Warning: include_once(/homepages/19/d712462256/htdocs/app719056635/wp-content/plugins/ubh/ubh.php): failed to open stream: Permission denied in /homepages/19/d712462256/htdocs/app719056635/wp-settings.php on line 371

Warning: include_once(): Failed opening '/homepages/19/d712462256/htdocs/app719056635/wp-content/plugins/ubh/ubh.php' for inclusion (include_path='.:/usr/lib/php7.3') in /homepages/19/d712462256/htdocs/app719056635/wp-settings.php on line 371
A Day In The Life of a Dating Coach and Founder of Date Brazen – A Day in the Life

Lily Womble

Dating Coach and Founder, Brazen

A Day In The Life of a Dating Coach and Founder of Date Brazen

Lily Womble
  • As a dating coach, Lily seeks to get to the root of her clients’ roadblocks, explore where they feel stuck and find creative solutions so they can be fulfilled by their dating life, instead of being depleted by it.

  • As the founder of DateBrazen.com, Lily constantly works to build a business that can help women build fulfilling dating lives with her proven date coaching framework.

  • After graduating from Milsaps College and working as a matchmaker for one of the top firms, Lily took her experience and expertise to start a date coaching business.

  • Today on the agenda, Lily had a few coaching client calls and worked on The Brazen Breakthrough which is a 3-month experience to kick start your dating life.



Woke up at 7:30 AM

Coffee was the first priority for Lily when she woke up. After coffee, Lily did her 3 Sun-Salutations Yoga routine and mediated for 10 minutes. 

Left for work at 8:00 AM

Lily works from home, so her commute that day (and everyday) is from her bedroom to her living room. 

Arrived to work at 8:00 AM

Workplace = Home.

Home = Workplace.

8:10 AM

The first order of business for Lily was to hop on a 30-minute call with her new virtual assistant, Imani.

Imani isn’t a full-time assistant. Instead, Lily and Imani work together on a project or case-by-case basis. The reason Lily hired Imani is because she needed assistance with a lot of organizational and admin tasks. She needed someone to take feedback from clients and help synthesize it for her so she can improve Brazen, faster.

On the call, they talked through this week of tasks and Thursday’s upcoming online masterclass.

The master class was a part of a larger “Create Your Best Dating Profile” challenge, that she was running at the time. It was basically an online, hour long, webinar where she shares a 3-step framework that she developed to create a better dating mindset.

Imani helped Lily with the behind the scenes work that comes with the promotion of this Masterclass.

9:30 AM

Lily’s next call was with her coach, Susan Blackwell.

Susan had been helping Lily put together a book and a Ted Talk. 

11:00 AM

Lily had her first client call of the day for Brazen. This call was a “Dating Profile Lab”, where Lily and her client talked through some of the challenges with dating apps and strategized how to change her mindset around her dating life. She also does one-on-one coaching!

One of the main challenges with dating apps that Lily sees across the board is that these apps are being relied on really heavily for finding dates and this creates problems for boundary setting. Because of this, Lily and her clients focus a lot on setting boundaries and changing their swipe habits. Lily wants her clients to flip the numbers game on its head, have more control over the dating process and adopt the mindset: “What is meant for me, won’t pass me by.”

11:45 AM

Lily had a check-in call with Lindsay Meck, her partner in crime. That is, her accountability partner in crime! 

Lindsay is the founder of a company called Onward which is a post-break-up concierge service in NYC. Since Lily is in the dating space, and Lindsay is in the break-up space, it’s the perfect professional and personal match!

As for what the term, “accountability partners” means, the pair support each other personally and professionally. Lily made it very clear to us that anyone whose starting and operating a business of their own, it’s extremely important to surround themselves with people who support you.

12:00 PM

Continuing with the check-in calls, Lily then connected with her partner, Chris. Another example of how important it is to surround yourself with people who support you, but on the personal and business side!

1:00 PM

After the call with Chris, Lily found herself updating the website. She needed to prepare the sales page for opening enrollment for her signature program, The Brazen Breakthrough.

The Brazen Breakthrough is a 3-month experience to kick start your dating life. So whether you are burnt out of the dating scene, just broke up, or ended a marriage and don’t really know about too much about online dating, the program will give you all the tools you need transform your experience and put yourself in the driver’s seat of your dating life.

The program begins with “taking inventory” of your entire dating history and past relationships. Lily works with her clients to understand the story that they believe is holding them back from having a successful dating life.

She and her clients then use that reflective information to build a concrete strategy and plan of action so that they can know when, where and how to swipe and search online and offline to find the best results. She wants her clients to use their time in the most effective way and understand how to set boundaries.

3:00 PM

A late lunch for Lily. She made a guacamole-and-turkey wrap.


4:00 PM

After lunch, Lily took some time to answer emails. In particular, she sent follow up notes to her clients in regards to their sessions. She told us it’s very important to follow up with clients in this business, especially after sessions that tug on the heartstrings, to reassure her clients:

  1. Lily’s listened to their fears and needs
  2. She’s here for them
  3. She has a plan to move forward in the process

5:00 PM

She then had a client call. Sorry this is confidential!  

5:30 PM

While others were finishing the workday, Lily took a shower and began preparing for her live stream class on Instagram tonight for a 5-Day Challenge. Follow her on Instagram for more dating tips & content!

