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!

Have you been wanting to start that next big project or creative hobby this year? Get ready to ignite your creative flame with this episode featuring the hosts of The Spark File podcast, Susan Blackwell and Laura Camien! Lily is thrilled to welcome Susan and Laura to the show, together they dive into a candid conversation about creativity and overcoming perfectionism.

In this episode, Lily opens up about her creative journey, from battling self-doubt to manifesting her dream of writing a book. Discover how Susan and Laura's New Year's Creativity Kickoff planted the seeds for Lily's inspiring ideas and fueled her audacious declaration to write a book and start a podcast.

Tune in for moments of celebration, insightful reflections on the creative process, and a deep dive into the challenges of increased visibility. Grab your favorite beverage, cozy up, and join Lily with guests Susan and Laura for a chat that's equal parts inspiration and real talk. 

Links:
Pre-order Lily's upcoming book, Thank You, More Please!
The Spark File 2024 New Year Creativity Kick Off
The Spark File

Show notes:
http://datebrazen.com/blog/sparking-your-creative-power

 

How was your year? How have you grown?  In the last episode of 2023, Lily shares her epic year in review, sharing some of her favorite brags and lessons. As you listen, we invite you to do the same - reflect, practice self-compassion, and celebrate your most cherished brags.   

Lily also answers listener questions, revealing insights into how she stayed grounded, who supported her through the challenges, and the mental shifts that were game-changers on her book-writing journey.

Join in celebrating the achievements, reflecting on the lessons learned, and looking forward to a new year filled with growth and empowerment.

Links:
Download the free Guide to Your Essence-Based Preferences

Show notes:
http://datebrazen.com/blog/my-epic-year-in-review-2023

 

Have you ever found yourself in a dating rut, unsure how to break free and progress? The key to moving forward is within reach. If you're feeling paralyzed, questioning where to begin, or navigating the uncertainties of being single, the solution lies in identifying your essence-based preferences.

In this episode, Lily shares the essence-based preferences tool that empowers you to attract the most fulfilling relationships. It is the tool that has allowed Lily and countless Date Brazen clients to attract the best relationship of their lives. Tune in and unlock the potential for positive change in your dating journey.

Hot-takes and topics:

• When you learn to trust what you want, you will set more boundaries and know when you are in the presence of the right kind of people.

• One tool for building self-trust is creating your essence-based preferences!

• The two categories of essence-based preferences: logistical and personality traits/values

• Lily explores how to ask for what you want in your dating life out loud (hint: this is where your co-conspirators come in!)

Links:

Download the free Guide to Your Essence-Based Preferences
VIP One-on-One Coaching with Lily
135. How to create your essence-based preferences

Show link:
http://datebrazen.com/blog/create-essence-based-preferences-with-ease

 

If you've ever felt behind in love or life, this episode is for you. On pub day for her new book, End Emotional Outsourcing: A Guide to Overcoming Codependent, Perfectionist and People Pleasing Habits, Beatriz Victoria Albina joins me to talk about how to stop centering everyone else's needs at the expense of your own—and start dating with self-worth.

We unpack:

💎 What "emotional outsourcing" is and why it keeps you stuck in people-pleasing, perfectionism, and codependency

💎 How to reclaim your agency and desire without guilt

💎 The BRAVE framework for building self-loyalty, step by step

💎 Why being a late bloomer is often an act of brilliance—not failure

Her book is out today! Go grab "End Emotional Outsourcing" wherever books are sold and start building the love life (and LIFE) that puts you back at the center.

Order your copy → https://beatrizalbina.com/book/

💥 Work with Lily:

→ Main Character Dating: datebrazen.com/waitlist

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

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

Follow Lily everywhere:
📲 Tiktok
📸 Instagram
📺 YouTube Channel

Hello, gorgeous friends! This week on The Date Brazen Podcast, Lily is diving into a simple 4-step framework to help you escape comparison mode in your dating life, especially during the holiday season. 

Whether at a holiday party or hanging with friends, dealing with triggers from engagement stories or past relationships, this framework will help you get into more massive, messy, courageous action toward your desires.

Tune in, save this episode, share it with your best friend, and let's kick off a season of self-care and courage in your dating journey.

Episode Topics and Hot-takes:

• "Eliminating comparison is a perfectionistic fantasy." Comparison is human.

