Episode Spotlight: Your Mid-Year Dating Plan: From Late Bloomer to Main Character
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: ✨ How to create your Essence-Based Preferences to vet potential dates ✨ The IRL dating plan that actually works (even if you're socially anxious) ✨ What to say on dating apps and how to write a profile that’s magnetic AF ✨ And why what you want isn’t too much—it’s the key to finding the right match Download the free Essence-Based Preferences Creation Guide: datebrazen.com/workbook Get the book, “Thank You More Please”: datebrazen.com/book 💻 Learn how to work with Lily: datebrazen.com Let’s connect: 📲 TikTok 📸 Instagram 📺 YouTube You've got this—and I’ve got your back.
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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 “behind” in dating (especially as queer late bloomers) The emotional labor we carry as single people and how to release it How to trust yourself again after a breakup or identity shift The shame-desire cycle and how to break it Liz’s journey coming out later in life and finding queer love with deep emotional resonance What self-trust really looks like after pain Whether you’re newly single, starting to date again, or exploring your sexuality later in life—this conversation will meet you with compassion, truth, and the reminder: you’re not too late, and you don’t have to settle. Work with Lily: 3 Steps to Attract the Right Partner as a Late Bloomer If you’ve felt behind in dating, this free training is for you. Learn how to: Release embarrassment and claim what you really want Attract dates without overthinking or scarcity Build a joyful, unbothered dating strategy rooted in feminist self-trust RSVP here- https://www.datebrazen.com/training 🔗 Learn about Main Character Dating: datebrazen.com/waitlist 🔗 Book: Thank You More Please 🔗 YouTube Channel 🔗 TikTok 🔗 Instagram
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242. “I Want Love—But I’d Like to Skip Dating, Please”-- Live coaching session
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 pressure late bloomers feel to already know how dating is supposed to work. Michelle shares how: → Dating apps make her feel panicked in 3 minutes or less → She’s afraid she missed the memo on how to flirt or date → All she really wants is a partner to laugh with at a family campsite, but dating feels like an IMPOSSIBLE way to get there. We talk about self-compassion, letting go of judgment, and what it means to stop settling—not just for the wrong relationship, but for a miserable dating life. 📺 Or watch the video version on YouTube! (@datebrazen) Work with Lily: 🔗 Free Live Training on June 17th: datebrazen.com/lets-go 🔗 Learn about Main Character Dating: datebrazen.com/waitlist 🔗 Book: Thank You More Please 🔗 YouTube Channel 🔗 TikTok 🔗 Instagram
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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 she didn’t even want to be on How to process feeling behind in your dating life The surprising strategy shift that gave Ellie permission to want what she wants How to practice self-compassion and build dating resilience in real time so you can put yourself out there and attract the right people If you’ve ever felt behind, unchosen, or like you’re "too late" to find what you want—this episode is for you. 🎉 And don’t miss Lily’s free live training: ✨ 3 Steps to Attract the Right Partner as a "Late Bloomer" ✨ on June 17, 2025. Sign up at datebrazen.com/lets-go Work with Lily: 🔗 Learn about her signature program, Main Character Dating: datebrazen.com/waitlist 🔗 Book: Thank You More Please 🔗 YouTube Channel 🔗 TikTok 🔗 Instagram
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Episode Spotlight: How to Shoot Your Shot (Even If You Feel Awkward)
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 take bold action in dating ✅ Why making the first move 100% of the time is a game-changer for attracting the right relationship ✅ How to bounce back from rejection (without losing your confidence) Work with Lily: 🔗 Free Live Training on June 17th: datebrazen.com/lets-go 🔗 Learn about Main Character Dating: datebrazen.com/waitlist 🔗 Book: Thank You More Please 🔗 YouTube Channel 🔗 TikTok 🔗 Instagram
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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