#5 Relationship Goals with Lily Womble

Updated: May 11

Lily Womble, Creator of Date Brazen, talks dating & relationship goals.

Content Discussed:

Date Brazen

The Irresistible Dating Profile Guide

Social Media Profiles:





Brene' Brown

Seth Godin

Rachel Hollis

Amy Riordan "What is meant for you will not pass you by." - Unknown  

Amy Riordan Welcome to The Amy Riordan podcast. They say owning a business is a journey in self development, so I decided to explore just that. Whether you're an entrepreneur or looking for fulfillment in your day to day life, get inspired here through interviews, life stories and proven self help techniques. What you do with the information received in this podcast is completely up to you, but if you act, you will alter the course of your life in ways you never could have possibly imagined. I'm Amy Riordan. Let's do this.  

Amy Riordan Today's interview is with the lovely Miss Lily Womble, who is the owner and creator of Date Brazen, and if you haven't heard of Date Brazen, you can check it out using one of the links below. It's an incredible company that's all about creating programs for people who are looking for that amazing someone to connect with, but also to build this relationship with themselves. The Date brazen motto is, "Build a clear path to the best relationship of your life." Not only does this program and this process that Lily's created completely embody that, but it also actually has a process that completely allows you to learn about you. So I feel like it really connects with what we're saying here. And I know you're gonna love this interview. So here it is.  

Amy Riordan Hi Lily! Thank you so much for joining us. We're so excited to have you on here.

Lily Womble Hi. I'm so glad to be here.

Amy Riordan Aw, thank you. So the first thing I want to discuss is, just tell us a little bit about yourself.

Lily Womble Yeah, totally. So I'm Lily Womble. I'm from Birmingham, Alabama, originally. I live in Brooklyn, New York now, but, a couple of years ago, I was in need of a side job because I was trying to be a performer and that was slow going in New York City. So, I found myself as a matchmaker part time at a national firm. So that was a very weird side job; I never intended to be in the dating space professionally. And so, I went through the rigorous application and interview process, Got the job, was sort of... it was a trial by fire, you know, started matchmaking women and found that I loved this work of meeting women in this vulnerable space, this vulnerable moment in their life. And helping them, right? They were in a moment in their life where they were ready to ask for help. And so, I was able to set them upon dates. And that seemed to be a really rewarding process, right? I got good at it. I was one of the most successful out of 160 at that firm, and I, you know, after a few years liked the job, but it was increasingly evident to me that only about 5% of matchmaking clients across the board were finding long term success with matchmaking. Because... my, my theory was that it's a silver platter solution and because it sort of assumes that I know how to match you better than you know how to match yourself. it is taking the power away from the client, right? And so many clients; most clients would come in depressed and burnt out in their own dating lives, and they'd leave feeling the same way because, they didn't find the love of their life in three months of matchmaking. So, I hated that. But I loved the work of dating. Meanwhile, while I was matchmaking and figuring all that out, I was in a toxic relationship myself and I was accepting far less love than I deserved. And I didn't know what to do about it because my therapist didn't have the right advice. You know, I love my therapist. I love therapy. But she didn't have the right advice, besides, break up with him. And then I was like, but then what? Right? My friends were just like, you need to break up with him and I was like, but then what? Right? They didn't have the right advice either. And I knew that matchmaking didn't work for my clients, and so I didn't want that either. Right? So date coaching became something I was experimenting with for myself to save myself from this terrible relationship and to hopefully move on and find someone better. Date coaching, I defined it is getting beneath the surface of what you say you want to what it is that would make you really come alive across the table, to examine the stories in your dating life that are holding you back from believing that you are worthy of extraordinary so that you can then claim the love that you really deserve, which is abundant and beautiful. So it's sort of the reflective work meets tactical strategy. And so when I did that date coaching work with myself, I found the courage to leave that relationship. I also found the courage to be single for a while and loved it. And then I was able to meet my partner, Chris, and accept the love that he wanted to offer, which was SO scary because he was so different than anybody I'd ever dated before. And for my matchmaking clients, I was date coaching them on the sly right, and they started to find better dates for themselves than anybody could find for them. They were meeting people in the sweet green line, on the subway, on a dating app, and they felt powerful and purposeful in their dating life for the first time. So I broke up with matchmaking. Ah, and I started Date Brazen, which now is my full time job. And now I get to help women across the - all around the world to create boss stating lives that they're proud of and that lead to amazing dates and successful relationships.

