Does the idea of making the first move in dating make you feel awkward AF? You’re not alone. In this episode, I’m breaking down exactly how to shoot your shot as a late bloomer—without spiraling into self-doubt or waiting for someone else to make the first move.

You’ll learn:

✅ The mindset shifts that make it easier to take bold action in dating

✅ Why making the first move 100% of the time is a game-changer for attracting the right relationship

✅ How to bounce back from rejection (without losing your confidence)

 

Work with Lily:

Free Live Training on June 17th: datebrazen.com/lets-go

Learn about Main Character Dating: datebrazen.com/waitlist

Book: Thank You More Please

YouTube Channel

TikTok

Instagram

Show transcript:

Lily @ Date Brazen (00:00.247)

Okay, let me know if this is you. You’ve been climbing the ladder at work for so long and you’ve gotten promotion after promotion. Basically, you’re kicking ass. You’ve also been single most of that time, which has become a part of your identity. Maybe you think of yourself as the single friend. Most of your friends are coupled and they don’t really get your dating struggle. You’re super independent and you’ve been told your success is quote, intimidating to people you could date.

You’ve also been told stuff like, you’re too much or are you sure you’re not being too picky? I mean, I was told those things over and over and over again. So you default to not talking about your dating life at all or making it a joke for some frothy dinner conversation. But under the surface, you have a secret. You really want to find the right partner and build a life with them, but it feels impossible because you feel so behind. If this resonates with you, then my upcoming training called

three steps to attract the right partner as a late bloomer is going to change your life. Because if you feel behind in any way in your love life, whether you’ve never been in a relationship or you just got out of a 10 year relationship and don’t know where to start, this process and this proven framework that I’m going to teach is going to feel like an exhale and a big old hug all at once. It is the sponsor, this live training is the sponsor for today’s episode of the Date Phrase in Podcast.

and I cannot wait to coach your face off inside. On June 17th, 2025 at 6 p.m. Eastern, you can go to datebrazen.com slash let’s dash go to sign up right now.

Lily @ Date Brazen (01:42.744)

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 show you exact steps you need to attract a soul-quenching partnership and feel amazing about yourself along the way. This is the Date Brazen podcast.

Hello gorgeous friends. Welcome to another episode of the Date Brazen podcast. I am so glad that you’re here. Today’s episode, as I just mentioned, I’m very passionate about it because it is one of my hottest takes. It is something that a lot of people disagree with me on, which is why I’m so excited to bring this lesson to you. This lesson is something that I’ve seen make a marked difference in my client’s ability to attract the right

partner. It has made the biggest difference in their main character energy in their love life. It’s made the biggest difference in them being able to show up as themselves in their love life and attract people who like them as they are. And it is something that made the difference for me between like not getting up with Chris and ending up with Chris. And it’s this. I want you to make the first move 100 % of the time.

Oh, Lily, no, what are you talking about? I hear you. I hear you. And I’m going to address all the questions and all of the resistance. Now, I think that this is really important, this lesson of making the first move 100 % of the time. And believe me, I’ve got caveats. I’ve got next steps. I’ve got, you know, I’m type A as hell, so I’ve got a step-by-step process for this as well. So here is what I believe about making the first move 100 % of the time. It means

that you are being proactive. It means that you are showing the fuck up for what you want. It means you are admitting to yourself what you want and you’re asking for it out loud and often, which is the skill that I’ve seen lead to my clients finding the best relationships of their lives. It means that you’re not playing games, okay? It means that you’re not sitting around waiting to be asked out to the dance. You are taking an active step.

Lily @ Date Brazen (04:07.279)

toward your joy in your love life by making the first move 100 % of the time. So here are the things that you will need to believe about yourself, your future partner and your dating life to fully buy into the making the first move 100 % of the time lesson that I’m teaching you. And by the way, if you feel resistance right now or you feel fear right now or you feel like, Lily, no, you’re wrong right now, AKA resistance, then just go with me.

