Date Brazen with Lily Womble


Date Brazen with Lily Womble

As many of you know, my primary job is not recording this podcast, it’s running my company, the Financial Gym. I don’t have as much time as I would like to be thoughtful about my podcast scheduling, so you can imagine how excited I was to realize that when I looked back on a number of the podcasts I recorded, I saw a theme of entrepreneurship.

The month of September has officially become entrepreneurs month here on the podcast, and today I’m featuring Lily Womble, founder of Date Brazen. Lily spent years as a successful matchmaker only to realize that most of the dating work had to begin way before the matching could take place. She joins me to share her entrepreneurial journey and how we can all have more fulfilling and meaningful dating lives.

What Are We Drinking?

Lily — Black Cherry Schweppes with Vodka

Shannon —  Grapefruit Schweppes with Vodka

Podcast Notes

  • Lily is from Birmingham, Alabama, she lived in San Francisco, and now lives in New York City. 
  • Shannon met Lily at an event at the Financial Gym. After that, Lily became a fixture in the Gym.
  • Lily is a dating coach, but started her career in matchmaking. She moved to New York on a whim.
  • She had a stable job at a non-profit in San Francisco. She studied international relations in college, but hated it the job.
  • She had a life-long dream of being a broadway actress and quit her job to move to NYC. She had no job or friends there, just a plan to study musical theater and audition. 
  • Lily did a lot of different jobs after being in non-profit communications. She was a nanny, a music teacher, she worked at at church in Hell’s Kitchen in exchange for her rent, and she was a balloon hat maker at a restaurant.
  • She had no intention of going into the dating industry at the time.
  • Lily had a friend who had a side job as a matchmaker at a national firm, and they were interested in hiring women who were self starters and who wanted to work independently. 
  • Lily’s friend encouraged her to apply. She went to her interview and had no idea what the matchmaking job would become. It was a very rigorous application and interview process. 
  • There are many matchmaking firms in the country. They are generally looking for women and men who are highly emotionally intelligent, who have the stomach for hard conversations, and who have a strong intuition.
  • You need to read between the lines of everyone you are meeting, you need to have a strong instinct about people, and you need to know the right questions to ask. 
  • The interview process would include questions like: You are sitting at home and your client is sitting at the table in the restaurant waiting for her date to show up. The date just texted you and said he found her online, is unattracted, and he is not showing up. How do you break the news to your client?
  • There is not much difference between people who use online dating and those who use matchmakers. The main difference is access to resources. You need to have a couple thousand dollars, minimum, to work with a matchmaker one on one, and you have to be at a certain level of burnout in dating.
  • She worked with people who were really high earning who just didn’t have time and she also worked with women who worked at non-profits who saved all of their pennies to afford the service. 
  • Lily really liked meeting women at this point in their lives, showing up for them, working with them, and helping them see that love for them was possible. 
  • Lily became the third most successful matchmaker out of 160 at her company. The metric to define success at this company was, after the first date, on their feedback form, they both indicated they wanted to see each other again. A second date was success.
  • Only about five percent of clients were finding long-term success with matchmaking.
  • For most people, specifically women, they would come in disheartened and dissatisfied with dating and with the dating resources, and they would leave the matchmaking experience thousands of dollars poorer, feeling the same level of burnout. 
  • Lily was dissatisfied with that and wanted to create something more long-term with her matchmaking clients, which is why she started dabbling in date coaching and it led her to start her own company.
  • Matchmaking: Sit down, talk about your preferences, Lily would get a list of what you are looking for and narrow it down, and she would go off and vet matches and set up a date for you, then evaluate how it went and move forward from there.
  • Date Coaching: Helping you become your own matchmaker by helping you get beneath the surface of your checklist, what you say you want, to what it is that would actually make you come alive across the table.
  • Lily spent hundreds of hours swiping on Tinder and Bumble. 
  • To find matches, Lily would look in the database, which was people who were clients, people who were recruits, and people from online dating resources.
  • Lily had about 2,000 phone calls with men for her female clients over three years.