Amy Riordan I love Date Brazen, and I will say that I wish it was something that I had had when I was dating. I got lucky and found my guy, and I know he's one for sure. But it's just - I really love the method of attack that Date Brazen has for people. And I love what you said. It's these people going out and finding these relationships for themselves. It's way better than then a matchmaker could do for them. That's huge.

Lily Womble Yeah, and I think there are some, I don't want to knock matchmaking on the whole, because there are some wonderful couples that have been, you know, brought together by matchmakers. Great on them. I think that for most people it's really expensive solution, and it doesn't work for most people; it works for. you know, a few for whom it was right, you know, um and I appreciate you saying that you love Date Brazen. I love it too. It's such a fun job. I had a woman say to me the other day, at a workshop I was running, she was like, "So this is your job? You do this for a living? You talk about dating for a living?" And I was like, "Yeah!" She was like, "That's kind of crazy." And I said, "Yes. It is and it's so rewarding." Because I think that, when you're able to date on your own terms, it's such a game changer. And that's what I'm all about.

Amy Riordan Wow. So tell us a little more about the process that Date Brazen has and I love the motto, 'Build a clear path to the best relationship of your life." 

  Lily Womble Yeah.  

Amy Riordan Beautiful.  

Lily Womble Yeah. So I love working with women about, you know, on their dating lives. I think that it's important to say that I don't want my clients to necessarily be quote good at dating, right? A lot of my clients come to me, and they're like, I don't wanna be good at dating. I just want to find a relationship. And so, I think it's really about taking a step back and doing that reflective work of, "Okay. What did my past relationships teach me, right? What stories have I created from my past relationships? From my past dating experiences?" Because beliefs are simply, you know, interpretations of things that have happened to us. So when I was a kid, I was very bossy and very enthusiastic and loud and a bold, brazen leader of a little girl. And because of those traits, I was labelled as "too much" by a lot of people, you know? Including my parents, who meant well, you know, who loved me. And they saw that I was really bossy and the final figure me out and trying to parent me through that. So, I received this message of, 'I'm too much', right? And as I grew up, because I had that belief about myself or because I interpreted my experience as a kid as reinforcing that I was too much. I then sought out men who also believed that I was too much, unconsciously, because my experience is lead to a belief, my belief influenced my behavior and therefore I sought out men who - one literally broke up with me - citing 'You're too much. I don't want to be with you, you're too much," So I was like, "Oh my God, it has to be true!" And we all have the version of, 'Your too much,' Right? It's either 'I'm not enough' or 'I'm too big', 'I'm too little' and 'Too old,' I'm too... whatever to find the love that I desire. So the work really begins with examining those beliefs and sussing out the truth from the fiction. And then once you've done that work, I think it's about moving forward with a clear strategy. So looking at dating apps as a tool, and nothing more. So I think that it's dating apps are very prevalent, obviously, there are 33.9 million active dating app users in the United States right now. They are 1500 dating apps. So it's an overwhelming place to be. And I think that I see so many people, women specifically, getting so overwhelmed by their dating life, so overwhelmed by dating apps and what everybody else thinks they should be doing in their dating life, that they can't see the forest through the trees. And so really, again, separating the fact from fiction of like, what do you really need to do in your dating life to meet great people? Is it beyond a dating app? Is it figuring out how to date in person? Is it, you know, what dating up is best for your personality? How can you set up your profile to be authentically joyful so you can qualify and disqualify dates with ease? You know? So it's equal parts reflective work and tactical strategy that I do and it's the best. It's the best work ever.

