The Fairy Tale: Rewrite The Dating Myths and Live Your Own Love Story Damona’s website The Dates and Mates podcast Damona on Instagram @damonahoffman Damona’s Date Tracker Show notes: http://datebrazen.com/blog/shedding-dating-myths-with-damona-hoffman

May 21, 2024 • 43min
197. Taking back your brain from a sexist society with Kara Loewentheil
Want to reclaim your self-worth and challenge societal norms? Then, get ready for a fantastic episode because we’ve got Kara Loewentheil, the powerhouse behind the School of New Feminist Thought, on this week’s podcast! Kara’s new book, 'Take Back Your Brain,' just dropped, and I can’t wait to share our conversation with you. In this episode, Kara and I dive into romantic socialization's history and social impacts. We bust myths about love, marriage, and self-worth and discuss the difference between empowerment and true personal power. We urge you to root your self-worth in yourself instead of seeking external validation. Kara’s insights are a game-changer. She offers a roadmap for embracing self-compassion, challenging patriarchal norms, and building mindsets that lead to a more fulfilling life. Don’t miss out on this powerful conversation! Tune in now and start taking back your brain! We get into: The brain gap: what it is and how to overcome it. Why the goal is to be grounded in your self-worth and not your relationship status The four traps of romantic socialization Body positivity vs body neutrality The beauty and power in the phrase “How human of me…” Links: Take Back Your Brain Unfuck Your Brain Podcast Show notes: http://datebrazen.com/blog/take-back-your-brain-kara-loewentheil