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
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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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🌐 Website