How to Get a Girlfriend with Connell Barrett - 21 Flirty Ways to Make Her Feel Authentic Attraction (How to Escape the Friend Zone, Part 2)
Episode Date: August 5, 2026You know what sucks? Thinking a date went well only to hear her say, “I didn’t feel a connection.” Dating coach and bestselling author Connell Barrett gives you a practical roadmap to avoid the ...Friend Zone—before, during, and after a date. He shares playful pre-date texts, flirting strategies on the date, and funny next-day messages that make her laugh. Get ready to start hearing, “So when are we going out again?”DO YOU STRUGGLE WITH FLIRTING OR TEXTING? BOOK A FREE CONSULTATION WITH CONNELL: DatingTransformation.comGET A FREE COPY OF CONNELL’S BESTSELLING BOOK, “DATING SUCKS BUT YOU DON’T”: Email: connell@datingtransformation.com (Write “Free Book” in Subject Line)
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So don't be mysterious.
Don't play it cool.
Play it clear.
Let her know you like her and you want to see her again.
Welcome back to how to get a girlfriend.
I am your host, dating coach Connell Barrett, helping you meet women, flirt, make romantic
connections, and yes, get a great girlfriend.
And do it all by being authentic.
This is not about sketchy pickup artist tactics.
It's about being your real self and learning how to lead that dating dance.
So you can get a great girlfriend.
And this is part two of the two-part friend zone mini series.
In the last episode, I talked about these three channels.
There are only three social channels on which we communicate,
not counting our family members.
The three channels is men that we're going to talk to people in one of three channels,
is friend to friend, business slash transactional,
or man to woman.
And if you ever get stuck in the friend zone, it's probably because you're speaking to women
on dates or in conversations, women you're attracted to on that friend-to-friend channel, most likely.
Or you go on a date and you're friendly with her, but you don't flirt.
And so that was the last episode.
I'm not going to repeat all of the concepts from the last one, but check it out if you missed
part one.
Today for part two, I'm going to give you, gosh, 20 plus practical tips to not just stay out of the friend zone, but to make sparks happen before the date even begins.
What if you could get out of the friend zone and start making flirty sparks happen before you even met that woman?
Yes, it is possible.
So that's what we're going to talk about.
Here we go.
Let's get right to it.
First, I want to say that before we talk about the moves.
the mechanics, the flirty things to say and do, all of this is built on the foundation of you
knowing and feeling your worth as a man. Basically, you're enough. I can and will teach you
all the things I teach my, I've had over, I've had over 2,000 clients in my dating career,
2,000 men who I've worked with one-on-one, almost 2,000 men, I should say, almost.
2,000. And I'm only as good as my clients because romantic connection and a woman choosing a guy to be
her partner, she's not going to choose you because you flirt well. She's going to choose you
because she sees that you bring so much to her life and that she sees you as a man of worth,
what I call a radically authentic man. That worth, that value has to be there. And for her to feel it,
you have to feel it first. So please know that your romantic worth comes first. And all these moves that
I'm about to teach you, they're only going to work as well as you feel and know that you're a man
who's a great catch. So think of flirting as the frosting and your romantic worth and value to women.
That's the cake. Flirting makes the cake taste good, but man, that cake has to be there. So by the way,
if you struggle with wondering if you're even enough, if you feel like, oh man, maybe a
I'm not in the league of most women. Maybe I'm just not what women want. Then please work on that.
Work on that. Find ways to discover and on earth your personal self-worth because it's everything.
My book starts off with a story where I'm hyperventilating in the bathroom stall at a bar,
about to go approach women for the first time. And what was happening there is I was so afraid I was
about to find out women just didn't want me that I was worthless. So I hope you don't feel that way.
if you do, you got to get that handled because the best flirting moves in the world are only going
to work as well as the foundation that it's built on. So if you really struggle with this, you can
book a call with me. One of the core things I do with my clients is I help them get their confidence
level sky high so that you see yourself as a true man of worth and value. So go to my website.
If you want to work with me, Datingtransformation.com, or if you just want to talk about how my coaching
works. Primarily, I help guys who really struggle with self-doubt. They just feel like maybe I'm not
what women want. So if that's you, work on it or help me, let me help you work on it, and I can work
on it with you. Go to datingtransformation.com. Okay. Now, when you have that confidence, you do truly
believing yourself, then it's really about how we talk to women and romantically communicate.
In other words, flirt. And before I go through all these things,
different friend zone techniques and strategies. Let's just keep it simple. Flirting actually isn't
complicated. Flirting is just play. It's playful communication. Logical informational conversations,
that's the friend zone. How are you? Where'd you go to school? How long have you worked there?
Flortation is fun and playfulness. It's basically the friend zone is Mr. Spock and flurts.
connection is Captain Kirk. Captain Kirk is emotional, visceral. Spock is logic and facts and figures.
You want to be a lot closer to Kirk than Spock. And flirting is just about light playfulness.
Okay. So you're going to see, you're going to notice the theme here, all the different ways we
smashed out of the friend zone. It's about bringing that light, playful, flirtatiousness.