• Ask, what thought is useful and true?

• Self-compassion is a strategy to help you move forward powerfully.

• S.O.F.T.: Self-compassion, Owning your needs, Feel your feelings, Thoughts not facts. 

Links:

1:1 Coaching with Lily
69. Worthiness + Winning Results with Simone Grace Seol

Show link:
http://datebrazen.com/blog/get-out-of-comparison-mode

 

 

This week, Lily welcomes female friendship coach and educator Danielle Bayard Jackson to the show!  As the founder of Friend Forward, Danielle is dedicated to empowering women with practical strategies for building and maintaining meaningful platonic connections.

Lily and Danielle explore pressing topics such as common barriers hindering sustainable female friendships, establishing healthy expectations for adult friendships, and navigating inevitable conflicts with grace.  The episode also addresses the challenges of making new friends, recognizing when it's time to end a friendship and the crucial role of time in cultivating lasting connections.  Don't miss this episode as Lily and Danielle dive deep into the complexities and joys of female friendships.

Episode Topics and Hot-takes:

• The most common barriers to building and sustaining friendships  

• Healthy expectations of what a friendship should be as an adult

• Healthy conflict is inevitable in all relationships. Danielle explains how to navigate conflict in friendships.

• Friendship breakups: How to know when it's time to end a friendship 

• "One of the key ingredients to friend-making is time." 

Links:

Register HERE for the upcoming live training- Dec 7th, "How to thrive during the holidays as a single badass"

Join Danielle's "Group Chat" Find out more at: https://www.betterfemalefriendships.com/group-chat

Danielle's website

Danielle on Instagram: @friendforward @daniellebayardjackson

Danielle on TikTok: @thefriendshipexpert

Show notes:
http://datebrazen.com/blog/fighting-for-our-friendships-with-danielle-bayard-jackson

 

This week, Lily addresses questions she's gathered from her TikTok community, centered around navigating the holidays while single. She delves into the complexities of solo celebrations, sharing her hottest takes, fiercest encouragement, and spiciest support.

Whether you're wondering how to handle prying relatives, seeking advice on thriving as a solo adventurer during the holidays, or craving solidarity, Lily's got you covered. Tune in for a dose of wisdom, a dash of humor, and a sprinkle of festive cheer as Lily guides you on thriving this holiday season as a single badass.

Register HERE for the upcoming live training- Dec 7th, "How to thrive during the holidays as a single badass"

Download the Free "Guide to Essence-Based Preferences" HERE.

Financial therapist Aja Evans joins Lily this week to discuss money and your dating life. The conversation is meant to inspire you to take up space in your financial life, challenge limiting beliefs, and prioritize relationships that align with your values and aspirations.

Aja is a Licensed Mental Health Counselor who specializes in financial therapy. In this episode, she helps us understand the connection between emotions and money and explores the varying dynamics of partnerships and money.

Episode Topics and Hot-takes:

• You don't need to make yourself smaller to accommodate a potential partner's ego.

• Aja helps us understand how to move through financial shame. 

• How to talk about money and finances on a date 

Links:

Aja's website
Aja on Instagram

Show notes:

http://datebrazen.com/blog/money-and-your-dating-life-with-aja-evans

 

This week, Lily welcomes Shirin Eskandani to the podcast! Shirin is a former opera singer turned coach who, in this episode, opens up about her quest for fulfillment beyond external achievements. From navigating the challenges of dating to discovering the unexpected depth of inner work in coaching, Shirin shares the transformative power that led her to pursue coaching with a commitment to inclusivity and decolonized perspectives.

Shirin shares her mission to diversify the coaching world, highlighting the need for more inclusive certifications. Lily and Shirin also dive into the concept of being "wholehearted," exploring themes of empowerment and the profound impact of coaching on personal and professional aspects of life.  

Listen in to hear this fantastic conversation that empowers self-discovery and self-trust.

Hot-takes from this episode:

• Nothing outside of you will ever make me feel fulfilled or enough. That is something you have to be working on yourself.

• "It isn't just about my dating life. It isn't just about my work. How we do one thing is usually how we do all or most things."

• Decolonizing is about questioning and getting curious about what you value and believe and whether those values and beliefs were handed to you from society or family. Then, decide that you get to choose what you value and believe and how you want to move forward.

