The Feminist Dating Show25 Nov 2025

257. Self-Trust for Anxious Overthinkers: How to stop dress rehearsing tragedy

If you're stuck in a spiral of overthinking — replaying conversations, asking 15 friends what to do, imagining every worst-case scenario — this episode will feel like a deep exhale.

Overthinking isn't you being "careful."

It's a self-trust deficit.

And that is a skill gap, not a character flaw.

In this episode, I break down:

• Why anxious rumination feels so real and so urgent
• How patriarchy, people-pleasing, and fear of rejection trained you not to trust yourself
• The difference between careful planning and dress rehearsing tragedy
• Why outsourcing decisions to friends keeps you stuck
• What self-trust actually is (and why it's messy, imperfect, and learnable)
• Tiny, doable steps to rebuild your self-trust today
• How this plays out in dating, boundaries, and big life decisions
• A framework to stop overthinking and start acting from your gut

If you've been doubting yourself for years — in your dating life, your friendships, your career, your boundaries — this episode will teach you how to finally have your own back.

Self-trust is a skill. And you're about to learn it.

Work with Lily

✨ Main Character Life Mastermind — Applications Opening soon!
Sign up for my free training-- Stop People Pleasing and Build a Stupidly Joyful Life-- on Dec 3rd to be the first to apply. RSVP HERE

📚 Read my book — Thank You, More Please
A feminist guide to breaking dumb dating rules and finding love
Order here: https://datebrazen.com/book

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