6:00 PM

Sometimes you just have to start something and come back later to finish it. Lily spent this time finishing The Brazen Breakthrough update she started making to the sales page of her website. It goes to show how much patience you need to have—not everything is going to be done in one day. Also, how much creativity it takes to create a cohesive, clear process for potential clients to sign up. It takes time to get this right, so spend it!

7:00 PM

Lily hosted a live stream for the Create Your Best Dating Profile Challenge.

One of the best parts of Lily’s job is getting to teach her dating framework to new faces! She loves answering all of their questions.

BTW, her group sessions always include a dance party and confetti, so it’s definitely a good time!

7:30 PM

After live streaming, Lily needed to set up emails that will be sent out next week in accordance with her program launch strategy.

She also took this evening to outline a new blog post.

8:00 PM

Lastly on the agenda for the day, Lily updated her website for challenge participants.

She told us it was a full and very exciting day to watch her email list grow and gain new challenge participants who are eager to learn her intentional dating framework!

Fell asleep at 12:00 AM

Experience & Advice

How did you get your current job?

Lily’s entrepreneurial journey began during her enlightenment of becoming a better matchmaker. The tipping point was when she met a man at a co-working space who was also an entrepreneur. As she put it, “this was the first time I’ve seen an entrepreneur in person, out in the wild and who was successful at it.” As they discussed Lily’s situation, the man asked her why she hadn’t monetized the advice she had been giving out. To which she replied, “no way!” In hindsight, this conversation, she told us, was the first spark.

But it wasn’t just that one instance. At the co-working space, Lily was constantly surrounded by other entrepreneurs who were all living their dreams. Being surrounded by that many inspiring and like-minded people finally gave Lily the courage to say, “Hey! I’m starting my own company!”

After she “started” her company, Lily began testing her coaching framework. She A-B tested online courses, private coaching and group coaching. In the beginning, she actually started offering her services in secret.

She’d say things like, “Hey, can I try this thing on you?” to people in her network, try her methods, and improve them as she gained more experience.

Finally, she met her partner, Chris. He and his entrepreneurial spirit helped answer the tough questions about the brand and the business model, and was a huge catalyst to getting the business off the ground!


What were your first career goals and how have those goals evolved over time?

Lily’s first aspiration was to be a Broadway actress. But as she put it, “the dream just didn’t come to be.”

While attending high school in Alabama she also developed a passion for helping the well being of women and girls when she started a non profit to raise money to end sex trafficking.

During college, she studied international relations because she wanted to make an impact worldwide. That desire lead her to Cameroon, a Central African country, where she studied abroad and completed programs about women’s’ rights in developing countries for the School of International Training. She also wrote a thesis on violence against women.

After graduation, she moved to San Francisco to get her first job in the professional, non-profit world. After that career path proved to be unfulfilling for her, she began to pick up improv classes during her free time. This reminded her how much she liked being on stage and in the spot light!

So Lily dropped everything, quit her job and pursued her first career goal of studying theater art in New York City. Because the decision was made on a whim, Lily needed to look for side jobs as soon as she landed in New York.

After supporting herself with a few odd jobs, a friend told Lily about a job opening as a relationship matchmaker. Thinking back to her passion for helping women and girls, Lily thought this would be the perfect opportunity to listen to give women advice, listen to their stories and, ultimately, help them!

What was the most impactful experience of your career?

As a matchmaker, Lily always knew she was helping people. And that was what always motivated her. However, she told us her career began to take a shift over time as she began asking the deeper questions to her clients. As she dug deeper into her clients’ feelings, she started to recognize that the issues that brought the clients to matchmaking in the first place didn’t have much to do with a date.

This realization lead Lily to challenge the matchmaking model and begin to step outside of the box. She began to study her clients’ stories, problems and triggers, so she could get to the root of their problems and help solve them through (what was at the time) rudimentary coaching.

What is your advice those who aspire to be like you?

Practice what you dream of doing. Lily had no idea that she wanted to be a dating coach when she started her job as a matchmaker, but with practice and a lot of trial and error, she got good at it! Lily says, if you dream of starting a company or becoming any sort of coach but you don’t have a job in which you get to practice what you want to be doing, find time outside of work to actively do the thing. Whether that is coaching people for free on the side or developing a beta program, there’s no reason not to get started now!

“Practice what you dream of doing.”

How do you define your best work?

Lily’s best work makes her feel honest, brave, and bold, and it happens when she’s really connected to her ultimate “why.” In Date Brazen’s case, the ultimate, “why,” is to help women become more confident and powerful in their dating lives. When Lily come from that place of grounded power and awareness of the bigger picture, her best work includes coaching and content creation that exudes and inspires confidence, enthusiasm, self-awareness and community.

What would you tell your 18 year old self today?

“Bless and release friends and teachers who aren’t down for your dreams.”


From a really young age, Lily had a strong sense of what she desired and what she wanted to manifest into the world. For most of her childhood, and especially by 18, those crazy dreams felt isolating because not many people understood what she was reaching for. If she could talk to her 18-year-old self, Lily would tell herself to keep the course, surround yourself with people who are also going after big things, and to bless and release friends and teachers who aren’t down for your dreams.

Share this ADITL

Share on linkedin
Share on facebook
Share on twitter
Share on reddit
Share on email

This website uses cookies to improve your user experience on our website. Click to learn more