Links:
One-on-One Coaching with Lily
Wholehearted Coaching: The Podcast
Whole Hearted Coaching Certification
Shirin on Instagram @wholeheartedcoaching
Wholehearted Coaching Certification Program on Instagram @wholeheartedcertification

Show notes:
http://datebrazen.com/blog/decolonizing-coaching-and-building-self-trust-shirin-eskandani

Farnoosh Torabi joins Lily on the podcast this week! Farnoosh is a leading financial expert, host of the So Money podcast, and author of So Money, Psych Yourself Rich, and When She Makes More. In this episode, she discusses the teachings and insights from her new book A Healthy State Of Panic, Follow Your Fears To Build Wealth, Crush Your Career, And Win At Life. The book (and this episode) illustrates how fear can be your superpower in this heartfelt and clever guide to maximizing your success to live richer and happier. Lily also parallels the topics in Farnoosh's book (related to fear) and how they can apply to the dating world. This is a fun, thoughtful, and heartfelt episode!

Featured Conversation Topics:

• The difference between harnessing fear and indulging it?

• How to build a healthy relationship with fear

• The fear of rejection, loneliness, and exposure in dating

• As you listen, think about one action step you can take to move with your fear in a more healthy manner. 

Links:
One-on-One Coaching with Lily
So Money with Farnoosh Torabi
A Healthy State of Panic, Farnoosh Torabi

Show Notes:
http://datebrazen.com/blog/harnessing-your-fears-with-farnoosh-torabi

 

Get ready for a healing and hilarious episode! Lily introduces a special guest who radiates "Main Character Energy" in every aspect of her life.  Devrie Brynn Donalson, the creative force behind the book, "You're Gonna Die Alone (& Other Excellent News)," unpacks her life-altering choices and journey.

Devrie reflects on her inspiring journey to Scotland, her struggles with body image, and her pursuit of self-discovery. Lily and Devrie also delve into the compelling dialogue on personal growth and societal pressures.

This episode is a rollercoaster of emotions, filled with humor, wit, and authentic storytelling. 

Don't miss this captivating conversation on the Date Brazen podcast!

Featured Conversation Topics:

• Devrie shares the story of her bold decision to move to Scotland, a journey sparked by friendship breakups and a quest for self-discovery.

• Discover how Devrie makes life-altering decisions by imagining herself as the main character in her story, ultimately guiding her choices.

• The challenges of growing up in a culture fixated on body size and appearances and the impact it can have.

• Devrie's thoughts on the fear of being unlovable and how it influenced her choices and relationships.

Links:
One-on-One Coaching with Lily
Devrie on Instagram & TikTok @devriebrynn
You're Gonna Die Alone (& Other Excellent News) 

Show link:
http://datebrazen.com/blog/healing-hilarity-and-mce-with-devrie-donalson

 

This week, we're breaking down the journey to creating a dating life that's joyful, boundary-filled, and confidently your own. Michelle, a Brazen Breakthrough client, joins Lily for a fantastic conversation about how she went from dead-end dating to only great dates. Plus, hear how she learned to stop compromising her desires and find joy in all areas of her life. 

🔥 Hot-Takes Alert! 🔥

• Ever wondered, "What if I do this thing and it doesn't work for my love life?" We're diving into that fear and breaking it down.

• It's time to stop compromising your desires. Learn how to permit yourself to want what you want without apology.

• The "shoulds" – we all know them, but how do we escape their grasp when it comes to dating, life, and love?

• 🗨️ Michelle reminds us, "Dating feels less like a 'life or death thing' when you are having fun in other areas of your life." 

Links:

✨Join The Brazen Breakthrough Now! ✨ The doors to Brazen Breakthrough close on Oct 27th at 11:59 pm EST

 

Lily is bringing you a bonus episode! If you missed her free live training, Create a Confident and Joyful-as-Fuck Dating Life, or want to hear it again - you're in luck! Today, Lily is sharing the entire training on the podcast. This training will help you build confidence, practice self-compassion and self-trust, and ease in your dating life.

In this episode, you'll learn:

• How to create a fiercely confident as-hell dating life (without the overwhelm, anxiety, and burnout).

• How to be completely dating-app optional and find juicy dates in person

• The anxiety-relieving plan of action that will make the right relationship inevitable.

• You'll also get a special invite to join us in my signature program, The Brazen Breakthrough.