So the cool thing about getting out of the friend zone is you can do it before you even meet here.
Here's a quick story. When I first started,
cracking the code on what does work with women. I was about a year into working on my dating life.
This was nearly 20 years ago. Actually, it was 20 years ago. I'm working on my dating life,
and I'm starting to figure some things out. And all of a sudden, I realize, you know what,
I can get women excited about meeting me even before we go on the date. I would have a lot of
playful, fun bantery texting with women. I remember a woman named Jennifer I met on
match. Match.com back when it was a website, not an app. And I remember Jennifer and I were
playfully bantering and teasing and flirting back and forth. I was getting the hang of it.
And I remember I'd never had a woman say this to me. She texted me, I can't wait to meet
your smart ass tonight. And she was just so excited about meeting me. And that was new to me.
And so the point is you can get a woman excited about you and get out of the friends
zone before you even meet her. So before the date, here's how we start getting out of the friend
zone. Make sure we stay in that man to woman, romantic, flirty zone. First things first, before the
date, when you ask her out, ask her out with certainty and clarity. Make it clear that it's a date.
You're not hanging out or getting together. So you don't want to text things like, hey, we should
get together sometime, maybe hang out. No, you want to ask her out with clarity. You want to ask her out
with clarity, hey, let's grab a glass of wine this week. You're very charming. And I kind of want to
see if you're as charming in real life as you seem here on the app or by text. So that's really
important. Women like a man who leads. And clarity is an important first rule of flirtation.
You want to be clear. I have two little catchphrases you might have heard me say. I say this on
Instagram a lot. So you might have heard this if you know my social media at all. My two little
catchphrases are flirting is play. It's just playful conversation. Playful back and forth.
Other words, it's not a game of win or lose. It's a game of tag. Tag you're it.
The other thing I say a lot is is just be clear. Say, hey, I like you. And flirting can be about witty,
fun back and forth banter, which I love. I love to do and love to teach. But the bottom line
is it's just be clear first. Hey, I like you. I want to take you on a date. So be clear when you ask
her out. Use the word date. I want to take you on a date or make it clear you're asking her out.
And I like to ask out to be clear. And I love this phrase. What nights are you free this week?
So basically I want to take you on a date.
When I started doing this, I would message a woman, hey, I want to meet you.
You seem awesome.
And I want to see if you're as wonderful in person as you seem here on the dating app.
What night's are you free?
And women were like, yes, sir, yes, sir.
I'm free Tuesday and Friday.
Tell me where to be.
Women love a man who leads.
And another thing you can do after you start sending this clear askouts, she says yes,
then play a little bit, tease, before the date as you lead into it.
One of my favorites back in my single days was I loved sending a woman a message like,
this is one or two days before the date.
I would say, hey, just so you know I'm looking really handsome, just got a new fresh
haircut.
So you better bring it tomorrow night.
And that turned into a fun one-upsmanship back and forth.
She's like, well, I'm thinking of wearing this out.
What do you think?
And then all of a sudden, this girl is sending me a cute selfie.
And I'm like, I don't know.
I give you like a seven and a half out of ten for the outfit, but my biceps are popping or whatever.
So you can banter back and forth playfully like that.
So that's like a, that's a confident, playful, predate flirt flirtatious text.
You can send a fake nervous predate text, which is also a fun bantery text to send before the date.
You can send something like this.
Say it's the day of the date.
You text her about noon, 1 p.m.
Hey, I'm at the gym.
Getting my pecs huge.
So I'll look amazing tonight.
Parentheses, nervously twiddling my thumbs.
So you make a joke about how nervous and scared you are about the date.
That's actually, you're actually conveying the opposite by saying that.
but you're playing the part of the nervous guy.
It's just fun banter.
Another thing, oh, I used to send this a lot, too.
I would always get to the date early, five or ten minutes early.
So I'd usually say something like, hey, I'll probably be there early.
Look for the dashing redhead trying to fight off all the other women.
It's a faux arrogant thing to say.
Obviously, I don't actually mean that.
but that sort of pretend feigned arrogance is very attractive to women who like that kind of bantery humor.
So if this is not authentic to you, don't steal my lines if it's not you.
But if this does sound like something you might say, feel free.
Another pre-date texting tip to not get friend zone.
It's actually not even about friend zone.
It's about how to not get canceled is don't confirm the date.
like you're confirming a business lunch.
Don't text.
So we're still on for tomorrow night, right?
None of that.
Don't do that.
You want to confirm the date.
You do want to confirm the date because you don't want to show up
and all of a sudden you find out she had a change with plans
and just telling you.
So you want to confirm the date in a playful light way.
You know, you want to say things like, oh.
So yeah, you're going to love the cheesecake at this place tomorrow night.
It's going to blow your mind.
can't wait to meet you.
What's your favorite cheesecake?
And then when she answers you, she's basically confirming the date, but you're doing it
with some confidence and some warmth.
And last thing I used to do, your mileage may vary, but I had a lot of success with it.
