Celebrating Your Singleness with Lily Womble

Podcast episode (Get Your Guy Coaching) featuring Anwar White interviewing Lily Womble (CEO/founder of Date Brazen) about dating, self-trust, and celebrating single life. They discuss Lily’s transition from matchmaking to date coaching, practical frameworks (checklist vs. essence preferences), a three-day “Celebrate Your Single Self” challenge (bragging, self-compassion, ‘for the few’ mindset), and personal stories about growth and finding a partner.
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Hey, girl. Welcome to the get yout Guy coaching podcast. My name is Anwar White, but you can just call me your own personal dating and relationship coach. Each week you'll hear actionable advice, tips, and strategies that you can implement in your own love life. I'm talking about healing your heart, dating effectively, and understanding men so that you can, you guessed it, get your guy. Are you ready to level up your love life? All right, let's go.
I never felt the way I do without anyone but you.
Hello, my loves, and thank you so much for joining me today. I have a special guest here in the get yout Guy coaching podcast. I have my dear friend and colleague, Lily Womble. She is the CEO and founder of Date Brazen. And it is all about feminist dating and dating on your terms. And Lily, just thank you so much for being here. I'm so happy that we're talking and getting to get together again.
Me too. I'm so honored to be on your podcast and you're killing it.
Well, thank you so much. And I just want to let everyone know that I was on her podcast a few months ago and we had so much fun and I think we're probably going to have even more fun today.
Yes.
I'm just really excited to have her here because I want you all to know that there are different ways to date and just like different ways to date. There are different dating coaches out there. And I think it's important for you to figure out which one you really vibe with. Right. Which one you feel a certain connection with. And it may not be me, and that's okay too. It may be Lily. It might be someone else. Finding a dating coach is very similar to dating. And so I think it's important for you to figure out which one's going to be best for you. So, Lily, enough about my little diatribe there. Talk to me about who you serve and everything about your business.
Yes. So I started my career in the feminist advocacy space. So I was working in nonprofits for the well being of women and girls around the world. And burnt out of the nonprofit space, took a hard right turn to New York, had 50 jobs, including making penis balloon hats at Senior Frogs in Times Square. Iconic. Iconic was not worth the panic attacks in the back from the strobe lights that were all over Senor Frogs Square. But meanwhile, I got a job sort of randomly as a matchmaker at one of the top, largest matchmaking companies in the us And I thought it would be a funny story about how I was a matchmaker that One time. But it blossomed into a career because I realized that dating was a place where women could learn how to thrive in not only in dating, but in their lives. And so using matchmaking as a tool at the time to help women to realize what they wanted was possible was really great. And I was also really good at it. So I was like the third most successful out of 160 at the company. I know I, you know all these details, but I want to tell you.
But I want to ask you about that. Why do you think that you were so successful? What did you do differently than some of these other people as it pertains to matchmaking?
Well, it's interesting because if you are going to listener at home, sign up for a matchmaking service or work with a dating coach, always, always, always ask the company or the person, what is your metric for success? How do you measure success? Because I was really good at connecting with my clients, being emotionally intelligent enough to read beneath the surface of what they were saying, ask them the right questions, really sort of nudge them and push them in the direction of, you know, be open to being surprised, you know, have your preferences, desires. But, you know, maybe you should go on this date with somebody you wouldn't have chosen for yourself. I was good in all of those respects. But the matchmaking company that I was working for defined success as going on a second date.
Okay.
So I was really good at helping folks pick a date that was good enough to go to a second date. The problem with that is they weren't using a long term success metric like a relationship or a partnership. And that's why people pay thousands and thousands of dollars to work with a dating professional, you know, to find extraordinary, to find their person. And so only about 3 to 5% of people in general from matchmaking were finding long term love. So that's when not so great that, you know, day that I was said, you were one of the most successful. Great. Hoorah, hoorah, hoorah. Then I started digging beneath the surface of, okay, what does that really mean here? What do I want for my clients? And I wanted something deeper for them. I wanted them to have the tools to find something better than just a first date. And meanwhile, while I was matchmaking, I was in a toxic relationship where I was accepting very little love because I was living with this limiting belief that I was too much, too intense, too bossy, too loud, too in your face, too feminist, too whatever.
I'm a part of that club.
Too cool. I mean, now my motto Is like, if you think I'm too much, like, cool, we don't have to be friends or anything. You can go live your life. I get to live my life. Hooray. But at the time, I was accepting very little from somebody who believed that I was too much. So I was attracting a mirror to my own limiting belief. And I remember one really day sharply where I was crying on his bathroom floor, and then 15 minutes later would take a call with a matchmaking client and say, you deserve so much better. Let's get you out on some great dates. There was a total disconnect. So through examining. And my therapist didn't know what to say to me about my dating life besides break up with him.
Right.