Literally just like take a deep breath. Ask yourself how might this be for you right now and take what you need to leave the rest. As always, I just know that this lesson is fire and that it’s going to change your love life if you embrace it. So here’s what you need to believe about yourself, your future partner and your dating life to make the first move 100 % of the time. Number one, that you’re powerful, that the right person will be

delighted when you show up. That’s number one, that you are powerful and the right person will be delighted that you showed up. Number two, that the right person will co-create when you show up. So that means that they will ask you questions back. That means that they will be like, if you think of a volley, like a volleyball game, I myself tried out for the volleyball team in ninth grade and epically failed.

Epically did not make the practice squad. I was so bad But I do remember the feeling of elation when I would like throw the ball up or like set it up whatever I don’t even know the words I would set the ball up and Somebody else would like set it back to me or spike it back to not spike I don’t even know that I shouldn’t be getting into volleyball language if I if I’m not able to pick up the ball

the volleyball language. But you get what I mean. Like when the ball is being tossed back and forth, it’s sort of, it’s very exciting to see a volley take place. It’s very exciting to participate in a volley. And that’s what’s going to happen when you make it your standard that you make the first move 100 % of the time is that the right people will volley with you. They will keep the ball up in the air with you. The wrong people for you will let the ball drop.

Lily @ Date Brazen (06:24.483)

They will not respond. They will not care. They are not right for you. They have seen themselves out. Bless and release. Even if you haven’t had a relationship, you can still bless and release somebody who doesn’t volley with you, who isn’t game to play. So the right person will co-create when you show up. They will be in a volley with you. I also want to say to all of you, have so many like, wait, I’m going to wait on that. I’m just too excited. Hold on, hold on, on. Okay. Third.

third thing that you will need to know and believe to make the first move 100 % of the time, to increase the likelihood of you meeting your person. You will need to believe that it will be awkward and that that’s totally fine. It will be awkward and that’s totally fine. I hear so many people saying, I feel so awkward. What they’re really saying is, what does that mean about me that I feel and am so awkward?

The thought, am so awkward and that’s a problem or that is repulsive to the right people or that that’s something that I need to fix is trying to make yourself more of a robot and less of a human. What if you just embraced that this life is weird and awkward and that you’re a squishy, gorgeous human being who’s gonna be awkward and that that’s totally fine. Welcome, okay? Welcome to…

The land in which your humanity is seen as just right. Your awkwardness, quote unquote awkwardness, is seen as just right. Remember the thing that I say all the time, you can’t say the wrong thing to the right person? Yeah, it applies here too. It’s going to be awkward and that’s totally fine. It doesn’t mean anything about you. That’s number three. Number four, you need to believe that trying this imperfectly

Trying this lesson, I make the first move 100 % of the time, trying imperfectly gets you closer to meeting your person. You need to believe that every shot you take is celebratory. Every shot that you take is getting you closer to meeting the right people, is getting you closer to the right opportunities, is getting you closer to the right new friendships, is getting you closer to what you want because you’re taking an active role in attracting it and asking for it. Now,

Lily @ Date Brazen (08:47.191)

I want to get into in a minute this idea of attract, not chase and how this is not chasing, but I’ll get into that in a moment. Okay. That was number four. And number five, the fifth and final thing that you need to believe in order to make the first move 100 % of the time successfully is that you’re resilient as fuck and that rejection won’t kill you. I got a message from somebody on Instagram that was like, making the first move wrecks my nervous system.

They said, my body is in shambles when I even think about making the first move. And that’s like social anxiety, anxiety, rejection, fear 101, right? Those are normal feelings. If this is the first time you’re listening to the Date Brazen podcast, I cite this all the time that our bodies fear rejection like we fear death. Why? Because when we lived in caves, our cave dwelling ancestors literally would die if they were rejected because it meant being put out onto the street and dying of exposure.

