You Like Her, But You’re Trapped in the Friend Zone. Flirt Like This to Escape (Live Coaching with Matt)

Summary

Podcast Summary:

How to Get a Girlfriend with Connell Barrett
Episode: You Like Her, But You’re Trapped in the Friend Zone. Flirt Like This to Escape (Live Coaching with Matt)
Date: April 7, 2026
Host: Connell Barrett
Guest: Matthew (Return coaching client)

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Episode Overview

This episode focuses on practical, actionable advice for men struggling with being “too friendly” and getting stuck in the friend zone, especially after making initial dating app connections. Connell Barrett, dating coach and author, gives live coaching to his client Matthew, a 40-year-old California business owner working to improve his flirting and dating outcomes.

Connell and Matthew dig into specific sticking points—including how to re-engage matches who go quiet, escalate banter off the apps, avoid coming off as just friendly on dates, and confidently express romantic interest to escape the friend zone. The tone is casual, encouraging, and honest, with plenty of real-life stories and direct language.

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Key Discussion Points & Insights

1. Managing Conversations on Dating Apps

(02:09–13:46)

• Problem: Matthew’s matches often go quiet after a few days of messaging, right before suggesting to move off the app.
• Connell’s Principle: The main goal of app messaging is to get to a real-world date, not to maximize banter.
  • Guidelines:
    • Aim to ask someone out after 8–10 total messages exchanged (not per person) (04:25).
    • Once you’ve discussed one or two topics, it’s enough to ask out—don't over-banter.
  • Quote (05:08):
    “The goal of messaging a woman on the app isn’t to banter... It’s to get her on a date.” — Connell
• Suggested Scripts:
  • Use a playful, leading line:
    “I’m curious—are you as charming in real life as you seem here on [app name]?” (07:33)
  • Respond playfully to snark (“I’m boring as hell...”) with “I love a challenge” or “Boring women are my favorite. Let’s meet up.” (08:27)
• Why women go quiet: Many are waiting for the man to take the next step and ask them out.

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2. Re-Engaging When a Match Goes Silent

(09:41–17:36)

• Connell’s Approach: When re-engaging, don’t just repeat the ask or go straight for the date. Instead, offer value—a fun question, a playful tease, or an emotionally engaging topic.
  • Quote (11:02):
    “Persistence plus charm equals dates... when a woman goes quiet, it’s better to make her smile, giggle, laugh, or just make her intrigued.”
• Personalization Pays Off:
  • Reference something specific she cares about (her dog, beach trips, art).
    • e.g., “Pop quiz, Jessica. What is the cutest thing your dog does that just makes you melt?” (14:17)
• Connell’s Real Example: Revived an artist’s interest by texting her a photo of an art installation and asking her professional opinion, rather than sending a generic “hey” (15:06).
  • Quote (15:10):
    “I didn’t think what’s in it for me? When I messaged her. I thought what would make Jennifer respond? Oh, she loves art, she’s an artist.”

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3. Timing & Frequency of Messaging

(16:22–21:00)

• Don’t Overthink Timing:
  • Avoid early mornings (stressful commute times); prefer afternoons or evenings when people are more relaxed (17:08–17:38).
  • Playful banter can work anytime—e.g. sending a “coffee porn” picture in the morning as a light opener (17:08).
  • Wait no more than 24–48 hours to follow up, or you’ll fall down her queue of matches (19:03).
    • Quote (20:31):
      “If you wait three or four days, you’re just going way down the queue.”

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4. Flirting vs. Friendliness on Dates

(21:00–27:00)

• Matthew’s Challenge: Coming across as “nice but not my type”—possibly too friendly, not flirty enough.
• Connell’s Solution: Kind and friendly is good, but add an edge—a clear, authentic statement of romantic intent.
  • Actionable Line:
    “You know what’s really sexy about you? [Trait]” (e.g., “You’re so quick-witted and funny.”) (23:59)
  • Focus praise on traits/personality over just looks; be specific and honest.
  • Quote (25:02):
    “Ask yourself, what is the deepest, truest thing I’m thinking about this woman? And just say it. As long as it’s not vulgar and as long as it’s not crazy needy.”
• How to Avoid Awkwardness:
  • Don’t undercut your statement by second-guessing or apologizing for it—commit to your words (26:07).
  • Quote (27:00):
    “There’s nothing creepy about being honest, as long as you’re speaking from a true, authentic place.”

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5. Preventing Awkward Silences & Keeping Conversation Flowing

(27:00–29:56)

• Lower the Bar: Don’t hold yourself to a perfect standard of conversation.
• Back Pocket Topics: Prepare one or two topics in advance (travel stories, her interests from dating profile) as conversation fallbacks.
  • Connell’s Tip: Review her profile before the date for cues to ask about (29:28).

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6. Post-Date Texting—How Soon, How Much, How Honest?