My friends just wanted to swipe for me, and I saw that matchmaking wasn't working for most people. So I was like, what am I going to do? And I arrived at date coaching as the solution that both I needed and my matchmaking clients needed, but they didn't know it yet. So now I get the pleasure after breaking up with the matchmaking industry about three years ago.
And that toxic guy.
And that toxic guy. Huh? Hello. Hello. That was a fiery, fiery beginning, middle, and end, let me tell you. I'm sure in that process, I became. I mean, I don't want to make a hyperbolic statement, but I feel like I was reborn at that moment where I was done accepting less. I knew that I needed to do deeper interrogation into why was I accepting less? What was beneath the surface of that? What did I really want? What were my deeper preferences off the page, outside of the checklist? And how was I going to use this tactical knowledge that I had as a matchmaker for my own dating life paired with the deeper emotional strategy? So when I did that for my matchmaking clients, they started finding dates on the subway and, like, finding dates for themselves that were amazing on an app and finding, like, approaching men at a restaurant, which they never would have done, you know? And so it was a powerful solution, and now I get to offer that powerful solution and to help women date on their own terms and find extraordinary love while remaining in their power and confidence.
Yeah, I love that you spoke about something really interesting about this notion of being too much. And I'm pretty sure a lot of my listeners are feeling like that as well. How were you able to kind of get out of that point and move outside of that? Obviously, we're all, you know, evolving and changing and moving toward who we are supposed to be and really realizing ourselves. But how did you Kind of make that shift for yourself.
That's a great question. And I think I'm still shedding a lot of old beliefs about myself. I mean just today realizing I'm entering a new place in my business where I can believe that I change people's lives and not apologizing to for that and really owning it. And I just sort of have these ahas pretty regularly. Cause I do a lot of work on myself with therapy and coaching. But I think I started by acknowledging the historical context of why I believed that narrative, why I believed I was too much. It started with therapy. It started with looking back at my relationship with my mom who was wonderful but who at age 12 told me, you're such a strong personality, you're going to have a hard time finding a husband, you know, and believing that and.
Really feeling different. So look, as an adult woman sort of revisiting my child self and saying what does she need me to tell her? What does she need to say to me now? And it was hard won that work. A lot of past self stuff. Talking to my former self and my smaller self and then also.
Really sitting with and looking around at my life and taking inventory of what in my life was that way. Because I used to believe that I was too much.
Yes.
So then the process of forgiving myself for making decisions when I didn't believe in myself like that process of self forgiveness was really important. I think that's so important.
I'm so glad that you pointed that out because even just making those connections are so powerful where it comes from. Right. Because when you can pinpoint where it comes from, it almost minimizes the power of that belief that wasn't serving you. It's almost just like, oh, now I get it. Because as a child this is how I thought of it and it just kind of stuck. Right. But now I'm a grown ass woman.
Yes.
I can choose to make another decision or choose to have a different belief about myself or the world or dating or men or whatever.
Yeah, absolutely. And I think that playing small is a trauma survival response. Yes. And so looking at, it's not that I'm not awesome and confident and beautiful, it's that I have a past and I need to work through the trauma and come into being emotionally safe today.
Yeah.
Like what you're talking about when you, when you focus on it this way and do some self forgiveness work and, and really go there with yourself, that no longer is my context. My context is no longer, oh, I was, I'm too much my context is now I'm Lily. And that means a lot of different things, you know? Yeah, I love that.
And also I can be whatever I say I'm gonna be.
Yeah, absolutely. Yeah. And I think that so many women in their dating lives specifically dictate a narrative early in their dating life that says something similar to. And I wonder what you think about this. That says, well, I, I have to do it this way. I have to date according to these old fashioned rules because I want to be successful or I can't be the badass and the kind person in my dating profile. I have to choose one identity or the other.
Right.
To present myself. And I think that those, those choices are rooted in old stories and old survival mechanisms that need to be examined.
Yeah, definitely. I love that you mentioned this and I feel very much the same way. And I'm always like when I'm talking to clients. No, you're you. And we're going to figure out who you are in this space and I'm not going to tell you who you are. You're going to figure it out for yourself.
Right, right. Because by the way, I'm not the person that's going to live with your partner. You are.
Right, right, exactly. Sometimes my client, sometimes clients freak out because they're like, well, I don't know what I'm supposed to be. That's great. We're going to figure it out for sure.
And I do think there's some perfectionism in that. Like, let me do it perfect. Let me be perfect. Let me showcase myself perfectly. When that's super boring, a b, it usually leads to inauthenticity and more stress and burnout. So I love, I love talking to you and love doing the work that we do because I really believe that it is about more than dating that we, that I focus on dating. You focus on dating.
But it is everything.
The work that we do is life changing.
Yes, very.
That.
