In this week’s Date Brazen Podcast episode, Flirting 101: My 3-Step Process to Flirt, Know If Someone’s Into You, and Ask Them Out with Ease, I’m breaking down my 3 step process to exactly how to flirt, know if someone’s into you, and ask them out with ease.

 

Here’s the deal:

Flirting is a learnable skill.

Awkwardness? It’s just a sign you’re human (not a dealbreaker).

With 10 seconds of courage, you can change the course of your dating life.

 

In this episode, we’ll dive into:

✔ What IS flirting? Like, what actually is it and how can you do it YOUR way.

✔ How to become rejection-proof.

✔ A simple 3-step approach to make flirting feel natural.

✔ SOFT practice for tough times

 

If you’re ready to stop overthinking and start shooting your shot, this episode will be your new dating secret weapon. Let’s do this!

This episode is brought to you by my free, live SHOOT YOUR SHOT CHALLENGE: From “late bloomer” to confident dater in 5 days ✨

Links:

✨  SHOOT YOUR SHOT CHALLENGE: From “late bloomer” to confident dater in 5 days ✨

Get Lily’s Book, Thank You More Please HERE.

 

Follow Lily on Instagram and Tiktok.

 

Subscribe to Lily’s Youtube channel HERE.

Show transcript:

0:00  

Hey, gorgeous friends, welcome to another episode of the date brazen Podcast. I’m so glad that you are here. We are talking about flirting. 101, okay, because flirting, or shooting your shot IRL, or just like making eye contact and making conversation, feels so elusive to most people, I think for a lot of reasons, we’re out of practice of in person connection. It feels really scary, because the potential for rejection feels high. And I know that flirting for a lot of you seems like something that you’re like friend is great at, but you’re just terrible at. And I want to let you know that flirting is a learnable skill, and this isn’t like flirting is a learnable skill, and here’s how to play the game. I’m going to show you how to make it so freaking simple that you can start flirting IRL and even ask someone out, starting this week. So in this episode, you’re not only going to learn how to flirt, you’re going to learn how to tell if somebody’s into you and what to do next if they are so buckle up. It’s gonna be a good one. Let’s get into this episode.