  • Lily mostly worked with women. She enjoyed serving them the most. Women tend to be the majority of matchmaking clients. 
  • ”Problem areas” with clients at the Gym tend to be Amazon and Uber, no matter the gender. It is rare that personal care, fashion, and retail are problem areas for men.
  • Women are held to a different beauty standard than men, and companies spend a lot of money marketing to them. There is a reason women spend more. 
  • Dating is a minefield of triggers and gremlins that we have accumulated from the very first day we had a thought. We’ve been accumulating experiences, from which we create stories, from which we create meaning and belief systems in our lives. 
  • If you believe you are incompatible with long-term relationships and that you aren’t going to find love because you are too overweight or are too much, that could become a self-fulfilling prophecy. 
  • Lily can help women create a fulfilling, joyful dating life on their own terms. 
  • Lily isn’t a licensed therapist like Jenny, from Forward in Heels, who was on the podcast in April. Lily highly recommends therapy and Jenny.
  • Lily always recommends that her clients work with a therapist, in addition to working with her. Date coaching is a good supplement to move you forward. 
  • Long-term, date coaching and therapy are better for you than a done for you solution. You are the expert of your own story, and you need to have the long-term skills to be successful no matter what. You need to have the skills to date on your own terms in a way that feels good to you.  
  • So much of dating and happiness comes from you. The challenge with dating when you are younger, is if you are not in a good headspace yourself.
  • Shannon remembers feeling a desire to have a happy, fairytale life, because she didn’t have that growing up. She was convinced she could have that for herself.
  • Shannon was a serial monogamist and was engaged in college, but that relationship ended right before she graduated. Her mom realized she was not ready and said she wasn’t going to let her get married.
  • Shannon then got into another serious relationship after that, and after it ended she tried a dating website and met Bill right after her 24th birthday. After their first date, she told her friends that she met the man she was going to marry.
  • Shannon was married at 25 and divorced at 38. She was so convinced she was going to have a fairytale relationship, but she didn’t have that skillset. The divorce rate is 50 percent, but she didn’t think it would be her. 
  • Shannon had so much baggage and she dated a series of guys who made her feel like it was worse than it was. Two of the guys had parents that were married for 30 years and what seemed like perfect marriages. Shannon felt like she had skeletons in her closet, because her parents had been divorced.
  • On her first date with Bill, she threw out all of her family baggage, and it wasn’t a big deal to him. He wasn’t threatened by her making more money than him, because he was a teacher. Shannon was attracted to him, because he embraced what she felt like were the barriers, or hurdles, to loving her. A challenge later on was that she was almost bullying him, because she has a strong personality.
  • Push back in a relationship always felt like judgment and she didn’t welcome that from him. He made her feel safe when she was 24, because she had so many insecurities. 
  • All anybody really wants is for their gremlin voices to be proven wrong. At the same time, it feels safe to live within the status quo. 
  • Lily believed for many years, based on what family and friends said to her, that she was “too much”. Her mom said from a young age that she was going to have trouble finding a man because of her strong personality.
  • Lily dated men who believed she was extra and they broke up with her because of it. She was seeking out people who was proving her belief right.
  • Brene’ Brown talks about the gremlin voices we accumulate, the mean shame voices that say you aren’t enough. If you are living bravely and courageously with vulnerability, you know those voices are going to show up, but you save them the cheap seats. You save the good seats for people who are in the arena with you.
  • Embrace the gremlin voices. You aren’t going to get rid of them. Look in the mirror and find the things that are right about you. There are more things that are right about you than wrong. It is so easy to believe the negative. We need to love ourselves and see ourselves the way our friends see us.
  • Everybody falls prey to feeling bad about themselves. It is all about developing that resilience and the practices you need to put in place when you fall into feeling terrible.
  • If you believe you are too much, you will reinforce it by meeting other people who believe you are too much. Creating a new belief about yourself takes a lot of work.
  • You need be able to have an honest conversation with your friends about how you speak about each other in a group or how you speak about yourself within the group.
