If the holidays bring up nerves about being single — the questions, the pressure, the comparisons — this episode is your Holiday Dating Survival Guide. It's a warm, grounding replay packed with self-compassion, boundaries that protect your peace, and real scripts for handling conversations about your dating life.

Inside, Lily shares:

• how to release the self-judgment we've all internalized from patriarchal socialization (that says that coupled women are "ahead" of single women)
• why self-compassion is the antidote to self-judgment (and how to practice it daily)
• three phrases from Dr. Kristin Neff's work to use when you're feeling nervous, jealous, conflicted, or despairing
• how to identify the desire underneath your fear so you can move forward from a grounded place
• what to actually say when someone asks, "So… how's your dating life going?"
• how to use boundaries, a self-care plan, and a joy-building plan to support yourself this season
• why you don't owe anyone your story — and how to practice unbothered energy
• how to feel less alone, even if you are the only single person in the room

This episode is a reminder that no matter what happened in your love life this year, you are worthy of celebration. You get to take up space. You get to be proud of yourself. You get to feel belonging.

✨ This is the final episode of 2025. The podcast returns in January 2026.

🎧 Listen on Apple Podcasts
🎧 Listen on Spotify

Work with Lily
Read Lily's book: Thank You, More Please
Explore programs + resources: datebrazen.com

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Laura sat on her dream for years.

She had already moved abroad, left her marriage, rewritten her book, built a whole new life in a new country… and yet the next thing she actually wanted to build — a business supporting women after divorce — stayed in a drawer.

In this conversation, you'll hear exactly how she went from:

• paralyzed by fear of judgment

• hiding the work she'd been doing for years

• waiting to feel "ready"

• thinking she "should've figured it out by now"

to owning her CEO energy, talking publicly about her work, pitching her idea in real life, and getting her first clients.

We break down the exact moment things clicked, the messy middle, and the main character energy skills that helped her finally do the thing.

If you've been circling a dream for months, years, or a decade… this episode is going to open something up for you.

Work with Lily

✨ Main Character Life Mastermind — Applications open now.
A 6-month container where you'll choose your main character project, release people-pleasing, build rock-solid self-trust, and take massive, messy action with a community that has your back.

The 10-minute application will increase your main character energy on its own.

Apply HERE

📚 Read my book: Thank You, More Please
A feminist guide to breaking dumb dating rules and finding love. Order HERE


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In this episode, Abby shares her late bloomer story with so much honesty and clarity. We talk about what it was like to be in her mid-30s, never having been in a serious relationship, carrying a loud "I'm behind" and "I'm weird" narrative, and feeling totally unsure how to talk about her dating history without spiraling.

Abby opens up about moving to a new city, trying to date while feeling embarrassed about her experience, and struggling with the not good enough voice that made her avoid connection. She also shares what shifted for her as she started to process shame, build community, and trust herself enough to take up more space at work, in dating, and in her daily life.

Inside this episode, you'll hear:

• how Abby learned to identify and quiet the "I'm weird" and "I'm behind" voice
• how belonging helped her stop self-isolating and start connecting
• what helped her ask for what she wanted (down to "I need 25% more texts")
• how she advocated for herself at work while doing two jobs
• how she built friendships, community, and eventually a healthy relationship
• what she wishes she could tell her past self, who felt so far behind

This is a powerful example of what can happen when you stop avoiding your desires and start trusting yourself enough to move toward them.


Work with Lily

✨ Join the live training: Stop People-Pleasing and Build a Stupidly Joyful Life live training-- December 3rd: Sign up HERE

✨ Apply to Main Character Life, my 6-month mastermind where Abby did this work — the space to release people-pleasing, build self-trust, advocate for what you want, and go after the life you've been circling for years. Apply HERE

✨ Get my Book — Thank You, More Please, Buy the book + grab your bonus HERE


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If you're stuck in a spiral of overthinking — replaying conversations, asking 15 friends what to do, imagining every worst-case scenario — this episode will feel like a deep exhale.

Overthinking isn't you being "careful."

It's a self-trust deficit.

And that is a skill gap, not a character flaw.

In this episode, I break down:

• Why anxious rumination feels so real and so urgent
• How patriarchy, people-pleasing, and fear of rejection trained you not to trust yourself
• The difference between careful planning and dress rehearsing tragedy
• Why outsourcing decisions to friends keeps you stuck
• What self-trust actually is (and why it's messy, imperfect, and learnable)
• Tiny, doable steps to rebuild your self-trust today
• How this plays out in dating, boundaries, and big life decisions
• A framework to stop overthinking and start acting from your gut

If you've been doubting yourself for years — in your dating life, your friendships, your career, your boundaries — this episode will teach you how to finally have your own back.

Self-trust is a skill. And you're about to learn it.