And a lot of my clients have is, so you get to the bar, you get to the venue.
And what happens so often with so many people, women, she's late.
She's four or five, six, ten minutes late.
Very normal.
So I did this literally 50 times.
I get to the bar.
I tell her where I am.
Hey, I'm the tall, handsome ginger up at the bar fighting off the ladies.
Better hurry, LOL.
And then she writes back, ha, ha, ha.
Oh, by the way, I'm running late.
And then I might just put a little more fun teasing pressure on her and say,
okay, well, you owe me one drink for every minute you're late.
And I like the good stuff.
So hope you brought your Amex.
Again, very bantery, very playful.
And it lets her know, wow, this guy is really bringing some energy here, right?
Okay, those are some pre-date tips.
During the date, here's how we stay out of the friend zone.
First, when she arrives, no handshake.
Warm, quick hug.
It's a date, not a business collaboration.
Next, sit next to her if logistics allow.
Let's assume we're talking about a classic first date for drinks.
Sit at the bar if you can.
I recommend that you, if you're a drinker, if you're going to be at a bar for the date,
then grab a spot at the bar.
That way you're next to her, and it creates a physical proximity that allows the two of you
to just literally and physically be closer to each other.
and perhaps have a little bit of a flirty touch, excuse me,
flirty touch as the date goes on.
Another first date tip.
Oh, here's something you do before the date starts,
but you're at the bar, you're waiting for her to come in.
Check in with your vocal tonality.
Beware of up-talking or sounding really kind of, you know, soft.
There's something about loud, not loud,
but there's something about a confident resonant vocal tonality that just makes women attracted.
I think it just comes down to evolution, you know, the alpha male, the tribal leader on the African Savannah,
when we were all evolving hundreds of thousands of years ago, he was probably the loud guy.
So don't be, I'm not saying be loud.
Just make sure your vocal tonality is dialed in.
What I used to do is I'd get to the venue and I would take my,
phone out and I would have a pretend phone call. I would grab my phone and say, hey, what's up?
I just got to the venue and I ordered a vodka and soda. I'm just waiting for her. Yeah, just
waiting. And I wasn't talking to anybody. I just wanted to get my voice accustomed to the environment
and be one or two or three percent louder than the environment. Here's what gets you stuck in
the friend zone. She walks in and you're like, hi, nice to meet you. How are you? How are you?
You look nice. You look great. Oh, you look so much better than your photos. It's like, that's not how
anybody talks. You don't talk that way when you're with your good buddies. When you're with people,
you're comfortable with. So the first thing that goes when you're nervous at the beginning of a
first date is going to be your voice. So do that little vocal tonality check in. Another tip for the
date, stay out of that front zone is lead, lead. You're always leading the date. Not always.
but mostly leading. Dating is a dance. Women generally want the man to lead during this courtship
phase. So you're leading, you're choosing the venue, or at least you're suggesting the venue for
her to sign off on. You're the one asking her out. You can choose, or for lack of a better term,
steer the conversation topics. I remember I was on a first date once with a woman. I'll call her
Joanna. It's not her name, but I'll call her Joanna. And Joanna, early in the date, she started
talking about a really bad experience she had in grad school. She had a tough, difficult situation
in grad school. She's talking about this for two, three, four minutes. And I heard this little
voice say, this is not helping the date. Change the topic. And I said, hey, we'll come back to
that in a second. But didn't you tell me this funny, didn't you mention this funny story about
the stray cat you adopted? And her face lit up. She's like, oh, yeah, the cat story. And then
she started talking about the cat story. And the date went from a really tough, rough start to,
she was lighting up and smiling, just talking about this cat. And what I was doing is I was monitoring
the topic, noticing, not monitoring, but noticing the topic. And just,
saying this is not a good topic. Here's a little thought experiment or a little visual that
always helped me. While you're on the date, imagine there's a little Steven Spielberg or Martin
Scorsese, a little movie director who's watching the date. He's sitting on your shoulder, watching
the date like it's a movie. And if the scene is going well, if the vibe is very light, playful,
or at least just good conversation that you're both enjoying, keep it rolling. However,
if you find yourself talking about politics for five minutes or Bitcoin,
or she goes on and on and on about what a mean jerk or boss is being,
and you're like, oh, God, this is not helping the rom-com movie of this date.
Yeah, I'll cut, cut, cut, cut, and then change the topic.
So that's part of how we stay out of the front zone.
take control of the topic of the date. I don't mean to be controlling. I do want you to be present
and in the moment and in the flow. Women love a guy who's present and in the flow. So don't be like a,
don't be like a, you know, a control freak about it. But just kind of notice, oh, my little Spielberg
on my shoulder, just notice the scene is not going well. Cut, new scene. In other words,
new topic. Another, oh, this is really important. Again, the essence.
of flirting is play. That's the essence of it, meaning playful light conversation.
So think as the date starts and begins to hopefully build momentum, begin to inject emotion
into the conversation. Less logic, less information, more stimulation, more emotion.