Amy Riordan So tell me a little bit about - I know you have, like, a step by step plan on here. You've got the dating roadmap, which I feel like you kind of covered already there. But what about this self care action plan? I feel like that's something, even when you're just setting general goals that you need to remember.

Lily Womble Yeah, yeah. So, let's talk about goals for a second. Goals are generally big, right? We think about things that we want to accomplish. And I love the quote... I don't know who is who is by - 'We will overestimate what we can do in a year, but we will underestimate what we can do in a decade.' Same goes for we will overestimate what we can do this week, but will underestimate what we can do this month. And so when it comes to setting goals, I think it's important to keep that mind set, that it's the small steps along the way that lead to the big results. So when we're talking about something like building a dating life that you're proud off and finding a relationship. When you're talking about something as big as being happy in your day to day life or doing things you've always dreamed of doing with the bucket list you know in mind, we need to break that goal down into very small steps. And then once you break that goal into very small steps, you gotta create this systems to support those small steps and in turn - when we're talking about dating, self care is one of the major aspect of creating a dating life that is fulfilling and successful, because if you're not filling up your tank, if you're not fueling yourself with good things, then you're not going to be able to continue to date with purpose, cause you're gonna get burnt out and frustrated and you're going to start to interpret (back to the beliefs), you're gonna start to interpret you're dating experiences as truth, right? And then create beliefs like men must suck. All men must suck, because my experiences show me X Y Z. When in fact, I think if you're pouring into yourself, if you're setting boundaries with your time, if you're protecting your heart time, which I say is any time you're spending talking about dating or swiping. If you're not protecting that time, then you are going to create beliefs that don't serve you and your dating efforts. So self care includes things as simple is cleaning your room right? That's a small step to feeling satisfied. You know, it's a simple as creating a bedtime routine and a morning routine. You know, it's - that that's pretty complicated, actually takes so much work and time to create those things, but it's about looking at the bigger picture and then helping people break down the bigger picture into very small next steps that allow them to pour into their home life, their body, their, you know their mindset. Therapy is a big part of self self care for me personally, and I recommend it to all of my clients. In fact, I generally don't work with clients unless they work with a therapist in tandem, a licensed therapist. Just because we're digging into some hard stuff and self care is about looking at the hard things and allowing feelings to come up and pass through and change so that you can grow.

Amy Riordan This is huge because people don't talk about that, when you're talking about dating. They never talk about how you need to love yourself first.  

Lily Womble Yeah.

Amy Riordan I know that's like a theory people, you know, people look at it like a theory like it's something maybe, maybe I'll help you. But no, it's huge.  

Lily Womble


Amy Riordan And you have it as like a main step. That's like very obvious.

Lily Womble A guide post. Yeah.

Amy Riordan Yeah, I love that. That's incredible. I feel like there's so much more to that than people realize. There's a lot. I mean, you know, we go through a lot of self doubt. All of us do.  

Lily Womble All the time, all the time. And if you don't, I think that a part of - I love this this idea - again, don't know who to attribute this quote to, but self care doesn't always feel good in the moment. It's a lot about giving gifts to your future self, which is a Brook Castillo quote. I love Brooke Castillo. She's a great life coach. She has a great podcast. And she has this great episode about giving gifts to your future self. And I think therapy is a gift to your future self. I think that, you know, journaling is a gift to your future self. I think that, making your bed can be a gift to your future self. Future self could be five minutes from now or it could be 10 years from now. What sort of relationship is going to be a gift to your future self? Right? To invite in your life? And yeah, I think that it's very important to focus on self care. One tip that I give to all of my clients and I want to share with your listeners right now is that before you start swiping, you need to journ - I recommend journaling for five minutes before you even open a dating app. So journaling for five minutes and trying to do what I call 20 in two, which is 20 things you love about yourself in two minutes, which is really hard. But you get better at it, the more you try. And so that's like a guide post of the Brazen Breakthrough experience, which is my signature coaching experience. But yeah, every time you swipe, before you swipe, you need to journal about why you love yourself.

