If flirting feels awkward, forced, or like a foreign language—especially because you feel “behind” in dating—this episode is your new playbook.

Lily breaks down her step-by-step approach to flirting IRL with courage and ease. You’ll learn how to strike up a conversation, gauge interest, and shoot your shot—without spiraling or second-guessing yourself.

Want the visual breakdown?

Watch it on YouTube: https://www.youtube.com/@datebrazen

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✨ 3 Steps to Attract the Right Partner as a Late Bloomer ✨

You’ll learn how to:

✔️ Release shame about being a late bloomer

✔️ Build rock-solid confidence in what you want

✔️ Start dating successfully this summer

RSVP here: https://datebrazen.com/lets-go

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Show transcript:

Lily @ Date Brazen (00:00.355)

Hey gorgeous friends, welcome to another episode of the Date Brazen podcast. I’m so glad that you’re here today. I am giving you the Late Bloomers guide to flirting. How to flirt. I’m going to make it so simple for you. And if you haven’t joined me on YouTube yet, go over to YouTube at Date Brazen because I am going to give you a visual breakdown step by step by step of how I teach my clients who are late bloomers how to flirt seamlessly. So

If you like the audio only version, stay here. If you want a visual guide to flirting 101, how to flirt, especially if you feel like a late bloomer, especially if you feel awkward or behind, then you’re going to want to get over to YouTube and just subscribe because I’ve got some great stuff going over there as well. So y’all, this is the late bloomer series. This is episode three of our late bloomer series where I’m going to teach you how to flirt. Here’s the deal.

There’s no magic pill you can take to avoid awkward interactions in this life. Awkwardness is the price of admission for connection. I’m going to say that again because I want you to really let that seep in. Awkwardness is the price of admission for connection. There are people in your life probably who you feel maybe a little envious of. they have such seamless social interactions. They don’t seem to be as awkward. They don’t seem to have as many stumbling blocks in their

language or they know what to say and I just don’t know what to say. Sure, there are people in your life who may be more extroverted, may be more seamless communicators, maybe that’s their gift that they’ve just had since they were a child. Both and that’s not most people. Most people feel super awkward when they flirt, feel super awkward and nervous when they meet somebody new, whether or not it’s a romantic connection.

And I wanted to say this because so many late bloomers that I speak to, and I’m thinking of myself 10 years ago as well, were so petrified of being awkward because of the risk of rejection. Right? So it feels safer not to try because the risk of rejection feels so dang high. And then your brain makes the rejection or the potential rejection mean that it’s really never going to happen because you’re going to be rejected by everybody. Right?

Lily @ Date Brazen (02:20.866)

This dress rehearsing tragedy that I see late bloomers doing and again, I did it 10 years ago again and again, the dress rehearsing tragedy or future casting the worst case scenario of being rejected at every turn. It is a normal survival mechanism in your brain. So be really kind to that version of yourself. Acknowledge that you just want to be safe, totally normal. Then offer a kind reframe. Like it might be safe to…

try something new. You’re increasing the chances of connection. You’re also increasing the chances of rejection. So I want you to really acknowledge that rejection resilience is a skill that you can build because if you have self-compassion, like we talk about almost every week on this podcast, if you have the skills of emotional granularity where you can name what’s happening in your body and you can breathe into it and like be with yourself through it,

then you’re unstoppable. If you’re willing to feel those uncomfortable feelings, if you’re willing to see your thoughts as thoughts, not facts, when you face something so tender as flirting and connection or flirting and rejection, if you’re willing to feel anything, then you are unstoppable in your dating life. So I’m here to tell you as a late bloomer, it’s not too late to learn this, even if you’re 25, 35, 45, 55, 65, it’s not too late and you’re here to learn a new skill. So.

Let’s get into how to flirt, especially if you feel like a late bloomer.

Lily @ Date Brazen (03:59.214)

Hey, I’m Lily Wangle, 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.

