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Today on the podcast I'm telling you exactly how to go from friend zone to flirty in any conversation. In this episode: The one question that takes you from friendly to flirty, and when to ask it. What the right people say when you ask, and what the wrong people say My rejection resilience plan to bounce back no matter what. My unconventional definition of flirting Why shooting your shot isn't desperate when it comes from desire, not scarcity How clients went from "I don't know how to flirt" to getting asked for their number, asking someone to coffee, and sending the bold text   🌟 Join Stop Freezing, Start Flirting, a three-day coaching challenge for late bloomers to confidently flirt and land a date IRL, October 25-27, 7-8pm ET: https://datebrazen.com/challenge   Work with Lily: 📖 Get the book, Thank You, More Please: https://datebrazen.com/book 🌟 Join the Main Character Dating waitlist: https://datebrazen.com/dating ✨ Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook 📸 Follow me on Instagram: https://www.instagram.com/datebrazen/ 🎵 Follow me on TikTok: https://www.tiktok.com/@datebrazen ▶️ Follow me on YouTube: https://www.youtube.com/@DateBrazen

If you want to date IRL and find your person, but you see someone cute and your body locks up, this episode is for you. Freezing is a somatic response. It is your nervous system protecting you from fears like: What if they reject me? I'm definitely not their type. They're probably coupled. Why even try? In this episode, I'm naming each of these fears for what it is, and giving you the reframes and in-the-moment tools to move through the freeze. Fall and winter are a high value, high opportunity season for your IRL dating life, so this is the moment to start. In this episode: The reframes for the fears that keep you frozen: fear of rejection, fear of not being their type, and the fear that they're coupled Why you need to stop being your own helicopter parent The somatic tool I learned that helps you move through the freeze What to do in the bathroom the moment you see a cutie The five parts of a rejection resilience plan Client brags from Main Character Dating, including the client who made a credit union teller blush   Work with Lily: 🌟 Join my free 3-day live challenge, Stop Freezing, Start Flirting (Oct 25-27): https://datebrazen.com/challenge 📖 Get the book, Thank You, More Please: https://datebrazen.com/book 🌟 Join the Main Character Dating waitlist: https://datebrazen.com/dating ✨ Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook 📸 Follow me on Instagram: https://www.instagram.com/datebrazen/ 🎵 Follow me on TikTok: https://www.tiktok.com/@datebrazen ▶️ Follow me on YouTube: https://www.youtube.com/@DateBrazen

How do you date men when you hate men? It can be a tough question, especially if you've never seen that what you want and who you want exists. Both/and in this episode, I'm your feminist dating coach. And especially if you date men, I'm here to show you how to attract the feminist, emotionally intelligent, fights-for-women's-rights kind of man you desire. You are for the few, not the many. And this kind of man is rare. But rare things exist. And I'm here to help you find them. I would tell you what I'm gonna tell you in this episode. In this episode: Why it's ok to hate men AND date to find your man. You can be a feminist and want a relationship. A complete dating system that vets for not only what they say, but how they behave ACK: acknowledge, compassion, kind reframe If you date men, you're not just looking for any man, you're looking for your man. This episode is the pep talk you need to double down on your boundaries, your vetting process, and your high standards.   💎 Join my free 3-night challenge, Stop Freezing, Start Flirting (Oct 25-27): https://datebrazen.com/challenge 📖 Get my book, Thank You, More Please: https://datebrazen.com/book ✨ Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook 📸 Follow me on Instagram: https://www.instagram.com/datebrazen/ 🎵 Follow me on TikTok: https://www.tiktok.com/@datebrazen ▶️ Follow me on YouTube: https://www.youtube.com/@DateBrazen

You don't have to be on dating apps to be "trying" in your dating life. This episode gives you the alternative strategy that has worked for hundreds of my clients (and worked for me to meet my husband). In this episode, you'll learn exactly how to date IRL. Inside episode 284: → Why "I don't chase, I attract" is one of my least favorite pieces of dating advice, and how it is negatively impacting your IRL dating life → My rule for feminist dating that I've seen work for hundreds of people who felt too behind, too late, too much, not enough → What to say when people tell you they don't know anybody single → Why awkwardness is the price of admission for connection 💎 Register for my free live 3-day coaching challenge, Stop Freezing, Start Flirting (Oct 25-27): https://datebrazen.com/challenge 💎 Listen to my Vox Explain It to Me interview: https://podcasts.apple.com/us/podcast/explain-it-to-me/id1042433083?i=1000789331580   Work with Lily 💎 Get the book, Thank You, More Please: https://datebrazen.com/book 💎 Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook 💎 Follow me on Instagram: https://www.instagram.com/datebrazen 💎 Follow me on TikTok: https://www.tiktok.com/@datebrazen 💎 Follow me on YouTube: https://www.youtube.com/@DateBrazen

