241. “I Stayed for a 4-Hour Date I Didn’t Want to Be On” — Live Coaching Session for Late Bloomers

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.

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

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

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  

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

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, Compassion, Kind Reframe). You’ll also get a powerful challenge to reconnect with your body and spark self-trust this week.   🎧 Prefer to watch? Head to YouTube for the full episode.   📆 And don’t miss Lily’s free live training on June 17th: 3 Steps to Attract the Right Partner as a Late Bloomer – save your seat now: datebrazen.com/lets-go   Links + Resources: 📚 Buy Lily’s book Thank You More Please: datebrazen.com/book 💖 Work with Lily: datebrazen.com 🎥 YouTube Channel 📱 TikTok 📸 Instagram

If flirting feels awkward, forced, or like a foreign language—especially because you feel “behind” in dating—this episode is your new playbook. Lily breaks down her step-by-step approach to flirting IRL with courage and ease. You’ll learn how to strike up a conversation, gauge interest, and shoot your shot—without spiraling or second-guessing yourself. 📺 Want the visual breakdown? Watch it on YouTube: https://www.youtube.com/@datebrazen Don’t miss Lily’s FREE June 17th, 2025 training: ✨ 3 Steps to Attract the Right Partner as a Late Bloomer ✨ You’ll learn how to: ✔️ Release shame about being a late bloomer ✔️ Build rock-solid confidence in what you want ✔️ Start dating successfully this summer RSVP here: https://datebrazen.com/lets-go 📚 Grab Lily’s book Thank You More Please: https://www.datebrazen.com/book Follow Lily on: ✨ Instagram ✨ Tiktok Learn how to work with Lily: https://www.datebrazen.com

Are you a late bloomer wondering, “How the hell do I even start dating?” In this episode, Lily breaks down the exact 6-step roadmap to go from anxious and avoidant to confident and aligned in your love life. You’ll learn how to drop shame, claim your essence-based preferences, use dating apps with boundaries, and build your IRL dating strategy—messy and awkward and powerful.   Here’s how to work with Lily: ✨ On Demand Training: 3 Steps to Attract the Right Partner as a Late Bloomer ✨ Buy her book: Thank You More Please: https://datebrazen.com/book ✨ Download the free "Create Your Essence-Based Preferences" Guide HERE   Follow Lily on: ✨ Instagram ✨ Tiktok ✨ Youtube

In this kickoff to the Late Bloomer Series, Lily gets real about how to tell a date you’ve never been in a relationship—without spiraling, oversharing, or self-abandoning. If you’ve ever felt behind in love, this episode will help you embrace your story, communicate with confidence, and stop making your dating history mean something it doesn’t.   ✨ Grab Lily’s book Thank You, More Please + get the bonus Podcast Listening Guide: https://datebrazen.com/book   Get on the waitlist for Main Character Dating: https://www.datebrazen.com/waitlist   Learn how to work with me: https://www.datebrazen.com/   Follow me on ✨ Instagram ✨ Tiktok ✨ Youtube   🎧 Full show notes + transcript at: https://datebrazen.com/podcast

Are you tired of living for everyone else's expectations... and ready to step into your own dang spotlight? 🎬✨ In this behind-the-scenes episode, I’m sharing practical tools to stop people-pleasing for good — and start building the stupidly joyful, self-trusting, main-character life you’re meant for. Inside this episode: What people-pleasing really is (it’s deeper than being “too nice”) Why releasing people-pleasing is so damn hard (and why it’s not your fault) How to start rebuilding self-trust in small, powerful ways Three practical steps you can take today to enter your Main Character Era If you’re feeling the heart pull to live bigger, braver, and more joyfully — the doors to Main Character Life are open right now. 🎟 Apply for Main Character Life (closing May 2!): HERE This is my six-month small group mastermind where you'll learn to: Release people-pleasing as your default Build rock-solid self-trust Take massive, messy action toward your dreams Create a stupidly joyful life that finally feels like yours   Work with Lily: Learn how to work with me: https://www.datebrazen.com/ Order my book, “Thank You, More Please”: https://www.datebrazen.com/book   Follow me on ✨ Instagram ✨ Tiktok ✨ Youtube