This bonus replay is jam-packed with Q&As that cover many dating questions and questions about what it's like being a part of The Brazen Breakthrough. There is so much good stuff - this is such an informative (and fun) episode!

Links: 
✨Join The Brazen Breakthrough Now! ✨ The doors to Brazen Breakthrough close on Oct 27th at 11:59 pm EST

Anna joins Lily to share her experience in the Brazen Breakthrough (Lily's proven feminist as fuck group coaching program). In this episode, Anna shares what led her to join the Brazen Breakthrough and how it helped her feel supported, get unstuck, and stop panic dating. This episode is going to be so freaking good! 

We're excited for you to listen to Anna's story. If it resonates and you are listening on the day it airs - October 17th - join Lily for a live free training.   In this live free training, Lily will teach you how to be dating app optional, how to create a dating life with more ease, joy, and power, and how to make the right relationship inevitable. You'll also learn about the Brazen Breakthrough. It's going to be an amazing time. Find all the links below; we hope to see you there! 

Hot-takes from this episode:

• How to approach finding a partner in a way that is sustainable for your mental health and move away from panic dating

• "You're for the few and not for the many."

• When you learn the skill of self-advocacy and step deeper into agency in your love life, what you believe is possible is inevitable.

• Anna shares how understanding what she wanted in her dating life led to her going on a great date!

Links:

Join Us TONIGHT, October 17th, for the Free Live Training → ✨ Creating a Confident and Joyful-as-fuck Dating Life That Makes the Right Relationship Inevitable ✨

The Brazen Breakthrough

Show link:
http://datebrazen.com/blog/stop-panic-dating

 

Taylor hasn't been in a relationship since she was 19. Now, at 31, after eight ghostings and countless near misses, she's wondering: "Why not me?"

In her words:

"Hope is scary."

Because every time she's let herself hope, she's been let down—and she's started to believe maybe she's just not worth the effort.

In this raw and powerful live coaching session, we unpack what's really underneath that fear—and build a brand new belief:

✨ "Massive change happens when I trust myself and advocate for myself."

In this episode, you'll learn:

💎 How to move from "I know the tools" to actually feeling them work

💎 What to do when self-compassion feels completely out of reach

💎 The thought error that keeps so many late bloomers stuck in shame

💎 Why practicing hope (even when scared) is the bravest dating move you can make

If you've ever felt behind, broken, or like dating is a hopeless slog—this one's for you.

💥 Work with Lily:

→ Main Character Dating: datebrazen.com/waitlist

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

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

Follow Lily everywhere:
📲 Tiktok
📸 Instagram
📺 YouTube Channel

If you think you are "behind" in your dating life, this episode is for you. Lily is going to teach you how to start dating with confidence.  Your "lack of romantic experience" is not a dealbreaker for finding love. 

If you've never been in a relationship…
If you've never been kissed…
If you've never had sex…

There's ZERO wrong with where you've been. There's only the invitation waiting in front of you to build what you want NOW and move forward.

Don't NOT go to the party because you're afraid you're too late. The best stuff happens at a party once it's started, anyway. 

Hot-takes from this episode:

• "If you believe that your lack of experience is embarrassing, then that is holding you back from finding love on your terms."

• "The idea of being a late bloomer rushed me into dating to "fix it."

• "Your assumed late-bloomer status does not have to be your identity."

• Neutralize your dating history with self-compassion. History does not mean anything about what is possible.

• Build a strategy that honors your power

• Bring on a community that supports the hell out of you 

Links:

Join Us on October 17th for Free Live Training → ✨ Creating a Confident and Joyful-as-fuck Dating Life That Makes the Right Relationship Inevitable ✨

Show Link:

http://http/datebrazen.com/blog/start-dating-as-a-late-bloomer

 

This week's episode is all about in-person dating!  Lily is sharing step-by-step how to build confidence and become the version of yourself who approaches people in person with empowered action. 

This in-person dating lesson isn't meant to make you micromanage; it's to help you SHOW UP for your desires. The advice inside this episode will help you approach somebody in person in the next 30 days. You've got this, and Lily and the entire Date Brazen community have your back.

Episode Hot-takes:

• Permit yourself to be in progress, and stop self-blaming for being "bad" at dating. 

• "How do you get out of self-blame? By practicing self-compassion."

