Today we’d like to introduce you to Lily Womble.
Hi Lily, so excited to have you with us today. What can you tell us about your story?
I was raised in the south — Birmingham, Alabama to be exact — and now call Brooklyn home. From the time I could speak, I was sensitive, loud, opinionated, and enthusiastic. And subsequently was labeled “too much” by many.
In a world where women are told to be small and take up less space, I really didn’t fit in.
I was also raised around people who measured women’s value on whether or not they were married. (then and now, I don’t believe that a romantic relationship is the gold standard of existence).
The well-being of women has always been my purpose. From starting a nonprofit to end sex trafficking in Alabama to working for an international women’s rights organization. I never thought I’d work in the dating world until during one fateful career change. I needed a new job to make ends meet in NYC, and I became a matchmaker at a national firm.
In that role, I realized that the dating world was a way I could help women be well. Because from my own story and from the stories of hundreds of clients, it was clear that dating was a microcosm of every fear, hope, insecurity that we have in this life.
Dating really matters to our overall well-being.
After setting up hundreds of dates, I became the third most successful matchmaker out of 160 around the country.
But something wasn’t right… I was in a toxic relationship. He was everything I said I wanted on my checklist, and still, I felt numb. I was accepting so little love and didn’t know why or how I could find something better for myself.
I remember crying on the floor of his apartment and 15 minutes later taking a matchmaking call telling a client, “You deserve so much better!” There was a huge disconnect.
I needed help.
—> Matchmaking was a first-date solution, and I needed something much deeper than a first date.
—> I looked to my friends, and all they knew to say was, “Play the numbers game! Let me swipe for you!” which wasn’t going to work.
—> And I asked my therapist, and she hadn’t dated in 30 years.
I knew something had to change. But where could I get help to never settle again? How could I gain the confidence to show up for myself and my dating life like the bold woman I was yearning to be?
So, I started to create my own solution. I explored beneath the surface of my checklist to uncover what it is I actually wanted. I saw clearly that I needed to heal from my self-limiting beliefs, define my deeper preferences, and craft a dating strategy based on what I uniquely needed. And that I’d need to be bold as hell in the pursuit of this extraordinary love.
The results spoke for themselves: When I coached my matchmaking clients, they started to find better dates for themselves than I or anyone could find for them. On a dating app, in the Sweet Green line, on the subway. (yes, really)
And for me, this work meant that I was able to break up with that toxic relationship, love being single for a while, and it was the reason that I was able to recognize and accept the love of my life partner, Chris (who was not on my old rigid “checklist”).
I broke up with matchmaking to build Date Brazen in 2018, and just a few years later, I’ve helped hundreds of women around the world create joyful dating lives that lead to the best relationships of their lives.
I started my podcast, The Date Brazen Podcast, in 2020, which has become a top podcast on the US relationship chart. I hang out with my 138k followers on TikTok daily to share my feminist dating wisdom. And my book, Thank You, More Please: A feminist guide to breaking dumb dating rules and finding love, comes out with Legacy Lit on June 11, 2024.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
Building a successful coaching business has been so joyful and not always easy. The ups and downs of entrepreneurship have been challenging, and I’m grateful to my friends and coaches along the way who supported me.
Other obstacles include that toxic relationship I talked about in the previous question that made me feel eternally stuck and destined to be in less-than-fulfilling romantic relationships. I’m so glad that I was my first client so I could heal that belief and build a love life that attracted the right person and that felt aligned with my power and agency.
Appreciate you sharing that. What should we know about Date Brazen?
I started my company, Date Brazen, in 2018 and have since helped hundreds of feminist humans build dating lives that feel like an act of self-care and that lead to extraordinary love.
The conversation about dating is stuck in the patriarchal, heteronormative, conventional dark ages. My work and business interrupt the status quo to help people find freedom in their love lives — which in my mind, is the last frontier of personal development.
I’ve developed a proven framework to help singles heal from past patterns of settling, claim all their deeper preferences, build joyful online and in-person dating plans, and start dating — all so they can stop shrinking in their dating lives, release dating anxiety, and receive more than they thought possible. This framework is the basis of my signature program, The Brazen Breakthrough, as well as the basis of my forthcoming book, being published by Legacy Lit — Thank You, More Please: A feminist guide to breaking dumb dating rules and finding love.
We all have a different way of looking at and defining success. How do you define success?
Success to me is measured in how deeply my clients trust themselves, ask for what they want, set boundaries with ease, and pursue their joyfully. The bonus is how many clients land in the best romantic relationships of their lives.
Success for me personally means how much I trust myself.
Pricing:
- My book: Thank You, More Please: A feminist guide to breaking dumb dating rules and finding love. $29, on pre-order everywhere books are sold
- My signature program: The Brazen Breakthrough (to create a joyful AF dating life that makes the right relationship inevitable), 12 months of coaching + our proven course. $2,000
Contact Info:
- Website: https://www.datebrazen.com/
- Instagram: @datebrazen
- Facebook: https://www.datebrazen.com/book
- Other: @datebrazen- TikTok
Image Credits
Damaly Shepherd