(29:56–36:23)

• Show Interest, Don’t Be Needy:
  • It's not needy to say, “I want to see you again” or “I had an amazing time.”
  • Neediness = multiple insecure messages, apologies, or seeking validation.
  • Quote (32:12):
    “Two of the sexiest words in the English language to a woman is when a man who she had a date with says, I want...”
• Connell’s “Sydney Sweeney” Test:
  • If your dream woman texted first, you wouldn’t think she was needy—apply that frame to yourself, recognizing your own value (32:39–34:10).
• Abundance Mindset: Remind yourself of your own value and options, like a “regular guy 10.”

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7. Flirting & Breaking the Ice in Real Life (Not Apps)

(37:00–39:39)

• Connell’s “What to Say” Framework:
  • When meeting women in person (e.g., supermarket or farmer’s market):
    • Ask a Question: Something situational or about their selection.
    • Make an Observation: Comment on something genuine happening around you.
    • Give a Compliment: Keep it G-rated and specific.
  • Example: “Hey, I see you take a little bit of coffee with your sugar.” (Observation, leads to banter)
    • Quote (38:09):
      “It’s 90% rejection proof because there’s nothing sexual. There’s nothing creepy. It’s just simple, basic, friendly social conversation.”

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Notable Quotes & Moments

• Connell on Modern Flirting:
  “What is flirting? Flirting in a word is play. It’s literally described... as playing at love.” (17:36)
• Banter vs. Intentionality:
  “The goal... isn’t to banter, although I love banter. It’s to get her on a date.” (05:08)
• On Owning Your Intent:
  “There’s nothing creepy about being honest as long as you’re speaking from a true authentic place.” (27:00)
• On Not Overanalyzing Messaging:
  “Don’t overthink it that much... as long as you’re giving value, you’re not going to come off as needy.” (21:00)
• On Post-Date Follow-Up:
  “You’re giving her certainty, and you’re being the man of certainty, which every woman wants in her life.” (31:09)

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Key Timestamps

• Managing App Conversations: 02:09–13:46
• Re-Engaging Quiet Matches: 09:41–17:36
• Optimal Messaging Timing: 16:22–21:00
• Flirting vs. Friendliness: 21:00–27:00
• Conversation Flow on Dates: 27:00–29:56
• Post-Date Texting: 29:56–36:23
• In-Person Icebreakers: 37:00–39:39

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Action Steps Recap

• On Apps: Move things off-app after 8-10 total messages—not per person.
• If She Goes Quiet: Reference a known interest, send a playful or curiosity-sparking message.
• On Dates: Always give at least one clear, genuine statement of romantic interest—mentioning traits, not just looks.
• Post-Date: Don’t fear being direct about wanting to see her again; “I want” is powerful.
• IRL Approaches: Use the Question-Compliment-Observation framework for breaking the ice.
• General Mindset: Remember and project your own value; abundance mindset beats playing hard to get.

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For listeners stuck in the friend zone or finding their texts ignored, this episode is packed with practical lines, confidence-boosting mindset shifts, and easy-to-apply frameworks to help turn friendly connections into real romantic chemistry.

Transcript

[A]

Stop thinking so much about what's the right thing to say. Instead, ask yourself, what is the deepest, truest thing I'm thinking about this woman? And just say it. Welcome back to the how to Get a Girlfriend podcast. I'm your host, dating coach Connell Barrett. I am here to help you know what to say and to flirt like you mean it. That's my new tagline, by the way. I hope you like it. Anyway, speaking of flirting like you mean it and a guy who has really achieved some incredible dating successes, I'm joined today by my client, Matthew. Matthew is making a return appearance to the show. He and I have been working together for a little while and he came to me long ago, struggling with flirting, struggling with first dates, just having some tough issues getting first dates to convert. And he's back to ask me a few more flirting and dating questions. Welcome back, Matthew Connell.

[B]

Thanks for having me again. Yeah, I Connell, I just want to start off by saying I can't thank you enough. The success you've helped me.

[A]

Thank you. Thank me as much as you want. Go.

[B]

I can keep on going. But no, I can't thank you enough. You know, you really helped me open up a new flirting channel and a new way to engage women that I never thought was possible. So I can't thank. Nice.

[A]

Well, you and I are both businessmen and we talk about things like funnels and bringing in business success. And I kind of like to, I like a guy to look at his dating life almost like we're launching a, a new business funnel, but for his love life. And we need to get that funnel filled with quote unquote leads. Right, The Glengarry leads. The dates, in other words. And your main funnel of Glengarry leads of really cute quality women, by the way, just for those of you who never met Matthew, he's 40, California business owner and single man who is just trying to find the one. And you're on the dating apps, right? That's how you're getting most of your dates?

[B]

Yeah, I'm on Hinge and Raya currently and which kind of leads me to an interesting question I wanted to ask you. I seem to be getting some good kind of banter conversations going and some even good conversations going, but then they seem to drop off after three, four days. I'm wondering if you had some ideas on kind of how to re engage in like a flirty kind of fun way that's not, hey, you know, cheesy and one liney, but something that'll kind of draw them back in and re. Engage in the conversation. So obviously we can take this conversation off the app and hopefully meet in person.

[A]

So you're saying before you've met her? You mean right before?