• "Commit to getting messy and practicing. You are not good at in-person dating because you haven't practiced yet." What if you just took one action step today?  

• Celebrate yourself! "Self-celebration is an in-person dating strategy. Celebrate every time you practice in-person dating!"

Links:
SAVE YOUR SPOT for Creating a Confident and Joyful-as-fuck Dating as a Burnout Feminist Badass

Show notes:
http://datebrazen.com/blog/approach-in-person-dating-even-if-youre-scared

Today, Lily is sharing an incomplete list (because the list just keeps on growing!) of the dumbest dating rules. She also offers her hot takes on how to break them. The "rules" covered in this episode include:

Dumb Dating Rule #1: You have to be on a dating app to be trying
Dumb Dating Rule #2:  Playing the numbers game - by constantly going on dates.
Dumb Dating Rule #3: "Give them one more chance. You NEVER KNOW"

This episode is going to help you free yourself from standards, rules, and pressure that are not serving you or your love life. 

Some Episode Hot-Takes:

• "A dating app can be a really powerful tool when you use it with boundaries; specifically when you see it as a tool and not the answer to your dating life."

• "Know your preferences deeply and choose dates intentionally. You get to trust yourself."

• "Pursuing the numbers game myth in your dating strategy is a quick ticket to burnout."

• "Hold your expectations to growth, not perfection."

Links: 
SAVE YOUR SPOT for Creating a Confident and Joyful-as-fuck Dating as a Burnout Feminist Badass
131. How your coupled friends can help you
135. How to create your essence-based preferences
162. The complete dating detox guide

Show notes:
http://datebrazen.com/blog/breaking-dumb-dating-rules

 

This week, Lily takes you through the complete dating detox guide. This guide will help you release the pressure on your dating life and create more spaciousness and ease. A Date Brazen listener inspired this episode when they asked:

"I have just decided to take a break from everything. Even though I'm good at taking this break, do you have any methods for healing or building back good feelings around dating?"

The dating detox guide will help you make way for more time and mental energy to envision the right partnership apart from the dating noise. Lily is going to tell you exactly how to get the clarity that you need and reignite your dating life with even more forward momentum than you've had before.

Some Episode Hot-Takes:

• "So many people are in that download, delete cycle, download, delete cycle. During this dating app pause, plan to get the most out of this time because intentional effort leads to intentional results."

• "Allow the worry to be seen through the lens of self-compassion."

Dating Detox Guide Steps Recap:

Step 1: Detox from Dating

Step 2: Detox from other's dating advice

Step 3: Detox from dating worry

Links:

SAVE YOUR SPOT for Creating a Confident and Joyful-as-fuck Dating as a Burnout Feminist Badass

140. My bless and release strategy for letting go

Show notes:

http://datebrazen.com/blog/the-complete-detox-dating-guide

 

We are back with brand-new episodes! This week, Lily provides an in-depth and actionable coaching answer to the question, "Am I doing enough in my dating life?" Listen to Lily's take on why you may ask yourself this question. Plus, she shares ten suggested action steps that will help you create momentum in your dating life and lead to the right relationship. 

"If you are not treating yourself like you would your best friend in your dating life, if you are swimming in self-doubt, self-blame, shame, and you're not addressing those things first, then doing these action steps in your dating life is not going to get you into the best relationship of your life."

If you do just one of the things mentioned in this episode, know it is beautiful enough. Celebrate yourself today (and every day)!   Print out the checklist below and give yourself a heaping dose of self-compassion.

Some Episode Hot-Takes:

• "I don't care about you getting into a relationship. I care about you knowing how to get into the best relationship of your life. Which begins with how you treat yourself."

• "Allowing yourself to be yourself will lead to the right relationship online and in person."

• "Celebration is a dating strategy."

Links:

121. Dating apps: Ask me anything
131. How your coupled friends can help you
135. How to create your essence-based preferences
Braving the Wildnerness, Brené Brown
Self-compassion.org
Kara Lowentheil's podcast, Unf*ck Your Brain
The Loveland Foundation
Psychology Today
National Institute for the Psychotherapies

Show notes:
http://datebrazen.com/blog/am-i-doing-enough-checklist

==========================

"Am I doing enough?" Checklist

1. Am I practicing self-compassion? 

2. Have I done my Essence-Based Preferences? 

3. Have I chosen my co-conspirator? 

4. Am I getting my brain coached/supported by the right coach or therapist? What support could I bring to my team to start making strides forward? 

