
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.
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This episode is your mid-year reset, late bloomer style. Whether you've been dating with no luck, stuck in swipe fatigue, or haven't dated in 15 years, this seven-step feminist dating plan is your guide to attracting the best relationship of your life. In this replay of one of our most popular trainings, you’ll learn:

Episode Spotlight: Finding love as a queer late bloomer, building self-trust, and healing after heartbreak
In this vulnerable and wisdom-packed episode, Lily sits down with Liz, a former Main Character Dating client, to talk about what it really takes to come back to yourself after a heartbreaking, sudden breakup—and how that healing work can lead to the most aligned love of your life. Together, they discuss: Why we feel “b
Today's podcast episode is a coaching session with Michelle. She's in her 50s, divorced after a 24-year marriage, and getting back into dating after being with one person her whole adult life. In this raw and powerful coaching session, we unpack the overwhelm of dating apps, the anxiety of being “naive,” and the pressu

241. “I Stayed for a 4-Hour Date I Didn’t Want to Be On” — Live Coaching Session for Late Bloomers
In this very first live coaching session on The Date Brazen podcast, you’ll meet Ellie—an amazing, big-hearted late bloomer who's never had a romantic relationship, and who thought dating was something she missed the memo on. Sound familiar? Together in this episode we explore: Why Ellie stayed on multiple 4-hour dates
Does the idea of making the first move in dating make you feel awkward AF? You’re not alone. In this episode, I’m breaking down exactly how to shoot your shot as a late bloomer—without spiraling into self-doubt or waiting for someone else to make the first move. You’ll learn: ✅ The mindset shifts that make it easier to
If you’ve ever feared that you're not attractive or desirable because it’s never happened before, this episode is a must-listen. Lily breaks down the internalized fears many late bloomers carry—and how to reframe those thoughts with compassion, context, and confidence using her signature ACK mindset tool (Acknowledge