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Use these 5 Moves for Great First Dates

Featuring NYC Dating Coach Connell Barrett
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Want to learn how to have great first dates? Listen to this episode of the Dating Transformation podcast to find out 5 moves that'll tip the odds in your favor.

First dates can be scary. Will she like you? Will you run out of things to say? Will there be awkward silences? Will she dump you for the cool bartender with the man bun? Questions, questions…

Fear not. Your host, dating coach Connell Barrett, has had more than 1,000 first dates. In this episode of the Dating Transformation podcast, he shares the 5 essential moves that he and his clients use to have great first dates with wonderful women.

Stop going on lame dates and start making sparks fly. Listen now!



"Good texts before a date are like movie trailers -- they build buzz and get her excited for the main event."

-Connell Barrett

Featured in the episode

Connell Barrett
Founder and Executive Coach of Dating Transformation


00:00 - Introduction
00:55 - Transforming Lackluster First Dates into Spark-Filled Connections
04:19 - Unlocking the Art of Flirty Texting Before Your First Date
08:37 - Creating Excitement with Fun and Engaging Texts
11:45 - Building Anticipation: Preparing Her for a Memorable Date
14:26 - Light-hearted Delays: Turning Lateness into Playful Banter
16:29 - From Jackass to Awesome: How Vulnerable Stories Win Hearts
19:25 - "Opening Hearts: The Magic of Raw and Real Storytelling
23:10 - Fun and Connection: Games That Elevate First Dates
24:51 - The Magic of Eye Contact: Staring Contests and Romance
27:31 - Outro

Produced by Heartcast Media

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Because nothing is worse on a 1st date than awkward. Silences.


Connell Barrett:


Welcome back to the dating transformation podcast. I am your host, Dating Coach, Connell Barrett. I'm here to help you learn to flirt, gain self confidence, and get a great girlfriend. All before the end of this episode. I'm that good. It's gonna happen in about 23 minutes. You're gonna meet her in about 5 minutes. No. Okay. Anyway, maybe not that fast, but quickly. That's what I do. I help guys get great girlfriends all by being authentic. Radical authenticity, I call it. And today, I wanna talk to you about 1st dates and how to go from lame, boring, fine, so, so, first dates to first dates that have sparks. 1st states where you and she are just so connected. 1st states where you're having a blast together. I'll bet you if you're getting 1st dates and you might not be. And if you're not, don't worry about it. It's very fixable. But if you are going on 1st dates, occasionally, I'll bet that you are struggling with things like running out of things to say. You might fall into interview mode. Oh, dreaded interview mode. You might have good conversations, or you feel like they're good conversations where the conversation flows, but then you find out a day later when she texts you that she's just, quote, unquote, not really feeling it. And that's really frustrating because you say, oh, what did I do wrong? Through everything I thought we had a good vibe. And or even worse, you might have been struggling with 1st dates where you have those long awkward silences. You know? So here's the thing about awkward Think about awkward slots. Awkward. Awkward. Sorry. What was that? Was that awkward? Did I make it awkward for you? That's the thing about awkward silences is if you're having those on 1st dates, then you're probably not having second dates with her. So we wanna fix this. Because nothing is worse on a 1st date than awkward. Silences. We don't want that. So let's talk about fixing this. So what I did was before this podcast, I was just thinking, alright. What are 5 essential elements that have been on every or almost every good first date I've had? And I jotted down the first five things that came to mind. Today's today's episode, I'm gonna give you my 5 essentials for great first dates. Or put another way these are the 5 things that have happened on pretty much every 1st date I've had that went really well. And I've been on a lot of 1st dates, roughly a 1000. That's right. Roughly a 1000 first dates. Because I am old, dear listener, I am so old that I used to swipe right on an abacus. Okay. Sometimes my jokes are stupid, but just know that I've been dating a long time. And so I've been on about a 1000 first dates. And I realized recently, you know what? There's a handful of things that I did on the very best first dates I've had. So I'm just gonna go through my top 5. Let's call these my top 5 first date musts. My top 5 first date musts. So here we go. In no particular order, Number 1 is texting before the date. Leading up, I should say I should say fun, playful, flirting, flirty texting before the 1st date. That totally changed the game for me on 1st dates many years ago when I first realized the art of how to do it. I think texting before a date is the same as a movie trailer, and the date itself is the movie. And I respectfully disagree with some of my dating expert cohorts out there. Some of them teach, oh, you know, just use texting. Use texting as a tool to get the date. Texting should be just about logistics, and I disagree. I think texting can be a tool that dials up the fun flirty banter. Texting is a tool that makes her excited about meeting you, puts you on her mind, and gets you on her mind in a really good way. Why wouldn't we wanna do that? So nothing wrong with texting just for logistics, but you're missing an opportunity if you're not using it. So, yeah, think of texting as a coming attraction, and the first date is the movie. I remember I had a first date. This was so many years ago. This is way way back when I first got into this. And the late actually, this is the middle double zeros. Because I've been training and working in this area since 2005. 2005 was when I first said, okay. I need to start working on my dating life. And about a year into this, I had been getting really good at the predatory texting, funny, flirty texts that lead up to the 1st date. And I remember I was going back and forth with the woman I was gonna meet that night. And I just remember her writing to me saying, about 2 or 3 in the afternoon for a planned 8 o'clock date. And I remember her saying, hey. I can't, I can't wait to, I can't wait to meet your smart ass tonight. I remember that. She was really excited about meeting me because we had texted a lot up to that point. And I in that moment, that was, like, an epiphany for me realizing, woah. You know what? We can use texting to get her super excited about the date. And then the date went great. The date went great with this woman from many years ago, so I always remember that.