Basically, facts and figures will lead you to the friend zone. Emotion and emotion and
passion is what women want. I was on a first date with a woman named Jessica many years ago.
Rooftop bar first date. She is a 12 out of 10. Beautiful, stylish, so incredibly smart,
part-time model artist, good gracious, just an incredible dynamite person. And we're on this rooftop
bar in Manhattan and it's going pretty well. It's going pretty well. I'm doing my thing.
And I remember the topic of first states came up.
And she even said, oh, I hate it when guys just want to know all this, these facts about me.
I don't go out to like talk about facts.
I want to have fun.
I just want to laugh and have fun.
And that was just a great little moment of Jessica sort of saying, hey, this is what we want.
So here are a couple of tips to help you do that.
start sentences with, here's how I feel.
Or how do you feel about blank?
So let's say you catch yourself asking two or three or four informational questions.
That's okay.
Not the end of the world.
Don't panic.
You just asked her when she graduated, what her degree is and where she went to college.
Facts, facts, facts.
Notice that and say, well, what did it feel like when you graduated?
Or you, wow, you're a, you're a turn.
You're an attorney, you're a lawyer.
Tell me about the first case you ever won.
What did that feel like?
The word feel is a powerful word.
Because when you start sentences with feel, you're priming your mind to speak more emotionally.
And women want to talk from an emotional place.
I don't mean emotional like, oh, my God, facts and feelings and opening up.
I'm not saying that kind of emotion.
I just mean infusing emotion in your words, conversation.
And so start sentences with, I feel.
Here's how I feel.
Try it.
Just do it in your regular life, just as a fun exercise.
Men are so, we're just wired to talk about this happened today.
Here's my fact.
Here's the information.
And that's okay.
Nothing wrong with you or me.
I'm the same way.
But women on a date, they don't want to find out what happened to you.
They want to find out how you feel about what.
happened to you. This was a freaking brain-melting, awesome game changer for me when I kind of
started to get this. They want meaning and feeling. To help you get that, here's another tip.
Use love and hate. Use those words literally in conversation. You're having tapas on a tapas bar on a
first date. Say how much you love the food.
oh my god i love this i hope and hopefully you love it in other words have a strong point of view
love love love and a little bit of hate not a lot but a little bit i remember i was on a first date
once and the music was great and all of a sudden a country music song came on and i said oh my god
i fucking hate this song who is this is this garth brooks this makes me want to jump off the roof
and she just laughed.
I wasn't saying anything especially witty or funny,
but there's something powerful about making a strong emotional stance.
So use I love.
Pepper your conversation with I love.
I love this.
I love that you said that,
but I hate that you said that.
On my first date with my girlfriend, Jess,
I don't remember this for sure,
but if I recall,
I said,
oh my God, I love that you're so into Italian food.
She's Italian.
heritage. I love that you're so into Italian food and that you come from this big family of Italians
and we were talking about that. But I hate that you dislike ketchup because we had a fun little
debate on our first date about foods we love and hate. It was very playful. Again, playful.
So I'm like, I don't know. I don't know, Jess. I don't know if I can date somebody who hates ketchup.
That's a deal breaker for me. I mean, I just want a wonderful woman, beautiful, charming, witty. You're all those
things, but if you hate ketchup or if you like ketchup, I hate it. I don't think it's going to
work out. She's like, yeah, I guess we should call it a day. I guess we're not right for each
other. So you hear that banter, hear that that, that little bit of sarcasm, teasing,
light playfulness. That's what I'm getting at here. That's what I'm getting at. Let me jump in and
make an important point. I talk a lot about play and flirtatiousness. And I talk about man to woman
communication. Man to woman communication is that that's the sweet spot for you. Go back and listen
to episode one of this little two-part series if you need to. Thing is, let's not overlearn this lesson.
Some of my clients think, okay, well, I'll just be super man to woman, flirt, tease, joke, sexual, this,
that, no. Next tip, follow the 80-20 rule. What's the 80-20 rule? 80% of you conversing with a woman on a date
It's just you being authentic, yourself, just sincere, normal you.
20% is the play, the tease, the flirting.
In other words, 80% cake, 20% frosting.
So don't make the mistake I made back in the day.
I hired too many coaches.
I got too into this world of learning all about how to talk to women and connect.
And I got so into this, I thought, oh, well, I've learned all these techniques.
I'll just do all of it.
And I would just like rapid fire machine gun, flirt, tease, joke, neg, story, this, that.
And it wasn't relatable.
And it was also just hard.
It was really hard.
So you don't need to do that.
80% of you talking to a woman on a date or texting and flirting on an app, whatever it is,
any communication with her, it's just you being yourself.
but it's that 20% we want to add, okay?
What I call flirt, well, flirtation, man to woman communication.
Next tip, here's the simplest thing you can do to get out of the front zone or to keep
yourself out of the front zone.
I call it a clear statement of romantic intent.
Clear statement of intent.
It's the simplest thing a guy can do.
Look her in the eye if you're in person and just say, I like you.