[B]

Yes, this is before. So we might have been chatting for a couple days on the apps. You know, kind of some messages here or there. Hey, tell me, maybe like, what's your favorite restaurant? You know, something engaging. And then there might be two or three, maybe four days max of silence. And I'm always kind of wondering, okay, should I. Should I re engage them? How should I re engage them? What's a good message? Or do I just say move on to the next one? I'm trying to kind of figure out thinking more of the messaging, though, more of how to get them back.

[A]

Ballpark number. How many messages have you sent back and forth with the typical woman you've matched with when they go quiet?

[B]

That's a good question. I was like, should I go look at my phone right now? Probably usually three or four messages. I think it's like right at the cusp of asking for the number of trying to get off the app.

[A]

Okay, so like three or four from you, three or four from her, and then silence.

[B]

Yeah. Yes. Three or four from me, three or four from her. And then like, right. It's literally. The next message would normally be like, hey, do you want to connect off this app and meet up? I want to take you out on a date. Again, something along those lines. Right.

[A]

So like one or two topics would you say you've reach or maybe one topic?

[B]

That's a good question.

[A]

Food. Ballpark number. I'm asking for diagnostic reasons.

[B]

Yeah, no, it's usually about three.

[A]

I'd say topics.

[B]

Three topics. Yeah. Okay. All right. I'm a big kind of banter guy. I like to kind of throw different topics in there. Kind of, you know, nothing like changing from, let's talk about the weather, but something maybe like, you know, like restaurants, and then maybe we're talking about vacations or trips.

[A]

Okay. I would say all things equal and every woman's different. But if you want a general thought here, once you get to 10 total messages, ask her out. Even eight total. So you might already think of it as eight messages total, maximum. Ask her out. And. Or you could also think of it as once you. Once you're done with a first and are in a second topic, that's enough to get her off the app. So I think my best advice for you here would be preventative measures. Now I'll tell you what to say when they go quiet, but they're actually not going. They're going quiet because they're probably waiting for you to ask them out or to move this off of the app.

[B]

Okay.

[A]

I'd rather you hear from them. Hey, why don't we text. I'd rather you ask her out and send like two or three messages and then say, here's a really good. Here's, here's, here's talk about what to say. Here's a really good thing to say. I'm just looking at dating profile. Let's see here. So here's a woman I matched with on Bumble. And by the way, this is for coaching purposes. I have a girlfriend with whom I'm madly in love. We have two beautiful little orange tabbies. So for what it's worth, dear listener, this is just for coaching. I'm not meeting women, but I am on the apps. I have a really weird job anyway, so I matched with a woman. I'll call her Brooke. Okay, Brooke and I matched. Beautiful, attractive, stylish. Just fantastic. Hey, Brooke. She just wrote, hi, I'm Bumble. I wrote, hey, Brooke, TGI Monday, if there is such a thing. My second message. I'm curious, are you as charming in real life as you seem on your Bumble? Thinking emoji, happy face emoji. She writes back, haha. Well, you have to find out in person. So we are now three messages in. She's only sent one, and now she is basically saying, ask me out. So something. You don't have to act this quickly if you don't want to, Matthew, but something you could do is one, because you like to banter. So do I. But the goal of messaging a woman on the app isn't to banter, although I love banter. It's to get her on a date. So I would say try to find a nice middle ground banter for three or four messages total, about one topic and one topic only, and then transition to asking her out or getting her off the app. Does that make sense so far?

[B]

That makes sense. So we're saying four messages. Sorry, six to eight messages total. Total, not per person.

[A]

Right. And that's a guideline. You want to read the room, read what she's giving you, not say Connell said eight messages. So eight messages. How long I wait? Don't do that. I would rather you ask her out sooner rather than later because that shows intentionality. It shows you're a guy who goes for what he wants.

[B]

Okay.

[A]

And I think some of these women are going quiet because they're maybe they're not banterers like you are. Or maybe they. And there's other reasons why women go quiet. But if, if you want one of my. It's the simplest line in the world I've sent. I've had many dozens of clients send this. And here's a. This is so copy and paste it's not even funny. I'll say it again. I'm curious. Are you as charming in real life as you seem here on insert app? It's a leading question. I should have been an attorney. It's a leading question, right? Because most women say, well, of course I'm. Of course I'm as charming in person. What is she going to say? And then what would you say, Matthew?

[B]

I'd probably say something lines of, well, I need to see this in person to verify this.

[A]

There you go. Perfect. Yeah.

[B]

Okay.

[A]

Or some women are a little snarky like you and I are. And some women have said to me, oh, I am absolutely boring as hell in person. I'm a total drab. I'm like a zombie. And then what would you say to that? No. Wrong answer. I'm just curious.

[B]

I usually like to come from a playful kind of challenge place. So I'll say something maybe along the lines of, well, I'm always up for a challenge. Let me see if I can change this.

[A]

I love it. I was about to say the same thing. I'm deputizing you as my assistant coach.

[B]

Yeah, I wish.

[A]

I love a challenge. Or the idea of in improv they say in improv there's this concept called yes and you say yes to the premise and then you add to it. So, oh, yes, I love boring women. Boring women are my favorite. Let's meet up. You don't even have to talk. I'll do all the talking. How about Friday night? So you basically you just agree and add to it. Bottom line is, I think preventative measures are going to be a bigger help for you than what to say next. But let's say she goes quiet for whatever reason, three, four or five messages in, she just goes quiet. What is your current strategy, if any, that you're using?