And I just wanted to complete your thought too, because this whole notion of perfectionism, which I think is very prevalent in our clientele is also affects us in dating. Because if we're perfectionists about ourselves, we're going to be perfectionists about our future partner. And if that's the case, then we're not going to ever truly accept him or her. Right. We're always going to be wanting them to be perfect and not just accepting because we can't necessarily just accept ourselves as we are. We have to be something else or some unattainable thing. Right. Okay. We've been talking and Skating around some of your dating philosophies. But I want to hear from you kind of how you think about dating and relationships and love and all of that.
Right. So I think of dating as a potential tool to express self care like that dating can be an act of self care for yourself. Because I think of dating and have seen over the course of working with thousands of people over the last few years that dating is a microcosm of everything. Every hope, dream, desire, insecurity, you know, fear. Everything that you have as a human being is right. Wrapped up into your dating life. You are doing yourself a disservice if you try to simplify dating into its own little silo of, you know, dating is its own separate thing. I have a career, I have friends. And then dating is. No, dating is everything. The way you date is reflective of how you're doing your life. Yeah, I think I hear so many women struggling with, how do I do this? How do I pick the right people? For me, maybe they've come from an abusive relationship or they've come from a 12 year relationship that just ended or would have you in there questioning, am I gonna be alone forever? Am I gonna. Why is this so hard?
Yeah.
And I think that you need to go back to the drawing board of what have you learned from your past relationships? Again, those trauma stories, how can we unpack those? And then how can you date in a way that is honoring your essence based preferences? So when I say essence based.
Yes, yes, girl, educate the masses.
Yes. So I think of preferences. In two buckets we have checklist, which is. And I want to hear, if you'd agree, disagree. I want to hear all the things checklists, which I think of as age, height, location, you know, attractiveness, preferences, you know, checklist. Great. Have your checklist preferences. We should interrogate them a little bit to see, like if you only want to date somebody six, five to six six, we probably need to talk about that.
Girl, stop.
So, yeah, right, right, right. And then essence based preferences are your personality traits that you want, the way you want to feel across the table, the values that that person has. And I think what people do generally is make a list of the personality traits, values, and then they stop there and they put it in a drawer. And you know, that's what they think is going to manifest the love of their life.
Or they've had that list since high school. And it changed right after watching like, you know, all of those teeny Bopper movies. Princess Me.
Yes.
You're like, I want my guy to be just like, whatever. I don't even know 10 things I hate about you. I know that's something that was big. She's all that I know. You know, like.
Right, yeah. I want Patrick Dempsey on a lawnmower to come and rescue me from this world. Exactly. So, no, I think essence based preferences need to be a living, breathing document. And dating can be an expression of what you're learning about yourself too. So saying, oh, here's my preferences and they're not going to change is sort of gating your opportunity to grow too. And so asking yourself, how do I want to feel based on this preference? If funny is a preference or compassionate is a preference, what does compassionate mean to me? What does a compassionate person do in my opinion? Because what I found is that compassionate to me is very different than compassionate means to you. And you have to know on a granular level what you're looking for. And, and then you can set boundaries around your dating life to find more of what you want. So that's the boundaries is especially in the self compassion is especially how dating can feel like self care.
I love that. I love that girl. You are giving us all of the tea that we need with these essence preferences. I love.
How do you feel about preferences? What's your philosophy on preferences?
What I know for sure is that love comes in a package that you generally do not expect.
And that whatever you prefer, something weird about the universe, or at least this has been my experience, that it generally comes very differently. And like the preferences that you have, I think are really great and I think says something about what you value, which I think is an exercise in and of itself to understand who you are, how you navigate this world.
Right.
What you find to be important. And again, it's not even about the other person because generally what they think about what they want in the other person really reflects about what they feel about themselves and what they perceive as something to have or to strive for. And so the question is why?
Yeah, yeah, absolutely. Absolutely agree.
Yeah, so it's really interesting. Okay, so let's talk a little bit about. Because we have a lot of single women out there listening. What advice do you have for them while they're single?
Hmm, in what regard? I could talk about that for days. What place?
Well, I think like single and ready to mingle and ready and open for love and really just wanting, I guess, to be fully prepared before they make that jump.
Yeah. Well, my first piece of advice is work with Anwar or myself.
Easy. There we go.
Easy.
Done. So what's Next.
What's next?
Yeah, because. Because here's the deal. You need to. If the question I love to ask is how supported can you stand to let yourself be? Support is hard to receive, especially for women who are used to doing it, quote, all on their own. Right. So I think that taking inventory of what support would be really yummy to receive in your dating life. Where do you feel stuck? Where do you feel lost? Where do you feel frustrated? That is an excellent opportunity for you to ask the universe. Ask, you know, yourself. What do I need to move forward here?
Yeah.