  • Lily recommends taking a negative talk vacation for a night. If you are feeling hopeless or down about dating, try to take a night off about speaking negatively about it and see what that does for your psyche and spirit.
  • When you get out of the habit of downing dating and your body, you realize how much you are doing it. Take inventory of when those negative feelings come up for you.
  • There is so much money spent in the dating process and it adds up. Shannon doesn’t love when she sees spending happen in bad relationships. 
  • Women waste so much money, because of the negativity that is related to dating. 
  • The financial impact of a bad relationship, whether you see it or not, is costly. 
  • Lily does not believe that success in her work is whether or not you get into a relationship. Success to her is defined by a healthy relationship with yourself. If you don’t have a healthy relationship with yourself, it is going to be very difficult to be in a healthy romantic relationship.
  • For women who are making very drastic spending decisions based on the relationship they are in, Lily would ask what’s your why? What is your why beneath this decision? Do you want him to feel taken care of? Ask yourself how are you being taken care of in this scenario. Are you playing out a scenario you saw between your parents? Does he not want to see you or spend time with you if you are not spending this money on him or her? That’s an answer you need to take a look at.
  • People are not examining the whys beneath their decisions, because it is difficult work to do on your own. We are sort of trapped in our own head, mindset, and what we grew up seeing, and it is hard to imagine something different, if you grew up with a negative connotation around relationships or money.
  • Healthy romantic relationships start with a healthy relationship with yourself and your money.
  • Ask the why beneath the why question. 
  • It helps to sit down and evaluate how you are being served in a relationship. In a healthy relationship, you should be serving someone else and they should be serving you an equal amount. 
  • Lily has a Relationship Reflection Guide available on her website. It takes you through, step by step, asking those questions and it’s for after you end the relationship. If you are in a relationship and you feel that maybe it is a bit of an unequal split of love, affection, or money or if there is anything that feels like the seesaw is tipping toward the other person and you are feeling left up in the air by yourself, you need to take a journal, a glass of wine, put on some music, and get real with yourself or a best friend. 
  • Ask yourself what attracted you to this person in the beginning, why you were drawn to this relationship, and how is it supporting you in your dreams and your future. If it isn’t, why not?
  • How does this person show up for your in the hard times? Why? Are you making excuses for them? 
  • A big red flag are the excuses. How many of those do you need to have? The key to healthy dating is loving yourself. The ultimate question needs to be: Is this person taking you to the next level, in whatever way that means, on a regular basis? Otherwise, why not be by yourself? You can take yourself to the next level.
  • Sometimes we leave gremlin voices unexamined, because we think examining them will be too painful to bear. If you are examining them with a licensed therapist in the clear light of day, it is a lot less scary than looking at them by yourself, in your room, at night, alone. 
  • Acknowledging who they are, what they look like, and why they came to be can be a really powerful process and can really transform your relationship with yourself. You learn to level up yourself.
  • If you take the time to address the gremlin voices and start to rescript them with a kinder truth, you can transform what you think is possible in your dating life specifically and with all parts of your life.
  • Lily’s clients get to level up their own concepts of themselves within the context of dating.
  • Lily started date coaching, because she was in a toxic relationship with a guy she met on Bumble. On paper, he was everything she said she wanted. He was super smart and he had a lot of compassion for people, he was funny, and they fell in love quickly. 
  • They went to Paris in the second month of their relationship. A friend was getting married in Amsterdam, but they took too much of a vacation, when she didn’t have the money to spend.
  • When they were in Paris, he said he wanted an open relationship. Because she was not grounded in what she desired in her own worth as a woman and as a human being, she said yes. She didn’t think anyone else would love her like he did, and she thought there was no one else out there for her that would handle her version of extra like he did. 
  • She stayed in the relationship and she became very unhappy. She hated most of the time that she was in it, but she was addicted to the idea that she didn’t have to be alone. She accepted far less love than she deserved, but she couldn’t admit it to herself.
  • Lily’s why beneath her decision of going to Europe and accepting an open relationship and being in it for a year, was that she truly didn’t believe that she deserved extraordinary love. She didn’t believe she was worthy of being loved really, really well. 
