Cora left an unhealthy marriage, deconstructed her entire evangelical upbringing, bought her first house, and raised two 16-year-olds solo. Then she met someone really good on Hinge. Who met all of her essence-based preferences. And she almost talked herself out of it. Not because he did anything wrong. Because she felt ashamed for wanting partnership after working so hard to become independent. In this live coaching session on The Feminist Dating Show, I coach Cora through the spiral in real time. We build her an "if this, then that" plan for the anxiety. We upgrade the questions she's asking herself. And we talk about why "desire is your birthright" (in the words of Dr. Juliana Hauser), not something you have to earn after you've suffered enough. If you have ever felt like wanting love was a betrayal of your hard-won independence, episode 266 is for you.

Work with Lily:

Read Lily's book: Thank You, More Please

Watch on YouTube: youtube.com/@datebrazen

Follow on TikTok: tiktok.com/@datebrazen

Follow on Instagram: instagram.com/datebrazen

Explore programs + resources: datebrazen.com

If you have a great life and dating just doesn't feel like part of it — this one's for you.

In episode 265, I'm coaching Christina live. She's 36, has a great life, one long-term relationship under her belt, and is asking the question a lot of you are quietly asking: is it even worth it to try dating after so much disappointment?

She's frustrated by the single tax — the emotional and financial cost of being the only single person in her circle, coordinating everything alone while everyone else has a built-in teammate.

She wants a partner more than she lets herself admit.

And she's bi, but feels like an adolescent there compared to her experience dating men — and keeps wondering if it's even worth exploring.

In this episode, we dive into ALL of this, and come up with a concrete plan to make dating a part of her amazing life-- with permission, boundaries, and a plan to attract more.

Work with Lily:

Read Lily's book: Thank You, More Please

Watch on YouTube: youtube.com/@datebrazen

Follow on TikTok: tiktok.com/@datebrazen

Follow on Instagram: instagram.com/datebrazen

Explore programs + resources: datebrazen.com

Here's the secret of flirting... Every single person you've ever wanted to talk to — the cute stranger on the subway, the guy at the coffee shop, the woman you keep seeing at the farmers market — is also in their head. Every. Single. One. And yet most of us walk around convinced that WE are the only ones who are awkward, anxious, and completely clueless about flirting. This week on The Feminist Dating Show, I brought in flirt coach @benjamincamras to change that story so you can feel like the confident badass you are while flirting and connecting with new cuties. In Episode 264, we cover: → What flirting actually IS (hint: it's not what you think) → The 4 flirt styles — and how to find yours → How to handle rejection without spiraling into a shame tornado → What to do when your mind goes completely blank mid-conversation → The subway flirt role play you didn't know you needed → How to flirt safely when you hold marginalized identities → The one thing to do THIS WEEK to build your flirt muscles This is not about performing. It's about becoming your most confident, authentic self — and you already have everything you need.

Follow Benjamin on:

• TikTok
• Instagram
• Flirtations! Podcast

Work with Lily:

Read Lily's book: Thank You, More Please

Watch on YouTube: youtube.com/@datebrazen

Follow on TikTok: tiktok.com/@datebrazen

Follow on Instagram: instagram.com/datebrazen

Explore programs + resources: datebrazen.com

If you've ever opened a dating app and immediately wanted to throw your phone across the room — this one's for you.

In episode 263 of the Feminist Dating Show, I'm coaching Kayla live. This episode is for you if you relate to any of this:

• You open a dating app and immediately spiral into, "What if they make me uncomfortable?" or "what if I say something stupid?"
• You avoid swiping because judging people by their photos makes you feel like a bad person
• You watch your friends get matches and wonder what you're doing wrong
• You feel like a late bloomer, a re-entry dater, or just behind
• Deep down, you're afraid the real problem is that you're just not lovable...

In this episode, I help Kayla name what's underneath her dating avoidance. We name what makes dating apps so dang difficult on our brains/bodies/nervous systems (they are such a flawed tool!). AND we build a simple "if this, then that" plan for dating that soothes her anxiety. In this episode, you'll learn to swipe without abandoning yourself, without judging yourself for your attraction preferences, or without lowering your standards.