Amy Riordan That is excellent. Yeah, so that's the swiping action guide that you...

Lily Womble That's a piece of it.

Amy Riordan That is... See this is - I mean, I feel like people need to be doing this before they create their bucket lists. Like in its entirety. It's not just I mean, it's not just good for for dating, but yeah, for life in general. You should be doing this regardless. I mean, aside from the dating roadmap, you know, if you're married, you probably don't need to be doing a dating roadmap. Aside from maybe like a marriage roadmap.

Lily Womble Yeah, I mean relationship roadmap, it's really important. To create and note your intentions for your day, your hour, your relationship on on the whole, you know.

Amy Riordan So let's talk about the scariest part about starting your own business. What was the scariest for you? Or do you have lots of scary parts?

Lily Womble That's a great question. What was the scariest part about? Money. Money, let's be real. I was a full time matchmaker, and I was not fulfilled in that role. And so I needed to figure out how to make enough money to start growing. Because I I didn't hit the ground... I wanted to hit the ground running. I wanted to have built, you know, a 1,000,000 clients by month one, and that sort of thing. But that's not how it worked out. It was a very small idea at first, and I had to work full time plus some side jobs, to make enough money to start investing in my business. And it began with a blog that nobody read or nobody watched my videos at first, right? It was super scary. It was, you know, my first venture with this company was creating an online course. And I invested thousands of dollars into this online course; into its promotion and everything. I did a beta test. It went well, I thought, and nobody bought the online course. So, I'm so - this is a couple years ago now, but I'm so grateful that I had that failure because it became clear to me that I needed to keep my day job, right. I was thinking, What if I launched this online course and the first time I launch it I'm gonna be able to sustain myself and my, you know, my partner Chris, and will be able to, you know, conquer the world in month one. I'm so grateful that I got that message to keep my day job, not because I shouldn't be pursuing Brazen, but interpreting that message as like, 'Oh, it's gonna take time and I'm here for it. I'm on the ride. I'm going to stick with this, even though I just lost a couple $1000,' right? Which I didn't have in the bank. It was debt and so that's scary too, right? So I guess the scariest part was how do we make money and in tandem with that is something that is guiding me through this entire process is like, 'What am I gonna create that's actually going to help people?' Because I don't want to make money if I'm not helping people more than the money I'm making, right? That's what my focus is, like creating an experience that over delivers, and that women feel is worthy of investment. And that took years to figure out how to do. And right now, we have 21 active clients in the Brazen Breakthrough, which is very exciting. And we've been able to serve, even more women this year, and I'm so grateful that I stuck with it and so grateful that I kept my day job and that I was that I listen to my body when it was time to quit that day job. So yeah!

Amy Riordan So how did you, in terms of listening to your body to quit that next job...  

Lily Womble Yeah.  

Amy Riordan How What was it that your body was saying?

Lily Womble How did I do that?  

Amy Riordan Yes.  

Lily Womble Oh, she was just saying like, "It's time now", right before I think that my choices, my - Because every single month I was like, 'Is this the month?! Is this the month that I'm gonna quit? Is this a month I'm gonna quit. Is this the month I'm gonna quit?' And I could tell that my answer result was coming from an anxious place. It was always coming from a place of anxiety and not enough. So when I got the message that it was time to quit from my body, my beautiful body, she was not anxious about it. I mean, of course, I was scared and nervous, but it wasn't coming from a place of scarcity, or I've got to do this now or it's never gonna happen. It was just like you can fall. You can; you can trust fall now, right? Um, so that's what I would say.

Amy Riordan So did you feel like there was a big enough difference between you and the company you work for to separate the people, like do you know what I'm saying? Like, like they were matchmaking and you are telling these people to go figure it out on their own... well, you know, through you. Did you have, like, an anxiety with that? That you felt like it was...

