
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

Mar 5, 2024 • 36min
186. How to bless and release the wrong people
Are you striving to let go of the wrong people? What if we told you that the extent to which you're willing to bless and release the wrong people is directly linked to your path toward the right relationship? In this episode, Lily reveals her strategy for blessing and releasing the wrong people in your life, enabling your mind to shift its focus towards the right connections for you. "Blessing and releasing" is a radical step towards fulfilling your desires. So, grab your note-taking tools because this episode is full of practical how-to's on this transformative process. In this episode, you will learn: Having people in your life who are not suitable for you is about the underlying fear that what you want is not possible or not worthy of what you want. That is worthy of your curiosity and compassion. Categories of when to bless and release (B&R) someone Different levels of connection deserve a different approach to blessing and releasing. Tips for outlining a B&R moment for a breakup Lily breaks down an incomplete roster of individuals to bless and release, including: the stonewaller, the Eeyore, the most intense human, and the pen-pal. Reflection questions to help you determine if you need to bless and release someone Text and out loud scripts for B&R like “Hey, thanks for hanging. I’m not feeling a romantic connection, wish you the best.” Links: Pre-order Lily’s upcoming book, Thank You, More Please! 124. The “Thank You, More, Please!” Challenge! Radical Alignment, Alexandra Jamieson and Bob Gower Show notes: http://datebrazen.com/blog/how-to-bless-and-release-the-wrong-people

Feb 27, 2024 • 46min
185. Getting nerdy with the research and cultural impact of dating with Faith Hill, journalist at The Atlantic
Today, get ready to geek out with us on the podcast! We're thrilled to have Faith Hill, a staff writer at The Atlantic, joining Lily for an insightful conversation about research and its cultural impact on dating. We get into topics like dating dynamics, dating yourself, social connections, and being single. Together, Lily and Faith dive into Faith’s latest articles about exploring love, dating, and the complexities of singlehood. What's particularly captivating about Faith's writing is how she addresses those burning questions that naturally arise as you delve into the research she shares. Tune in for a chat that sheds light on the intriguing intersection where love, society, and human connections meet! 🎙️✨ We get into: Dating culture and its problematic value of coupled people over singles What the research showed regarding dating “spark vs. slow burn.” The assumption that we'll be happier in a relationship The emotions that get stirred up when examining this statement, “As your friends get coupled, it could feel like a ghost town.” Hot-take: “Spending all your time with your partner is not great for your relationship or friendships.” Allowing for messy intimacy with friendships or partners Perception and feelings about solo dating: how to release the narrative that taking yourself on a date means you are lonely, and how to bring more pleasure to solo time Hot-take: “Solitude is not antithetical to connection.” Links: Pre-order Lily’s upcoming book, Thank You, More Please! 130. How to find and create "exhale" friendships with Blake Blankenbecler 173. Fighting for our friendships with Danielle Bayard Jackson Faith’s articles referenced in this episode: No, You Shouldn’t ‘Date ’Em ’Til You Hate ’Em’ https://www.theatlantic.com/family/archive/2023/11/awkward-modern-dating-the-spark/676039/ Don't let love take over your life https://www.theatlantic.com/family/archive/2023/09/relationship-balance-love-friendship-autonomy/675321/ Take yourself on a date! https://www.theatlantic.com/family/archive/2022/12/seeing-movies-alone-solo-date-in-public/672363/ Show notes: http://datebrazen.com/blog/research-cultural-impact-of-dating

Feb 22, 2024 • 8min
Brazen Breakthrough Series: What I promise inside The Brazen Breakthrough
Doors to this round of The Brazen Breakthrough close 2/23/24 @ midnight EST. Here's the LINK TO JOIN US. If you're catching this after the fact, then add your name to the waitlist with the link above.

Feb 22, 2024 • 11min
Brazen Breakthrough Series: "How does The BB help me find better dates?"
Doors to this round of The Brazen Breakthrough close 2/23/24 @ midnight EST. Here's the LINK TO JOIN US. If you're catching this after the fact, then add your name to the waitlist with the link above.

Feb 22, 2024 • 7min
Brazen Breakthrough Series: "Can I DIY The Brazen Breakthrough from the podcast or book?"
Doors to this round of The Brazen Breakthrough close 2/23/24 @ midnight EST. Here's the LINK TO JOIN US. If you're catching this after the fact, then add your name to the waitlist with the link above.

Feb 22, 2024 • 5min
Brazen Breakthrough Series: How much time does it take?
Doors to this round of The Brazen Breakthrough close 2/23/24 @ midnight EST. Here's the LINK TO JOIN US. If you're catching this after the fact, then add your name to the waitlist with the link above.