So it’s normal to fear rejection like you fear death. The problem is that you’re treating that fear as if it were a fact. You actually haven’t tried enough to prove to your body that you’re not going to die. So all you have to do is go up to the step before this and the step before that. It will be awkward. That’s okay. And trying imperfectly gets me closer to the right people. Trying baby step trying and then celebrating your efforts.

of shooting your shot, of making the first move, is exactly what will help you create resiliency in the face of rejection. Because rejection, while painful, doesn’t mean anything about you. It means that the person that you spoke to or asked out or said hello to or made eye contact with that rebuffed or wasn’t interested, means that they weren’t in the place to reciprocate or that they weren’t your person or they weren’t interested. Whatever. Just that’s all them shit.

You get to be into your shit. You are the main character of your love story. Okay. So I want you to be, I won’t even say rejection proof because that implies this state of perfectionism in which you would be totally fine being rejected all the time. No. What if you expected it to suck a little bit or a lot, but then preparing for it to suck shortened the amount of time that it sucked and not preparing for it to suck like

Lily @ Date Brazen (11:14.147)

like breast rehearsing tragedy all the time, but just being like, if it happens, I know what I’m gonna do to shorten the window of time that I feel shitty after experiencing rejection. And the way that you shorten that amount of time is by SOFT. SOFT, I’ve talked about this a few times on the Date Brazen podcast. It’s a self-coaching framework that I teach inside of my programs.

SOFT, so important and it is going to allow you to be rejection bounce back central. You know I don’t want to say rejection proof. So now I’m going to say like, I’m going to figure out a word in the moment. Rejection buoyant. Rejection like bungee. I don’t know. Like we’ll figure something out, but something a little more playful that’s like, yeah, I bounce back quickly because I have SOFT. S, self-compassion.

Here’s an example of in the moment if you shoot your shot if you make the first move and you’re it’s rebuffed Okay, the person’s like no, I don’t want to talk to you That sucks. Okay, that really sucks and hurts. Ouch. Ouch. Ouch. Softs Self-compassion says of course you’re feeling like shit And of course you feel like you want to hide into a hole and die and of course you feel embarrassed and maybe some shame like of course it makes total sense because of neuro neurobiological

wiring because of our cave-dwelling ancestors, because you were taught that being rejected in this way meant that you were a loser or that you were somehow less than or that somehow you were missing something that you should have known already. So of course you feel this way. Self-compassion says, of course. It doesn’t say, over it. It doesn’t say, everything sucks and is awful and nothing’s ever going to change in this chair. It’s not wallowing.

And it’s also not moving on really quickly. is a scientifically backed resource, scientifically proven resource that has proven to reduce cortisol and increase resilience. Two things that you need to continue into OFT, S-O-F-T. Self-compassion says, of course, it could look like a hand on your heart. It could look like a deep breath. It could look like a five minute meditation on self-compassion.org by Dr. Kristin Neff. It could look like writing yourself a little self-compassion letter in your journal that starts with, hey, Lily.

Lily @ Date Brazen (13:36.653)

I’m so sorry that you were rejected. That really sucks. I’m here for you. You’re not alone. Of course you’re struggling with this because insert your context here. S, O, own your needs. Own your needs. If you are rejected, what do you need? Maybe you need to go to the bathroom for a second. If you’re at a bar and somebody didn’t want to talk to you and you shot your shot and it didn’t work out, O, own your needs. Go to the bathroom, take a break, take a breather. Maybe you need to go home. Yeah. You don’t need to push yourself.

Maybe you just need to say, ouch. Maybe you need to call a friend. Maybe you need to text a friend. Maybe you need to move your body a little bit to move some of the anxiety around and move through that anxiety. I don’t know, what do you need? Own your needs. This is saying so many people, when they experience rejection, internalize it, blame themselves, say it’s, how could I have done that? I set myself up for failure. I’m a loser. Nobody wants to be with me, right?

