In this episode, I break down exactly how to start dating with confidence, self-care, and intention.– especially if you’ve never dated before!

You’ll get a step-by-step guide to move past fear, own your desires, and create a joyful dating life on your terms.

 

Here’s what you’ll walk away with:

✨ How to start dating from a place of power (not pressure).

✨ Why your thoughts are not always facts—and how to shift them.

✨ The “Thank You More Please” challenge to clarify what you really want.

✨ How to release perfectionism and embrace the messy, fun, real parts of dating.

✨ The truth: You are uniquely qualified for the right person.

_________

WORK WITH LILY:

✨ Get my free “Create Your Essence Based Preferences Guide” HERE

✨ Order my book, “Thank You, More Please”: https://www.datebrazen.com/book

✨ Get my FREE training, “3 Steps to Attract the RIGHT Partner as a Late Bloomer”: https://www.datebrazen.com/training

 

Links:

Follow Lily on Instagram and Tiktok.

Subscribe to Lily’s Youtube channel HERE. 

Show transcript:

Lily @ Date Brazen (00:00.046)

Hello, gorgeous friends. Welcome to another episode of the Date Brazen podcast. I’m so glad that you’re here. Happy New Year. Happy, happy New Year. Okay, so today is gonna be great, because we’re gonna talk about how to even start. If you are somebody who wants this year to be beautiful and expansive and juicy in your love life, if hell, you just want to feel like,

it’s happening, like your love life is happening or your dating life is happening. You wanna feel excited about this area of your life or empowered in this area of your life. You wanna be out of your anxiety and into your agency in this part of your life. This episode is for you. Today I’m talking about how do you even, where do you even start to create an intentional dating life that feels like self-care and that leads to extraordinary love.

So whether you’ve never gone on a date in your life, whether you’ve never been in a romantic relationship in your life, whether you just got divorced or you had one relationship a long time ago but haven’t really dated very much since, this is to support you in starting with power and with confidence and with self-compassion. So be sure to have something to take notes. Maybe it’s your notes app, maybe it’s your

notebook and pen because we’re going to get really like step by step tactical today. I’m going to give you my roadmap. So before I get into that, I do want to tell you that this episode is brought to you by my signature program, the brazen breakthrough. This is my step by step feminist as fuck program that’s going to teach you how to build a dating life that feels like self care, how to do that reflective work to get beneath the surface of your patterns.

to build new narratives in your dating life that serve you and your worthiness. You’re gonna learn how to define your essence-based preferences and use that reflective information to build a tactical strategy so that you have more clarity and ease as to how to meet somebody on a dating app with less anxiety and how to build a joyful as fuck dating profile, how to use a dating app effectively to your benefit where you’re in control.

Lily @ Date Brazen (02:13.25)

where you are in the driver’s seat, how to build an in-person dating life and love life that feels juicy and exciting and courageous as hell. There’s also monthly group coaching calls where I’m going to lead you through and coach you through all of this content and you’re going to build community with the badasses in those group coaching calls. It is the place to be if you want to create a love life on your terms, if you want more ease here and you want a clear path forward, you deserve it.

You can go to datebrason.com to find out when the next live info session and coaching session is to learn about the Brazen breakthrough. Go to datebrason.com. Info is there, also in the description of this episode. So with that, let’s get into where do you even start?

Lily @ Date Brazen (03:05.294)

Hey, I’m Lily Wonville, former top matchmaker and founder of Date Brazen. After setting up hundreds, I realized that with coaching, women could match themselves better than anyone else ever could. With my unconventional feminist approach, I’ve helped women around the world build courageous and self-trust-filled love lives, and now I’m here to support you. Get ready, because I’m about to share the exact steps you need to attract a soul-quenching partnership and feel amazing about yourself along the way. This is the Date Brazen podcast. Number one.

Why am I doing this episode? I’m doing this episode because I hear so many people stuck in overwhelm, stuck in fear of starting, stuck in the stories of like, what does it mean about me that I haven’t been on a date yet, or I haven’t been in a real romantic relationship yet, or I haven’t been in one in so many years, right? So first I’m gonna invite in a deep breath.

Lily @ Date Brazen (03:58.862)

breath is always available to you. And I want to also acknowledge like thoughts are not facts. Thoughts are not facts. Thoughts are emotional interpretations of the world around you, usually built to keep you safe after traumatic experiences, after seeing things that you do not want. Your brain is creating stories to protect you. And those stories have been older coping mechanisms that used to serve you. They may not serve you anymore. And it’s time to acknowledge that and start to rewrite.

piece by piece, how you can bring more agency into your dating life, into your best next step, because you’re powerful, right? You’ve created so many incredible things. You are brilliant. You are gorgeous. I’m just gonna claim it. You are irresistible to the right people for you. And I hope that you can get off on yourself a little bit. Look, it’s the first of the year. Let’s acknowledge how much you’re bringing to the table in so many ways.