And I would say the first, I'm doing this Celebrate youe Single Self challenge starting on February 3rd. Yes. Yes. So I believe that there are three tenets to building a dating life that feels like self care. And that's what we're going to do in these three days. It's also leading up to the opening of my coaching experience, the brace and breakthrough full transparency, which is so juicy and amazing.
But celebrating your single self. I come from Alabama. Right. Where women's value is. I grew up seeing that women's value is very much connected to her being married to a cisgendered straight white man usually. And. And I always felt so out of alignment with that messaging. I mean, I went to a college in Mississippi where women were getting engaged in my sorority at age 19, 20. And, you know, if that's the choice you want to make, great. Good for you. I hope that that's, you know, your person and that they treat you well. The problem that I saw was that in that sorority, women were celebrating an engagement more than any other choice in a woman's life.
Yeah.
And I found that to be really problematic. So at that time, I've just decided to launch into a story about this.
Go do it. I want to hear, girl, give me all that tea, girl. This is what I'm here for.
Great. So at the time when I was like, you know, 1920, seeing all these other 1920 year olds get engaged, I thought, okay, it's beautiful that we have the ceremony to celebrate an engaged sister in this group.
Yeah.
What about a ceremony to celebrate her employment opportunities? What about a ceremony to celebrate her decision to go in this direction with her life and her career and her, you know, what about the other parts of her life? Right.
Or getting amazing grades that semester or whatever?
Right, right. And to facilitate celebration. And I was told I was called by the president of my sorority when I started to ask people about, like, what do you think about this? Called by the president of my sorority by the way, I was in the car on the way to, like, a feminist human rights conference.
I got a call, and she was like, hey, Lily, a lot of people have been coming to me and telling me that you have been espousing this, you know, belief that we should be celebrating employment just like we celebrate engagements. And I'm here to tell you that marriage is in no way as important. Like, basically, professional development is not as important as marriage. Marriage is a sacrament in my religion. You have insulted not only me, but the other women who have gotten married to suggest that we should celebrate in this way. This has been around for 100 years. It's never going to change. By the way, it's all about leadership. Because, you know, a decade later, that sorority is the first to accept transgender women. And, like, it all depended on who that leader was. Right. And whose beliefs are at the driver's seat. And her beliefs were that marriage was the most important thing. And I was shamed for that. And I wish in that moment I could tell you that I was like, okay, bye. This is totally. You're wrong, and I don't agree with you. Bye. No, I cried, and I apologized to her. And because I felt so ashamed for wanting more for myself and my fellow members than just marriage, that sort of was the fire that I was born in in a way that I walked away from that year. I ended up quitting the sorority shortly thereafter. But I walked away knowing that there was something really powerful about women standing in their power and talking about what they were proud of.
Yeah.
And by the way, at that time, I said to people, when I was, like, sharing this idea, I was like, well, I'll go first. I have an internship. I want to celebrate, and then I know five other women who will go after me. And I was accused of being self aggrandizing in that conversation with the President. I know.
So you couldn't win.
I get. I could not win. But I knew that when I got in my toxic relationship, I was not in the practice of owning why I was awesome. I was not in the practice of bragging about myself. I was not in the practice of, you know, being proud of my accomplishments out loud. And that was one of the reasons that I got into a horrible relationship. And so now with the Celebrate youe Single Self challenge, my mission in this season and with Brazen, is to help women own their awesome and to invite other women to own their awesome together. And bragging, not in a way that sucks air out of the room on a date, but invites mutual sharing. Invites mutual pride. And so that's day one of the celebrate your single self challenge. Day two.
So let's talk about that bragging for a second. Because I think sometimes people will hear bragging be like, that makes me feel a little bit uncomfortable. I don't know if I want to do it. How does that really relate to my love life? So can we talk a little bit about that? And how can my listeners at least take that first step into getting into their bragging selves to really level up their love life?
Absolutely. So I think that this question is really rooted in how are you socialized? How are you socialized to behave? And in a lot of cultures around the U.S. you know, let's say North America, because, you know, I know you're a Canadian now. Yay.
I mean, I get that some cultures, it's not appropriate to like, talk about your accomplishments at the dinner table. I have some clients, I ask my clients before every session, what's your brag? And some clients are uncomfortable saying my brag is. So they instead say, my gratitude is you don't dip your toe in the water however you want to. But I think it's so funny that.
You asked that because I asked what is their highlight of the week, which obviously has to be a great, amazing thing that they've done. Something has happened.
Right.
To get into that habit of being able to express the good and the not so good. I also ask them, they're low light too. Right. Because in a relationship you have to be sharing these things about yourself.
Yep. And I think that so much of the time, and I hope this thread will make sense. I have been listening very carefully in the last few weeks to my clients share a lot of no's. No, I don't want somebody who does that. No, I don't want to feel this way. No, I don't want to. And that's the first step to self awareness, is recognizing what you don't want.
Right.