1:09  

Hey, I’m Lily Womble, 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. I created this flirting 101 class for my clients inside of my program, main character dating, and it’s really good, so I wanted to share it with you. Inside of main character dating, I have a flirting flow chart that I’m gonna outline for you here, and I’m so excited to dive in. So what is flirting? Flirting, Put very simply, is joyful courageous connection. Literally, just three words, joyful courageous connection. It’s not necessarily batting your eyes and laughing a certain amount of times. It’s not having the right line to hook them in early flirting. At its core is just joyful courageous connection. You can flirt with anybody, whether romantic or platonic or just, you know, in your day to day adventures, you can just flirt with people. Flirting is only joyful, courageous connection. Here’s the deal, it’s going to be awkward. It’s going to be awkward. So just, why don’t you accept that and keep it pushing so many of you are avoiding trying to flirt because you’re afraid you’re going to feel awkward or be awkward, and then you’re afraid of what stories your brain is going to tell yourself about yourself as a result of that. So for example, if you flirt and it feels really awkward and you get rejected, your brain might make up a story that says, See, I told you you were too awkward. You always have been so awkward, and it pushes people away, and there’s no way you’re gonna find the right partner, because you’re so dang awkward. I have news for you. You know who is human on this earth? Everyone? You know what humans are? Awkward, weird. There’s no playbook for social interaction in which you will avoid feeling awkward all of the time. It just comes with humanity. It’s a part of the human condition. So instead of fighting it, instead of trying not to be so awkward, why don’t you just give yourself permission to be freaking awkward. The right person is going to be so glad that you started a conversation with them. The right person is also looking for a relationship with someone exactly like you. You are uniquely qualified for the right relationship, even if you feel awkward, especially if you feel awkward, awkward, just awkward just means that you know you have an expectation of how a social interaction is going to go, and it feels uncomfortable when it happens and doesn’t go so smoothly. So so the right person will be able to have a conversation with you, even if you feel awkward, or even if something awkward comes up again. I’m going to repeat myself from a couple weeks ago. You cannot say the wrong thing to the right person. If you’re willing to feel awkward, you are unstoppable. I’m going to repeat that. If you’re willing to feel awkward, you are unstoppable in your dating life and everywhere. So the point of flirting, 101, this lesson that I’m teaching you, is that you’ve got to practice, you’ve got to be willing to feel awkward, and you’re going to find your version of flirting along the way, your version of flirting and my version of flirting might be different. That’s okay. It’s all at the end of the day, just joyful, courageous connection. And again, the only rule is that you cannot say the wrong thing to the right person. Okay, here’s the How to Okay. Are you ready? You’re gonna take notes. Buckle in, open your notes out. Get ready. Number one, you’re gonna see some. Somebody that you want to start a conversation with. It’s going to start as a little bit of small talk, and this is IRL flirting. So for example, you’re at a bar, or you’re at a restaurant where people are milling about, or you are at a festival, or you’re at a pottery class, or you’re at a comic book store or a Comic Con, wherever it is, you’re going to see someone that you want to strike up a conversation with, and you’re going to go up to them and give them a genuine like question or little bit of a compliment. Hey, I love that book you’re reading. Why’d you pick it up? Or what do you think about it? Start with small talk and a smile. Super simple, small talk and a smile. You can’t say the wrong thing to the right person. Ask a genuine question or give a genuine compliment. Like, oh my god, I love that book. I love that shirt. How are you doing tonight? Like, just literally open up the door for the conversation, and, if possible, ask a question about something you notice that you’re genuinely curious about. So here’s how to know if someone is game to have an interaction. It’s very simple. If they give you a one word answer, a polite smile, or they don’t smile at all, and they physically like turn away from you. Their body language turns away from you, they’re not interested in having a conversation. You can just move on with your life. It might feel awkward for a moment, it might sting, and it’s okay. You shot your shot. It didn’t work out. Let’s keep it pushing right. You did nothing wrong in this scenario. You asked a question, you tried to connect. They weren’t interested moving on. If they respond with a yes and approach, yes and meaning they respond to your question, and they maybe turn physically a little bit toward you. They don’t turn away from you. Maybe they turn a little bit physically toward you, and maybe they follow up with their own question or their own like, yeah, this book is really great. I love this author. Are you reading Have you read it before? Whatever? Then they’ve opened up the door to conversation, and your job is to pick up that ball and toss it on back. This becomes a sort of game of volleyball, in a way of for flirting to happen with another person, there has to be an equal co creation, an exchange. And you could just, like, start having a conversation with this new person about the book or about the movie or about the you know, whatever it is, the drink, the cocktail that you’re having. Start that conversation. It’s a yes and conversation at that point. So that’s step one. Just open up the conversation. See if they respond with a yes, and if so, keep going, if they respond with a no body language wise and only a one word answer, then keep a push and move on with your life. I was taught so many dumb dating rules growing up that I needed to be less picky, that I needed to be less intense, less sensitive, that I needed to stop being too much in order to find somebody. I was also taught that a single woman is behind a coupled woman in life. I was taught that in order to find a relationship, I needed to shrink in order to belong and be attractive and as an adult, that led to me settling in tons of situationships. It led to me shaming myself for feeling behind my coupled peers, and then once I became a top matchmaker and learned these matchmaking tools, once I it did this work myself and uncovering my preferences and relearning what it meant to take up space in my life and my love life, specifically, I attracted not only the best relationship of my life, but I felt more joyful in the process. And every step that I used to find the love of my life is now written in my book. Thank you more, please. And it not only worked for me, this book and this material has helped 1000s of single, badass humans around the world to create joyful as hell, dating lives that lead to the right relationships, dating lives that feel like an act of self care, and if this sounds like you that you need to get your hands on my book. Thank you more please, which you can find wherever books are sold, and you can go to date brazen.com/book

