The Date Brazen Podcast

Dating can feel like a rollercoaster of emotions—excitement, hope, fear, and sometimes, pure panic. In this episode, we’re tackling the fear that keeps so many incredible people stuck on the sidelines. If you’ve ever thought, What if I get rejected? What if I say the wrong thing? What if I’m not enough?—this one’s for you. I’ll walk you through how to move through dating fear with self-compassion, community, and a whole lot of self-trust. Because here’s the truth: fear is normal, and it doesn’t have to be in the driver’s seat. You don’t have to be fearless to find love—you just have to be willing to take messy, brave action toward what you want. Hit play, and let’s reframe your fear into power. Takeaways: ✨ Self-compassion isn’t just nice; it literally helps your body handle stress better. ✨ Feeling afraid to date? That’s human. You’re not alone. ✨ Messy action beats overthinking every time. ✨ The right person won’t need you to perform or say the perfect thing. ✨ If you desire more, it’s because it’s possible for you. Let’s go get you what you want. 💫 Get your free Essence Based Preferences Guide ​here​. Work with Lily: Get Lily’s Book, Thank You More Please HERE.   Follow Lily on Instagram and Tiktok.   Subscribe to Lily’s Youtube channel HERE.

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

Feeling like a late bloomer in the dating world? Discover a powerful 6-step roadmap to boost your confidence and embrace your unique journey. Learn to overcome shame, define your relationship preferences, and set healthy boundaries. Dive into practical strategies for engaging in real-life connections while celebrating small wins along the way. With self-compassion and intentional communication, you'll find that dating can be a fulfilling and empowering experience.

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