I gotta tell you that this episode is brought to you by my live training coming up on June 17th called Three Steps to Attract the Right Partner as a Late Bloomer. In this training, you are gonna learn how to release your shame about being a late bloomer. You’re gonna learn how to build confidence in what you want. And I’m gonna help you build a step-by-step plan to help you start dating successfully this summer. You’re not gonna wanna miss this training. It’s totally free and it’s live with me.

So you can go to datebrazen.com slash let’s dash go. Again, that’s datebrazen.com slash let’s dash go to sign up. Because you want something, right? The right relationship. You wanna feel confident in yourself finally. You wanna feel like that late bloomer, heavy weighted vest is finally off your body so you can start flirting and start shooting your shot and start going on joyful dates. You wanna become a magnet for the right kind of people for you.

You want something? It’s not here yet. So let’s fucking go. That’s what you’re gonna learn in this training. How to go from feeling like a late bloomer to a completely confident dater who has a successful magnetic dating life. So again, go to datebrazen.com slash let’s dash go to sign up. At that free training, you’re not only gonna get my entire playbook for how I and hundreds of my clients went from feeling like late bloomers to magnetic confident daters.

You’re also going to get a special invitation to join me in my signature program, Main Character Dating, which opens on June 17th, 2025. So you’re not gonna wanna miss it. There is an extra special bonus that I am revealing at that live training. And so get yourself signed up. Like come learn a new skill with me. Come learn how to release your shame, build rock solid confidence in who you are and what you want and build a step-by-step process to date with joy.

Lily @ Date Brazen (06:21.012)

successfully. Now let’s get back into the episode. Alright this is going to be quick and dirty. I’m going to give you a visual breakdown if you’re watching on YouTube exactly how to flirt. How to flirt, how to know if somebody’s into you, how to shoot your shot, IRL. This will also apply to texting or messaging but I’m really talking about IRL flirting because it’s about to be sexy summer. It’s about to be your sexiest dating summer yet and I want you to have the skills to

Go out of your house, get off your couch joyfully, make new connections, flirt your face off, have fun doing it, and attract amazing juicy dates as a result. This is the process that I have guided my clients through again and again and again, and it freaking works. Even if you’ve never flirted, even if you’ve never approached somebody, even if you have social anxiety, I’m gonna break it down so simply. So let’s get into that visual, shall we?

And if you’re not yet on YouTube watching, go over to YouTube, at date brazen, to watch this visual breakdown. And if you like the audio version better, obviously you’ve got that too. Okay, so now we’re into the visual step-by-step of how to flirt, especially if you feel like a late bloomer. And again, go to at date brazen on YouTube, if you’re not watching already, to see this visual breakdown. I think it can be really helpful, especially if you feel anxious about this topic, just to see it broken down visually really simply.

Let’s get into it. So first and foremost, what is flirting? Flirting is joyful, courageous connection. That’s all flirting really is. So if you’re overthinking it, just know that flirting is joyful, courageous connection with a splash of like, are we attracted to each other thrown in? Right? You’re looking for that curiosity. If you’re like curious about someone, if you’re curious about like, they’re kind of cute or like, they’re really interesting.

then you go over to them and you start having a joyful, courageous connection. That’s literally all it is. Human beings were meant to connect. And I think flirting has been sort of overblown as this like, what is the secret language of flirting? I think it’s just like taking a deep breath, being present with yourself and then joyful, courageous connection. It will be awkward as I say again and again and again, it will be awkward. And if you’re willing to feel awkward,

Lily @ Date Brazen (08:43.06)

you are unstoppable in your dating life. You can flirt with anyone. You get to practice. It is a buildable skill set that you need to practice, and you will find your version of flirting. That’s why I don’t like prescriptive dating advice that tells people exactly how to flirt in the way that the person teaching it flirts, right? Because everybody is different. The relationship that you are going to be in is very different than anybody else’s relationship that you know.

It’s going to be uniquely qualified for you. And so if you’re flirting for romantic connection possibility, then you’re going to figure out your way of flirting as you practice. And this step-by-step system is going to be a framework to jump off of. The only rule, the literal only rule is that you cannot say the wrong thing to the right person. Step one, you start with small talk and a smile.

ask a question or make a complimentary comment. If they say a one word answer and their body language points away from you without eye contact, they probably aren’t interested, move on. Okay? So this could be at a comic book store. You see a cutie, you obviously share an interest, you go over to them, hey, like how you doing today? Like, my God, that’s my favorite comic. And then if they pick up the ball, right, it’s a co-created thing.