9:09  

to get an extra special bonus. The bonus is the dating life fix my top podcast episodes to get you unstuck right now and again. You can get that bonus and my book at date, brazen.com/book or get the book wherever books are sold and grab that bonus at date, brazen.com/book you’ve got this and I’ve got your back. Now let’s get back to the episode. Step two. Look for the fun, connect and talk. That’s all you got to do with step two. You just keep the conversation going. It doesn’t have to be for very long if during this step, you realize that they’re in a relationship, they mention a partner, or they you see a wedding ring, or whatever you can just like, keep chatting. You’re connecting with another human being. And it’s not expected that this is a romantic type of flirting. You’re just literally connecting with another human being. Remember, flirting is just joyful, courageous. Connection, and you can either, like, move on with your life. If you realize they’re in a relationship and you’re flirting with the intent of potentially some romantic curiosity, just keep it pushing, keep it moving. Or you can just connect with this person and move on when it feels right from the conversation. If the conversation continues to feel fun and flirty and you have no indication that they’re in a relationship. They haven’t said anything. You don’t see a wedding ring, and if their body language is pretty consistently pointed toward you, and it feels like physically safe to do this next step, remember, check in with your body. If you’re in an environment where you’re feeling like, I can do this. I can ask a qualifying, disqualifying question that I’m going to reveal in a moment. Then may moment. Then make a courageous next step in the form of step three. After five to 10 to 20 plus minutes, you’re going to ask, Hey, so are you single? Literally, that’s all it takes. You’re connecting. You’re getting that yes, and you’re getting that affirmation with the body language. You’re getting that back and forth. It may feel awkward, but that’s okay. The right person is gonna be so glad that you struck up a conversation after five to 10 to 20 minutes of consistently yes and conversation, you can ask, Hey, so are you single? You can ask even this way. I know this is really random, but are you single? Literally, that’s all you have to do to get clarity. This question is fun, flirty, low stakes. The problem is that a lot of y’all are thinking that this is going to be a high stakes conversation, and that if you receive an answer that you don’t want, or you get rejected, or whatever, that it’s going to be the end of the world when you have the skills that I teach you in this podcast, self compassion, right? Self Compassion is proven to reduce cortisol and increase resilience, two things that you need to move on after after being rejected, it happens because you’re shooting your shot, more your odds of finding the right person increase, as do your odds of experiencing rejection. That’s just playing on a bigger stage. You with the skill of self compassion, of turning toward yourself with kindness, of feeling those feelings and and being willing to like process any feelings that come up along the way, you’re basically building a bigger, better surfboard to ride bigger and bigger waves. Bigger waves mean more epic views. It also means sometimes you’re gonna wipe out. That’s okay, because with these skills, your your surfboard has got you, and when you wipe out, you’ll have the skills to pick yourself up, back up, and get back up on the surfboard as soon as you can after taking a beat. So I want you to know that you’re good no matter what that like you shooting your shot, and whatever happens as a result of you shooting your shot doesn’t really have to do with you. It’s just that you’re for the few, not for the many. You’re engaging in something really vulnerable and courageous, which is increasing your odds of getting what you want, and sometimes you’re gonna wipe out. That’s okay. So I want you to dispel this myth that like, if I ask them, Are they single? And they answer, no, I’m not single. I’m gonna be so embarrassed, and I’m gonna not be I’m gonna have to leave the restaurant or the bar or whatever. Okay, leave. No big deal. A lot of you are letting that get you out of the pursuit of what you want because of self judgment and maybe some shame and fear, and with self compassion and with the permission to be awkward, the permission to connect, the permission to be human, you’re unstoppable. So if they say, No, I’m actually not single, you can be like, Oh, okay, well, have a good night. Here’s the most awkward way I can think of that. Going okay, so you’re you’re flirting. It’s going well, 510, 1520, minutes past, you’re flirting, yes, and balls going up in the air. You’re both tossing it back and forth to each other. Hey. So random question, are you single? This is the most awkward way

13:52  

it could go. No, I’m actually not single.