Feb 22, 2024 • 15min
Brazen Breakthrough Series: What's inside The Brazen Breakthrough?
Doors to this round of The Brazen Breakthrough close 2/23/24 @ midnight EST. Here's the LINK TO JOIN US. If you're catching this after the fact, then add your name to the waitlist with the link above.

Feb 20, 2024 • 34min
184. Being in the right relationship with Brazen Breakthrough member Maddie
What does it feel like to be in the right relationship? Join us on the Date Brazen Podcast as we get into this intriguing question with Maddie, a former client whose journey may inspire you. From discovering deeper essence-based preferences to finding her now-husband during the Brazen Breakthrough program, Maddie's story is a testament to the transformative power of belief in self and taking courageous action. This episode is a beacon of hope, reminding you that what you desire does exist. Through inspiring stories like Maddie's, we witness firsthand that with bold action, the love and fulfillment you seek are not only possible but inevitable. Hot-takes and episode topics: Just got out of a relationship - is it too soon to do this work? The most impactful lesson Maddie learned that translates beyond dating Maddie shares her sparkly experience meeting her now husband on a dating app Overcoming doubt about whether or not you are in the right relationship How does it feel to be in the right relationship, and what is the work after you find it? Centering yourself in what you want sets you on a different path; there is transformative power in believing in the possibility of what you truly desire Links: Pre-order Lily’s upcoming book, Thank You, More Please! Creating a Confident and Joyful-as-fuck Dating Life That Makes the Right Relationship Inevitable Show notes:http://datebrazen.com/blog/being-in-the-right-relationship

Feb 13, 2024 • 17min
183. Why you need to fire your coupled friends from giving you dating advice
This week, Lily serves up some real talk about why it might be time to bid farewell to dating advice from your coupled friends. You’ll hear why it's crucial to take the reins of your dating life and stop relying on well-meaning but misaligned advice from friends in relationships. In this episode, Lily encourages you to set boundaries with friends who may unintentionally trivialize or patronize your dating experiences. She emphasizes cultivating supportive communities of single friends who genuinely understand and uplift your dating struggles. The goal of this episode is to leave you feeling empowered to take control of your dating journey and assemble a crew of friends who've got your back. Hot-takes and topics: Your coupled friends don’t know your love story. Hot-take: They don’t know more than you because they are in a relationship and you’re not. If dating advice friends give makes you feel small, or your dating experience is entertainment for them, it is time to fire your coupled friends from giving you dating advice. Surround yourself with people who get your dating struggle and who are moving forward with you. Links: Pre-order Lily’s upcoming book, Thank You, More Please! Creating a Confident and Joyful-as-fuck Dating Life That Makes the Right Relationship Inevitable Danielle Bayard Jackson, Friend Forward Podcast Show notes: http://datebrazen.com/blog/fire-coupled-friends-from-giving-dating-advice

Feb 6, 2024 • 42min
182. My Qualifying/Disqualifying questions strategy so you never go on a bad date again
Have you ever wondered what questions to ask when you first meet someone? This week, Lily unpacks why qualifying/disqualifying questions are the ultimate game-changer and can transform your dating experience from emotionally exhausting to intentional and amazing. In this episode, Lily shares the ONE question that will revolutionize how you vet potential partners, ensuring you never waste time on lackluster dates and conversations again. Drawing from the program, The Brazen Breakthrough, and her upcoming book, Thank You, More Please, A Feminist Guide to Breaking Dumb Dating Rules and Finding Love, you get the tools and mindset needed to navigate the dating landscape confidently. Grab your notepad because this episode isn't just about strategy - it's a journey into reclaiming control of your dating narrative and steering towards the relationships you truly desire. Episode Hot-takes and topics: “Give yourself permission to want what you want and start showing up for what you want in your life.” Qualifying/Disqualifying questions lead to higher-quality dates: you don’t need to cast a wide net. You need to be very specific about the type of person you seek. “Most people are going to be wrong for you. You are for the few, not the many.” Stop sending bespoke messages and extending unnecessary emotional labor Q/D questions that get deeper than surface-level convos allow you to vet people quickly Ask the right questions and tune into your body to see how the answer makes you feel. You want to feel intrigue or curiosity or excitement. If you don’t, bless and release. . Other Q/D questions we LOVE and Questions we DO NOT love when you're first texting Links: Pre-order Lily’s upcoming book, Thank You, More Please! Creating a Confident and Joyful-as-fuck Dating Life That Makes the Right Relationship Inevitable Free Guide to Your Essence-Based Preferences Show notes: http://datebrazen.com/blog/qd-questions-strategy