“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