Lily Womble, Founder of Date Brazen

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We just love when our lady friends cnnekt us to other lady friends who just do amazingly, cool, influential stuff. That is this case with Lily, the founder of Date Brazen via Emily Merell of Six Degrees Society. Date Brazen is a dating coach service and offers great tools (including IRL events) to date smarter. Lily is honest, intelligent, and warm, upfront. All qualities that we admire. Lily tells us about her career path and why she finds coaching women how to date better and become their true selves so fulfilling, in today’s spotlight.

Lily, what was it about being a matchmaker that made you want to transition to a dating coach and launch your own business? And how are the roles different from one another?

I was one of the top matchmakers at the largest firm in the country.  I worked with hundreds of clients, all of whom were exhausted from the dating game and unsure how to find the right sort of people on their own.

Though matchmaking was a good solution for some, only a few had long-term success. After matching hundreds, I realized that with coaching, women could match themselves better than any professional ever could.  I began date coaching to provide a long term solution for my clients where they felt in-control, fulfilled and joyful in the process.

A matchmaker sets clients up on dates. A dating coach like me helps people work through their dating roadblocks to find high quality dates on their own.

I created Date Brazen to provide a dating solution for women who felt at the end of their rope. I now provide one-on-one and coaching to help women gain clarity in what they’re looking for, identify the patterns and stories standing in their way and develop a search and dating strategy tailored to their personality and needs.

And why do you find what you do so fulfilling?

I love what I do! Most single women I encounter feel very isolated and lonely in their dating lives. Conventional dating wisdom is stressful, friends and family can give the wrong advice and a good therapist can only do so much to help you find solutions in dating. It’s such a gift to interrupt lonely dating with unconventional strategies that work. Also, I love cultivating a community of single women who are encouraging and lifting each other up.

You’re connecting with all these women in building their personal lives, and in the process, it’s also learnings. What have you learned about yourself in these women?

Love this question.

Mostly, I’ve learned that I still have work to do on myself. When discussing dating roadblocks and the self-limiting beliefs of my clients, I’m aware of the work I still have to do on my own roadblocks and self-limiting beliefs.

Just like my clients, negative beliefs about my desirability and worthiness are deeply ingrained into my psyche, and these beliefs take a lot of time and work to rewrite.

I’ve also learned that I need to be vigilant about asking for support from my community. As an entrepreneur, as with dating, it’s easy to push through hard times on your own. The fear of being a burden is real, but acting from that fear means being isolated. Which means burnout. I have learned to proactively reach out for the support of my community, and that’s made a world of difference in my mental health and in the success of my business.


In your event, Swipe with Intention you talked about your little gremlins (mean voices in our minds) said: you are too much. How did you fight off that little gremlin?

Honestly, that gremlin voice is still sometimes loud AF. The “gremlin voice” idea is one I borrowed from Dr. Brené Brown. She explains that our gremlins are the voices in our head who say “Uh, uh. You’re not good enough.”


In my own dating life, I experienced what I call the “You’re too much” gremlin. I believed (and am still uprooting this belief btw) that I was too loud, too bossy, too silly, too controlling to find love. This gremlin voice was sometimes debilitating and also caused me to make some not-so-great choices in men.

I worked to uproot that gremlin voice by slowly accepting and loving what I bring to the table, loud laugh, and bossiness and all. When I sensed that gremlin voice coming back up, I would say, “If I’m too much for you, then you’re not enough for me.” Recognizing that my “too muchness” was the essence of what made me special and lovable to the right person was so empowering.

You touched on being in a relationship as not being a “success” in life, can you explain why you feel this way?  (super feminist view and we’re all for it!)

Finding the right relationship is a random. I don’t believe that it “happens when you least expect it,” I don’t believe that it happens when you’re playing the numbers game.

There isn’t anyone who can put a timeline on meeting your person. And in the process I firmly believe that dating doesn’t have to suck. In fact, I know that dating can feel joyful, exciting and fulfilling when you have the right strategy and boundaries in place.

My favorite Brazen success stories aren't necessarily when someone finds a relationship. They are when I see a woman start to trust her intuition before, during and after dates, feel confidence to put herself out there in new ways and develop boundaries to fiercely represent herself in her dating life.

What are some challenges of developing your business—and what about your successes?

One of the challenges I’ve faced in building Brazen is that women aren’t used to seeking professional help in their dating lives. It’s been a process to educate people on the fact that dating can be a fulfilling experience.

One of our major successes came after launching Date Brazen Membership, an affordable one-on-one and community coaching experience for women around the country. I love building this community and providing even more women with necessary support and guidance in the dating realm.


Lastly: what is the next milestone you are looking forward to?

I’m looking forward to getting on more stages to talk about the positive impact of swiping with intention! I’m excited to continue interrupting the “dating has to suck” conversation with actionable tools to change the game. Thank you so much for featuring me and Date Brazen!!!

To swipe more with intention, visit the website here. To attend an upcoming event in New York, click here. Want to work with Lily on some one-on-one? Read testimonials now.

Interview by Chary

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