“Why do I have to do all this work just to be given a chance?”

In this deeply moving live coaching session, Lily talks with Caleigh—a brilliant late bloomer feeling burned out and heartbroken after years on dating apps.

On the surface, it’s dating fatigue. But underneath, they uncover how internalized misogyny shows up in dating: feeling like you have to be less intense, less emotional, or hide your anger just to be seen as desirable.

In this episode, you’ll hear:

✨ Why dating can feel like Groundhog Day, especially for late bloomers
✨ How grief and shame linger around never having had a serious relationship
✨ The truth about anger—and why feeling it might change everything in your love life
✨ How perfectionism sneaks into dating and keeps you stuck
✨ Concrete tools to raise your standards without giving up hope

If you’ve ever wondered why dating feels like so much work, or worried that your big feelings make you “the problem,” this episode will make you feel seen—and give you practical ways to keep going without losing yourself.

Work with Lily:

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 Channel

If rejection makes you want to hide under the covers and never date again—this episode is your roadmap back to brave action.

Lily shares one of her most painful rejections from her dating life, how it nearly derailed her belief in love, and the five-step Rejection Resilience Side Quest she created to help late bloomers build the skill of shooting their shot without spiraling.

Inside this episode:
⚡️ Why rejection feels so dangerous (and why that makes total sense)
⚡️ A 5-step framework to depersonalize “no” and take bold action anyway
⚡️ A rejection aftercare protocol that actually helps you recover faster
⚡️ How building resilience leads to getting more of what you want in love and life

This is the most essential skill in dating that no one teaches—until now.

💥 Want more support?

Work with Lily:

🔗 Learn about her signature program, Main Character Dating: datebrazen.com/waitlist

🔗 Book: Thank You More Please

🔗 YouTube Channel

🔗 Tiktok

🔗 Instagram

Ever catch yourself thinking: “Why would they like me? What’s wrong with them for wanting me?”

This sneaky belief keeps so many late bloomers stuck in self-doubt, playing small, and avoiding the very love they crave.

In this episode, Lily gets personal about how this thought showed up in her own love life—even when she met her now-husband—and shares the powerful mindset shifts and tools you need to bust through this myth for good.

Inside:

✨ Why this belief is so common for late bloomers
✨ How it blocks you from trusting healthy connection
✨ The ACK tool to start rewiring your brain for worthiness
✨ Real-life reframes to help you believe, “Of course they like me!”

Listen now and start stepping into your main character energy—for love, dating, and beyond.

Work with Lily:

🔗 Learn about her signature program, Main Character Dating: datebrazen.com/waitlist

🔗 Book: Thank You More Please

🔗 YouTube Channel

🔗 Tiktok

🔗 Instagram

Think dating apps are the only way to find love—but secretly hate them?

Same, friend.

In this episode of the Date Brazen Podcast, I’m sharing my complete, no-BS guide to using dating apps in a way that protects your sanity and increases your chances of finding the right relationship.

Inside, you’ll learn:
→ Why deleting and re-downloading apps keeps you stuck
→ The exact rules for stress-free swiping (hint: 20 minutes a day)
→ How to write a profile that qualifies the right people—and filters out the wrong ones
→ Why you should never, ever try to be “chill” in your dating bio

Plus, I’m revealing my personal photo rubric and conversation starters that actually spark connection.

Dating apps are flawed—but with this episode, you’ll know how to make them work for you.


Work with Lily:

🔗 Learn about her signature program, Main Character Dating: datebrazen.com/waitlist

🔗 Book: Thank You More Please

🔗 YouTube Channel

🔗 Tiktok

🔗 Instagram

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:

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