Or you're charming.
or you're sexy.
Use clear, simple language.
The simplest way to flirt.
And for a lot of women, the most powerful way,
is you just tell her what you think and feel about her.
You just say it.
You just say it.
The first chapter of my book opens with this dramatic story of me.
I'd approached a woman named Kelly.
We're hitting it off on a rooftop bar.
I leave her alone.
I come back and these three Wall Street guys are talking to her.
And she's really flirting with one of them, this wavy-haired guy.
And I'm basically boxed out and she's like ignoring me.
And they're sort of pushing me away.
And with the help of my coach, I drum up the courage to walk over there.
I take her back.
I take her by the hand and say, hey, come with me.
I want to talk to you.
And I pull her away from these guys.
And I sit her down and I said, it's not cool of you to flirt with me.
You're with me tonight.
I'm a guy who goes for what he wants and I want you.
And I never made a woman swoon until that moment.
38 years old.
It took me 38 years to make a woman swoon.
Better late than never.
And yeah, so it's not about magic word.
It's about clarity.
It's about crystal clear statement of intent.
that's aligned with how you're feeling.
So you've got to be feeling it.
So on a date, or doesn't even have to be on a date, it can be before the date.
Text the woman.
By the way, you are very charming.
I can't wait to meet you tonight, see if you're as charming in person as I hope.
Then on the date, tell her.
Use these incredibly powerful two words.
You're sexy.
And tell her why she's sexy.
And if you really want to take this clear statement of intent up to like the nuclear
level, tell her she's sexy, tell her why, and make the reason why something that's not about
her physical appearance, make it about her very traits as a woman, her intelligence, her soulfulness,
her warmth, whatever it is. That's what she wants to hear. And because you're communicating
from an authentic place, I hope, she's going to see that it's real. On my first date with my
girlfriend, Jess, were on my rooftop at my apartment at the time, having a couple glasses of wine.
We met at a bar, had a couple drinks, then went back to my apartment for a rooftop beverage,
a glass of wine, two glasses of wine. And I was so blown away by how witty and funny she is.
I still am to this day. Anyway, and I looked through in the eye and I said, I have to tell you the truth,
you are so witty and so funny. That's so sexy to me. I'm not usually.
so impressed. Usually I'm the funny one on a date. I'm just trying to keep up with you. And she later
told me how much she loved hearing that. Because a lot of guys said to her over the years of dating,
you're cute, you're hot, you're sexy. But I think I was one of the few, if not the first,
who told her that the girl inside, the woman inside was sexy. Her very essence is a person,
her wit, her intelligence. And yes, she's very, very pretty. And I was also physically attracted
to her. But damn, I was just so, I was just so, I was just,
so drawn to her intelligence. She's so quick-witted. It's one of the things I love about her and one of the
things I started to fall for on the first date. I told her and it impacted her and here we are years later.
Okay. Next tip about staying out of that friend zone on the first date. Tease, but do it playfully.
Here's the secret to teasing. A lot of guys are like, okay, tease. Teasing is the secret to flirting.
Well, no, it's a tool. But it's a powerful tool. But here's the way to use it. You want to tease only about something that she would not take personally. You don't want to tease about like an identity level thing. You want to tease about like surface level behaviors or or tastes. So if she says she loves Garth Brooks, great. Tease her about that. I tease my girlfriend about like,
Michael Bublay. Nobody's perfect. So teasing about her favorite movie, her favorite band,
little small traits like she snorts when she laughs. That's a good thing to tease.
Don't tease about something that she could take personally. My client, Nick, once made the mistake
of teasing a woman. He was trying his best. God bless him. He was teasing a woman because she had
like three drinks on the date. And he joked about her being an alcoholic. She did not find that funny.
That's a serious thing that maybe she has a source spot about. So don't tease about something that a
reasonable person could take offense to. I once teased a woman I approached or I teased the fact that
she had this little shih Tzu dog. And I'm like, oh my God, your dog was like a little rat.
I'm basically calling her most prized friend in the world a rat.
It's stupid of me.
She did not like it.
So don't do that.
A couple more things you can do on dates to stay out of the friend zone.
So think of the date like the first 30 to 60 minutes of a date.
Light, playful.
As that goes on, then you want to start open.
opening up a little bit more. You want to let a lot of the teasing, playful, flirting,
schick, the compliments, the jokes, let those start to fall away and be increasingly open.
Be increasingly open. Here's a great way to do that. Tell a personal, vulnerable story about
yourself that is true and that doesn't make you look good, but that you've learned from.
Let me say that again, a personal story that doesn't necessarily make you look good, but it's compelling and somehow it shows that you learned or grew in some way, shape, or form.
For example, I talked often on many first dates about my failed nine-week marriage.
I had a nine-week marriage that was over quickly nine weeks.
And I started to do that.
Not strategically.
I just did it because I just said, you know what?
I'm going to be really myself.
I'm just going to be so authentic and real with women.
I don't care anymore.
I'm just going to be open.
And I started opening up about that.