I'm gonna read your mind. Ready? I'll bet that you would love to confidently approach women. Get great matches on the dating apps, flirt with charm, and attract your dream girlfriend. Right? But fear keeps you from approaching. You're not sure how to flirt. You struggle on the apps and desirable women just don't seem into you. Well, I have great news. Dating coach, Conor Barrett, can help. He's guided thousands of men like you to more confidence and help them attract their dream girlfriends. So book a free strategy called today to see if Connell's coaching is right for you. On your call, Connell or a team member will give you personalized advice to help you have more confidence, more dates, and more fun. Oh, and you'll be dating women as your best self. A charming gentleman. That's because Connell does not teach creepy pickup artist tricks. He unlocks your most confident self so you can make authentic, romantic connections. Your next steps: Book your free call today at dating transformation.comforward/contact and grab a time that works for you. Then you'll be on your way to more confidence, better results, and attracting bright, beautiful women. So you know, soon, Connell will stop taking on new clients. So book a call today while you still can. Go to dating trans dot com forward slash contact and transform your love life. Bye.


It was that moment for me where I realized, hey. Texting is a trailer coming attraction, and the date is the main movie. So let's talk about best practices for doing this. A lot of guys ask me how much I should text her before a date? And my answer is It doesn't matter. Lot or a little as long as you're giving as long as your text messages are giving her value. They're making her smile. They're not asking for much. They're basically getting her excited about the date. So don't worry about how often you text. As long as you're giving her value and as long as the message, the frequency, I should say their reciprocation is roughly 5050, maybe 6040. Don't worry about it. So that could be 10 text messages a day if you and she are pinging each other back and forth, which is great. It's probably gonna be less than that, though. Might just be 1 or 2 texts per day or every couple days, but Don't worry about how many texts you send. Worry about the quality of the text messages. If you're giving value, if you're sending good little memes, jokes, fun callbacks to things that you and she have talked or laughed about, asking her good questions. If you're, in other words, making her smile, she's gonna want more. So less is not more if your text messages are good, more is more. She's gonna be loving it, and then you're gonna start getting messages from women. Like I get where they say a day before the date, day of the date. Oh my god. I can't wait to meet you. I can't wait to see you tonight. I'm finally gonna meet you. I'm so excited that many women say that to me. I'm not trying to brag or anything. I'm just saying, This is why I coach this stuff, and I want you to get those kinds of reactions too. So don't worry about how often or how many messages worry about the quality. Make them fun, funny, interesting. Filter all of your pre date text messages through this lens. Will this make her smile? Is this likely to make her smile or keep her interested or get her wanting to write to me back. And if what you're about to send does not meet that criteria, don't send it. Don't ask the boring question. How was your day? How was your weekend? Don't do that. Make it, make it give value, make it fun. How do we do that? Couple strategies here that I like to use, and my clients use all the time. First of all, I just like to keep the fun banter going. Right? I like to send messages 1 or 2 days before, like, One of my favorite ones is I'll text the girl. Oh, hey. Just letting you know that I'm at the gym getting my pecs ripped for our big date. And then parentheses, nervously pacing and twiddling my thumbs. And, I've had women write me back with a big LOL, writing me back with weightlifter emojis, but all the things they're doing before our big date, one of the messages I like to have my client send, and we personalize it. I don't literally have a copy and paste version of this. But I like them to write, like, actually, like, 2 or 3 hours before the date starts. You send her a message that says, Oh, hey, Katie, just so you know, I look really handsome tonight. So you have been warned, winky face. That kind of cheeky foe, arrogant