  • Lily comes from a divorced parent household and didn’t know what anything else looked like.
  • Women are naturally caregivers and we put other people in front of us, even in relationships. We don’t think enough about how we are being served, because we are thinking about how much we are serving.
  • While Lily was in the relationship, she had just begun the matchmaking job. She realized this because she was telling her clients they deserved love. She did this thousands of times to hundreds of clients.
  • Finally, by speaking those words out loud and being surrounded by family and friends who loved her, those two things collided and she realized her relationship was terrible.
  • Her partner, Chris, came into her life and he made his interest very clear. She felt one door closing and another one opening.
  • Lily was singing in a cabaret show, and the man she was seeing had to leave ten minutes in. Meanwhile, Chris was sitting in the front row with flowers. 
  • Lily ended her relationship and couldn’t be with Chris at the time, because she needed to heal. She took some time away from being in a relationship to start to forgive herself and heal the relationship with herself. 
  • She then began to realize that Chris was here, very present, very loving, with a huge personality, and loved how extra she was. It was a scary prospect. This was something bigger than she thought she was ready for.
  • It was a lot of work to come to terms with how much love he was willing to give her. It was uncomfortable for her to get out of the pattern of behavior that she had been in with accepting so little. 
  • It is work to change that paradigm of behavior and belief, to transform from someone who believes they need to give every cent and every piece of energy to another person to be loved to someone who believes they are worthy of extraordinary and they don’t need to give any money or time that is beautiful or true to them to prove that.
  • Success in dating is feeling fulfilled and joyful. It can even feel like self care, because you are learning about yourself and you are treating yourself well in your dating life.
  • The number one mistake Lily sees women making, is they treat dating like it is a numbers game. It is a conventional dating myth and it doesn’t apply to us today. The myth encourages people to put themselves out there ad nauseam, even if they are really burned out and desire rest. The numbers game says you need to increase your odds by going out and putting yourself out there for every single opportunity.
  • The numbers game mentality doesn’t necessarily increase your odds of meeting someone. What it does is guarantees that you will experience burnout faster and you will have a lot of dating dissatisfaction. 
  • Lily encourages people to examine they ways they have treated their dating life like a numbers game and then make a shift to a minimum viable market mentality. 
  • Seth Godin defines this as the smallest amount of people that are right for you and your business. In your dating life, it is the idea that you are for the few and not for the many. You should be swiping and dating like that, but you shouldn’t be so picky that you aren’t open minded.
  • Dating like this looks like thanking people who ghost you or don’t text you back or don’t seem interested in meeting, because their gift is getting you closer to the smaller number of people who want to meet you. 
  • People are experiencing cognitive overload in the dating space these days, because we have too much access. There are hundreds of thousands of options, especially in a big city like New York, and our brains, scientifically, can only handle nine options at a time before we experience cognitive overload. This means we shut down higher functioning, so we don’t make the best decisions possible for ourselves.
  • Limit the amount of time you are swiping – 10 to 20 minutes maximum per day. Choose a time where you feel good about yourself.
  • What is meant for you will not pass you by.

TAKEAWAY: My biggest takeaway is that dating costs money. It’s not just the cost of getting ready for, and paying for, the dates, but a lot of times there are costs associated with unfulfilling and bad dating situations. The smarter you can date, the better your finances will get. I promise you!

Random Three Questions

  1. What is a food you hated as a kid and do you hate it now?
  2. What is a show you like to binge watch?
  3. If you won a million dollars, what would you do with it?

Connect with Lily


Instagram: @datebrazen

If you’d like to talk to my team at the Financial Gym to help you prepare, at least financially, to start a business or help run yours better, I hope you’ll reach out to us at the Financial Gym. The number one employer at the Gym is “self employed”, so it’s certainly an area we’re comfortable working in. The great news is that Martinis and Your Money listeners get 15% off Financial Gym services. So head over to, or send friends to, to get signed up today.

Leave a Reply