Today on the podcast I’m telling you exactly how to go from friend zone to flirty in any conversation.

In this episode:

• The one question that takes you from friendly to flirty, and when to ask it.
• What the right people say when you ask, and what the wrong people say
• My rejection resilience plan to bounce back no matter what.
• My unconventional definition of flirting
• Why shooting your shot isn’t desperate when it comes from desire, not scarcity
• How clients went from “I don’t know how to flirt” to getting asked for their number, asking someone to coffee, and sending the bold text

🌟 Join Stop Freezing, Start Flirting, a three-day coaching challenge for late bloomers to confidently flirt and land a date IRL, October 25-27, 7-8pm ET: https://datebrazen.com/challenge

Work with Lily:

📖 Get the book, Thank You, More Please: https://datebrazen.com/book

🌟 Join the Main Character Dating waitlist: https://datebrazen.com/dating

✨ Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook

📸 Follow me on Instagram: https://www.instagram.com/datebrazen/

🎵 Follow me on TikTok: https://www.tiktok.com/@datebrazen

▶️ Follow me on YouTube: https://www.youtube.com/@DateBrazen

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Shownotes:

lily (00:00.76)
Hey gorgeous friends. Today on the podcast I am telling you exactly how to go from friend zone to flirty in any conversation. You’re gonna want to listen to this episode and take notes. And I want to invite you to my upcoming challenge called Stop Freezing, Start Flirting. How late bloomers can go from fro blah blah blah blah blah.

lily (00:30.36)
Stop freezing, start flirting, a three-day coaching challenge for late bloomers to confidently flirt and land a date IRL. We are running this challenge. I am leading this challenge from Sunday, October 25th, which if you’re watching listening to this buttla, if you’re bananas, if you’re listening to this live, then that is coming up on Sunday. And it’s gonna be Sunday, Monday, Tuesday from 7 to 8 p.m. Eastern on Zoom with me. And you’ll be in a coven cheerleaders.

doors open to main character dating during that live challenge. And for those who are live, I am offering a special gift that I have never ever offered before. If you join main character dating while we’re live on the call, you definitely are gonna want to be in this room to learn how to stop freezing and start flirting this season. Why? Because fall and winter is the best time to do IRL flirting and dating, because

Of all of the parties that you will attend, that you will be invited to, that you have opportunity to go to because of the events that people are gonna host, you need to have the skill set of feminist flirting so that you can effectively connect with people and attract dates confidently. It is possible for you, even if you never have before, even if you’re introverted, even if you’re shy, I’m going to account for all of those things. And it’s really for you if you wanna connect with people, if you wanna connect with men, women, humans in person.

For your dating life and attract dates confidently as a result, then this is for you. So you can stop freezing and start flirting, finally to attract the right relationship without the dependence on dating apps. So with that, let’s get into the episode. And if you wanna come to the challenge, go to datebraison.com/slash challenge to get your butt signed up. When you RSVP, you’re gonna be given a QA form to ask me.

anything about flirting if you feel like a late bloomer, about dating, if you feel like a late bloomer, especially. or no matter where you’re coming from, right? If you feel behind in your dating life, if you haven’t been in a right in a relate bananas, if you haven’t been in a relationship or haven’t been in the right one, you can ask me anything and I’m building the challenge content off of your questions. So go ask the question that you’ve been burning to ask about your dating life. Is it even possible? And I’m gonna build content around what you want to learn.

lily (02:47.049)
in addition to bananas. And and I will create podcast episodes and challenge content off of what you’re wondering and what questions you have. So go register, add the links to your calendar for our Zoom calls and and ask me anything and get ready to stop freezing and start flirting to make the right relationship inevitable without the dependence on dating apps. With that, let’s get into the episode.

lily (03:21.527)
So you’re so you’re probably great at being friendly. And there is one thing that takes bananas. There is one magical question that takes any conversation from friendly to potentially romantic flirtyville. Okay? I wanna talk about the best friend role versus the main character role before I get into this script. The best friend waits and hopes, they sit on the sidelines.

They don’t go to the dance floor because they’re waiting to be asked, or they don’t ever think they’re going to be asked. So they’re resigning themselves to sitting on the sidelines and and looking at all the dancers on the dance floor. the best friend sits around in hopes. The main character asks for what they want. The main character doesn’t sit around wondering. The main character decides that they are the decider and the chooser and that they can shoot their shot, right? So the one question.