[B]

I try to keep it, usually after two to four days of being quiet, like if we. Okay, if we've had some good banter or some good conversation and messages are flowing pretty frequently, I'll try to obviously take it to the next level. Meet, meet or connect off the app. But if it again goes quiet after that, I'm usually just sending a follow up, like, hey, would Love to take you out on a date. Wondering if you're free, obviously next week. Next week. Something very kind of basic, but I think it needs more. More of an umph. But I can't figure out what it would be.

[A]

You're a business guy, right?

[B]

I am, yeah.

[A]

Let's say you're. You're sending a marketing message to somebody on your mailing list. You're. They're interested in your product, possibly, and they. You want them to buy, but first you have to get their attention. What do you think would work better? You ask them to buy when they've gone quiet, or you try to engage them with something that maybe a tip or an insight or something emotionally stimulating to get them responding to your quote, unquote, reach out. What do you think would work better?

[B]

I think the tip's gonna be. The tip's gonna get more engagement.

[A]

Yeah. And that's a good way to think about the next message to send when a woman goes quiet. When a woman goes quiet, it's usually there's multiple reasons. Beautiful, attractive women especially have hundreds and hundreds of options coming in, sometimes thousands, but hundreds of people are matching with her. So the way we stand out is persistence plus charm equals dates. And I would say by charm, I just mean you're giving value. Right. You're seeking to make her smile. So when a woman goes quiet, I wouldn't message her and say, hey, do you want to go on a date? Because she wants some kind of emotional engagement. Most likely better to make her smile, make her giggle, make her laugh, or just make her intrigued by something she finds interesting. So without naming names or identifying anybody, can you give an example of a woman you matched with recently on an app? And you were like, oh, man, what could I have said to her? We can use a quick little case study if you want.

[B]

Yeah, I was gonna look through my phone. I think I know I was messaging this girl named Jessica.

[A]

Okay.

[B]

Yes. And we had some nice banter, some conversation today, you know, obviously earlier in the week. And then it just went quiet the last three days. And I think I let. I sent her the last message. I can read it to you if you want me to. I'm not.

[A]

What was your last message to Jessica? Sure,

[B]

let me pull it up. We were talking. My last message to her was, hey, explain yourself in five emojis.

[A]

I like that. I like that. That's not bad. That is asking her to do a little work, but it's not hard work. It's fun. So that's a great example of Trying to talk to a woman on that emotional wavelength. So I like that it didn't work, though, for whatever reason, it might not have been anything wrong with the technique, for whatever reason that didn't engage her. Or maybe she read it in the middle of doing 17 things at work, and then. And then 12 other guys went to the top of her queue. Right. So based on what you know about Jessica, what are a couple things about her that, you know, she cares about or that are relevant to her?

[B]

That's a good question. I know she has a dog. We've talked about that. We've talked about our favorite things because we live kind of close to each other in Los Angeles. So we talked a little bit about that, and we talked about both loving the beach.

[A]

I love it. So, yeah, I would say if a woman like that goes quiet, rather than asking her out, I would say, ask yourself, what does she care about? What would she like to. What would.

[B]

What.

[A]

What would she like to message about what might engage her? In her case? She likes the beach. She likes her dog. Loves her dog. So you might say, hey, pop quiz, Jessica. What is the cutest thing that your dog does that just makes you melt? It's like, what dog mom would not want to answer that?

[B]

I see. Okay. Yeah.

[A]

I'm looking at my phone from many, many years ago, but I was trying to get a really attractive and frankly, just cool, dynamite, smart, what I call a wow. Girl from Bumble to respond to me after a few messages. She went quiet after a few messages. And she is an artist, an actual literal painter. And so I thought, how do I get. I'll call her Jennifer. How do I get Jennifer to write me back? I'm looking at the message right on my phone right here. And I was out and about in the city, and I saw this art installation, like an outside art art installation that showed a cow covered in. I'm not very articulate at describing art, but like, with paisley, multicolored. Pick a paisley. Imagine a paisley cow.

[B]

Okay, okay, I've seen this.

[A]

So I. So I took a photo of it, and at this point, we were texting, but same difference. I took a photo of it and I said, okay, pop quiz. One of my little pet phrases. Okay, pop quiz. Since you're an artist and therefore an expert, is this a legit art or B, just a damn cow? And she immediately wrote back. And I can't even read her response. I mean, I can. It's just. It could go on forever. She wrote back saying, oh, my God, I love that. I Love what that artist did with the colors. I've been where you took that back back engaged. And we ended up meeting up having a date. So bottom line, I didn't think what's in it for me? When I messaged her, I thought what would make Jennifer respond? Oh, she loves art, she's an artist. That's probably a good way to get her engaged. So I prefer a personalized, a message that engages her on something she cares about, her dog, her favorite hobby or whatever has already worked with her in the past. Is a good place to start. Make sense.