In episode 283, I'm getting personal about how people pleasing made me settle in dating, friendship, and work, how it led to panic attacks on my lunch break, and the three-step formula I used to quit, one small choice at a time. → I thought I was and wanted "too much," and how that kept me in a relationship where none of my emotional needs were met → How people pleasing was showing up in every relationship in my life, from texting clients at 10 p.m. to making every single plan for my friend group → How you can go from feeling sick with people pleasing, like I was, to building an expansive, joyful life as the main character → The unconventional way to use guilt as your roadmap to give yourself more permission → The three-step formula I used to quit people pleasing and build main character energy, even when I was afraid Main Character Era -- my small group 6-month mastermind for people-pleasing burnt-out feminists to build rock-solid self-trust and finally get what they want in love, friendship, and work -- applications close tonight at midnight. 💎 Apply for Main Character Era: https://datebrazen.com/era   Work with Lily: 💎 Get the book, Thank You, More Please: https://datebrazen.com/book 💎 Join the Main Character Dating waitlist: https://datebrazen.com/dating 💎 Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook 💎 Follow me on Instagram: https://www.instagram.com/datebrazen/ 💎 Follow me on TikTok: https://www.tiktok.com/@datebrazen 💎 Follow me on YouTube: https://www.youtube.com/@DateBrazen

Jackie was burnt out to a crisp. She was in a job she felt trapped in, because the story was that she had to be of service no matter how she felt. She had taken a sabbatical that was supposed to be two or three months, and it took her a couple of months just to relax. She came back and was immediately depressed. She couldn't see the forest through the trees. She had no vision. She just wanted to lay down. She also knew she was a background person who wanted to be a main stage person, and she couldn't say that out loud without shame about abandoning her community. Inside Episode 282 of The Feminist Dating Show, Jackie share your story of how she quit people pleasing as her default inside Main Character Era Mastermind (formerly Main Character Energy Mastermind), and what happened in the six months after. She left the job. She started her own company. She moved abroad, got the apartment she wanted in Edinburgh, and started dating with a lot more freedom. Inside episode 282:   → The difference between rest that hides burnout and rest that heals the burnout → How the skillset of self-trust changed Jackie's dating experience for the better. → The micro inflection points where your brain wants to dress rehearse tragedy instead of claiming that it's working, and how to catch yourself and redirect toward the best case scenario. → How Jackie built a self-care action plan she runs the second she notices herself spinning, instead of waiting until she's already spiraled   💎 TONIGHT: Join my free live training, Quit Being the Best Friend: How to Stop People Pleasing and Finally Get What You Want in Love, Friendship, and Work Without Overthinking and Anxiety.   You'll learn how to stop people pleasing, build rock solid self-trust, and become the main character of your life: https://datebrazen.com/best-friend   Work with Lily: 💎 Get the book, Thank You, More Please: https://datebrazen.com/book 💎 Join the Main Character Dating waitlist: https://datebrazen.com/dating 💎 Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook 💎 Follow me on Instagram: https://www.instagram.com/datebrazen/ 💎 Follow me on TikTok: https://www.tiktok.com/@datebrazen 💎 Follow me on YouTube: https://www.youtube.com/@DateBrazen

The way you do one thing is the way you do everything. So when you're stressed about the question "when is the right time to have sex??" and outsource your answer to another dating expert or another tiktoker, I hear an opportunity to build a life changing skillset that will create clarity for this question (and all questions).... That skillset? Self-trust. When you build the skill set of self-trust, with sex, with friendships, with romance, with work, it all gets more easeful. Episode 281 unpacks what this question is really asking and gives you a framework to come to your best answer, whatever it is. Not just for this. For everything. Because the skillset of self-trust will help you get clarity everywhere. Inside this episode: → Self-trust defined: the firm reliance on the integrity of yourself. It does not mean everything goes your way. It means you will have your back no matter what happens. → ACK. Acknowledge, compassion, kind reframe. The self-coaching tool Lily teaches in main character dating, applied to a decision you have been agonizing over. → The small self-trusting decisions that you can make today that will start to build self-trust.   💎 Join my free live training, Quit Being the Best Friend: How to Stop People Pleasing and Finally Get What You Want in Love, Friendship, and Work Without Overthinking and Anxiety: https://datebrazen.com/best-friend 💎 Get the book, Thank You, More Please: https://datebrazen.com/book 💎 Join the Main Character Dating waitlist: https://datebrazen.com/dating 💎 Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook 💎 Follow me on Instagram: https://www.instagram.com/datebrazen/ 💎 Follow me on TikTok: https://www.tiktok.com/@datebrazen 💎 Follow me on YouTube: https://www.youtube.com/@DateBrazen