I am most interested right now in what are you a yes to? Okay, we know what you're a no to. We know what you don't want more of. So what are you a yes to? And I want everybody that I work with and everybody in the world to be a yes to themselves, to be a yes to their own power, to be a yes to what they are able to create in the world, whether that be a beautiful job, a beautiful relationship, a beautiful home. I want them to be a yes to what they they desire. And the first step to that is talking about what makes you uniquely qualified for the love of your life, talking about why you are amazing and proud of yourself. So I guess the first question might be to tap a best friend of yours, Tap a friend that you really trust and say, hey, let's do this crazy thing where we text each other one brag today and we text you. And the brag can be, I want you to say my brag is because it's really powerful to say. My brag is like, make yourself uncomfortable and say one thing that you're proud of. Hey, My brag is that I did a peloton workout today and it felt really good. My brag is that I felt in appreciation today. I felt in flow. My brag is that I asked for a raise or I set a boundary. It doesn't have to be accomplishment based. It can be around your self care as well. Yeah.
One of the other things that I kind of am all about is also so many women out there have journals. Right. That they use that they implement on a daily basis. I always think that also creating, at least every day there's something that you're bragging about. I also kind of recommend too, having another journal that's just a brag book.
Of just, like, love a brag book.
All of the things that you've ever accomplished in your life that will continue to reaffirm you and to, you know, reiterate how much of a badass bitch you are.
Yeah, absolutely.
Even if it was like winning the spelling bee in fourth grade, girl, write that shit down. You're everything.
Yes. You've done it. You own it. And I think that it's beautiful just to go on a bragging journey. And two months into a bragging practice, a month into a bragging practice, you can look back at your first brags and be like, oh, my God, I've grown. Because I can see that I can write down 15 more things than I could a month ago. Or I've grown because my brags have become bolder and more embodied because so many of my clients, I don't know about you, forget the success that they've achieved.
Of course. So they're like, they just knock it off. They have this goal, they rock it out, they check it off. No time to celebrate, and they go on to the next.
Yep, yep. You got to carve out that celebration time. It is more important than ever. So that's how I'm doing this challenge. That's why I love bragging.
I love it. So bragging is the first day.
What's the second Day girl second day Self compassion.
Tell me all about that self compassion.
So I think that we are a push it, push through it kind of people. At least how we're socialized to be in this capitalist society that we live in. You know what I'm saying? So I want you to stop and say, no, I deserve compassion for myself. If dating is hard, don't push through it. Don't try to download another app. Don't try to go on one more date even though you're burnt out and exhausted and feeling terrible. Sit down and say here is a sentence to get you started in a self compassion letter. Hey Lily, it sucks the dating is so hard. I am really sorry. I am here for you. And of course it's hard because your parents are divorced. Of course it's hard because you have all of these stories that you're untangling and you're doing a lot of personal development work. It's all happening at once and it's hard, you know, instead. And taking time for self compassion can feel self indulgent, but it's actually giving yourself the necessary juice and fuel that you need to continue. Pushing forward is not the answer. Pushing through your feelings are not the answer. Feeling your feelings is the answer to moving forward. So that's what Day two I love that.
And I also love the fact that like oftentimes I know quite a few of my clients and some of my listeners will just not want to address those feelings right. Feelings equals weakness equals they're just going to hold me back. I have goals to hit and accomplish. They're not going to help me. And one thing that I want to offer to them is that if you're having these feelings, it means that you're on the right track. It means that there's something that needs to be overcome so that your path to your ultimate goals, you're going to actually reach it instead of always being hindered by these variety of different things that are happening that maybe you've ignored or avoided in the past.
Yeah, absolutely. And I also want to I know that we are a fan of thought work or working with thoughts and thinking about what your thoughts are. And you know, for anybody that doesn't know what I'm talking about, I believe that thoughts are emotional interpretations of the world around you and that your feelings are inspired by your thoughts. So if you are feeling anxious, depressed, generally sad or defeated, if you're feeling despair, feel those feelings. Their feelings are for feeling. And in your self compassion practice, you can more ease it when you slow down, you can more easily recognize. Oh, wow. I'm feeling this way because my thought is that I'm actually not worthy of what I want.
Yes.
And I'm really sorry that I was taught to think that and that that's how I've survived by now. Oh, my gosh. I've got your back, Lily. And we're get through this. And that thought is a choice. And I can make another choice. Yeah.
Yeah, definitely. Okay, so day two is self compassion.
Yes.
Girl. What is day three?
Day three. And this is where you and I, I think kind of I want to hear your opinion on this. It's my mega mindset. Shift.
Okay.
Around. And again, we're dating like, it's self care with this challenge. So going from the numbers game to I am for the few, not for the many. So it's all about what if you could date like you're for the few, not for the many? What actions would you take? What boundaries would you set? How would that belief or thought influence your behavior? Because I see so much anxiety and stress in people's dating lives stemming from this idea that I have to be out there all the time. I have to be dating all the time. I have to be doing everything per perfectly, and I want people to slow down and only.