[B]

That makes sense and kind of a. An interesting sub kind of question from this. Is there a better time to message? I mean, obviously, is it during the day, is it at night? Have you noticed any sort of.

[A]

6:37pm On a Tuesday is the perfect time. Only message women on that day and time, otherwise you have no chance.

[B]

No, I was interested. Yeah, no, I was like 6:30, I'm like, oh, okay. I think I can make that work. I only got Tuesdays. I like this. But no, I was, you know, I love the, you know, I'm trying to figure out like, is there, is it before work, after work? Obviously. I feel like, you know, it's a very interesting. I mean, look, some people are on their phones all day, some people aren't. So I didn't know if you had any suggestions on that as well.

[A]

I wouldn't overthink it. If I'm going to give you a guideline. I would say maybe don't ask her out at 7:15 in the morning when she's commuting to work and all stressed out and worried about what her boss is going to say. Yeah, but that might be a great time to send her coffee. Porn. Take a picture of the cappuccino you just ordered. Send her a picture of the cappuccino.

[B]

Okay.

[A]

It's like my coffee can kick your coffee's butt or something like that.

[B]

Yeah, flirting and engaging. I get it.

[A]

It's like giving value. I used to say give, give, give, ask. Put another way, play, play, play, pull the trigger. What is flirting? Flirting in a word is play. It's literally described, defined in the Oxford dictionary as playing at love. That's what flirting is. It's play. So think play, play, play and then pull the trigger. Pull the trigger of course means ask her out. Okay, but if she's not playing with you, pulling a trigger, you're gonna, you're gonna get blanks probably once you get her playing with you again.

[B]

Oh, ha ha ha.

[A]

Oh, my God, here's my coffee today. And then all of a sudden, you're messaging about coffee, which is a perfectly light topic to be messaging about. And then you might. Then you can ask her out at that point. But the guideline is, I would say, yeah, you do want to be cognizant of what time of day it is. Monday morning, I wouldn't ask her out, but, you know, maybe in the afternoon or evening, may, it's happy hour. That's not a bad time to send another message. No, People are in a. Typically in a better mood at the end of a workday than they are on their way to work. So you want to. Don't overthink it that much. But I would say asking a woman out would make sense to do in the afternoon or evening, generally speaking. That said, doesn't matter what time of day. Somebody like you can get a woman to be like, hell, yeah, I want to go on a date with this amazing guy no matter what time it is.

[B]

I see what you're saying. Okay. Okay.

[A]

And I would not wait more than 48 hours, maybe even 24 hours. But 24 to 48 hours is the most you should wait before you message a woman again. Do you know why? Pop quiz.

[B]

No. No, I don't. I wish I did.

[A]

You've been on many dates, right? Have you ever by any chance asked one of your dates to let you see her inbound messages from men Unhinge or Raya?

[B]

No, I'm going.

[A]

Have you ever, on your next date, ask. Or on your next first date, ask her how many matches she has or how many likes she has. It'll blow your mind. How many men are trying to match with her and date her?

[B]

I'm sure. I mean, I can't imagine. Yeah, yeah.

[A]

So like, Sydney Sweeney wouldn't have as many matches as some women I've seen. I was. I was on a first date many, many moons ago. It was actually right before I met my girlfriend, because I remember in the lead up to meeting Jess, but I was on a first date with a woman from Bumble. Very attractive single mom, 40 plus, very pretty, very successful, but not like cover model, just like an attractive, dateable single mom. And I looked at her bumble. She had 4,000 likes. 4,000. 4,000. So my point is simply that you got to stay on her mind. If you wait three or four days, you're just going way down the queue.

[B]

Okay?

[A]

So persistence plus charm. Give, give, give, ask, ping her once a day or at the most, don't wait more than 48 hours. Otherwise you'll just be out of sight and out of mind. And as long as you're giving value, you're not going to come off as needy. You're not going to bother her because you're that guy who is asking the charming question about her dog or sending her the funny coffee photo or the picture of your cat doing backflips or whatever.

[B]

No, that's. Yeah. And that kind of. It's interesting. It kind of leads me to kind of my next kind of question I have. Obviously it's like, you know, I'm going out on these dates, which, which is great, you know, but I think sometimes I come off kind of too friendly and not, not flirty enough. But, but I don't want it to sound like forceful or awkward or kind of weird. So I'm trying to. I don't want to be awkwardly flirting. So I was wondering if you give me some kind of advice on that. Like, I think I'm coming across too friendly on these dates, but not flirty enough.

[A]

Can you elaborate what you mean by that?

[B]

Yeah, like, I'm going out on dates and I've had a couple dates where girls are like, oh, you know, at the end of the day they're like, oh, you seem really nice, but just not my type. So I think I'm maybe getting put in the friend zone or maybe I'm coming off like I'm not flirting or maybe I don't, I don't want to sound awkward, so I don't want to like flirt with them, but I don't know how. It's like a. I don't know how to put it. It's an interesting question, but I guess more of it's. It's like I'm getting on first dates, I'm going and then I'm there, but I don't know how to flirt. And I don't know if it's flirting or if it's. I'm coming off too friendly to them like, or what it is. Right.