That takes you from best friend to main character, that takes you from friendly to flirtyville with the right people. Is so random question, are you single? Random question, are you single? This question is how you take any conversation, you’re like, I don’t know if they’re interested, I don’t know if they’re single. You just say random question, or are you single? And you use 10 seconds of courage to do it. And then whatever they say next is kind of secondary.

To you becoming the version of yourself who shoots their shot, who is the main character of their dating life. Because what happens when you’re in the in the way of opportunity more by asking this question is that you have more access to opportunity instead of wondering if your crush likes you back, instead of wondering for months or years if that person is single and they’re interested too, right? The right person might shoot their shot before you can, but

I that’s kind of secondary. We’re not in control of what anybody else does. You’re only in control of yourself and how you behave. And I want you to be in the practice of talking to somebody, vibing, having a good time after five, 10 minutes. So random question, are you single? Or after a few weeks of volunteering with someone, so random question, are you single? Who you’re, you know, you’re into. You think they’re cute. Or you know, someone that you worked with a couple years ago and you haven’t been in touch for

lily (05:40.628)
A long time and you get coffee or a drink or something, and you’re vibing, and you’re like, so random question, are you single? It’s a magical question because it puts you in the way of opportunity and it makes you the main character of your love life. Okay. When you ask this question, the right person will say, Yeah, I am. And are you?

And you’ll say, Yeah. And then you’ll say, K do you want to take my number? Or you’ll say, D can I get your number? You’ll be awkward about it, probably. And that’s fine, because awkwardness is the price of admission for connection and you can’t say the wrong thing to the person. And the wrong people will say, No, I’m not single. The wrong people will say, Yeah, I am, but I’m not interested. The wrong people will stumble over their words and run away and say, No, they’re the wrong people for you.

And that’s when we would would engage your rejection resilience plan, right? Which we talked about last week in the episode, and in other episodes I’ve talked about it. It’s like five things. It’s planning for your brain to be mean to you with the sentences that it would serve up about, of course they weren’t into me. I’m not attractive enough. I’m not desirable enough. I’m not whatever enough. Blah, blah, blah. Your brain’s gonna be a human brain. Then you plan for SOFT, self-compassion, owning your needs, feeling your feelings, thoughts, not facts.

Self-compassion sounds like, of course, I’m struggling with rejection. Human beings don’t like rejection because we fear it like we fear death. Because when we lived in caves, rejection meant dying. It makes sense neurobiologically why I’m having this experience of feeling like shit. And I’m really proud of you for looking at this. I’m not alone. I’m proud of you for owning what you want and trying anyway. How courageous and awesome are you? Right? Active kindness without self-compassion, owning your needs. You might have the need of running away.

After being rejected, you might have the need of calling a friend, jumping up and down, taking three deep breaths, laying on your couch, having a big cry, feeling your feelings. This is where you notice where the feeling is in your body after being rejected. Maybe it’s the feeling of hot shame. You’ll notice, okay, it’s in my chest or my stomach, and you’ll breathe into it just for 90 seconds. Hey, I’m willing to feel anything to be with you. There’s nothing you could say do or feel that would make me want to stop being your friend. Two thoughts I love by Coach Simone Sowell.

lily (07:53.966)
Feeling your feelings is not some magical, like, you know, ceremony that you have to do with 30 minutes. It’s like 90 seconds of mindfulness of like, where is this feeling in my body? What is this feeling? You can look at a feelings wheel, they’re really Googleable to just notice, okay, I’m feeling embarrassed, I’m feeling shame, I’m feeling dread, I’m feeling panic, whatever the feeling, breathe into it for 90 seconds. Thoughts, not facts. This is where you prepare.

To be kinder to yourself with the sentences that your brain is feeding you about you asking so random question, are you single? The thoughts could be the reframes, they have to be useful and true feeling right now and accessible. We’re not doing toxic positivity. We’re not saying it doesn’t matter. If it if you’re feeling like it matters, then let’s not fight your brain. Let’s actually say, ooh, that was hard. And my brain is just being a human brain. This will pass soon.