Let that story that happens when the experience of rejection happens, the story kicks in the default narrative that says it’s your fault. Go back to what you need to believe to shoot your shot, to make the first move 100 % of the time, the right person will co-create. Yeah? It will be awkward. Try and get you closer. So this default story, we got to rewire it. So S, self-compassion. O, own your needs. F.

Feel your feelings.

This is really tough because I hear you, I hear you saying, Lily, but I do feel my feelings and I feel like shit. Why do I feel like shit if I was feeling my feelings? No, no, no. You’ve got to do it intentionally with the framework that I’m about to teach you. Are you ready? Are you ready? Feel your feelings means sit down or stand somewhere, close your eyes, put your hand on your chest or on your belly, somewhere compassionate. Breathe into your body.

Lily @ Date Brazen (15:34.551)

Notice where the feeling is in your body. If it’s a tightness in your chest or a lump in your throat or a pit in your stomach, name it. Name it. If you were to look at a feelings wheel with all the different feelings words on it, I want you to pick out which word or words feels resonant to you. You can imagine it if you’ve seen one before and you have that kind of brain that can picture it or you can Google it, keep it on your phone, keep it as a screenshot. There are so many different feelings wheels that can help you. Why is this helpful?

Dr. Lisa Feldman Barrett coined the term emotional granularity. And she found that when you have a precise emotion word to describe your experience, you are that much more likely to move through that experience with agency. Yeah. So it’s about

owning how you feel, naming how you feel instead of just being like, I feel like shit, let me run away. Or instead of being like, I feel like shit, I’m just gonna sit here and just, I feel terrible and it’s just a fact that I feel terrible. know where it is in your body. Take a deep breath, have agency, take responsibility for caring for yourself like you would a dear friend. Name it with emotional granularity. No, name it in your body. Notice as you breathe into it and name it.

Does it shift? Does it change? Does it intensify? Does it shrink? Does it have a texture? Does it have a color? Noticing it and breathing into it will allow your nervous system to calm down a little bit. You will have more access to your higher functioning after you take this beat. You’ll have more access to confidence, to joy, to agency after you take this path.

of S, self-compassion, O, own your needs, F, feel your feelings, like breathing into it for like three minutes is gonna help. Naming it, breathing into it, noticing the shape and color, noticing sometimes what I’m feeling, like specifically what I’m feeling, shame, which comes up a lot with making the first move 100 % of the time. Shame comes up and I don’t wanna feel it. I would rather run down a slide of razor blades and into a vat of rubbing alcohol.

Lily @ Date Brazen (17:47.573)

then feel my feelings sometimes. Truly. I’m not perfect at this. I’m sitting on the park bench with you, doing this with you. I just know after years of practice that doing this actually makes me feel better quicker, helps me bounce back quicker, helps me comfort myself better and more effectively. Like I wanted to be as a child. Yeah. So this is the reparenting work that you need. This is actually going to shorten the gap of time that you’re freaking out about rejection.

So when I feel shame, what do I do? I put my feet on the floor. I take a couple deep breaths. I think the thought, this will only take a few minutes. I only have to be here for a few minutes, even at home, like, God, I don’t want to do this. And then I say, okay, Lily, I’m here for you. I use one of my favorite Simone Sol quotes. She’s a coach that I admire. There’s nothing that you could say, do or feel that would make me want to stop being your friend. I’m willing to feel anything to be with you, Lily.

And then I say, okay, I’m feeling shame, I’m feeling shame. Okay, it’s on my chest. God, it feels like somebody’s marching around on my heart, like really stomping hard and like panicked a little bit trying to figure, God, okay. Then I noticed the shame. say, I’m feeling shame. This fucking sucks. God, I’m here for you. And literally three minutes of that, of breathing and noticing and having my own back allows me to then be more resource to do the final step, SOFT, thoughts, not facts.

your brain is making up a ton of fucking thoughts about you being rejected, they’re not true. Okay? The thought that you’re a loser or that it’s over or that you shouldn’t have done that or you were stupid for doing that, shooting your shot, making the first move. Those are thoughts, not facts. The problem is that most of y’all are trying to go to toxic positivity land after you make the first move and you’re like, it’s okay, it’s okay. I did it and it’s gonna be okay.