5. Do I have a joy-building plan? Am I getting out into the world to do fun things?

6. Am I asking people out when I feel led?

7. When my energy allows, am I making new connections and discussing what I want in my dating life?

8. Am I swiping with the boundaries I need? 

9. Am I bringing community to my dating life? 

10. Am I celebrating myself?

Over the next two weeks, we are inviting you to enjoy Date Brazen Spotlight episodes. We're dusting off some of the most listened-to episodes and sharing them with you! This week,  In this episode, Lily shares some exercises that can help you better align with what you desire. 

"It doesn't take time; it takes alignment." 

With this new thought, you move from a place of stagnation to one of action. What action can you take to get into alignment?  Think about what you can do today to align with your values and move towards the life you desire tomorrow. 

SHOW NOTES:

https://www.datebrazen.com/blog/how-to-align-with-your-desires

 

Over the next three weeks, we are inviting you to enjoy Date Brazen Spotlight episodes. We're dusting off some of the most listened-to episodes and sharing them with you! This week, we are taking a trip all the way back to when The Date Brazen podcast first started, with an episode about how to be the boss of your dating life! Let's get into it. 

BAD ADVICE ALERT: "Dating is a numbers game."

Lily tackles one of the biggest problems people face in dating - the "Numbers Game."

This common piece of dating advice is hurting your dating life. Lily shares why and what you can do about it. Listen to this episode to hear the three steps to find better dates in less time!

Find all the info and links from today's episode in the show notes:  https://www.datebrazen.com/blog/episode-1

 

This week we have the pleasure of introducing you to Steph! Steph is a former Date Brazen client who joined Main Character Energy Mastermind last year to deepen her self-trust and self-pleasure and to date with unbothered energy. 

Lily and Steph get into topics such as bragging, being celebrated, and belonging. Steph also shares some of her breakthroughs from pursuing her desires and pleasures without apologizing or qualifications. No matter your circumstances, we know Steph's story will support and inspire you to embrace the main character energy in your love life. 

Hot-takes and takeaways from this episode:

• Breaking up with perfectionism and instead dating messy can be freeing

• Being witnessed and celebrated by a group of women cheerleaders

• The importance of normalizing belonging 

If Main Character Energy Mastermind resonates with you, applications are open. Click here to apply! 🎉

Show notes:
http://datebrazen.com/blog/a-coven-of-cheerleaders

 

This week, Hana joins Lily to share her main character energy story. Hana participated in the Main Character Mastermind last year. In this episode, Hana shares what it was like to invest in her love life and how she overcame the resistance she felt doing so.  

Main Character Energy is more than answering the question, "Can I date, and how do I do it?"  Prioritizing other areas of your life, as you'll hear Hana did, doesn't need to take away from dating. Engaging in play can amplify the results you see in your love life and beyond. This conversation is exciting and permissive as hell! 

Hot-takes and episode takeaways:

• Identifying resistance when it comes to investing in your love life 

• The importance of celebrating yourself! 

• Owning the ability to make your own rules and step into your power

Links:

Get on Main Character Energy Mastermind Waitlist!

Show notes:

http://datebrazen.com/blog/investing-in-your-love-life

 

Karin felt like a badass in every other area of her life and had so much joy - except in her dating life. When she came to Main Character Energy Mastermind last year, she knew she wanted to learn how to become a badass in her dating life.  In this episode, we explore perfectionism, specifically letting go of it, and how to create a dating life full of joy. 

Listen as Karin shares how releasing perfectionism helped her quickly create her desired results and how Main Character Energy seeped into every area of her life moving forward. 

Hot-takes and episode takeaways: 

• Releasing perfectionism is what creates results fast

• Creating a safe space for yourself in your life

• All of the answers you are looking for are inside you, and learning to internalize self-trust in a soft and new way

Links: 

Get on the Main Character Energy Mastermind waitlist!

Show notes:

http://datebrazen.com/blog/creating-a-joyful-dating-life

 

 

Becca came into this coaching session feeling stuck, frustrated, and deeply alone in her experience:

"I'm 37. I've never had a relationship. It feels like I'm missing something that everyone else figured out."

This episode is for the late bloomer who's never really seen their story reflected in dating advice—and is tired of wondering, "What's wrong with me?"