So if they pick up the conversation and keep it going with you, then they’re interested, keep talking. Whether or not romantically, they’re interested in connecting with you. If you’re at a coffee shop and they’re reading a book, my God, I love that book. Or, like that book looks so interesting, right? You can just make a comment and keep it moving, right? If you want to comment on like a shirt that they’re wearing or a watch that they’re wearing or whatever, that can be a good into. All you need is…

one complimentary statement or one piece of small talk to get in a conversation, see if they co-create with you, and if not, move on. If they respond with a yes and approach. So for example, they say like, yeah, that makes sense. They follow up, they ask another question, eye contact is consistently looking at you, they point their body toward you, right? They move from looking at the stacks of books or comic books to literally moving toward you.

Lily @ Date Brazen (11:06.978)

physically, like not in terms of a lunge, but they like physically turn and look at you, then they want to keep talking. You can trust that you’re not doing anything wrong by engaging another human being in conversation, even if it feels a little awkward. So keep going in that case, like keep going. Step two, look for the fun, connect, smile, talk. Look for the fun, connect, smile, talk.

you might need to practice keeping a conversation going if you’re interested in somebody. A lot of my clients in this process have asked, well, what if the conversation feels like it’s coming to a lull? And like, if you both are looking at each other sort of expectantly, and you want to keep the convo going, then you could do any number of things that I’m going to get into in this visual breakdown. But keep looking for the fun, keep asking questions, make sure they’re like, you know,

holding an equal weight in the conversation, make sure you’re not doing all of the emotional labor or all of the asking and peppering them with questions. Take a deep breath, be in your body, know that it might feel awkward and that’s okay because awkward is the price of admission for connection. If they make it clear, this is step three, if they make it clear that they are in a relationship that is monogamous, if you see a wedding ring on or if you are not interested romantically, just

keep things fun and flirty and casual in so far as you’re comfortable, then part ways. If you find out that they’re married and you’re just like, I don’t really want to talk to you anymore, I’m a little uncomfortable, then just dip. You can always leave. This is another skill that you need to build of self-advocacy, of leaving when you want to leave. So many people who were socialized as women really fear disappointing somebody, even if they’re a stranger. I know I have, and I still work on this to this day.

So just acknowledge that you are a human being who gets to take up space in this world. And if you want to leave a conversation, you need to practice leaving it, period. If you are on a date and you want to practice, if you don’t want to be on that date anymore, you need to practice leaving that date. You need to practice feeling uncomfortable in order to do what you want to do, in order to be the main character and self-advocate. This is a very important skill for not only you in your life,

Lily @ Date Brazen (13:26.616)

but for building the right partnership. So the other part of step three is if the conversation continues and feels fun and the body language is pretty consistently pointed toward each other, then you can ask a qualifying, disqualifying question like, what’s bringing you joy lately? Or like, who in your family makes you laugh the hardest? like, I have another one coming up that you’re gonna see. Now, caveat, you must feel physically safe to do this. I would recommend being in public. I would recommend…

and tuning in with your body, making sure you feel physically safe, especially for those who hold marginalized identities, especially those who are queer or trans, who unfortunately, because of our homophobic transphobic world may not feel physically safe to do this IRL. There are other ways to flirt that have more built-in barriers like using online dating. So make sure whoever you are,

that you feel physically safe when you’re doing this. And if you don’t leave immediately, okay, after five, 10, maybe even 30 minutes, because you might meet a stranger and connect and start talking and be like, my God, we’ve been talking for so long. Five, 10, 30 minutes, you say, you must say, this is the like leveling up of flirting, right? So random question, are you single? This is what distinguishes you from somebody who just has fun conversations.