And women loved it.
Not because there was anything magical in the story.
It was, I was not trying to impress her.
And the reason I had this marriage, nine-week marriage, look, it takes two to tango.
But I was insecure.
I was not, I had no self-confidence and I settled with the one woman who said she wanted to be with me.
And so I take a moment to talk about this on a date in the past because it shows a woman,
okay, this guy's got jokes. This guy's got a good personality. Hopefully she feels that way.
But also a woman wants to see the real guy behind the flirty moves. So opening up,
telling a personal story that about maybe maybe about a mistake you made in the past it could be
it could be about a personal failure you had but you want to talk about it not as a trauma dump
you want to talk about it as something you've learned you have grown and evolved that's really
important so the story needs to be framed as boy did I screw that thing up years ago but man
did I learn a lesson that's
one really good way to tell a story. Another good way to tell a story on a first date, it doesn't
have to be super vulnerable and open. It can just be like a fun story from youth. So like the, what's your
most embarrassing moment in high school? What was your most embarrassing moment in college?
That might be a great story to tell a woman on a date, whatever the answer might be. I do not try
this at home. Your mileage may vary, but I used to talk about my first sexual experience on some
dates when I was feeling really open and the woman was really game to like, let's get real.
I talked about my first time having sex. Not because it was a triumph for me. I was terrified,
petrified because I was so afraid of being bad at sex. And I talk about how it was over. How it was
over in literally three seconds. Poor Angie, my first, was so disappointed. So I tell the first
date story. I guess that'd be an example of actually a vulnerable story as well. So yeah,
being a storyteller, as the date goes on, be more open, more real, not that you're not being real,
but less like banter or jokey and more genuine and real, but still light, still yourself,
still yourself.
And then the other thing you can do on a first date to make sure you don't get in the friend zone
is a little bit of physical expressiveness.
It's okay to touch a woman on a date.
It is okay.
You are not going to be arrested by the Me Too police if you touch a woman on the shoulder
as you express a point.
Or you high five her when you and she find out you
both love the same, have the same favorite dessert. You both love Tiramisou. Oh my God, I love that
too. High five. Yes, you can touch a woman on a date. And different women have different preferences on
how they like to flirt. Some women love physical touch. Some women, not so much. Some women, it kind of
depends. So I do recommend that you at least experiment with some physical touch. Here's the way to do it
that makes it feel normal and not creepy to women.
Here's the secret.
This is so simple.
What not to do, here's what not to do and what you should actually do.
What not to do is don't touch at all.
Don't not touch at all.
That's no good because it's a date.
You want to be man to woman, not friend to friend.
But you also don't want to just touch like you are executing physical touch move
that some dating guru on TikTok said,
break the touch barrier.
I hate that.
I hate break the touch barrier.
Like executing touch is going to magically make a woman fall for you.
That's not really how this works.
Think of physical touch as just an expression, extension of your authentic expression.
You're making a point right now, if you can see me on the video version of this, you probably can't.
But I'm using my hands.
I'm moving.
we move our hands. If I was with you having a one-on-one conversation with you, I'd probably
like make my point and then, and then I'd touch your shoulder. Touch. So think of physical touch as an
expression, sorry, extension of your expression. And so that'll make it feel very normal and
human to her, this touch, because it is. And the other thing, the real secret that's just so simple
when I first learned this is have a reason for the touch. What not to do is what some guys
do when they say, well, I got to touch. And he just puts his hand on a woman's knee for like two
minutes. I had a former client. I don't even know if he hired me or not. But I remember I did a
consultation call with a guy. I'm pretty sure. I forget if I worked with him. But he said,
oh yeah, on my last date, I just put my hand on her thigh. And I just left it there. And I said,
okay, how'd that go? She's like, well, she kept moving my hand off. And then she walked
to the restroom. I said, well, yeah, don't do that. So the mistake is just putting your hand
randomly someplace is no good. Have a reason for the touch. Have a purpose, a very specific reason.
Here's a classic old school pickup thing that still can work. The jewelry inspection.
You notice she has a cool ring or a cool bracelet. You take her hand. Oh, hey, what's the story
behind your ring as you briefly take her hand and then give her her hand back? Or she's got a cool
bracelet. Hey, where'd you get this bracelet? What's the story there? And then you return her wrist to her.
If you just have a reason for why you're expressing that touch, it'll feel normal to women.
I had a first date with a personal trainer once. We were talking about physical fitness and training
and muscle tone. And I'm like, I said, make a muscle. And I made a muscle to tell her to, I gestured. And she
made a muscle and then I just touched her bicep. And I was genuinely interested. We were talking about
physical training, but it was woven into an organic conversation. And physical touch is one of the
ways that many women feel closer to a man on a date. Not all. Some women aren't into physical touch.
So that's why I hate the whole always break the touch barrier thing that other male gurus
say. Sometimes women love it. Sometimes they don't. Read the room.
Read the room. You'll be able to tell. If she likes the touch, you'll know because she'll touch you back.