So number one, notice what assumptions you’re having about yourself. Notice how those assumptions about yourself and your dating life are, how they’re affecting your decision-making. Notice how you’re feeling in your body. Be a loving witness. So you know when you were a kid and you were on the playground at school and you suffered a rejection from a friend who you thought was a friend and then they rejected you, told you, can’t play with us. my God, it hurt so bad.

hurt so bad and it was so confusing and hard and hurtful and you stand there and you’re upset and you’re maybe starting to cry. And then an adult in your life, maybe a teacher comes over and there are two versions of what that teacher could respond with, right? There’s the version where the teacher says, it’s okay, you’re okay, you’re okay, go play with somebody else. Figure it out, go, go, go, figure it out. You’re okay, you’re okay. There’s that version.

Lily @ Date Brazen (05:59.278)

And I understand that teacher’s perspective, right? They think they are doing what you need, like just get over it, right? I’ve had to do with so much code underneath, it’s like, this is life, kid. This is life, it hurts, get over it. It’s okay, just move on. And I understand that maybe that teacher’s going through a lot and they don’t wanna spend the time to, you hold space. You know, and both and. What does the child need? What does this younger Virjia, what’s the dream?

best case scenario for you on the playground. For me, it’s that that teacher comes over, gets on my level, says, what happened? And they listen with no agenda. They validate, they reflectively listen. They say, that’s so hard. I’m so sorry. That hurts really bad, doesn’t it? I’m sorry. Can I give you a hug? And then I say, yeah, you can give me a hug. And then we hug and I maybe cry some more. And the more that they’re just like present with me, not trying to talk me out of my feelings,

not trying to talk me out of this present moment, the more I become okay, the more I become like, yeah, I’m safe, I’m held, it’s okay, this really hurts. It doesn’t mean that the hurt goes away necessarily, but it does mean that I’m coming into more of an emotionally safe place with myself. So then I hear, inevitably, I hear some other kids playing and I wanna join them. And I say, okay, I’m ready to go. And the teacher says, are you sure? Do you need anything else? I’m like, no, I’m okay, thank you. Then I leave.

That is the kind of loving witness energy that you get to give to yourself here. That is so important when thinking about your dating life. Dating is not a silo. Dating is not something that everybody just has figured out. Dating is hard. It is vulnerable as hell. And it is a microcosm of every hope, joy, dream, fear, insecurity, desire that we have as humans. So when you tell me I’ve never been on a date or I haven’t been in a romantic relationship, my response is not,

Ugh, what’s wrong with you? My response is, yeah, I hear you. You just so happen not to have gone on a date. That doesn’t mean anything about you or your worthiness to me. That means that you’ve lived your life. You’ve made choices. That’s good. You’re human, right? I think the problem with that, not the problem, because all of us have human brains, the spiral comes in when you are punishing yourself for not being in a different place than you are right now.

Lily @ Date Brazen (08:19.576)

You don’t have to punish yourself anymore for that. You get to turn towards yourself with loving witness energy, with loving kindness and say like, yeah, I’ve been doing the best I can and that’s enough and that’s okay. What if my dating life didn’t mean anything about my worthiness? I fundamentally believe that dating and relationship status is not a reflection of our value as human beings. People are not in relationships because they’re more valuable than you.

They’re in relationships because somebody weird wanted to be weird, particularly with that brand of weird with somebody else. And it just means that you haven’t found your person or your, you know, like your brand of weird person yet. Like you are uniquely qualified for what you want. And yeah, you want something and it’s not here yet. And this space between those things can be painful. And your brain is trying to solve for the problem. Why have I not found somebody and my friend has? So your brain then creates stories.

to make meaning out of that scenario. The meaning that your brain has probably made of that scenario is maybe it’s me, maybe there’s something wrong with me. That is a cognitive distortion, not just. is. It is your brain trying to make meaning when that meaning that your brain is making is so much more about socialization, the patriarchal world in which we live that values coupled women, coupled people over single people.

the cultural norms that we exist within. I I grew up in Birmingham, Alabama, where that cultural norm was definitely Ring by Spring. If you don’t know what that is, God bless, bless your heart. You didn’t grow up in the South. And that may be something somewhere else. And if you did do Ring by Spring and are in a healthy, wonderful relationship, good on ya. I love that for you. Both and. Look at why your brain might have made that mean, your singleness mean that you were less than. So much to do

with so many complex factors. And your brain likes to be right, is the other thing. So your brain probably has gathered a lot of evidence, quote evidence, to prove that story right, that there’s something wrong or something you need to fix. When actually we’re just sort of clearing the deck, like being a loving witness, allowing your nervous system to reset if there’s any fight, flight or freeze here, as there is often in dating. And then looking at where might these stories be coming from?

Lily @ Date Brazen (10:44.322)

that my singleness means something about my value. And then what else might be true? It might not be impossible that I just haven’t met the right person yet. It might not be impossible that I have loving, healthy relationships in a lot of areas of my life. And it might not be impossible that there’s not a hierarchy to relationships, that romantic relationships aren’t that different. Maybe. What if you could play with that idea? So then.