But if you’re freaking out about rejection and you haven’t gone through self-compassion, owning your needs, feeling your feelings, that trying to map a new thought into your brain of like, it’s okay and I’m great and it’s all gonna be okay. If you don’t believe that, if your nervous system is not cared for, that is toxic positivity. It is a cheap plastic bandaid that will fall off the minute you get in hot water. So what do you do to not do toxic positivity to actually work with your brain to rewire it to believe something.

Lily @ Date Brazen (20:09.839)

a more positive, a little more hopeful that it’s authentic. You gotta go through S, self-compassion. O, on your needs. F, feel your feelings. T, thoughts not facts. So this is when you just notice what thought your brain is making up about the rejection. If you experience rejection, let’s just choose one. I’m stupid for having done that. Nobody wants to be with me. Okay. After you go through self-compassion, of course you think that, of course you feel however you feel. That’s really hard.

on your needs. Take a breather. Take a break. Take a walk. Call a friend. Text a friend. F. Feel your feelings. Okay, I’m feeling shame. It feels hot. God, it feels like red and spiky. Okay, I’m willing to feel anything to with you. Thoughts not facts. I’m having this thought that I was stupid for trying and that nobody’s going to want to be with me. Thoughts not facts. It might be possible that, put a baby step reframe in there. It might be possible that I’m human and that feeling awkward is part of it.

It might be possible that that person just wasn’t right for me. It might be possible that I haven’t met everyone. It might be possible that I’m learning something new. It might be possible that that moment where I shot my shot, where I made the first move is actually really brave. That’s how you move through rejection more easily and how you open yourself up to being even more in your main character energy and how you open yourself up to attracting the kind of people that you want to be around.

is with that level of having your backness, okay? Let’s get into how, okay, a lot of people especially, I need to do a whole podcast episode about this, I am the whole divine feminine, divine masculine thing and the whole, men need to make the first move and women need to receive the first move or whatever that is, is not for me.

It is not something that resonates with me. In fact, I find that language and that framing to be pretty problematic. Now, if you resonate, take what you need, leave the rest from this podcast episode. I do not. I find that like you need to be in your divine feminine, which is, which means you receive all of the, all of the first moves. I find that to be a really reductionistic narrative. And I want more for you than just taking a backseat of your love story. I want you to be.

Lily @ Date Brazen (22:28.682)

to be driving your own car toward what you want and you see another car that is your future partner and they pull alongside you and they drive parallel to you. They are also driving their own car. They co-create the relationship by showing up for you. You first have to show up for yourself and what you want, okay? So this idea of like attract, don’t chase, manifest, that’s what I mean when I say the right person will co-create.

The mindset of making the first move 100 % of the time does not mean that somebody else won’t make the first move before you do. It doesn’t mean somebody else might notice you before you notice them. It doesn’t mean that you’re cutting off everybody who would make a first move around you. It just means that you are in the driver’s seat of attracting more. And making the first move is also a really flexible term. It doesn’t mean necessarily asking people out 100 % of the time, though it could.