The good, reliable, everyone-comes-to-me best friend. You've been praised for that role your whole life. What if it's the reason you can't get yourself to shoot your shot, ask for more, or take up space with your desires?   This episode names the pattern hiding under all of it: people pleasing. Not being nice. The habit of self-abandoning in real time to avoid being misunderstood, judged, or abandoned. Lily breaks down where it lives and how to start unhooking from it.   Inside episode 280:   → The two categories of people pleasing: the interpersonal kind (the date you stay on too long, the resentment you never voice) and the internal kind (the imagined judgment that keeps you from hitting post, asking for what you want, or flirting IRL)   → Why people pleasing is self-protection dressed as politeness, and why it's actively emptying your cup   → The main character energy formula that moves you through the fear: permission, self-trust, massive messy action   → Why self-trust isn't one-and-done. It's small choices built on small choices   → The people pleasing detox: take inventory, choose one pattern, run it through the framework   Your richest, biggest life is on the other side of this pattern.   💎 Join my free live training, How to Quit People Pleasing: https://datebrazen.com/best-friend   Work with Lily:   💎 Get the book, Thank You, More Please: https://datebrazen.com/book 💎 Join the Main Character Dating waitlist: https://datebrazen.com/dating 💎 Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook 💎 Follow me on Instagram: https://www.instagram.com/datebrazen/ 💎 Follow me on TikTok: https://www.tiktok.com/@datebrazen 💎 Follow me on YouTube: https://www.youtube.com/@DateBrazen

You've been waiting to feel ready. Ready enough to launch the thing, shoot your shot, ask for the promotion you've been researching and figuring out the pitch for for months. Here's the hot take: you're stalling what you want because of the fear that you're not enough for it. The fear of failure, of judgement, of "not enoughness" has driven your car for long enough. So in this episode, I get a little messy and share my HOTTEST takes on exactly how to build the belief- and actions- of enoughness. Through a winding road of Matrix analogies and The Holiday references, you're going to realize in this episode that you are THE ONE. The One who is the main character. Who can create the love, friendship, and work life that you desire In the words of Mary Oliver, "What will you do with your one wild and precious life?" That's what this episode is here to help you answer. Get into it!   Work with Lily: → Join my free live training, Quit Being the Best Friend: https://datebrazen.com/best-friend 💎 → Get the book, Thank You, More Please: https://datebrazen.com/book → Join the Main Character Dating waitlist: https://datebrazen.com/dating → Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook → Follow me on Instagram: https://www.instagram.com/datebrazen/ → Follow me on TikTok: https://www.tiktok.com/@datebrazen → Follow me on YouTube: https://www.youtube.com/@DateBrazen

Here are 3 signs you're demoting yourself to the "best friend" role in love, friendship, and work... You're the designated listener in your friendships, always the one reaching out first, making the plans, overgiving and caretaking. In dating, you're hesitating to ask for what you want for fear of scaring them off, settling for good enough or settling for inaction. At work, you're logging in past 9p.m., trying to fulfill your coworkers' needs because you fear that shutting down your computer will let people down and mean you're not seen as the go-to person. It's exhausting to demote yourself to the "best friend" role. And it's time for your main character era. This week's episode is about the skill set that will take you from "best friend" to main character. Main character energy isn't something you're born with. It's learnable. In this episode, you'll learn the exact three-part framework Lily uses in her own life and teaches her clients to finally stop shrinking and start taking up space in your dating life, your friendships, and your work. Inside episode 278, you'll lear: ■ The three signs you've been demoting yourself to the best friend role across dating, friendship, and work ■ The three-part skill set that makes up main character energy: permission, self-trust, and massive messy action ■ How to build self trust (even if you've never had it before) ■ What it actually means to shoot your shot unapologetically in every area of your life   Ready to step into your main character era? Join Lily's free live training, Quit Being the Best Friend, on September 15th to learn how to break free from people-pleasing and finally get what you want in love, friendship, and work. Sign up: https://datebrazen.com/best-friend   Work with Lily: ■ Get the book, Thank You, More Please: https://datebrazen.com/book ■ Join the Main Character Dating waitlist: https://datebrazen.com/dating ■ Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook ■ Follow me on Instagram: https://www.instagram.com/datebrazen/ ■ Follow me on TikTok: https://www.tiktok.com/@datebrazen ■ Follow me on YouTube: https://www.youtube.com/@DateBrazen