Work with Lily:

Read Lily's book: Thank You, More Please

Watch on YouTube: youtube.com/@datebrazen

Follow on TikTok: tiktok.com/@datebrazen

Follow on Instagram: instagram.com/datebrazen

Explore programs + resources: datebrazen.com

This one's for you if dating has started to feel like a hamster wheel of painful experiences… and you keep thinking: I've done so much work on myself—why is this still so hard?

In this live session, I coach Quinn through:

• the loop of type vs. essence-based preferences
• the fear of being "too much" in dating
• what to do when uncertainty triggers a full-body spiral
• how to tell if your "picker is broken"… or if you've been trained to assume you're the problem
• self-compassion as a real tool (not a pep talk) to re-regulate and come back home to yourself
• how to update your EBPs so you're not dating someone you have to parent or beg for affection
• community + dating after a big move

By the end, Quinn says it perfectly: this session felt like closing a bunch of tabs in her brain and finally having the system run again.

If you've ever been in the mindset of "it's fate or it's me," I want you to hear this.

Work with Lily:

Read Lily's book: Thank You, More Please

Watch on YouTube: youtube.com/@datebrazen

Follow on TikTok: tiktok.com/@datebrazen

Follow on Instagram: instagram.com/datebrazen

Explore programs + resources: datebrazen.com

Have you ever wondered if you're "too late" because dating has never worked the way it seems to work for everyone else?

My client Liz joined Main Character Dating at 38 having never been in a long-term relationship. She felt behind, alone, and unsure how to even do dating.

What shifted for Liz inside Main Character Dating was hope.

No more dating shame.

And an action plan that helped her move toward the right dates with self-trust and support.

In this episode of The Feminist Dating Show, Liz shares how dating went from something she avoided to something that finally felt possible.

In this conversation, Liz shares how:

• Dating went from something she avoided to something that felt possible
• Community helped her realize she wasn't the only one
• Structure and feedback helped her interrupt old patterns
• She started dating with clarity, courage, and direction

Her words say it best: dating feels possible now.

If you've ever thought "Is it always going to be like this?" — this one's for you.

And I also want you to know this:

Main Character Dating is open for enrollment right now.

This is my year-long group coaching program for anyone who hasn't found a romantic relationship (or the right one), and wants a joyful dating life that makes the right relationship inevitable.

🗓 Doors are open until Monday, Feb 16th.

💖 Learn more and join us here: datebrazen.com/dating

No matter what, I know Liz's story will help you feel less alone—and more hopeful about what's possible for you.

Work with Lily:

Read Lily's book: Thank You, More Please

Watch on YouTube: youtube.com/@datebrazen

Follow on TikTok: tiktok.com/@datebrazen

Follow on Instagram: instagram.com/datebrazen

Explore programs + resources: datebrazen.com

In this episode, I'm sharing my 10 rules of feminist dating—the principles I know actually lead to an equitable, joyful partnership. No matter your past experience (or lack of experience), your age, or your sexuality, these rules are here to help you magnetize the right partner and feel amazing doing it.

These 10 rules are a response to outdated, patriarchal dating advice that teaches you to shrink, self-silence, and settle. I walk through what it means to date as the main character of your life, expect co-creation, stop doing unnecessary emotional labor, question inherited scripts, and reject the idea that you're "too late."

This episode is for late bloomers, restarter daters, and anyone who wants to date with power, alignment, and self-trust—without playing games or abandoning themselves along the way.

In this episode, I'm sharing a transparent update about the podcast: why I decided to rename it The Feminist Dating Show.

I talk through the intention behind the previous name, what I heard from listeners over time, and why I want the podcast name to immediately feel inclusive and clear—especially for people who are new to this work. Feminist dating has always been the value system underneath everything I teach, and this new name reflects that, while still serving the amazing late bloomers and re-entry daters we serve.

Nothing about the mission or the content is changing. This show is still for late bloomers, restarter daters, and anyone who's been taught it's too late or too much to find what they want.

Let's do this!

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 LilyRead Lily's book: Thank You, More PleaseExplore 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 PleaseA feminist guide to breaking dumb dating rules and finding love. Order HERE Follow Lily everywhere: 📺 YouTube Channel 📸 Instagram 📲 Tiktok 🌐 Website

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 Follow Lily everywhere: 📺 YouTube Channel 📸 Instagram 📲 Tiktok 🌐 Website