You touch her arm. You high five her. She touches you back. You'll feel that it's mutual.
And if she's given back a little bit, then you can keep going. And if she doesn't, you can, of course, pull back.
Hope that makes sense. And one more thing about the actual date itself, going for the first kiss.
Should you go for the first kiss or not? That is the question.
I get that a lot.
My answer is this.
If it's a nighttime date, if it's like your classic bar, dinner, nighttime date, I'm talking first date.
If the conversation flowed pretty well, if not very well, at least pretty well.
You know, she didn't end the date.
She didn't look at her phone the whole time.
She was present with you.
She gave you her focus.
Then I recommend that you go for a first kiss.
Or at the very least, you tell her you want to kiss her.
So you make some sort of first kiss action or gesture.
Here's why.
I have never, to my knowledge, and I went on a million first dates.
Not literally.
I counted once.
I think I was on a thousand first dates.
I never, to my knowledge, lost my chance with a woman by going for her first kiss and she turned the cheek.
I got plenty of cheek turns and quote rejections, although they weren't always rejections.
Bottom line is there were plenty of times I went for a kiss and didn't get it.
I never lost any of those women because I went for it, to my knowledge.
In fact, some of them ended up saying how much they liked it.
They just weren't ready yet.
However, I know for a fact that many times when I wanted to kiss a girl, but I went out,
I was afraid.
I know I lost her because some of the women told me.
I was on a first date with a girl named Brandy in Brooklyn once.
Sorry, second date, second date.
Had never kissed her.
Second date.
We're in a park, moonlight, very romantic, summer night.
She's giving me the eyes.
There's touching.
She's sitting there, like, pouting her lips.
Kiss me, Connell.
She's basically screaming.
And I whipped out.
I didn't go for it.
And she gets up and walks away and says, well, I'll call.
I'm going to call it a night now.
She starts walking away from me.
and I knew what I had done.
And I caught up to her.
I, I, and I said, oh, hey, wait for me.
And I caught up to her.
And I then tried too hard, tried to write the wrong.
And I went in for the kiss and she turned away and said, I'm sorry, no, you had your chance back there.
She said that.
Exactly.
You had your chance back there.
Painful, yes, but a great lesson.
Thank you.
Thank you, Brandy, in Brooklyn for teaching me that.
So I've never lost a girl by going for it that I know of.
I know for a fact I've lost the brandies of the world.
So that's why I'm going to say to you, go for that first kiss.
If it's a nighttime date, especially if there's alcohol, maybe dinner, go for that first kiss.
Or if you're not able to pull that trigger, then second best would be look her in the eye and say, I want to kiss you.
that clear statement of romantic intent, that'll tell you how she feels.
If she says, well, go ahead.
Or what are you waiting for?
Or if she just kind of blushes and holds the eye contact with you, boom.
She is saying, you may kiss me now.
If she turns away and says, no, no, not here.
That's okay.
So I would never say always or never, but I say almost always go for a first kiss or
tell her you want to kiss her if it's a nighttime date and it went pretty well. If it's a daytime
date or if it's like a quick coffee, if it's a, you know, a lunchtime date or a quick little 20, 30 minute
meetup, read the room. Read the room. You never know. Sometimes you can go for that kiss.
Sometimes you don't want to. Okay. Let's talk about after the date. After the date.
A lot of guys ask me, well, what should I text her?
and how long should I wait.
I don't give a fuck how long you wait.
Let me rephrase that.
I don't want you to give a fuck how long you wait.
You are a man, an authentic, sexual, healthy gentleman,
and you're just texting a woman you're into.
You don't need to worry about games.
You don't need to worry about, am I needy, am I insecure, am I a simp?
No, you're not.
You're a man who's going after what he wants.
So if you had fun on the date and you want to see her again, you can text her before she gets home.
Or you can wait till the next day.
It's up to you.
Don't think about it from a place of what's the right strategy.
As tempting as that is, I advise you to not think, what's the right strategy?
I advise you to rather think of it this way.
What can I text her that will make her feel good about the date?
Or what can I text her that's honest and authentic that will make her smile?
And you can send that whenever you.
you want. I've been on dates where, oh my God, it went great. We kissed. We were into it.
She's on the way home and I'm texting her before she's home. I'm not worried about coming off
is try hard or insecure. No, I know she's into me. I'm into her. It's not try hard or
insecure to do that. And that said, here's a couple of strategies for you. After the date, a few different
ways. A few different styles of the next day text. And I do recommend, if you want to see her again,
I do recommend this. If you want to see her again, text her the next day, something. Don't wait
longer than 24 hours. Okay. So next day, there's many different options. You could send her a funny text.
Hey, last night was great. Do you have a Yelp page where I can leave you a review? You can go kind of
funny. You can go, you know, funny and a little.
little cheeky. Hey, did you have fun last night? Text one for yes, two for hell yes. This is a
classic. The next one. I love this. Hey, I just wanted you to know that you had a good time last night
and you want to see me again. I sent that to my van girlfriend, Katie, or after our first date.
