Coming up on this episode of Flirtations, we’re joined by the marvelous Lily Womble—a feminist dating coach, former top matchmaker, host of the Date Brazen podcast and author of Thank You, More Please: A Feminist Guide to Breaking Dumb Dating Rules and Finding Love.
Lily is on a mission to help us break free from the beliefs the patriarchy has embedded in our love lives—and to ask for more.
In this conversation, we talk about what it means to date as a feminist. We explore everything from how the patriarchy shapes modern dating culture to why so many women feel like they're “too much” and “not enough” at the same time.
We’ll hear about Lily’s experience dating as a self described late bloomer, we’ll unravel the tension between wanting to be chosen and choosing for ourselves, how you can overcome a scarcity mindset - thoughts like, “It’ll never happen for me!” - by harnessing the power of desire.
We also get into black cat energy, the male gaze, and flirting, of course!
So, whether you’ve ever felt behind in dating, struggled to believe you deserve more, or found yourself following traditional gender norms and yet it’s not for you - you’re going to want to hear this.
Let’s do this Flirties, and meet Lily!
Don't forget to subscribe, rate, and review Flirtations on your favorite podcast platform, and share this episode to spread BFE - big flirt energy, all over the world!
Enjoying the show and want to support my work? Buy the Flirt Coach a coffee!
Work with me!
Take the FREE Flirt Styles Quiz
Get INSTANT ACCESS to my anti-anxiety flirting and dating guide
Download my FLIRTING AND TEXTING CONVERSATION GUIDE
Grab my FREE Dating App Survival handbook
About our guest: Lily Womble was one of the top matchmakers in the U.S. After setting up hundreds of first dates, she realized that with the right tools, high achieving women could match themselves better than anyone else ever could. She started her company, Date Brazen, five years ago and has since helped thousands of women become their own expert matchmaker with her unconventional, intersectional feminist approach to dating. She's on a mission to interrupt the patriarchal status quo found in the dating world to help women create love lives that are self-trust filled, settle-proof, and actively joyful.
She changes lives daily with her 85k+ TikTok community, Top 4 Relationship Podcast- The Date Brazen Podcast- , and sold-out coaching programs world-wide. She lives in Brooklyn with her fiancé, Chris.
You can find out more about working with Lily here, buy Thank You, More Please, follow Lily on Instagram, TikTok, and YouTube, and stream the Date Brazen podcast.
About your host: Benjamin is a flirt and dating coach sharing his love of flirting and BFE - big flirt energy - with the world! A lifelong introvert and socially anxious member of society, Benjamin now helps singles and daters alike flirt with more confidence, clarity, and fun!
As the flirt is all about connection, Benjamin helps the flirt community (the Flirties!) date from a place that allows the value of connection in all forms - platonic, romantic, and with the self - to take center stage.
Ultimately, this practice of connection helps flirters and daters alike create stronger relationships, transcend limiting beliefs, and develop an unwavering love for the self.
His work has been featured in Fortune, NBC News, The Huffington Post, Men's Health, and Yoga Journal.
You can connect with Benjamin on
© 2025 iHeartMedia, Inc.