It means approaching people. means saying hello. It means asking, are you single? It means asking, do you want a relationship once you’ve, you know, like gone on a date or like once you’ve been talking to somebody, it means showing up and expecting a volley, expecting a co-creation. And in that way, you are attracting the kind of people that want what you want. And you’re not that energy that I see with attract, people take the eye,

attract I don’t chase I think sometimes as I’m just going to sit down. And sometimes people need to rest. That’s totally fine. Like if this resonates, if this resonates, great. If it doesn’t, if you’re like, I’m just exhausted. I need a break, then go to the complete dating detox episode. It was episode like 130 something. And listen to that. I highly recommend a break if you need one. But here’s what I don’t want this energy of, you know, in Greece, when they are dancing.

and you see the row of people just sitting and looking and waiting for somebody to ask them out. I just want you to be on the dance floor. And I want you to make magic on the dance floor by inviting yourself to take up more space, inviting other people to come along with you. That’s why all of my programs are in groups. That’s why I really think that you need to build a community of people who have your back, who know what you’re going through and who are going through this dating process with you, alongside you, on the dance floor with you.

Lily @ Date Brazen (24:49.049)

This making the first move 100 % of the time is not saying you need to be the muscle or of all these connections. It just means that you’re on the dance floor friend. So here are the potential pieces of resistance that I hear in my brain that you might have. Number one, if I make the first move that I’m doing all the work, okay. Not true. Not true. You’re just showing up for the party. You’re showing up to the dance floor. You’re not sitting on the sidelines waiting for somebody else to make a bet. You are proactive.

you get to be proactive for what you want and the right people make themselves apparent. If I make the first move that I’m doing all the work is false. Yeah. It’s just showing up and expecting people to volley with you, to pick up the ball, to co-create with you. Number two, if I make the first move, it’s unattractive and I don’t want to look desperate.

The right people are also looking for you. The right people are going to be delighted that you showed up to the dance floor. The right people are going to be turned on by you making the first move. The right people are going to be so excited that you said hello. The right people are going to be so fucking into you. And you just need to get off on that vision a little bit more or a lot more. You spent so much time thinking about, guessing, what you don’t want next based on your past.

that I want you to get into, what are you a yes to? You’re a yes to somebody who wants you to show up. You’re a yes to somebody who wants a relationship. You’re a yes to somebody who is awkward with you. Third and final, I want them to make the first move to prove that they’re interested. This is a version of a game that you no longer need to play. Okay? I want them to make the first move to prove that they’re interested. If they’re interested, they’ll keep the conversation going.

or they’ll help you plan the date or they’ll ask you out on the date or they’ll pitch a date for the date or they’ll make the reservation. Right? I’ve talked about this a few times, but co-creation, it’s not muscling and it’s not taking your hands off the wheel. It’s co-creation, which means that you say hello. They say, hey, you say.

Lily @ Date Brazen (26:56.583)

I know this is kind of a weird question, but what’s bringing you joy lately or something like, I like that watch or my God, I love that book, whatever. They say, my God, yeah, I’ve been reading it for a while. It’s so interesting. What are you reading lately? And then you’re like, I’m reading the book, Thank You More, Please, by Lily Womble. And it’s like a feminist guide to date breaking down dating rules and finding love and it’s out now. And then they’re like, that’s so cool. Right. Co-created conversation. Let’s take it to an ask out. Hey, I’ve loved this is you.

Hey, I’ve loved talking on the app. I’d love to meet up IRL. What do you think? my God, I would love to meet up IRL. How’s next week? Amazing, next week’s great. How about this neighborhood? Great, how about this time? Great, how about this bar? Great, how about this? it sounds good. Maybe we could go this place after dinner for dinner. Amazing, I’ll make a reservation, amazing. Co-creation, period. In that way, the right person makes themselves a parent. You don’t have to play fucking games with the right person. You don’t have to…

default to like making them prove to you that they’re interested that fear of they’ve got to prove to me that they’re interested is coming from a place of I The last relationship was so shitty my last relationship didn’t he didn’t make she didn’t make any effort It didn’t work and I need the next one to be different So they need to prove from the moment we talk that they are different and that they are going to be interested and they’re going to be proactive That’s taking the stuff from your past relationship

and drag in that baggage into the future. Why don’t you start by practicing the thought, I’m learning the skill of self-trust, I’m learning how to discern who is right and wrong for me, and I am the kind of person who makes the first move 100 % of the time and expects the other person to also show up 100 % and co-create 100 % with me. There are so many first moves in the beginning of a relationship. There’s,

who asks somebody out. There’s who plans the first date, who plans the second date, who plans the third date. There’s who, you know, says, love you first. There’s who asks to move in together first. There are so many first moves and reducing who asks you out or who approaches who for the first time to it must be this or nothing. they must prove to me that they want to be with me with the first move or nothing. That’s so reductionistic. The right relationship will be long, friends, if we’re lucky, right?