If approaching a cutie in the wild makes you nauseous… If you "aren't the type of person" to make eye contact with hotties in the wild… If the thought of asking someone out in-person makes your butthole clench up… If you want to try in-person dating, but feel overwhelmed and anxiety-filled at HOW to start. This episode is for you.    💎 Get the book, Thank You, More Please: https://datebrazen.com/book 💎 Join the Main Character Dating waitlist: https://datebrazen.com/dating 💎 Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook 💎 Follow me on Instagram: https://www.instagram.com/datebrazen/ 💎 Follow me on TikTok: https://www.tiktok.com/@datebrazen 💎 Follow me on YouTube: https://www.youtube.com/@DateBrazen

If you've ever feared that you're not attractive or desirable because it's never happened before, this episode is a must-listen. Lily breaks down the internalized fears many late bloomers carry—and how to reframe those thoughts with compassion, context, and confidence using her signature ACK mindset tool (Acknowledge, Compassion, Kind Reframe). You'll also get a powerful challenge to reconnect with your body and spark self-trust this week.   Links + Resources: 📚 Buy Lily's book Thank You More Please: datebrazen.com/book 💖 Work with Lily: datebrazen.com 🎥 YouTube Channel 📱 TikTok 📸 Instagram

You want to flirt IRL. But you're scared to start... The Flirting Ladder is exactly how you will build the skills to become an expert, confident flirter! This is the exact tool Lily teaches inside Main Character Dating to take you from frozen with fear to flirting with confidence. In this episode: → Flirting is joyful, courageous connection. Not a performance, not a personality trait some people are born with. It's a skill set you build by doing. → Awkwardness is the price of admission for connection. It will be awkward, and that is not a sign you're doing it wrong. → You cannot say the wrong thing to the right person. The right person is looking for you too, and they will be delighted you walked up. → The flirting ladder itself: start with one second of eye contact and climb, one accessible rung at a time, until "so random question, are you single" feels doable. → The 10 seconds of courage tool that builds momentum from paralyzed to shooting your shot. By the time "random question" is out of your mouth, you're already halfway done.   Your flirting ladder lives right next to your rejection resilience plan from episode 267. Build both and you're unstoppable this summer.   💎 Get the book, Thank You, More Please: https://datebrazen.com/book 💎 Join the Main Character Dating waitlist: https://datebrazen.com/dating 💎 Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook 💎 Follow me on Instagram: https://www.instagram.com/datebrazen/ 💎 Follow me on TikTok: https://www.tiktok.com/@datebrazen 💎 Follow me on YouTube: https://www.youtube.com/@DateBrazen

Today we're talking about making the impossible happen. So if you think finding love is impossible for you, this is the episode for you. You've done it before. The friendship you didn't know you needed. The job that used to be a pipe dream and is now a no-duh. Your love life is next.   Work with Lily: ■ Get the book, Thank You, More Please: https://datebrazen.com/book ■ Join the Main Character Dating waitlist: https://datebrazen.com/dating ■ Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook ■ Follow me on Instagram: https://www.instagram.com/datebrazen/ ■ Follow me on TikTok: https://www.tiktok.com/@datebrazen ■ Follow me on YouTube: https://www.youtube.com/@DateBrazen

If rejection makes you want to hide under the covers and never date again—this episode is your roadmap back to brave action.   In this Episode Spotlight, 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. Work with Lily: 💎 Get the book, Thank You, More Please: https://datebrazen.com/book 💎 Join the Main Character Dating waitlist: https://datebrazen.com/dating 💎 Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook 💎 Follow me on Instagram: https://www.instagram.com/datebrazen/ 💎 Follow me on TikTok: https://www.tiktok.com/@datebrazen 💎 Follow me on YouTube: https://www.youtube.com/@DateBrazen