Together, we worked through:

– The fear that it's too late to have what you want

– How to shift from self-blame to self-trust (without pretending it doesn't still hurt)

– The exact first step to start dating from your real power

Becca left with a new plan—and a very different energy.

If you've ever thought "Maybe it's never going to happen," I want you to listen to this one.

🎧 The Late Bloomer Show, episode 250. Available now wherever you get your podcasts.

💥 Want more support? Start here:

→ Main Character Dating: datebrazen.com/waitlist

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

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

Follow Lily everywhere:
📲 Tiktok
📸 Instagram
📺 YouTube Channel

You are in for a treat this week because today, you will hear from a former Date Brazen client, Christine, who participated in The Main Character Energy Mastermind. You'll hear how Christine grew self-compassion and confidence, leading to a sparkly new relationship!  

Before joining us in Main Character Energy Mastermind, Christine did work on her dating life. Then she expanded her main character energy beyond dating. We are excited for you to hear Christine's perspective and her breakthroughs throughout this process.

Over the next four weeks, we'll showcase four client interviews to inspire you to embody your main character energy. These four individuals have so much wisdom to share, including their breakthroughs and how they learned to give themselves permission to trust themselves harder and take massive (albeit sometimes messy) action. 

Hot-takes and takeaways from this episode:

• What do you want your rules to be?

• Embracing the messiness of dating and doing self-reflective work

• How Main Character Energy Mastermind provides the opportunity to go deeper 

Links: 

Get on the Main Character Energy Mastermind waitlist!
Episode 129. Behind the Scenes of Main Character Energy Retreat

Show notes:

http://datebrazen.com/blog/christines-main-character-energy

 

 

In this episode, Lily shares the three cornerstones of Main Character Energy and how to start building them.

✨Add your name to the Main Character Energy Mastermind Waitlist HERE. 

This week we invite you to enjoy a Date Brazen Spotlight Episode! This episode is all about feelings. Lily created it as a practical guide for feeling your emotions, even the hard ones, and in the toughest times (like being rejected). You'll learn how to address your emotional needs with safety and self-compassion.  

Some hot takes from this episode:  

• Feelings are a bodily function, feeling them does not mean you'll get stuck in them, feeling them is a means for moving them through your body 

• You are not going to miss out on life when you slow down to practice self-compassion or feel your feelings - you are going to experience a more meaningful depth of life 

Show notes:
https://www.datebrazen.com/blog/feel-your-feelings-when-rejected/

This week we invite you to enjoy another Date Brazen Spotlight Episode! Lily will return very soon with all new episodes. Be sure to check out Episode 153 for some of Lily's recent updates on all things Date Brazen!

This spotlight episode answers the question, "How do I move on with my dating life after a really hard breakup?"  Lily gets really vulnerable and shares a story about an ex. Reflecting on your past relationships can be tough. And it's also the key to finding the best relationship of your life.

Let's supercharge your dating life (or current relationship) right now!

Show notes:
https://www.datebrazen.com/blog/episode-2

Lily is back this week with a new episode! She shares some big life updates that have transpired over the last few months. You'll hear about some of the most memorable moments from her wedding, get a brief behind-the-scenes glimpse into her writing process for her upcoming book, and get a front-row seat to an impromptu (and personal) Main Character Energy session. This is a fun and vulnerable episode we hope you'll enjoy!

Links:
Date Brazen on Instagram
Date Brazen on TikTok 

Show notes:
http://datebrazen.com/blog/big-updates-june-2023

 

Please enjoy this week's Date Brazen Episode Spotlight, a re-airing of one of Lily's popular podcast episodes. Lily will be back with new episodes very soon! In the meantime, visit the archives at DateBrazen.com/podcast for Date Brazen podcast episodes! 

Today we are bringing you a special replay of Lily's dating app ask me anything episode! Lily shares all of her dating app hot takes with you. Some of the questions answered in this episode include:  

• "How do you get someone to talk to you?!?!" 

• "What do I do when I am asking qualifying/disqualifying questions and the response I get is simply, 'You're pretty.'" 🤨

• "How do I respond to my family about why I don't use dating apps?"

• "Can Tinder be used for finding long-term partners and not just hook-ups?"

We hope you enjoy the episode!