[A]

Okay. I know that feeling and I remember feeling that myself because I'm the nicest, kindest guy in the world. I'd like to think on my better days. So it was really frustrating for me when I was struggling with that. The insight I want to offer you is there's nothing wrong with friendly, friendly kind. That's exactly what women want. We just want to make sure that there's an edge, there's a flirtatious risk taking side to you as well. And then you're giving women what they want, which is, oh, a kind, nice guy who also is not afraid to look me in the eye and make a clear statement of romantic intent. Which is what you always want to do on every first date with a woman you find attractive. You want to give her a clear statement of interest. Romantic interest. It could be as simple as saying, you know what's really sexy about you? It's blank. My first date with my girlfriend, my now girlfriend, I was just so blown away by how funny and witty she is that I looked at her at one point and said, you know what's really sexy about you? You're so quick witted and funny. I'm usually the funny one on a date and I'm just trying to keep up with you. And she later told me how that really resonated with her because she's used to guys saying, oh, you're so pretty, you're so cute. But I was the guy saying, okay, yeah, you're cute, but, but wow. What's really blowing me away is how witty and smart and intelligent you are. So fastest way to make an impact with flirting is, is tell a woman, let her know with clear, simple language what you like about her and why you like it. And ideally make it a trait, not just a physical thing. Do you do that on most first dates?

[B]

I don't, but now I'm going to.

[A]

Okay. And the thing about clear statements of romantic intent is that this is. It shows your interest. It shows you have the confidence to say it. It's also flirting. It's basically, hey, I like you. Do you want to go on another date with me? It's vulnerable, but it's all because it's vulnerable. It's also, it shows confidence in yourself and a willingness to lead that dating dance. And if anybody out there listening is struggling with what to say, stop thinking so much about what's the right thing to say. Instead, ask yourself, what is the deepest, truest thing I'm thinking about this woman? And just say it. As long as it's not vulgar and as long as it's not crazy. Needy. Okay, you don't want to be super needy. What I mean is, you don't want to say, oh my God, I haven't had a date in four years. I'm so glad you're here. Don't be that honest.

[B]

Okay?

[A]

But also don't say, I want to take you back to my apartment and do XYZ to you hot naked body. Don't say that first. Say that later in the night. When things are going amazing, there's that sweet spot in the middle. So simple. I don't want anybody to script out what they say. But if I had to give somebody the what to say, I would say, use the word sexy on a first date. You know what's sexy about you, Amanda? You're so bold and courageous in. You backpacked through Europe all by yourself. Oh, my God, that's so cool and sexy. I'm not used to meeting women like that. You have to. You have to believe it. You have to feel it. But, yeah, women like a guy who just tells it like it is. That's what the bad boys have going for them, quote, unquote.

[B]

I. I would love to say that, and I will. I just, you know, I don't want it to sound, you know, awkward or forced. But, I mean, I think it's a. It's a great idea. I'm gonna. I'm gonna implement it.

[A]

Awkward is mo. Most of what makes something awkward is

[B]

you

[A]

not committing to whatever the move is in this case. Clear statement of romantic interest. So if you say, you know what, Can I just tell you something? I hope. I hope this isn't weird. Oh, my God, Amanda, you're just really. You're really sexy. I'm sorry, is that creepy? Am I being creepy? Like, that's fucking awkward, what I just did there. What if you say, you know what, Amanda, you know what's really sexy about you? You just say exactly what you think. Your. Your brain, it's like you're all over the place in a beautiful way. It's like bumper cars up there. I love it. I love the ride I'm on. It's really sexy and cool. Just owning it. There's nothing creepy about that. So. So much of it is commitment. Commit commitment to what you're saying. It's hard to make that creepy or awkward. It's not. It's not. There's nothing creepy about being honest as long as you're speaking from a true authentic place.

[B]

I appreciate that. No, that's good advice. And then, you know, I mean, even on these days, I know you kind of. We talked about it a little bit, like, a couple minutes ago, but, like, I feel like I'm running out of things to say, like, And I don't want it to get awkward. And, you know, those have those moments you're like, oh, like, is she going to talk? Am I going to talk? What's going to happen next? Who's going to speak? Any suggestions on how to keep the conversation going?

[A]

You yeah. Running out of things to say. I feel you. I remember I used to bring a 8 and a half by 11 sheet with like 14 cool things to say and I put it in my back pocket back when paper was a thing in the world. And I would go into the men's room in the middle of the date and like, okay, say the cool. Tell her the cool story about my trip to Italy and say this or that. So I remember that feeling. Here's the. Let me hopefully shine a light on this for you. By the way, my cat is sitting on my lap as I, as I talk. But this happens not because you have to. You're not good at saying things, but because the bar is too high for how good what you think the conversation needs to be. So we want to lower the bar for how good the conversation is. And if you believe in whatever you're talking about, that's going to resonate with a lot more women. So don't think what's the right thing to talk about or what's how to talk about it an amazing way. That's like good content. Just think about, okay, let me share about my life. Let me share a travel story. Have a back pocket topic so that when you do get in your head, you can say, okay, I'm gonna. I'll tell her about my trip to South America. And if I really get in my head, I'll also ask her about the fact that she loves the beach and ask her what her favorite beaches. So give yourself one or two back pocket topics so that if you do run out of things to say or start to, you can just kind of break glass for topic. And the nice thing about this is having that emergency backup topic usually means you won't even need it because you're not worried about running out of things to say because you have something to lean on.