text sends a really good message to women because Only a very confident man would send that kind of cheeky text message. Right? You know, you're not actually telling her that you're super hot and handsome. You're actually making fun of the kind of guy who would say that. But by making fun of that guy, you're kinda getting the same stature improvement in her eyes. That is good for dating because she's thinking, what kind of guy would say that? Only a really confident funny guy. So I sent messages like, hey. I'm excited for our date. Here, I'm at the gym, getting my pecs and abs totally ripped for you. Just so you know, I'm looking really handsome tonight. I like to do that one. While you're by the way, you can text a girl right before she arrives. You know, you get to the bar and scope out a spot and get a really good seat for the 2 of you. And you can say, hey. Just letting you know I got to the bar, and I grabbed us a spot up at the bar. You might add something like, oh, and I'm the, I'm the handsome I'm the handsome well dressed man fighting off all the ladies. Better hurry. So those kinds of little fun, little playful playful jabs, playful comments, women tend to really like that. So, yeah, think of fun messages that lead up to the date. It's all about dialing up the fun, dialing up a little bit of romantic tension. And oh, and then invariably, many, if not most women, will be at least a little bit late. Before the 1st date. So when you send that message saying, hey. I'm at the bar. I'll see you in a few. She'll probably say something like, oh, okay. Cool. I'm actually running about 5 or 10 minutes late, just so you know. Then you can write this. You can say something like, Uh-oh. 5 minutes late. Okay. Well, you owe me one drink for every minute late you are. And I like the good stuff. So I hope you brought your credit card. So you can , you're putting some pressure on her, but it's not real pressure. It's its romantic playful tension. And, of course, it's a joke. You're not really expecting her to buy you 5 drinks. If you are, you have a drinking problem. Anyway, yeah, this is very effective. I've had, like I said, I had a couple different many women over the years say, hey. Gosh. I can't wait to see you. My girlfriend, Jess. I was so excited before our first date. She actually wrote to me saying we were texting back and forth fifty times, at least. From the moment we matched on this dating app, the league, to our first date, Jess, and, and I must have texted 50, 75 messages. And I remember her saying, The day of the date or maybe the day before she wrote and said, hey. I'm really liking our banter. She kind of broke character for a minute and just said, I'm really liking this. So, yeah, think about pre date texting as something that's gonna get her excited about the date. Okay. That's number 1. That was the one I wanted to spend the most time on. Number 2, another must for a 1st date is sharing a personal story. Come to a date ready to share an anecdote. A personal anecdote. You want it to be true, of course, and you want it to make you not look cool. Be vulnerable, in other words. So don't come to a date ready to tell a story about the time you hit the home run to win the high school game, or don't make it about how cool it makes you look. There's a real power in being vulnerable in sharing a story that might make you look like a Jackass in the past, but because your current awesome, amazing, authentic self is sitting next to her as you share the story. You actually look really awesome because you're willing to share a story about something you messed up, something you screwed up. On 1st dates, I've told the story about my my failed 9 week marriage, I told a funny story from high school about the time I faked back spasms to get out taking a test, I told the story about cheating on a test in high school, getting in trouble for cheating and how I was so scared of getting suspended. And then I've just told, like, crazy fun weird travel stories. So I will tell a great travel story about the time I got poorly mugged in Amsterdam. This guy tried to mug me, but he was so bad at it that I basically blew him off, and there's a funny story about how he was pretending to have a gun in his pocket, but he had a bomb instead and the cops came over. Anyway, think of true vulnerable stories that don't make you look good in the story, but make you look good now. You know? Yeah, be vulnerable. So share a good personal story.