Show notes:
https://www.datebrazen.com/blog/dating-apps-ama

 

Please enjoy another Date Brazen Episode Spotlight, a re-airing of one of Lily's popular podcast episodes. Lily will be back with new episodes in a few weeks. Visit the archives at DateBrazen.com/podcast for Date Brazen podcast episodes! 

In this week's spotlight episode, Lily shares three steps to get out of anxious spiraling or future-tripping and back into believing in what is possible for your dating life. You are worthy of having your needs met and prioritizing yourself, and it starts with how you treat yourself.    

Show notes:
https://www.datebrazen.com/blog/three-steps-to-get-grounded-in-your-dating-life

 

Please enjoy another Date Brazen Episode Spotlight, a re-airing of one of Lily's popular podcast episodes. Lily will be back with new episodes in a few weeks. Visit the archives at DateBrazen.com/podcast for Date Brazen podcast episodes! 

In this spotlight episode, Lily talks about how to meet someone in person. You'll hear practical advice and her five-step plan to help bring more joy and compassion to in-person dating. 

Show notes: 
https://www.datebrazen.com/blog/how-the-hell-to-meet-someone-in-person

 

This week, please enjoy a Date Brazen Episode Spotlight, a re-airing of one of Lily's popular podcast episodes. Lily will be back with new episodes in a few weeks! Until then, visit the archives at DateBrazen.com/podcast.

This week's episode is about the "Thank you, more, please!" challenge. This challenge is a powerful tool for those who were taught, "What you want does not exist." Listen in as Lily dares you to look for evidence that what you want DOES to exist in your love, professional, and beyond love life.  Tune into this short episode to learn how to implement this challenge today. 

Links:
Follow Date Brazen on Instagram
Follow Date Brazen on TikTok

Show notes:
https://www.datebrazen.com/blog/thank-you-more-please

 

This week, please enjoy a Date Brazen Episode Spotlight, a re-airing of one of Lily's popular podcast episodes. Lily will be back with new episodes in a few weeks! Until then, visit the archives at DateBrazen.com/podcast.

It's episode 100, y'all! Returning to the show is my partner Chris. He joined me for an Ask Chris and Lily Anything episode in 2020. In this episode, he joins me as my host and asks me some burning questions about dating, relationships, growing Date Brazen, and everything else. Join us for this fun and behind-the-scenes episode!

Hot-takes From This Episode:

• My favorite Date Brazen episodes

• The hardest part of our relationship: being human together. 

• What I am most PROUD to say "No," to.

• Do I believe in red flags? Hint: YES!

• Chris shares some of his favorite Date Brazen-isms

Show Notes:
https://www.datebrazen.com/blog/100th-episode-chris-asks-lily-anything

 

 

Today on The Late Bloomer Show, I'm coaching Dana.

Dana is a badass who's never been in a relationship—and she came to our session asking the question so many late bloomers carry:

"Are men going to see that as a red flag?"

In this episode, we go deep and get tactical.

💎 We create her Essence-Based Preferences in real time (including the exact words she'll use to vet potential dates)

💎 Build a clear vetting plan so she never has to waste a weekend on a "blah" date again

💎 Make over her dating profile so it reflects who she actually is: adventure traveler, joyful weirdo, emotionally aware, deeply feminist

We also talk through how to show up confidently when you feel behind, how to stop apologizing for your inexperience, and how to date like you're not dead yet.

💥 Work with Lily:

→ Main Character Dating: datebrazen.com/waitlist

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

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

Follow Lily everywhere:
📲 Tiktok
📸 Instagram
📺 YouTube Channel

This week Lily is sharing some behind scenes of her upcoming wedding day. Listen to this fun "Ask me anything about my wedding" episode, inspired by the Date Brazen Instagram community! You'll hear what Lily is doing differently and how she plans to bring main character energy to the special day.  

Links:
Date Brazen on Instagram
Date Brazen on TikTok

"Any time a guy asks me out on a dating app, I get nervous and cancel. Why am I doing this?"

Listen in for Lily's hot take and advice for this listener question.

Get my free Guide to Make Dating Feel Like Self-Care

Sign up for The Brazen Breakthrough Waitlist

Listen in for Lily's piping hot feminist take on a listener question about "Who should pay on a first date?"

Sign up for The Brazen Breakthrough Waitlist

Download my free Guide to Make Dating Feel Like Self-Care