[B]

Okay, that makes sense. So I. Okay, I like that. I actually have been going to the bathroom. I'm like, oh yeah, what was I going to talk about? So I'm glad. Glad I'm not the only one, Connell, who's scrolled through notes on their phone or piece of paper.

[A]

If you don't do this already, you could look at her hinge or her raya literally on the way to the date and say, okay, Emily, she loves musical theater and she's into science. Oh, and her family just did a trip to Ireland. Okay. And you can just have one or two of those topics ready to talk about. And you probably won't run out of things to say in Part because you're not worried about it, because you have your backup plan.

[B]

Okay, good call. And then I had a great first date last week. Monday. Good conversation, everything flew, and, you know, we really enjoyed each other. And then I kind of. I don't know what to do. Like, I'm like, I want to text. Do I text right after the day? Do I text the next day? I don't even know what to say. I don't want to sound needy and be like, hey, I had a great time, but, like, I don't heard a thing. I'm not interested. So I was wondering if you give me some advice on that.

[A]

Yeah, you want to show interest, but you don't want to come off as needy, but you don't want to go quiet. So you probably feel like you're stuck between a rock and a hard place with what to text. Is that what I'm hearing?

[B]

Yeah. Yeah. More of the rock than the hard place.

[A]

Okay, are you worried about double and triple texting or just not coming off as needy in your texting?

[B]

Oh, I already double and triple text, so that's not. That is, like, the least my, like. But it's more of, like, the needy. Like, you know, I don't want to sound like, oh, I'm desperate, but, like, hey, like, I had a lot of fun, but I want to see you again. So I don't know how to draw the line between needy and desperate, and maybe cool, I guess, is a good way to put it.

[A]

Okay, well, one of the core ways of flirting is letting a woman know what you want. Two of the sexiest words in the English language to a woman is when a man who she had a date with says, I want, it's not needy to say, I want to see you again, or, I want to take you out for a second date, or I want you to know how incredible tonight was. That's what I'm talking about. By clear statements of intent, leaning into that authentic self and letting her know that you're into her. There's nothing needy about that. What's needy? Would be sending her nine messages. Did you get my last message? Do you like me? How do you think the date went? Oh, I'm so sorry. I shouldn't have said that thing. And apologizing for yourself, that would be needy. But you letting a woman know you want to see her, you're actually giving her what she wants. You're giving her certainty, and you're being the man of certainty, which every woman wants in her life.

[B]

Okay, and then how soon after the date. Do you suggest texting? Is it

[A]

1 hour, 37 minutes and 12 seconds? You know, I'm very little Central Mountain time. And then that's totally different set of rules. Okay, let me ask you this. Who is your dream woman? What famous woman would you just be like, oh, my God, Connell, if that was my girlfriend, I would be over the moon.

[B]

Connell, when I was, like, 16, 17 was Keira Knightley. I'm so embarrassed to say this. Okay. Definitely changed since then. Probably right now. I'm going to go. Sydney Sweeney. I'm going to say.

[A]

All right, let me ask you a question. Here's a thought experiment, Matthew. You have a first date with Sydney Sweeney, and it goes pretty darn good. She's wearing her jeans, you know, because she's always marketing, and it goes really well. And Sydney Sweeney, before she gets back home in her Uber, she sends you a text and says, hey, I really had fun meeting you, Matthew. I can't wait to see you again. Would you a ghost her because what a needy bitch. Sad? Or would you say, yes, Sydney Sweeney's into me and take out a billboard telling everybody, you know,

[B]

I'm gonna go with B, but can we include C as probably text all my buddies and be like, hey, nobody's gonna believe this,

[A]

but okay, so why is it not needy when she messages you? That.

[B]

That's a great question. I guess it's because there's. The feelings are mutual, I guess. Or, like, because I feel that. I don't actually even know how to answer that. Yeah, I don't know how to answer that one. I'd hate to say this, but, yeah, I feel like it's. Maybe it's because there's a true connection and I'm truly interested in her. And I guess when you throw away.

[A]

Yeah, because you see value in her romantically, what she can bring to your life. Right. You want her to like you, right?

[B]

Yes. Yeah.

[A]

Because you see. Oh, my God, I would love to date this woman. She has so much to bring to my romantic table. Something like that. Fair to say, correct?

[B]

Yeah, fair to say.