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The thing about storytelling is when you're opening up and being really honest and raw and real with a woman, And talking about something you messed up or talking about something from your past or sharing a fun story, you're giving her the green light to then follow suit. And then have her share real vulnerable stories. So and then a really good date can just be two people swapping stories about their lives. That creates a great connection. So be a storyteller. Share a personal story. First date must be number 3. This is so simple, but powerful, so I'm psyched to share it with you. Number 3 is to give her a power compliment. Give her a powerful complement. What's a power compliment? It's something about her, the person, the girl, the woman, inside that you find sexy and beautiful and attractive. Tell her what it is and use the word sexy. Or or at least something that's romantically charged. Most men, if they have the courage to compliment a woman at all, they make it about her looks. And there's nothing wrong with letting a woman know she's physically visually attractive to you, but it's what every guy does. Or it's what it's what few guys who do compliment women. It's usually like, oh my god. You look beautiful. You're stunning. I love your dress. You look incredible. You're gorgeous. That's fine as far as it goes, but it's pretty common. And what's more powerful is to give her a powerful compliment, which is to tell her something internally about her that you really like. I remember I was on a 1st date once, and This woman just had an amazing mind. She was very articulate, funny, goofy, and had a silly sense of humor, And I just remember saying, hey. But you know what's really cool and sexy about you? You're so you have such a weird sense of humor. You're quirky and weird. I love the way your brain works. You make interesting connections, and that's really attractive to me. And I could see how she took that, and she knew it was genuine. But it really moved her because I was telling her that I was basically saying, hey. If any guy can see your outer beauty, I can see your inner beauty. So on that 1st date, notice what you notice about her, other than looks, notice what mannerisms or traits or inner qualities you find beautiful and tell her. It's not a big deal. You're not making a big deal out of it. You're just saying, hey, by the way. I can't believe you moved here at xyzage. All by yourself? Wow. You're so brave. You're so courageous and brave. That is really beautiful, really attractive. I like that about you. I'm not easily impressed, but you're impressing me. And, yeah, you use the power of a power compliment. Okay. First date must number 4 is movement movement, meaning don't just sit on the same bar spool for 3 hours. Go to a second place or at least plan to. Have a second spot in mind that you can go to so that you can change the scene. This kind of logistical movement makes a date feel like more of an adventure for both of you. It feels almost like if you go to two or three venues, on one date, then it's like going on 2 or 3 dates at one time. My client Teddy recently had a first date with a woman, and they went to 5 different places on that date. This was his first date. He just met her that day. He approached her during the day during a seminar I was doing with him here in New York City where I give guys in person coaching. Teddy walks up to this beautiful woman sitting at a coffee shop, having coffee. They went on a date that night. They went to five locations, and the six locations where they went back and they hung out at his place. So the power of changing locations, not only is it does it feel good to just move around and not have feet stuck on the same spot for 3 or 4 hours. It shows leadership. It gives our brain a nice sense of variety. And, also, if you and she want it, you might end up going back to her place or your place. It's a lot easier to do that if you've gone to 3 or 4 other places first as opposed to being on a bar stool for 4 hours and saying So, wanna come to my place? It's like, no. She's not gonna do that. But if you've already had a fun adventure where you've hit up 2 or 3 cool spots, your place or her place or wherever, That's just the next place for you 2 to hang out and get even closer. Okay. And then your 5th and final 1st date must is oh, this is so simple, and I can't wait to tell you about it right now. It's to play games. I don't mean being a game player. I mean, play actual games. Play a couple games on a first date. 2 truths in a lie. Have a staring contest. Thumb wrestle. I there's a bunch of games in my book in the the 1st 8 chapter of my book if you want more. Just play games. The simplest ones would be too too soon to lie. I love doing steering contests because I'll just say, okay. Here we go. Ready? Let's play a game. Let's do a steering contest. And the rule is you are not allowed to look away and you're not allowed to laugh or to smile. Are you game? Let's see who wins. And, of course, as soon as you tell your date, that you're not allowed to smile or laugh in a staring contest, she's gonna not be able to stop laughing. It's gonna be so hard to contain it. And plus the eye contact that comes with part of a steering contest creates a real strong emotional connection It gives you it gives you a reason to look deeply into each other's eyes, which is super attractive. And, and romantic. So I would say be a playing game. Like, I learned coin magic. I would do coin tricks for girls. Yeah. I know a lot of first date games. So find 1 or 2 first date games that they don't have to be they don't have to be amazing. It can just be, 2 lies, one truth, 2 truths and a lie. In my book, I talk about the question game, where we just take turns asking questions, but you have to tell the truth. I play a game called the first time where you take turns asking each other about the first time the other person did blank. So you might say, okay. Tell me about the first time you flew as an adult or flew by yourself on a plane. And then she'll say, okay. You tell me about the first time you had a date, had a first kiss, whatever it was. So it helps you take the often stiff awkward get to know you process of a date. It pours it into the container of a game, and everybody likes playing games. Everybody. Everybody loves a game. So play games and play games with girls. One final tip about that is two games per date should be a max. Any more than that, it comes across as a little bit gimmicky. So those are the 5 musts of a great first date. Text beforehand, kinda like a movie trailer before the coming attraction. Share her personal story number 2. Give her a power compliment number 3. Have some movements change locations. Take her to at least one or 2 other places. And then number 5, play some fun first date games. Alright. Until next time, you guys, remember your future incredible, gorgeous, cool, amazing girlfriend. She's out there. She already likes you. She just has to meet through real authentic you. See you next time.


Thank you for listening to the dating transformation podcast. For lots of free tips, videos, and other goodies, go to See you next time.


Produced by Heartcast Media.

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Dating Tranformation with Connell Barrett

Welcome to the Dating Transformation podcast. I'm coach Connell Barrett, and I help men build confidence + connect with women by being their own authentic selves.

dating sucks but you don't #1 Amazon bestseller

Get this Book & Attract Your Dream Girlfriend


NYC Dating Coach Connell Barrett

106 W 32nd St, New York, NY 10001

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