Lily @ Date Brazen (29:18.697)

The right relationship will be long. I’m just saying that because life is short. We are on this planet for a finite amount of time. Why not fucking shoot your shot? Why not make the first move 100 % of the time? Just to get the ball rolling. Just to get the ball rolling. Okay? Now a couple of like things that people ask that I wanted to bring up. Societal norms that the guy should ask you out or he’s not that into you. No, no. If he wanted to, he would is one of my least favorite pieces of TikTok dating advice.

because it’s cute and fits in the little pocket, little pocket piece of advice, but it’s so reductionistic, it leaves no room for nuance. It leaves no room for the magic of co-creation. You need to make the first move when you feel confident, when you feel like ready and available to be awkward and do it imperfectly, and you can expect that the right person will co-create with you. Again, the right person may make the first move before you just because that’s how it happens. It doesn’t mean…

that this mindset of I make the first move, I am proactive, I am the main character isn’t going to mean that the right person also won’t make a first move, right? Again, there’s so many first moves in a relationship. And I don’t know about you, but I wanted to be with someone who didn’t care about those societal norms. So with Chris, my now husband, he texted me a few times.

We were like in a mutual friend circle. had done all this work for my own love life. I was doing these steps. I was claiming my essence-based preferences and I was healing after my last breakup. It was a really hard breakup, really hard relationship, really terrible. I was wrecked. And Chris, I met him through a friend that I made through my joy building strategy. I went to an improv class. made a friend. She introduced me to her friends who introduced me to her friends who then brought me to Chris’s birthday party in 2017.

Chris and I met and I was, you know, nearing the end of that relationship. I broke it off. Chris ended up texting me and like texting me back and forth and I set a boundary. I was like, hey, I know you’re really great. I know you have a crush on me because our mutual friends have told me and I’m just not, I don’t want to chat anymore because I know that you have a crush on me and I just need to heal. need some space. He was like, okay, cool. A couple of months later, he was on my mind all the time.

Lily @ Date Brazen (31:37.575)

And I had dated some. I was like fucking around more. was having more fun in my love life. I was feeling more confident. I knew my essence based preferences. I knew how I wanted to feel in the right relationship. And so then I was feeling more like drawn to Chris. And I was thinking about Chris all the time. This is kind of intimate. I, not sex intimate, like kind of a peek behind the curtain. Sometimes I have dreams that

my body. I know my body is just telling me like, this is what your intuition is saying. And I think that’s kind of normal. Pretty normal. But I had two nights of dreams of him being my partner and holding his hand and just literally partners partner dreams like holding his hand, taking a walk together and I’d wake up with the sun shining on my face. was like, Whoa, this feels different. This feels intense. Whoa. So after that second night of dreams, I texted him and I asked him out after I’d rejected him a few months earlier.

And he responded like, yes, let’s do it. And we’ve been together ever since. So I just know that the right person will be responsive to your move, whether it’s the first move or not. Like the right person will be responsive to you because the right person wants to be with you. also, so in that case with Chris, like he made the first move and then I said no, and then I made the first move. It was just kind of messy like that. And that’s how human relationships work. Okay, so here are a few ways to make the first move.

IRL or on a dating app asking what’s bringing you joy lately. That’s the best opener that there is. I’ve used it many times. My clients have used it many times. It leads to intentional conversations with people that want to be intentional asking that question, saying hello in IRL, especially just like, Hey, how’s it going? Or like, love what you’re wearing and love that shirt. Love that watch. Love that book. Make a genuine compliment. Kick off a conversation from there. You don’t have to keep all of the conversation going.

