The Feminist Dating Show – Details, episodes & analysis

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

Follow Lily everywhere:
📺 YouTube Channel
📸 Instagram
📲 Tiktok
🌐 Website

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


Follow Lily everywhere:
📺 YouTube Channel
📸 Instagram
📲 Tiktok
🌐 Website

What do late bloomers most want to know about sex? In this episode, Lily sits down with Dr. Juliana Hauser—sex therapist, TEDx speaker, and author of A New Position on Sex—to answer the top 10 questions late bloomers have about sexuality, intimacy, and pleasure.

They cover everything from starting with little or no experience, to disclosing your sexual history (or lack thereof), to navigating body image, chemistry, pain, and more.

Whether you're 20, 30, 40, 50+ and wondering where to start, this conversation is a must-listen.

🎧 Listen in now and discover the tools, confidence, and compassion you deserve in your sexual journey.

📖 Grab Dr. Juliana's new book A New Position on Sex: A Guide to Greater Sexual Confidence, Pleasure and Authenticity available now right HERE

💥 Work with Lily:

→ Main Character Dating: datebrazen.com/dating

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

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

Follow Lily everywhere:
📲 Tiktok
📸 Instagram
📺 YouTube Channel

What does it feel like to be in the right relationship? Join us on the Date Brazen Podcast as we get into this intriguing question with Maddie, a former client whose journey may inspire you. From discovering deeper essence-based preferences to finding her now-husband during the Brazen Breakthrough program, Maddie's story is a testament to the transformative power of belief in self and taking courageous action. 

This episode is a beacon of hope, reminding you that what you desire does exist. Through inspiring stories like Maddie's, we witness firsthand that with bold action, the love and fulfillment you seek are not only possible but inevitable.

Hot-takes and episode topics:

• Just got out of a relationship - is it too soon to do this work?

• The most impactful lesson Maddie learned that translates beyond dating

• Maddie shares her sparkly experience meeting her now husband on a dating app

• Overcoming doubt about whether or not you are in the right relationship 

• How does it feel to be in the right relationship, and what is the work after you find it?

• Centering yourself in what you want sets you on a different path; there is transformative power in believing in the possibility of what you truly desire

Links: 

Pre-order Lily's upcoming book, Thank You, More Please!

Creating a Confident and Joyful-as-fuck Dating Life That Makes the Right Relationship Inevitable

Show notes:
http://datebrazen.com/blog/being-in-the-right-relationship

This week, Lily serves up some real talk about why it might be time to bid farewell to dating advice from your coupled friends. You'll hear why it's crucial to take the reins of your dating life and stop relying on well-meaning but misaligned advice from friends in relationships.

In this episode, Lily encourages you to set boundaries with friends who may unintentionally trivialize or patronize your dating experiences. She emphasizes cultivating supportive communities of single friends who genuinely understand and uplift your dating struggles. 

The goal of this episode is to leave you feeling empowered to take control of your dating journey and assemble a crew of friends who've got your back.

Hot-takes and topics:

• Your coupled friends don't know your love story. Hot-take: They don't know more than you because they are in a relationship and you're not.

• If dating advice friends give makes you feel small, or your dating experience is entertainment for them, it is time to fire your coupled friends from giving you dating advice. 

• Surround yourself with people who get your dating struggle and who are moving forward with you.

Links:

Pre-order Lily's upcoming book, Thank You, More Please!

Creating a Confident and Joyful-as-fuck Dating Life That Makes the Right Relationship Inevitable

Danielle Bayard Jackson, Friend Forward Podcast

Show notes:
http://datebrazen.com/blog/fire-coupled-friends-from-giving-dating-advice

Have you ever wondered what questions to ask when you first meet someone? This week, Lily unpacks why qualifying/disqualifying questions are the ultimate game-changer and can transform your dating experience from emotionally exhausting to intentional and amazing. 

In this episode, Lily shares the ONE question that will revolutionize how you vet potential partners, ensuring you never waste time on lackluster dates and conversations again. Drawing from the program, The Brazen Breakthrough, and her upcoming book, Thank You, More Please, A Feminist Guide to Breaking Dumb Dating Rules and Finding Love, you get the tools and mindset needed to navigate the dating landscape confidently.

Grab your notepad because this episode isn't just about strategy - it's a journey into reclaiming control of your dating narrative and steering towards the relationships you truly desire. 

Episode Hot-takes and topics:

• "Give yourself permission to want what you want and start showing up for what you want in your life."

• Qualifying/Disqualifying questions lead to higher-quality dates: you don't need to cast a wide net. You need to be very specific about the type of person you seek. 

• "Most people are going to be wrong for you. You are for the few, not the many."

• Stop sending bespoke messages and extending unnecessary emotional labor 

• Q/D questions that get deeper than surface-level convos allow you to vet people quickly

• Ask the right questions and tune into your body to see how the answer makes you feel. You want to feel intrigue or curiosity or excitement. If you don't, bless and release. .