Do things that serve them. And I think dating like, it's a numbers game, if you are self aware and you've done the prep work does not serve you. What do you think about this?
So I don't think it should be everything either. I always tell my clients, I just want you on the apps a little bit in the morning, maybe a little bit in the evening, but it should not take your entire up your entire day. I agree with you ultimately, but I think that the way that we get there is a little bit different because I do want my clients engaging with a variety of different men and talking to them just so that they can better understand themselves and who they are in the love game. It's not about trying to go through the guys and figure out do they like me or anything. Like, it's more about, okay, he said that to me. I didn't really like that. So we talk about that and understand. Get a better understanding of, like, what your boundaries are and why you didn't like that and what's coming up for you and what's being triggered and all of that. So I think ultimately we agree that, yes, you're for the few and not the many. And I always think that. I always tell my clients, like, nine out of the 10 guys that you talk to probably won't be the one. And that's okay too.
Yep, absolutely.
But there will be a one, right? There will be a one. And you have to figure out who you are so that when that one does come, you guys are coming to the table with a similar energy that you're like potentially ready to engage in a way that is going to move the relationship forward. But talk more about what sort of mindset does one need to be in when it comes to not being for the many and just for the few?
Because that is a shift, as you were saying before. Right. I think ultimately people feel like, oh, I guess I'll just put myself out there and like, I guess I'll be found.
Yeah, right, right. Well, I think it's about self trust. I think it's about the numbers game sort of is built on this belief that you can't trust what you. I don't know if you would agree. I think the numbers game is a piece of advice that folks give, usually parents and coworkers and, you know, friends, like just, just go on more dates, just download more apps, you know, try more. Are you being too picky? I think that that's generally dating advice that is given from the perspective of your friends and family don't want you to be suffering and they see how hard dating can be for you. So they tell you to play the numbers game because they don't want you to be in suffering. And giving you dating advice helps them feel a little more powerful and also eases their suffering that they're like, oh, I can just help her fix this. You know what I'm saying? I'm for the few, not for the many. Is a very self determining mindset. It is, it does. It doesn't really matter what you think about my dating life, mom. It doesn't really matter what you think about my dating life, coworker. I know my path. I have confidence in who I am and what I'm looking for because of this deeper work that I'm doing. Again with one of our coaching programs. We could help you with that. But I'm for the few, not for the many. Necessitate self trust, which I think is a huge game changer for a lot of people because they go from I don't know if my picker is broken, I don't know if I, you know, I don't know if I can do this on my own to, you know what, I can trust my body. And it takes work to recalibrate your body. Compass in that way to be able to trust your intuition. That takes work and practice. But those are some of the elements of the mindset. Shift to I'm for the few, not for the many.
And so that's going to be all about day three, right?
Yeah.
I love that so much. I know you have a famous line that you say often, and it's one of my favorite every time I hear your podcast. What's the name of your podcast?
The Date Brazen Podcast.
Yes, ma'.
Am. Yes.
So tell us that phrase and what it means. Because I think it's so important for people to kind of just take this in, internalize it and feel it.
Yes. So I will take you back to when I first heard the phrase. I was trying to be an actress in New York City. This is before matchmaking. So I was like, singing and dancing my ass off and auditioning. 4:00am you know, non union calls for, you know, non union Shrek, the musical, national tour, you know, like, totally crazy stuff. Yeah. So. And I was struggling, didn't have much money, didn't have any jobs to my name, and I went to a dance class and the teacher wrote on the mirror, what is meant for you will not pass you by.
Yes. Can you repeat that?
We gotta get. What is meant for you will not pass you by.
And it immediately put me at ease because I no longer had the anxiety of, should I have gone on that audition three weeks ago? And that would have been my big break. And I didn't go because I was tired and I was. I was feeling low, but I should have got that immediately put my mind at ease. And similarly, when it applied to dating, it put my mind at ease as well. It's like, you know, I applied it to my dating life after my toxic relationship, you know, but. Yeah, but. But it had to go through the learning. But in dating, it was like, no, I can. I can listen to what I. If I don't feel like going on the date because I need to rest because I'm so exhausted, like, what is meant for me will not pass me by. I can be honest with somebody that I like, because what is meant for me will not pass me by. I say, also, you can't say the wrong thing to the right person. If you need to set a boundary, if you need to tell someone what you need you don't have, you can choose to not be afraid of being honest because the right person will remain and won't care.
They want to hear from you. They want to know exactly how you're Feeling.
And mar. Do you know. Do you know about my first date with Chris? And what like I did my first date with Chris?
No, girl, but I wanted to talk to you about all of how you met your girlfriend. Oh, my God. Tell the story, girl, tell the story.