Lily Womble That it was the same?  

Amy Riordan Yeah.

Lily Womble Or that the people would be like... oh, yeah, I felt so many of so many fearful thoughts. 'Why would somebody want to do something like this with me? Why would somebody like why would somebody invest their hard earned money with me if they could get a silver platter solution?' You know, these fears that, like, 'I know, that that silver platter solution isn't a solution that I would want, so I need to create a new solution. but maybe nobody else will see that', right? And it was a lot of experimentation. It was a lot of, I mean, when I got my first client, she said she was on the matchmaking... she like had subscribed to the matchmaking blog that I used to work for; the company I used to work for and I guest blogged for them about my new company.

Amy Riordan Oh wow.

Lily Womble Not thinking anything about it, I thought, like, what a cool opportunity, but you know, maybe nothing will come with of this because those people have already, like, signed up for a matchmaking blog. But my first client came to me and she was like, 'Your article was the 1st one that I really resonated with, and so that's why I'm reaching out.' And so I think it's just about writing - writing what you feel is true and disregarding the fearful thoughts that are getting in the way of writing down what's true. Easier said than done, but I'm glad that I chose to do that. I'm glad I chose to write down the truth; what I thought was the truth. And my truth is not everybody else's truth. I love this idea of, um, that Seth Godin has, do you know, Seth Godin?

Amy Riordan Oh Yes.

Lily Womble Yes! He's a brilliant marketer and he has this idea of Smallest Viable Market Minimum Viable Market, and so it's this idea that businesses are marketing in general, when they don't have the smallest viable market mindset. Businesses are marketing toe way too many customers. They want to be for everybody so that they find the... so that they can get some business. But smallest viable market dictates that you need to define the smallest amount of people who will be so psyched to work with you; who are so your people. You know, there's this quote from the musical Title Of Show that's, 'I'd rather be nine people's favorite thing than 100 peoples ninth Favorite thing.' And so I, with the smallest viable market, I was like, OK, I'm gonna try to be nine people's favorite thing. I'm gonna try to find the smallest number of people who will resident with what I'm saying. In doing so, I then was able to find more and more clients around the world who resonated with the message and who wanted to do this work with me. So, there was obviously, there was so much fear. There was so much, you know, scarcity. Some, like, a lot of time I had a lot of scarcity thoughts, but I'm so grateful that I went through it because now I get to talk about abundance and scarcity in dating and speak from my own dating experience with that and also speak to my experience building this business and really feel like, 'Okay, I'm overcoming a scarcity mindset every single day. And what are the practical elements of that?' And I get to teach that now. It's awesome.

Amy Riordan I just have to say thank you so, so much for everything you've given us. I feel like there's... one of the goals for this podcast is to get people; give people as much tools as possible to get them through their week or hopefully even like a month or two. And I feel like this is just chock full of all sorts of good stuff that they can get, not only for their bucket list, but also for their dating life. I want people to set dating goals and relationship goals and self care goals.

Lily Womble Yeah, the one thing that I'd say is - to your audience about creating a bucket list is experiment with being extravagant. I think that so often our goals are rooted in - well, from the clients that I've seen and worked with and from my own life, my goals sometimes were in opposition of the crappy experiences that I had, right? So I'd look at my past toxic relationship and say, 'My goal is to find something better than that. But that wasn't an abundant goal. That wasn't an extravagant goal, that was in opposition to something terrible.  

Amy Riordan Yes.