• Other Q/D questions we LOVE and Questions we DO NOT love when you're first texting

Links:

Pre-order Lily's upcoming book, Thank You, More Please!

Creating a Confident and Joyful-as-fuck Dating Life That Makes the Right Relationship Inevitable

Free Guide to Your Essence-Based Preferences

Show notes:
http://datebrazen.com/blog/qd-questions-strategy

Feeling hopeless or panicked about in-person dating? Then, this episode will motivate you to prioritize your desires and step into the path of opportunity to create a juicy in-person dating life. Today, we are getting into the ins and outs of the Brazen Breakthrough and how it changed the game for member Chloé. 

Chloé opens up about what has been happening in her dating life and how she has been showing up differently. You'll also hear how she now embodies what it means for her to have permissive, joyful connectivity.  We are so excited for you to hear this episode. It is a beautiful example of a human creating the life she desires.

Episode hot takes and topics:

• Chloé on finding partnership: "It is not embarrassing or weak to say that my life would thrive even fuller with deep witnessing and intimacy."

• The lesson that changed how Chloé's outlook on dating and dating apps 

• "My feelings about dating have shifted dramatically." 

• How the Brazen Breakthrough helped Chloé create a juicy in-person dating life   

• Breaking patterns that take you out of the path of opportunity 

Links:

Pre-order Lily's upcoming book, Thank You, More Please!

Creating a Confident and Joyful-as-fuck Dating Life That Makes the Right Relationship Inevitable

Episode Link:

http://datebrazen.com/blog/juicy-in-person-dating

Prepare for an epic episode of the Date Brazen podcast, where former Brazen Breakthrough client Maya opens up about her rollercoaster journey through self-discovery and empowered love! Join Lily as she and Maya dive deep into intentional dating and the power of co-creating relationships. 

In this episode, you'll get the scoop on essence-based preferences and how Maya turned her dating game around. She shares how she embraced her needs and learned to communicate like a boss, and how she and her partner keep the romance alive with intention-setting actions.

If you're ready for a journey filled with real talk and self-love, this episode is your go-to. 💕

Episode hot takes and topics:

• "It is about my internal state. If I am full and whole. I can give of myself to someone else. It has to be a conscious activity."

• Mindset shifts that helped Maya believe finding love was possible

• Relationships are a co-creation: "You are co-creating the relationship. It grows, it breeds, and it shifts. That is what is so beautiful about relationships." 

• "What's meant for you won't pass you by - this is something I live by for everything in my life."

• How Maya learned to tap into her intuitive self to guide the way
  
  

Links:
Pre-order Lily's upcoming book, Thank You, More Please!
Creating a Confident and Joyful-as-fuck Dating Life That Makes the Right Relationship Inevitable

21. How Maya Found Love
Maya's Substack "On Holiday"
Maya on Instagram

Episode link:
http://datebrazen.com/blog/the-right-relationship-is-inevitable

Lily is sharing her complete guide to finding love on a dating app. You'll hear how dating apps can help expand your social circle, help you get to know your dating personality, your triggers, and how to take care of yourself. 

Lily drills down into her fiercest, most direct dating app advice so that you can find more success on a dating app while preserving your mental health and finding joy in the process.

This episode is fire! Take notes and get ready to dive into breaking the dumb dating rules of the dating app advice you've heard before that doesn't work and get a clear path forward.

Episode Hot-takes and topics:

• Dating apps are just one tool in your dating tool kit. 

• Choose the ONE dating app that works for you

• Create a cozy swiping routine and know your swiping tipping point 

• How and why to avoid unnecessary emotional labor 

• Lily's formula for your dating app profiles - what makes your profile magnetic to people is YOU!

Links:

Pre-order Lily's upcoming book, Thank You, More Please!
Free Guide to Your Essence-Based Preferences
Episode 89: How the hell to meet someone in-person
Episode 132: Before you swipe, try this meditation

Show notes:

http://datebrazen.com/blog/complete-guide-to-finding-love-on-a-dating-app

Pre-Order Lily's book- "Thank You More Please" HERE

This week, Lily peels back the curtain on the journey of writing her book, "Thank You More Please: A Feminist Guide to Breaking Dumb Dating Rules and Finding Love." Lily shares the vulnerable moments, the highs and lows, and the transformative process of birthing this creative endeavor. Get ready for an intimate conversation about the unconventional feminist approach that inspired the book, her challenges, and the ultimate joy of bringing this guide to life.

In this episode, you'll hear the behind-the-scenes details, Lily's writing routine, and the soundtrack that fueled her creative process. This episode is not just about the book; it explores Lily's growth, courage, and mission to help you create a joyful and love-filled dating life on your terms. Plus, learn about the exciting pre-order bonuses with "Thank You More Please." Tune in and be part of this journey to love and self-discovery!