13:58  

And then you, you’re like, oh,

13:59  

okay, um, okay, okay. And

14:05  

then you run away. That’s literally like it that’s the most awkward way it can go. And that is not gonna like mean anything about you, just means you had an awkward interaction. Ooh, you know, not a big deal. If you’re willing to feel awkward, you become unstoppable. And if they say, No, I’m not single, you can just like, bounce. You can leave. You can you can, like, turn to your friend afterward and be like, I just want to celebrate that I shot my shot. It didn’t go the way I wanted. And I want to celebrate that I shot my shot that is amazing, and it’s a thank you more. Please to your brain. You can do courageous things and celebrate yourself for it, that you are alive, you are vibrant and vital, and that you’re powerful, that you can do this. If they say, Yeah, I’m single, but I’m really not looking to date right now you can, you know, just say, okay, cool. Just like wanted to, wanted to check in, and then you can either leave. Or keep the conversation going, or go to the bathroom. I love a bathroom boundary for this reason, right? Anytime you’re feeling like overwhelmed or over simulated or embarrassed or whatever, just go to the bathroom and have a bathroom break. Take a deep breath in the bathroom, put a hand to your chest, somewhere compassionate and and then keep it pushing. Now, this step three of asking, so are you single it could lead to this outcome? Yeah, I am. Ooh, if you’re watching this on YouTube, you’re seeing my big facial reactions to this. Maybe some freaking out what happened, maybe some overwhelm, maybe some like excitement, maybe some PT pussy tingle, and they say, Yeah, I’m single. You can follow up with amazing, do you want to grab coffee sometime? I’m single too. I’d love to grab coffee or something like that. Like or you can just say, Yeah, I’m single too. We’d love to get together sometime. Can I get your number? Shoot your shot. It does not matter who starts the conversation first. They could very well ask you if you’re single before you get to it. They could very well ask you out before you ask them out. I’m just talking about here’s how to do it. If you want to do it, if you want to shoot your shot, if you want to flirt, IRL, if you want to ask somebody out. This is step by step, how you do it. It does not matter who shoots their shot first. It does not matter who asks who out first. It matters that the date and the conversation and the relationship is CO created. For example, if you say, hey, so random question, are you single? And they say, Yeah, I am single. And then you say, okay, cool, me too. Can I get your number? Would love to get coffee sometime? They give you, you know, their number, so you’re more in the driver’s seat of that texting interaction. You can always offer your number, but I know a lot of people like to receive it and then decide what they’re gonna do. And then they will say, How about like, we go out to coffee. I love this coffee shop down the road. And then you’re like, Oh, that’d be really cool. How’s next week? And then they say, next week’s not good. I have some work stuff, but the next week is good. How about this date? And then you’re like, amazing, that date works. And then they’re like, Okay, amazing. I’ll meet you there. Bye, that’s a co created date. In that way. You know that there’s equal buy in, there’s equal amounts of emotional labor. If you’re talking about a dinner date, you know? How about this neighborhood? Amazing. I know this restaurant amazing. I’ll make a reservation. I’m amazing, right? This like both yes anding of equal buy in. So it doesn’t really matter who goes first. It matters that it’s co created. And this is possible. This happens every single day with my clients inside of main character dating, they shoot their shot with such confidence and knowing that it will feel awkward along the way, because they just have this step by step process. And they practice now, if you ask, Are you single? And they say, Yeah. And you say, Do you want to go out sometime? And they say, Oh no, I’m not really looking to date. After you shoot your shot, It’ll sting, and it’s okay. Go to the bathroom, like keep it pushing, leave the bar, just know that you’re increasing your odds of getting what you want by showing up this courageously and being willing to do it awkward, do it scared, being willing to ride with yourself afterward no matter what happens, 10 seconds of courage is all that it takes to approach somebody and say hello and ask a question. 10 seconds of courage is all that it takes, really, for anything. If you’re talking about shooting your shot professionally, or you’re talking about shooting your shot with a friend, a new friend, shooting your shot romantically, 10 seconds of courage is really all it takes to get the ball rolling. So really, it’s just three steps to flirt. You open the conversation with a hello and a genuine question or compliment. Wherever you are, you have a conversation, and if it’s continuing, body language is good, it’s fun. And you ask, Hey, so are you single? That’s the second step. And then the third step, however they respond, is what you do next, right? If they say no, you go on with your life. If they say, Yes, I’m single and I’d like to go out, then you make a date plan. You co create it with them. That’s the three steps to flirting IRL and shooting your shot. So your homework after listening to this episode is to listen to it again. Take more notes. Take keep track of any like resistance thoughts that you have. I can’t do that because that’s not possible for me, because and just have compassion for that voice, for that version of yourself who is really nervous, because this is really fucking vulnerable episode 221, of the date brace. Podcast has my practice called S, O, F, T, self compassion, owning your needs, feeling your feelings and thoughts, not facts. This is what I recommend, running any of those like sticky thoughts through running them through that framework so that you can have compassion for yourself, know where that fear is coming from, and ultimately come up with a baby step. Reframe like it might be possible that I can try new things, and then suddenly you have more resilience. You have more more tools. You’re building new neural pathways that support your desire for the right relationship and a courageous love life. So listening to episode 221 will really help so that you can process any of that, like resistance or stickiness as it relates to shooting your shot and flirting. IRL, this week, I want you to flirt with someone, whether that’s a friend or a barista or someone that you have a crush on. I want you to flirt, and if you’re willing to take me up on the challenge, I want you to do all three steps, starting the conversation, keeping it going, if it’s like a good vibe. Body Body language is pointed towards you. Conversations like a good back and forth, yes, and we need to ask if they’re single. And then whatever happens, you move to step three, either keeping it pushing or continuing to co create a date. You never know what this is going to lead to. It’ll lead to, not only, deeper self trust, because you’re no you’re knowing like I have my back. No matter what, it’ll also lead to more experience flirting under your belt, so you’re just less and less afraid. It’s like immersion therapy, and again, it’s increasing the likelihood of you getting what you want. My clients meet amazing people to date and be in relationships with. Ultimately, IRL. IRL dating is not dead. It’s just a lost art that you need to start practicing with this flirting lesson. And anytime you’re nervous about flirting, just come back and listen to this quick episode to pump yourself up. This is figure audible. I’ve got your back and you fucking got this. I cannot wait to hear flirting updates. DM me on Instagram at date brazen. With any flirting updates that you have, I cannot wait to hear them, and I will see 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 date brazen.com/book The bonus is the dating life fix my top 10 podcast episodes to get unstuffed right now and be sure to subscribe so you never miss an episode. You’ve got this and I’ve got your back. You.