The right person will co-create, will volley. So release the perfectionism of like, I’ve got to say the right thing and just show up awkwardly, say hi, start making conversation and start practicing that now with just people around you, right? Like just saying hello, just like practicing the experience of shooting your shot, whether it’s romantic or not, will allow you to increase your resilience to making the first move IRL. That’s it.

Lily @ Date Brazen (34:00.635)

And so many of my clients end up making the first move on a dating app, making the first move IRL, making the first move, asking their friends for support. There are so many first moves that you get to claim and be in the driver’s seat for, and then the right people will co-create with you. Another one that I wanted to address, flirting with someone who’s already in a relationship unknowingly. Look to what you have to believe. It will be awkward. Yes, some people that you flirt with and say hello to and like make the first move with IRL, they might be in a relationship. And that’s okay.

You’ve done nothing wrong. This is a human, weird world and you get to shoot your shot. You get to make the first move and practice SOFT when and if, when because projection will happen when you start making the first move more. You know what also will happen more? You get more of what you want. You go on more joyful dates. You attract the kind of people that are turned on by who you are and what you stand for and how you show up in the world. If you’re introverted and you’re nervous to make the first move, that’s okay.

I want you to focus on baby steps, baby steps. So if any of these steps that I’ve outlined feel like, whoa, that’s too much, then why don’t you reverse engineer it into tiny, tiny baby steps, making eye contact with somebody. One of my clients called it a wink and run, like making eye contact and then running away, like tiny, tiny baby steps, just to prove to yourself that you are resilient.

that you are bold, that you are brave, that you can make the first move and being rejected isn’t going to kill you. Okay? And if you’re introverted and your social tank is lower, then just use your limited social tank on something that helps you make new connections and make it known to the people in your life what you want. That’s another version of a first move saying, hey, I’m looking for the right relationship and here are my essence based preferences. And you can create those by reading my book, Thank You More Please, A Feminist Guide to Breaking Dumb Dating Rules and Finding Love.

I take you through step by step. And if you want to work with me to create your plan, to create your essence-based preferences, to start shooting your shot, to know how to make the first move 100 % of the time with confidence and ease. And if you want to learn how to start attracting the right people with more ease and clarity and confidence, if you want to feel like you have your own back and you know how to feel your own feelings and move through any hard feelings with confidence, and if you want to like start creating…

Lily @ Date Brazen (36:22.365)

the most epic main character dating season of your love life, main character dating is opening very, very soon. So you can find out more about that with the link in the description of the episode. And you can also find the book link in the description of the episode. Book is more of a DIY vibe, still very good DIY vibe. Main character dating is I’ve got your back and coach you every step of the way every single day for a year.

to make sure that you step into the most epic season of your love life with accountability and support and coaching and community. So time to make the first move 100 % of the time. I want you after listening to this episode, either re-listen to it to hear the steps, or you took notes and can read these notes. How can you make a first move this week? Where can you make a first move this week? Where do you want to make moves? And how can you set yourself up to make the first move powerfully, awkwardly, imperfectly?

Trying this, doing this imperfectly means you are that much closer to meeting your person. And the right person is going to co-create the fuck out of this relationship with you. You’ve got this and I’ve got your back. And I can’t wait to talk to you next week. Bye. Thanks for listening to the Date Brazen podcast. If you liked this episode, then you’re going to freaking love my book. Thank you more, please. It’s my proven step-by-step feminist guide to breaking dumb dating rules and finding love.

You can buy it anywhere books are sold and then get a juicy bonus at datefrazen.com slash book. The bonus is the dating life fix. My top 10 podcast episodes to get unstuck right now. Be sure to subscribe so you never miss an episode. You’ve got this and I’ve got your back.