to someone who is flirting in order to connect with a potential date period. Yeah. So this is how you build an IRL dating life. Really. It’s how you practice the skill of IRL dating so that you cannot rely so heavily on dating apps to set you up. So, so random question, are you single? This is a fun, flirty, low stakes question for the right person. They’re going to be like, I, I, you know, right. I’m going to get into what they’re going to say next and how you respond, but like,

The right person is looking for you too. So you asking this question will be a relief to them. Also, this question is going to help you weed out the people who are unavailable. So random question, are you single? Fun, flirty, low stakes. If no, I’m not single. You just say, I it. Just wanted to ask, have a great day. Then you can bounce, right? One of my clients, when she was practicing flirting called her practice, winking runs. She would literally wink at a cutie and then run away.

Lily @ Date Brazen (15:49.388)

fine. It is about building up the tolerance to be courageous. It’s about doing that 10 seconds of courage so that you start getting more of what you want in your dating life and you start becoming unstoppable. If they say, yeah, but I’m not looking to date, that’s okay. This is practice. If you internalize that as a rejection, then you have the skills by listening to this podcast or by reading Thank You More, Please, the skills of self-compassion, the skills of

like emotional granularity of noticing, God, I feel icky in my body. Like it’s in my chest or it’s in my stomach. I can breathe into it. I’m willing to feel anything to be with you. A thought that I love by coach Simone soul. If you’re willing to feel anything to be with yourself, then you’re fucking unstoppable. So even if a rejection comes, then you can move through it because you’re not going to make it mean everything. Now, if they say, yeah, I’m single, you can say,

Yeah, me too. Want to grab a coffee or go to the comic book store, et cetera, some type, like insert thing you like to do here. I’m using the comic book store because I just think it’s such a fun way to meet somebody. And I’ve had a couple of clients who are passionate about, you know, comics come to me or Comic-Con even also a great place to meet people. If you’re into Comic-Con, it just is a fun example. So insert anything that you like to do here. You need to shoot your shot at that point, right? You’ve already asked. So are you single or random question?

Then they answer if they answer. Yeah. And they kind of like a anticipatory smile. You can say, I am too. Do you want to grab coffee sometime? And then it’s up to the both of you to co-create. This is not up to you to do all the work. This is up to you to pitch it, see if they pick up the ball and go from there. So co-creation would sound like, yeah, I’d love to go to coffee.

Do you want my number? Do you want me to take your number? And you say, yeah, here’s my number or yeah, I’ll take your number, whichever is fine. And then you start texting and a co-created date would sound like, Hey, love meeting you so random. Do you want to grab coffee next week? And then you would say, yeah, would love to. How about this neighborhood? And they’d say, yeah, would love to have at this place. Right. That’s a co-created date.

Lily @ Date Brazen (18:05.23)

versus a muscling date, which we don’t want, is you doing all the planning, all the work, all the reserving, all of the following up. No, no, no, no, no. The right person will also want to be with you and will want to go on a date with you. So if they say, yeah, me too, want to grab coffee, go to the comic book store, et cetera, sometime. If they say, ah, no thanks, it’ll sting. It’ll sting for a second. Ouch. And it’s practice. If they say yes, co-create a date plan, like we were just talking about.

Or just say, here’s my number, like let’s make it happen. 10 seconds of courage is all that it takes, gorgeous friend. So I want you to go and role play this with a friend. Like send them this episode, say, hey, can we role play this scenario where I meet somebody IRL? Or this can even help your friend set you up better because maybe they’re nervous to shoot your shot for you at a scenario where you’re talking to somebody and they’re like, you know, looking for you. They’re a co-conspirator.