You could also offer to yourself as a useful and true reframe, it might be possible that I am becoming my most flirtatious magnetic self. And this person just wasn’t my person. That’s okay. And it sucks right now, right? You’re gonna do the rejection resilience plan when you receive the answer you don’t want, which is the no. And you’re gonna bounce back quicker afterward.

But the point of all of this is asking the magical question while you’re talking with somebody. Really flirting is two things: joyful, courageous connection. I’m gonna add a third, awkward. It can be really awkward. Joyful, courageous, awkward connection. It it is asking a question to connect with somebody, offering a genuine compliment, co-creating a conversation with someone with whose body language is pointed towards you, who seems to want to be chatting with you.

Chat, chat, chat, five minutes, 10 minutes in. So random question, are you single if you’re interested in them romantically? And then you get your answer instead of wondering and beating yourself up. I didn’t shoot my shot. I didn’t do this. I know, you know, I never have opportunities like this, and that one passed me by. Just be in the way of like asking. Who cares? Be in the way of opportunity. You’ll get more of what you want because of it. So random question, are you single? Say that out loud right now to get it in your mouth and in your brain. So random question, are you single? Say it with me. So random question, are you single?

lily (10:08.267)
This is what it takes to move from feeling behind, like a late bloomer, like I felt, to moving into confident Daterville, to moving into like where I got to with these skills with my rejection resilience plant, like I would have like talked to people and like made them feel really fun and like I would have asked great questions. Like I had no problem talking to strangers, but in terms of flirting or assuming that somebody might be into me enough to ask.

So random question, are you single? Or in terms of like assuming anybody would want to date me, that was where I felt a total disconnect from my desires and what I did. Cause I would not ask dating-wise, are you single? I would not like assume that somebody was into me. And then actually, when I did, I’ve told the story on the podcast before. I met this guy at a party. We spent the whole day together. I was really attracted to him.

He took me, we walked through Manhattan together. It was like this magical day. It was like six hours long. We hung out. We were having the best time. He would take, we would go into bars and I would offer to pay for I would offer to split the bill. And he was like, No, I got you. And after a few of the like stopovers at restaurants and bars just to get a little bite, snack, again, long rambling day. He would say, No, I got you. I’ve got you. No, I want to treat you. And I was like, my God, we’re on a date. my God. So six hours then we’re at the final pub.

And we weren’t drunk or we were just like tipsy, happy, you know, fed, well fed. And I said, This is a date, right? A version of So Random Question Are You Single, but a lot more direct because I thought it was obviously a date. And he was like, No, why would you think that? Gut punch. I immediately welled up with tears. I had to immediately run away and leave. And I got in the lift and I was crying so hard in my lift that the driver said,

Ma’am, are you okay? It was so deeply embarrassing. I felt shame. And I I wish at the time I had had this rejection resilience plan, I would have bounced back. But this affected me for weeks and months. I thought, of course he wasn’t into me. I was foolish for thinking it was a date. And now I just have these act I have access to new thoughts and new reframes that said, like, no, it kind of sucks that he was leading me on in a couple significant ways. It sucks that.

lily (12:36.021)
know, I wish that I’d gotten clarity early on earlier on in the day by asking this magical question. So random question, are you single? And I wish I’d followed it up with, well, I think you’re really cute, something like that, to see if he thought I was cute. And he would have made it clear that that I wasn’t for him for whatever reason and and I would have known earlier. But I’m glad I went through that because it really like allowed me to talk to you in this moment of understanding of like, wow, sometimes this rejection thing.

After shooting your shot can really fucking suck and can be sort of like wood on the fire of believing your undesirability. But with the rejection resilience plan, with more unbothered main character energy, you are recentering yourself and decentering the people who are wrong for you and getting to the answer quicker of whether or not something is flirty or friendly for somebody else. If you feel it’s flirty or you feel that it’s romantic potential, you’re gonna get clear quicker.

And you’re gonna find the people who are right for you quicker and you’re gonna wonder less and you’re going to be in your power more. I wanna give you some examples of exactly what this has looked like for some of my clients because I think it’s really inspirational. sh this client flirted with a coworker and he asked for her number and to hang out soon. And she said, I was just saying I don’t know how to flirt and this will never happen for me. Five seconds of courage and bam.

So she was allowing herself to flirt with him and let him know that she was single and then she was looking and he ended up like asking for her number. It happens that somebody else can shoot their shot first when you are in the mode of flirtation, when you are releasing the freeze, when you are when you have your rejection resilience plan in your back pocket to bounce back from anything. And it’s possible to learn how to flirt if you never have.