Oh, my God. Have we talked about all of this?
A little bit. But by listening, to hear from it.
Okay, okay, okay. Because we're friends outside of this people, you know, we talk all the time.
Yes.
So I was in this relationship with this person who I never named because I, you know, send him all the best in the universe. We were terrible fit for each other in a terrible relationship. We were also in an open relationship, which is something that I, looking back, had forced myself into because I thought that this was. I was in love with this person. And I thought this is the only way that I can belong in this relationship. So I'm gonna take this crappy choice over being alone. And for people who do non monogamy and love it, love that for you was not for me. So it was that summer that my parents were getting a divorce and I was at the tail end of that horrible relationship that I was invited to a rooftop party, very fancy, in New York City for a friend of a friend's birthday. Okay. I was like, oh, okay, I'll go to this friend of a friend's birthday, whatever. And it was Chris's birthday party. And I didn't know Chris. I had heard about him. He was roommates with my friends. And I mean, I went and he immediately welcomed me. And he was cooking for everybody. He was grilling for everybody. And he was this like, gorgeous yellow shirt. And we all just sat up there and got really sunburned, or I did my very pale self. And we just laughed and talked and, you know, that was that. July 4th rolls around, his birthday's in June, July 4th rolls around. A couple weeks later, same rooftop, and I was invited. They go up to the rooftop. Chris and I, you know, we hang out. I don't think anything of it. I just think, oh, he's a nice guy. You know, he's cute. But I was in this toxic relationship at the time, so my radar wasn't like, on for other men. He comes up to me and it's like, hey, I think you're really cute. And it's a shame you're in a relationship because I want to sex you up.
Not to sex you up, girl.
I know. Quoting. I wanna sex you up. Like such a weirdo. Like, I was like, oh, this guy thinks he's gonna, like, make me blink with this brazen, right? I'm like, fuck him. I'm gonna. I look at him dead in the eye. And I was like, well, I'm in an open relationship, so let's go down to the bathroom right now and bang it out.
Oh, no, girl.
And he. Cause I knew he wasn't serious. I knew that, like, he was just fucking with me, right?
To get a reaction. Yeah.
And to get a reaction. And so I, like, like, volleyed it back at him, and he responds with, cool. Well, it's good to see you. It's good to see you. See you later. See you later. And meanwhile, years later, he was like, lily, I had told my friend to watch. Hey, watch me go do this. And my friend was staring at me the whole time and, like, saw my shame. But when he said, like, I have to admit, I got a pt. I call it a pussy tingle. I got the pt.
That's for the pt, girl.
Yes. So he. Chris was very, like. He, after a couple months, started courting me. Like, started telling people that he liked me, made it known. He started texting me, and I was like. Or started Facebook messaging me. I don't remember. And I was like, this is too much. Like, this guy likes me. What's wrong with him? That was my mindset.
Had other people courted you before? Like, this?
Never.
Because that's the thing that I want to highlight, too, because it's going to feel weird when someone actually is courting you and you have never been courted and showing up in a significant way.
Oh, my God. And you have to let it be known that there is some discernment that you need to do around. Like, is this creepy or is this cute?
Yes, for sure, for sure, for sure.
And the discernment for me was, okay, I know this. I know all of this person's friends, right? I have a read on how I feel. This is beautiful and cool, but also weird. Do you feel uncomfortable? So I was still with this guy. And it came upon August, like, literally, June met him. July, I want to sex you up. We can go bang it out. Then August, I was singing in a cabaret show. It was the last time that I ever sang on stage. So I was singing at this thing. All of my friends came. It was a $40 cover, like, crazy New York. And my ex came, too. He was late. My ex was late. He was freaking out. Like, I don't want to be here. Texting me right before I was about to go on stage. Chris, meanwhile, came with our Mutual friend. They brought flowers. They were in the front row of this show. And there was this juxtaposition. It was literally like a door closes. A door opens because right before I'm about to go on stage, my ex comes up to me and says, hey, I need to go. This isn't a good place for me. I think he was struggling with something at the time, but I was like, well, do you want to stay for my song? And he was like, yeah, yeah. And then I'll leave. And I got on stage. I shit you not. I sang a song called what you don't know about women.
And then I got off stage. I kissed him, the ex, which haunts me to this day, that I kissed him. Why did you know along the way, it's like, why didn't I break up with him then? Why didn't I break up with him that he leaves. Then I realized he hasn't paid his bill. I have to gather cash from all of my friends, like, pay his bill. I Venmo request him. I call him in a cab home. I'm like, this is unacceptable, right? Like, we need to. We need to have a conversation. And then we broke up. And the day we broke up, I devastated. More so because I had allowed myself to be treated like that. Less so that I was, like, missing him more so, like, wow, that was really traumatic for me. And that night, I was with a friend who cooked me dinner. And, like, the friend who actually introduced me to Chris. And Chris messaged me and was like, hey, I'd love to talk sometime. My friend told Chris the day that this guy and I broke up, and I looked at my friend Jesse, who I was at her house at the time, and I said, I don't know why I know this, but I know in my body that I'm going to be in a serious relationship with this person.