Lily Womble So experimenting with extravagant meaning, not saying, 'I want something better than that.' But saying, 'I deserve someone so extraordinary. I deserve someone who sees that I'm extraordinary. I deserve the most abundant, gooey ooey like love that I've ever seen in my life, right? Same with, instead of saying 'I dream of someday going to Italy', you know, like that's on my list of things to do. And my fear says, like, 'What if you don't ever have the money to take the trip of your dreams?' But then, like the extract - playing with the extravagant is sort of like 'I am going to rent a yacht in Italy on the Amalfi Coast, and it is going to be - Beyonce and Jay Z are going to come and, like, hang out on our yacht.' Experimenting with that extravagance, right? And seeing how that feels in your body, even if the goal is like, so outlandish, does that resonate with you?

Amy Riordan Very, very much so. I feel like people keep themselves in this box and...

Lily Womble Yeah

Amy Riordan I have really - I admire you for saying that people compare it to their past. You're right, like the past relationship. That's insane because, it's so true. People just think I want better than that. Well, no. You should be having, like, a 1,000,000 times better than that. Like, think, think higher, think higher.   

Lily Womble Yeah.

Amy Riordan Because you were, like, hitting your lowest low.

Lily Womble Yeah. You can't imagine how many, how many amazing experiences are waiting for you, you know? When I'm in sort of a cavey mindset, the Brene' Brown you know, I don't know. We don't. We might have not have time to get into this, but the Brene' Brown, like when you're in the cave moments, you know, it's this loneliness, desperation, shame feelings. It's hard to see the possibility. And one time I was in this cavey moment my mom reminded me like 'Lily, you're so, you're stuck in this moment so much that you can't see all of the gorgeous possibilities that are out there for you. I'm gonna believe them for you until you can believe them for yourself.' And so... Yes, sometimes it takes time. It takes other people believing them for you until you can believe them for yourself. And it takes some some gumption, right? To put it out there.

Amy Riordan I cannot agree more. Again, thank you so much for everything you've given us. I really; I have had a lot of self doubt about this podcast, and you're helping me, like, rope it back in I feel like, so thank you. This interview is one my favorites so far, so thank you very much seriously. 

Lily Womble Aw that's so nice. I'm so excited to be on this podcast.

Amy Riordan We're bringin' it in!

Lily Womble We're bringing it in. I mean, I think that the only difference... I love the Rachel Hollis quote - I'm just a quote machine today. The Rachel Hollis quote, 'The most outrageous thing that we did to succeed is not quit', you know? And everybody starting a business, beginning a dating journey, you know, feels fear; feels embarrassment sometimes, like 'Oh, my God, it's not what I wanted to be. Or, you know, this podcast isn't where I want to be yet.' Whatever the fear is, I mean, I faced this earlier today, I was recording Brazen TV episodes, and my lighting was weird and my lighting kept changing, and I was like, 'Oh, my God, this is terrible. I can't believe this is so terrible, everybody's gonna judge me!' And, you know it's recognizing that feeling and also saying, like 'Progress, not perfection.' You know? You've got this. I've got this and it's audacity. It's like, it's pretty audacious to say, like I'm creating something that will impact a lot of people. And that's how Oprah got started. That's how Rachel Hollis got started. That's how everybody that's done anything has gotten started is being audacious enough to say, 'I'm gonna do this and it's gonna impact people', you know?

Amy Riordan Yeah, well, thank you.  

Lily Womble You got this.  

Amy Riordan I'm gonna have to bring you back on here. We're gonna have to do an update later.

Lily Womble Pease! Please, please, please. So many things are happening in the Brazen Universe that I'd love to update you on.  

Amy Riordan Okay.  

Lily Womble Yeah. I'm excited to see where the podcast goes, it's going to go great.  

Amy Riordan Thank you! Me too! I'm so excited!

Lily Womble Yay, yay, yay!

Amy Riordan Ok, bye.

Lily Womble Thank you so much. Bye!

Amy Riordan Amy Riordan is a weekly podcast brought to you by me, Amy Riordan. Love this podcast? Leave me review and share it with friends. You can also find me on social media. Subscribe to this podcast for all new episode notifications. With questions, topic requests or interviewee nominations, visit AmyRiordan.com. Curious about specific content mentioned in each episode? Those details are linked below.

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