Another client said, I asked him to coffee and he said yes. On a Thursday evening at a dating event, this client was super nervous. She met one guy she was curious about, plus a few women for friendship. Afterwards, she went up to him and asked him to coffee. He said yes, and they’re co-creating their date. She said, I almost talked myself out of asking, but I’m really glad that I did. Like another version of are you random question, are you single? It’s like you’re at a speed dating event. It’s obviously this double opt-in thing. Shoot your shot.

lily (14:59.231)
Ask someone out, right? Like when you have your rejection resilience plan in your back pocket, you are able to go from friendly to flirty and like see who co-creates with you. Someone else said, another client said, sent the text. She’d been going in circles for a few days about a flirty text to her crush about getting together this summer. And she got coaching and main character dating. And the reframe that helped her most was: quote, regardless of the outcome, I want to be my most flirty and courageous self.

And she would make moves like this. So good, right? She said, My heart was racing. I hadn’t heard back when I hadn’t heard back when I posted this. And she felt like sure her most bananas. Her heart was racing when she sent it. And she felt like the most courageous version of herself. So the the version of you who asks so random question, are you single, or asks, so do you want to go to coffee, or says, Hey, I think you’re cute. Do you want to exchange numbers? That is becoming your most creative.

bananas, your most courageous, magnetic self. It’s when it comes from the thought, I am awesome and I deserve connection and I deserve romance and love, the feeling can be pride in yourself. And the actions are shooting your shot, not from a place of desperation, but from a place of desire. So some of you might say, it sounds so desperate to shoot your shot or it’s like chasing, not attracting. No, no, no, no, no.

When you are in your power and you are in your main character energy, you are connecting from that place. And it is not desperate. If someone else judges you as desperate, that’s a them problem, not a you problem. Now, if you were in your dating life like feeling scarcity and having the thought no one is right for me, and this person in front of me may be right for me, even though they don’t really meet all of my preferences. But I gotta like, I gotta lock them down or else.

Then it might feel desperate for you, to you, because you’re coming from this place of scarcity. But when you’re coming from this place of courage and self-trust and building main character energy, there’s no way that you’re gonna, you’re not in desperation. You’re coming from a place of abundance, baby. another client sent a bold text. This guy that she’d been casually seeing, but she was interested in him, was leaving for the country for a while.

lily (17:22.539)
And she sent a bold text to see him before he left. She said, I took action instead of waiting for him to reach out to me. And this is the power of feminist flirting. This is the power of stepping into your main character energy with the skill set of feminist flirting. And I am teaching you this skill set at my live challenge on October 25th, 2026. let’s see, is that right? Yeah.

Again, it’s called Stop Freezing, Start Flirting, a three-day coaching challenge for late bloomers to confidently flirt and find a date. IRL bananas. A three-day coaching challenge for late bloomers to confidently flirt and land a date. IRL, it’s October 25th, 26th, 27th from seven to eight p.m. Eastern. Everybody who registers will get the recording. But if you show up live, there is a special gift only for people that show up live when we open the doors to main character dating. Only for you. I’ve literally never offered this before. I’m so excited about it. So

Go to datebraison.com slash challenge to get your butt in this challenge. And know that if you feel like a late bloomer, if you feel like behind, you haven’t been in a relationship before, this is for you. If you are re-entering the dating scene after divorce or a loss, this is for you. If you are a start-stop dater, you like constantly download and delete the apps and you haven’t been in a relationship in a while, this is for you. If you are a situation chip alum and you have settled for less for so long, this is for you. Anybody

Who resonates with wanting to do feminist flirting powerfully? If you want to feel the fearless feel the little bananas, if you want to feel fearless and connecting with cuties, if you want to start making the right relationship inevitable by asking, so random question, are you single without so much fear? If you want to you know, have my feminist dating road bananas.

If you wanna have my feminist flirting roadmap, you wanna know how to talk to somebody cute without freezing and you want an action plan for this this fall and winter season to actually start IRL dating and eliminate your dependence on dating apps to meet the right person as soon as possible, then this challenge is for you. I can’t wait to coach your face off there. And I can’t wait to talk to you next week. Bye.