This will be helpful for both of you, whether they’re single or coupled. So practice flirting, practice asking if single, if yes, if no, practice those scenarios, practice asking somebody out just to build the fluency of your flirting practice. And your homework after this episode is to do SOFT for a week. That’s a practice that I taught in a previous episode. It is the practice of a 20 minute journaling exercise, self-compassion around the concept of flirting. Like if you’re freaking out specifically,

self-compassion, owning your needs, listing them out on a sheet of paper, feeling your feelings, breathing into your body, where am I feeling intensely about flirting or the practice of flirting or the possibility? And then T, thoughts, not facts. What thoughts am I having about flirting that are thoughts, not facts? And what is a baby step reframe that is a little more expansive, that is useful and true that I can practice this week? It might be true that I’m just learning something new. It might be true that…

I’ve got this. It might be true that I’m safe to try. It might be true that being awkward is not a deal breaker for the right person. It might be true that the right person for me is also awkward and we’re going to connect over that, right? Do that journaling practice for a week just to build the mindset work and the resilience to try because without mindset work, tactical action is going to fall flat and you’re actually going to keep being in a cycle of inaction or avoidance. So I really want you to address this head on and like…

Lily @ Date Brazen (20:29.906)

Go for it. Then you need to flirt with somebody, right? Like in addition to the mindset where go flirt with somebody imperfectly, ask someone if they’re single, ask someone out. You can do this. That was flirting 101. You can watch or listen to this episode as many times as you need to. And just know again, as I mentioned at the top, awkwardness is the price of admission for connection.

And so if you have the skill set to be kind to yourself when you feel awkward, if you have the skill set of noticing that you’re having a thought like, I’m awkward and that means that nobody’s ever gonna wanna be with me. If you can recognize that as a thought, not a fact, which it is, and practice something more useful and true, like most people are awkward when they meet somebody new. For the right person, that’s not gonna be a deal breaker.

the more you can get in the habit of building that neural pathway with compassion and not toxic positivity, right? It’s not the aggressive opposite of like, shut up brain, you’re wrong. I’m gonna do this. It’s gonna be great. That’s not gonna work. Cause your brain’s not going to like that new thought cause it doesn’t feel useful and true, right? The brain just wants to be safe, which is why you haven’t been flirting in your life before. So this is about doing flirting with emotional safety. Doing flirting with emotional safety means leaning on self-compassion.

noticing when you’re having hard thoughts, not facts about yourself while you’re flirting and then trying messily. The other piece is I want you to celebrate every win. No win is too small. So if you try this flirting 101 lesson and you go up to somebody and say hello and they say hi and they like kind of brush you off, you can just turn around and say, that sucks. It feels shitty to be rejected. You don’t have to do that where you’re at though. can.

You can just acknowledge, that feels shitty and I’m proud of myself for trying. I’m brave enough to try. Anybody who got anything that they wanted had to be brave enough to try and all it takes is 10 seconds of courage. So I want you to celebrate when you flirt and it doesn’t go well. I want you to celebrate when you flirt and it kind of goes well. I want you to celebrate when you flirt and it really goes well. Celebration, self-celebration is the key.

Lily @ Date Brazen (22:39.761)

to moving forward, especially as a late bloomer, because before you might’ve been organizing your lack of experience or your failed attempts before as evidence that what you wanted wasn’t possible and that you were uniquely unqualified. But now we’re flipping that script on its head. You want something, it’s not here yet, so let’s fucking go. It’s possible to learn a new skill, and flirting is just a skill that you haven’t practiced enough to feel fluency in it. So go practice.

this month and you got to be willing to do it messily. You’ve got to be willing to do it imperfectly. Be willing to do it awkwardly because what? Awkward is the price of admission for connection. I’ll talk to you next week. Just remember that you’ve got this and I’ve got your back. If you haven’t already, go to datebrazen.com slash let’s dash go to sign up for my next live training called three steps to attract the right partner as a late bloomer.

I cannot wait to see you there. Again, I’m going to teach you how to release the shame about being a quote late bloomer, the shame that’s been keeping you stuck in a cycle of isolation and self doubt and overthinking. I’m going to teach you how to build confidence in exactly what you want, even if you’ve never been in a relationship before, even if you just got out of a bad 20 year relationship. And you’re going to learn my step by step system to create a dating life that is joyful and magnetic, IRL and online.

It’s going to be a party. So you’re going to want to sign up at datebrazen.com slash let’s dash go. I’ll see you there. 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 datebrazen.com slash book.

The bonus is the dating life fix, my top 10 podcast episodes to get unstuck right now. And be sure to subscribe so you never miss an episode. You’ve got this and I’ve got your back.