Wow.
I resisted it because I needed to heal, you know, I needed space and time. Chris was pursuing me. I had to set a boundary. I had to be like, hey, please don't text me. I need some space again. You can't say the wrong thing to the right person. I then started having dreams about him being my partner. I had two nights in a row of dreams. And then, like, the sun shining on my face in the morning, I want to cry thinking about it. And finally I texted him. I was like, hey, let's. Let's get together and go on a date. Let's do this. And he told me before our first date, this is it, you know? Like, I know that we're gonna be. I've spent a lot of time thinking about this. I. We didn't really know each other, but we did. It was beautiful and weird and, you know, not something I'd ever experienced before. Okay, so this is an example of you can't say the wrong thing or do the wrong thing with the right person. Though I do regret some of my decisions. I was 45 minutes late.
Girl, why?
I was 45 minutes late to that date.
Oh, my gosh.
Can you believe. Can you believe he stuck around the restaurant, thought that I. The restaurant was, like, treating him like he was being stood up, which he was in the first. 45 minutes.
45 minutes. Yeah.
And I look back, and I had been going on a few dates, like, with different people. I was late to all of those dates, and I think it was an unconscious sabotaging.
Yes, that's what I was saying.
And conscious. And unconscious. And conscious. I was being late because I was not ready to receive this experience. And then my ass went on that date with Chris, and I talked about my ex for literally, like, 45 minutes.
Oh, my gosh. Girl. Cannot be the wrong thing to the right man.
I was hurt, and I was healing, and he was. He just felt like a friend. And as he was holding my hands and, like, it felt so beautiful and like a friend mixed with this, like, love that was building on the first date. It was. It was wild.
Yeah.
But eventually, after a few weeks of dating, he was like, hey, can we talk about your. Like, I really want you to be supported. I want you to talk to your therapist, but I don't. I don't know that I can hear about your ex anymore. We've talked about it so much, and I'm glad he set that boundary. Yeah, but that's the piece of, like, you can't say the wrong thing to the right person, and the right person will know what they need enough to ask for what they need.
Right.
So that's. And then after that first date, we were. We were together, and we've been together for three and a half years.
I love that. And congratulations on your relationship. I want to hear about these stories because I think it's important for my listeners to understand that it looks very different for everyone. It's not the same story. It's not how that happens. You do not run into somebody at the coffee shop, and that's it. Right. Maybe 5% of the time, but oftentimes it looks just like what you just described. You're having so much. Your sliding doors moment in that cabinet. Did you see that movie?
I did. I mean, of course. I mean, that was such a sliding doors. Such a sliding doors, lake house moment. We are when God opens a fork in the road, for sure. And I. I also want to say people are like, well, you didn't meet Chris on a dating app, and you teach people how to date online. A dating app is a tool to get to know yourself better. Right. And to meet somebody outside of your social circle. Had I not done the reflective work that I did, which I now get to help my clients with. I know you do reflective work with your clients, I would not have been able to receive the love that Chris wanted to offer. So I don't view our work or my work as just helping you online date. I see it as helping you find the most extraordinary relationship of your life, however it arrives.
I love that. I love it so much, girl. Thank you so much for sharing all of this amazing tea, both personal and professional.
So much. Right from the place of single girl.
I want more. I want more. I love it. So for my listeners who want to connect with you and are interested and celebrate your singleness, how can they get in contact with you?
Yes, the best way to join the Celebrate your single self challenge, you can go to datebrazen.comchallenge to sign up. My Instagram is also a great place to DM me. I love hearing from people who listen to our podcast Podcast at Date Brazen.
Slide into her DMs, y'.
All. Slide to my DMs. And if you're interested in a podcast with Anwar where I interview him, you can go to the Date Brazen podcast and look at our ANWR Lily episode of that podcast. I'm really, really excited to welcome more women into Brazen Breakthrough in February and really help more people claim the extraordinary love that they are worthy of and that they deserve. And I'm really grateful for you, Anwar, for being such a super connector and for offering, you know, an opportunity to talk about what we do in this way I think is so important.
Yes, of course, girl. Well, much love to you and thank you so much for joining me on this episode. I've had a blast.
Me, too.
And I hope that you have as well. Thank you so much for joining us, everyone. And as always, be well.
Hey, girl. Thank you so much for listening to the get yout Guy coaching podcast. If you like this episode and want to talk with me personally, please book a free consultation at www.getyourguycoaching.com apply or subscribe and leave me a review wherever you listen to your podcasts. Talk soon.
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