Work with Lily

✨ Main Character Life Mastermind — Applications Opening soon!
Sign up for my free training-- Stop People Pleasing and Build a Stupidly Joyful Life-- on Dec 3rd to be the first to apply. RSVP HERE

📚 Read my book — Thank You, More Please
A feminist guide to breaking dumb dating rules and finding love
Order here: https://datebrazen.com/book

Follow Lily everywhere:
📺 YouTube Channel
📸 Instagram
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🌐 Website

Feeling like the supporting character in your own story? This episode is your plot twist. We unpack Main Character Energy (MCE) as a buildable skill set—not a personality type—and show how tending to your needs heals burnout and expands your capacity to show up for the people and causes you care about.

In this episode, you'll learn:

• The 3-part MCE framework: Permission → Self-Trust → Massive, Messy Action
• Why MCE isn't selfish—it's the power source that fuels your impact (both/and)
• The tiny tool that changes everything: 10 Seconds of Courage
• Five rapid-fire ideas to practice 10 seconds of courage today (self-care, belonging, shoot-your-shot)
• How to stop "best-friend energy" (people-pleasing, perfectionism, over-functioning) and step center stage

• Free Live Training (Dec 3): Stop People-Pleasing & Build a Stupidly Joyful Life —RSVP HERE
  
  
• Main Character Life Mastermind — Get details + apply (when open) or join the waitlist HERE
  
  
• Main Character Dating — My signature program to build a joyful, self-trust-filled dating life and attract an aligned partnership. Learn more: https://datebrazen.com/dating
  
  
• Get my Book — Thank You, More Please Buy the book + grab your bonus: https://datebrazen.com/book

Follow Lily everywhere:
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Subscribe so you never miss an episode. You've got this—and I've got your back.

If you've ever found yourself doing everything right and still feeling exhausted, this conversation is for you.

In this episode, Lily sits down with Maureen, a writer, educator, and book coach who transformed her life from chronic burnout and perfectionism to joyful, sustainable main character energy.

They dive into:

✨ How perfectionism becomes emotional armor (and how to take it off safely).

✨ Why joy—not hustle—is the most powerful growth strategy.

✨ The role of self-celebration and community in creating a life that feels like your own.

Maureen's story is a reminder that you don't have to blow up your life to change it. You just need new tools for how you treat yourself while you grow.

Connect with Maureen:

🔗 narrative-drive.com

📝 narrativedriven.substack.com/

Work with Lily:

🌸 Main Character Life Mastermind — A 6-month small-group experience starting in January to release people-pleasing, build rock-solid self-trust, and become the main character of your life in 6 months or less.

Get early access + bonuses: https://datebrazen.com/life

Free Live Training: Stop People Pleasing and Build a Stupidly Joyful Life — December 3rd: https://datebrazen.com/joyful-life/

Get Lily's Book: Thank You, More Please HERE

Follow Lily everywhere:
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Ever catch yourself thinking: "Am I doing enough to find love?"

That question sounds productive—but it's usually fear in disguise.

Fear that time's running out.

Fear that what you want might never happen.

In this week's episode of The Late Bloomer Show, I walk you through the 10-step "Am I Doing Enough?" checklist—the one I give my clients when they start to spiral.

You'll learn how to:

💗 Practice self-compassion (so you stop hustling for worthiness)

🎯 Create your Essence-Based Preferences

💎 Bring in community and support

🎉 Celebrate yourself like it's part of the plan—because it is

You don't need to "just try harder" in your dating life.

You need an effective plan that prioritizes your self-trust along the way.

Work with Lily:

→ Free Essence-Based Preferences workbook: datebrazen.com/workbook

→ Read Thank You More Please: datebrazen.com/book

→ Learn more about Main Character Dating: datebrazen.com/dating

→ Learn how to work with Lily: datebrazen.com

Follow Lily everywhere:
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Should you wait for the slow burn? Or chase the spark?

This question keeps so many late bloomers stuck in overthinking, second-guessing, and dating people who aren't right for them.

In this episode of The Late Bloomer Show, Lily breaks down the real truth about attraction and connection, including:

The pros + cons of both the spark and the slow burn

Why both approaches can lead to wasted time

What to focus on instead (hint: curiosity > rules)

How to ground yourself with Lily's Date Feedback Compass

If you've ever stressed about whether you "knew" soon enough or felt enough chemistry, this episode will give you clarity and freedom.

🎧 Listen now and find out why curiosity—not binaries—is the most powerful dating tool.

Work with Lily:

→ Free Essence-Based Preferences workbook: datebrazen.com/workbook

→ Read Thank You More Please: datebrazen.com/book

→ Learn more about Main Character Dating: datebrazen.com/dating

→ Learn how to work with Lily: datebrazen.com

Follow Lily everywhere:
📲 Tiktok
📸 Instagram
📺 YouTube Channel