After you get clear on what’s happening beneath the surface in your brain, that you need to start a dating life, that you haven’t had one yet, or that it hasn’t been what you want yet, then I want you to pivot. I want you to pivot to the thank you more please challenge. You can look at episode 124 after this episode to learn more about the thank you more please challenge. So, because so many people who come to me and say, where do I start? They’re like, I don’t even know what I want. So this is how you get to know what you want. When do you feel supported in your life?

When do you feel excited? When do you feel lit up, turned on, emotionally, sexually, intellectually? How do you want to feel? And what relationships currently feel amazing and caring in your life? So this is about getting in the driver’s seat of noticing, noticing what you want when it is in front of you.

Confirmation bias, that idea of like your brain wants to be right, confirmation bias may have gotten you to pay attention to the everyone’s ahead of me, no one’s single in my city, my city is crappy for dating, like, et cetera. So it’s time to say yes and, yes and thank you brain for making a lot of meaning out of all of this. Maybe ask yourself, am I willing to be wrong about this? Am I willing to open up to a different possibility? It is time to notice. It is time to notice.

where there is evidence around you that what you want exists, where you are really adept at relationships, where you are the expert in what you want. And then the next step after that is to claim your essence-based preferences. And for that process, look at episode 135 of the Date Brazen podcast. What are the values that you want? What are the personality traits that you want? What are your checklist preferences and how do you hope they make you feel age, location, height, et cetera?

Lily @ Date Brazen (12:59.106)

with personality traits and values, what do these words mean to me? What’s my love life vocabulary? And I want you to make decisions rooted in your deeper preferences. This doesn’t mean like, where do I start getting on a dating app? No, no, no. This is about something deeper than a dating profile, something deeper than a rigid snapshot. It’s an impressionist painting of like, how do you wanna feel? So notice, like claim your essence-based preferences. Okay, so first we’re gonna recap really quickly.

First, you’re gonna notice what’s going on beneath the surface. How can I be a loving witness to myself? How can I really care for my nervous system, my brain, my body? Then do the thank you more please challenge. Notice what you want in the real world. Attune your focus to when am I receiving what I want? Where is there evidence that I have great relationships and I get to be cared for and I’m interesting and amazing and desirable, all these things. Then.

You’re going to claim your essence based preferences. See episode 135 for a step-by-step process. Then next step, start playing. This is your invitation to release perfectionism. Beneath the question of where do I even start usually is the desire for this like, just give me the three steps and then I’ll be fine, right? And of course I’m giving you some steps. I love steps. You know I’m type A. And.

This is not about rigidity, this is about play. This is about releasing the idea that there’s a perfect way to do any of this. Like this is about messiness. The best things in my life have come when I have been willing to like get messy and to play. And that takes a couple things. It takes some emotional safety, a lot of nervous system care to feel safe enough to get messy in play because previously I have organized safety around perfectionism and people pleasing.

And so this is about redefining like, I get to be in charge, you know? So start playing. That means asking for what you want out loud and often. Tell your friends about your newfound essence-based preferences. Have them join you in the thank you more please challenge. Send them episode 124 and do it together. Saying what you want out loud and often means to yourself. That means, you know, kind of getting off on what you desire, flirting with your desire.

Lily @ Date Brazen (15:17.41)

I desire the right relationship. Sometimes saying that out loud can be transformative for people. Getting on, you know, this can tactically look like getting on one dating app with intention. I have a great episode for that. Episode 121 of the Date Brazen podcast is a dating app, ask me anything, so go there. And then, you know, it could also look like joining us in the Brazen breakthrough, getting a community around you, getting a process around you that feels like self-care and that you get to play within.

approaching acute person in person, intention, like set your intention to be messy and to play, to be safe while you play. And then get messy, get messy, get messy. Like do it, go. Perfectionism isn’t a thing here. So last two steps, boundaries, right? Boundaries I recommend for your play, one dating app, not five. If you feel aligned with it, notice when you’re exhausted, pay attention, drop everything to care for your nervous system, have your own back super fiercely.

And I encourage you, last step is to joy build, right? And in-person dating life is very available. And it looks like deciding what brings you joy in the real world and doing it often, making connections when you do those things in the real world, looks like taking out your AirPods at the grocery store, looks like making eye contact with people, looks like saying hello to cute strangers. It looks like feeling like so nervous.

to do something courageous and doing it anyway, having your own back, celebrating the shit out of yourself when you do it. Play, play, play, play, play. Get messy. There’s no perfect version of this. Everybody’s awkward. Everybody’s weird. We’re all super intense and weird. And I think that social media has us comparing ourselves and saying like, oh, I’m not as cool or as chill as somebody else. Chill is not a thing. The right person for you is going to be so uniquely qualified for you. And you are going to be so uniquely qualified for them.

and the right person, the right people, right? Play, play, play. That is how to start. That is how to start. You’ve got this. You’ve got this. You’ve got this, right? And it’s about building. It’s about playing and learning and growing. There’s nothing to fix. It’s all growth. Love you. You’ve got this. And I’ve got your back. Talk to you soon.