[A]

Right. She's a 10, right. You want to look at yourself and project that version of yourself when you're on a date with a woman, which I know you are, you're. Because you're telling me how many. How loose and fun and in the zone you are. On first dates, you want to remind yourself that you're a. Well, I guess what I'm saying to you, Matthew, is you're as beautiful and sexy as Sydney Sweeney. Maybe not to me. You don't look quite as good as she does. But it comes down to the perception of value that that person has in you. And that's really what dating comes down to, is we look at the other person and say, is this person the kind of person I want in my life? And if that person is that kind of person, if they have a lot of. They have a lot to bring to your table, then you don't have to worry about you letting them know you're interested. A core tenet of flirting is just clear language, letting a person know you like them. And what we don't want to do is get too going, go too far down the rabbit hole of all the on tick tock and YouTube where it's like, don't, you know, play it cool. Don't let her think she's into you. Make her, make her wonder if she likes you. Maybe, maybe 25 years ago, that might have worked a little bit. But in the dating app world, when every attractive woman has hundreds of options, that doesn't work. Plus, it never even if it worked, it just feels bad. I'd rather you get in touch with your core worth. You know, you offer as a man that you're a regular guy 10. Sydney Sweeney is a society 10. You're a regular guy 10. I'm a regular guy 10. I like to think when I was single and you want to communicate with women from that place of, oh, I'm a 10, I'm a regular guy 10. Sydney Sweeney has countless dating options if she wants them. Right?

[B]

I'm sure. Yeah.

[A]

So do you, though. How many matches and dates are you getting on the apps? Tons and tons. Right?

[B]

Correct. Yeah.

[A]

You have an abundance of options. So I want you to project a side of you on dates that is, hey, I have an abundance of options. I'm an amazing guy. But tonight I'm with you. I hope we hit it off. And if you like her, there is nothing needy about a high value, authentically awesome man letting a woman know that you're into her and want to see her again. Nothing needy about that. If you came off as super needy and insecure and didn't have a good date, then that would be bad. But it's not about what you text. It's about what you're giving her on the date.

[B]

I see. Okay. Makes sense. And then, you know, some. Some other things that have also come up is, you know, picking up women not from the apps. Right. It's a farmer's market, supermarket, restaurant, bar. I Don't want to use cheesy pickup lines. But I also don't want to be boring. And I don't know how to flirt naturally in those situations. Any suggestions about how to break the

[A]

ice out in the real world?

[B]

Break the ice and then how to even break the ice with some flirting. Right. So it's not like a, hey, here's my pickup line. Oh, you're picking up the soup. Oh, let's. I don't know, you know?

[A]

Yeah, it's so scary to know you want to meet a woman out in the real world but then not know what to say. And my clients and I deal with this. I used to deal with it all the time. You don't need to say something amazing. You don't need to use some canned cheesy pickup line. If you use a scripted, planned pickup line, you're just going to sound like a robot. And that's not what women want. So what you want to do is give yourself one of three simple options. I call it the what to say framework. Here's how you know what to say. So you see a woman at the farmer's market and you choose. Either you want to ask her a question that makes sense, you want to give her a compliment that's G rated, or you want to make an observation about something that you notice, and then you use one of those three options as the way to break the ice. So question, compliment, or observation. So for example, my client Robbie was at Starbucks not long ago, and he saw this woman next to him and she put five sugars in a small or a tall coffee at Starbucks, five sugars. So he observed that instead of some planned pickup line, he said, hey, I see you take a little bit of coffee with your sugar. Just a dad joke. And she giggled and said, yeah, you caught me. I kind of have a weakness for sugar. And then they chatted for a couple minutes. Next thing you knew, he was getting her number and they went on a date the very next night. So he didn't need to use a planned pickup line. Just look at the situation and go, okay, compliment, question, observation. And whichever one you choose, it's 90% rejection proof because there's nothing sexual. There's nothing creepy. It's just simple, basic, friendly social conversation. And that's how you start a conversation that can lead to a date.

[B]

Okay. No, I'm going to try that. Appreciate that one. That's a good one. Okay. I think those are all the questions I had. Okay. For this week, I'm sure my question

[A]

for you Is when is your next first date? Any plan?

[B]

I think I have one this week, Friday, and then maybe another one Sunday as well. I'm trying to close the deal on that one.

[A]

Okay, fantastic. So on your next first date, I would say if, assuming you are genuinely liking her, look for a moment midway through the date when you just give her that clear statement of interest, you say, hey, you know what I like about you or what's charming about you or if you're really feeling it, you know what's sexy about you? Putting that, what I call man to woman communication out there. That's what keeps guys like you, me back in the day. That's what gets you out of the friend zone and getting a lot more second and third dates. And even if, even if she's not the one for you, long term, women just love a guy who just is not afraid to lead that dating dance and to flirt like you mean it. So yeah, flirt like you mean it.

[B]

I'll give it a try. I appreciate it, Connell.

[A]

Cool man. Hey, thanks very much for listening by the way. By the way, if you like, Matthew would like to talk with me about your dating results and taking them to a new level. And if you struggle with flirting, if you struggle with what to say, then go to my website, go to datingtransformation.com you can book a free consultation call with me and we can get on the phone and talk about how we can get you flirting like you mean it and getting you really good at what to say and flirting and getting you out of the. Getting you out of the friend zone and into a really good romantic chemistry with women on dates and in real life and on, on the app too. So go to datingtransformation.com until next time. Thank you so much.

[B]

Thanks, Anna.