She said she was reading, she was on her phone when that text came through and her girlfriend was
with her, like kind of watching the text come through to Katie from me. And she wrote back,
or she later said, we both laughed at that. That was really good. So a lot of women like that.
Hey, it's a very, it's cheeky. And if you're not a cheeky, smart ass like me, you don't need to
send that. I'm just giving you options. But that's a classic. I love that. Hey, you had a good time
last night and you want to see me again. Another funny one is you text for this, the, the, the, that you
pretend like it's not a text for her.
her. You text her, mom, dad, I think I met the one last night. I just hope she doesn't find out I live in
your basement. You can do that one. You could be more sincere. There's nothing wrong with very sweet and
sincere. Hey, I'm still wearing that smile you gave me from last night. Or, hey, I think we both
agree that this needs to happen again, right? You could compliment her. Let's say you kissed.
and I certainly hope you did on that first date.
Hey, I had this crazy dream
that last night I kissed the coolest, most awesome, incredible woman.
Was it real or a dream?
That's very flirty.
Yeah, it's really you choose.
Are you sincere, be sincere.
Are you a cheeky smart ass like me?
Be a cheeky smart ass.
Are you just like to crack.
jokes make it funny. Up to you. Beware of chat GPT. It's chat GPT AI sucks so bad at flirting. It's terrible.
It's almost like it's just it's mind-boggling how bad AI is at flirting. Here's chat GPT
flirting. Oh boy, you seem like trouble. Or so do you mind if I steal your curly fries?
on the date tonight, that's AI's version of flirting. So whatever you do, I do not recommend
you use AI. And this is not some dogmatic anti-AI belief I have. I'm totally cool with any
any cool technology. I just have tried it out and AI is terrible at flirting. Flusing awful.
So whatever your style is, you do want to send her that next day message just because it gives her
the sense of clarity and certainty. Hey, this guy is into me. And there is nothing needy or try hard.
Being mysterious doesn't work. If it ever worked 30 years ago, maybe it did. I don't know.
But in 2026, when women have a million options, apps, matches, guys wanting to meet them,
if a guy plays it cool, he's done.
So I don't think being mysterious and not try hard ever really worked very well, ever,
but it certainly doesn't work now.
So don't be mysterious.
Don't play it cool.
Play it clear.
Let her know you like her and you want to see her again.
But do it with some playfulness.
So just to recap here, think about this.
The date, before the date even starts, light, joking, maybe a little tease.
Hey, you better look good for our date.
I'm very handsome this week.
That's very different than every other guy.
And then she meets you.
You're genuine.
You give her a hug.
You're open.
You have emotionality in your conversation.
You're making her feel to feels.
And at some point during the date, maybe you're a little bit, you brush the hair out of her eyes.
You say to her, wow, you know what?
You have a very sexy laugh.
It's so feminine.
I love the sound of your laugh.
And you look her deeply in the eyes when you say it.
And then you open up a little bit.
You're a great listener.
You're very present.
But she can tell you're real.
You're not trying to impress her.
You're just expressing your true self.
And then as the dates winding down, you just see her looking at you with those eyes.
All of this masculine, authentic, warm, loving strength.
is coming from you and hitting her in that feminine receiving heart of hers.
And that's what makes her feel those feels.
And then you go for that kiss and she's so glad you did and you're making her feel the feels.
And you text her the next day, something that reminds her what an incredible time the two of you had last night.
Not only will you be out of the friend zone, you're going to be having her saying,
When are we going out again?
What are we going to do next?
When are you asking me out?
That's when I knew I'd gotten really good at this.
And by the way, I used to live in the friend zone.
I was terrible at this stuff.
I had to learn everything I'm teaching, sharing today.
But anyway, I knew I'd gotten really good at this.
I kept hearing the same sentence from different women.
So when are we going out again, Connell?
When are you asking me out again?
That was a wonderful.
That's so much nicer to hear than
didn't feel a connection. I'll leave you with a story. Quick story, Eileen. If you're out there,
Eileen, hope you're well. Eileen was this incredible dream girlfriend I had many years ago. On our first
date, I did all the things that you and I have been talking about today, or I've been talking with you
about. I remember at one point we met at this bar, and Eileen, by the way, beautiful Irish heritage,
freckles, dark hair, freckles, just and so witty and funny, a dancer, I just was crazy about her.
She was definitely what I call a wow girl, meaning she made me go, wow, this girl's incredible.
Anyway, on her first date, we have incredible chemistry, we're bantering really nicely.
At one point, I noticed how witty and funny she is.
and I said, hey, do me a favor.
Could you just dial down the charm and wit?
Because I'm the charming witty one here.
Do you mind?
In fact, and she said, okay, I'll try to be stupid now.
And I said, yeah.
You just sit there and look pretty, okay?
And she said, okay, and she took her makeup bag out and pretended to put on me.
I'll just sit here and put on my makeup and wait for you to talk.
It was great.
playing with me. So that's what kind of chemistry we had. We were doing this little role play.
Another point during the date, I remember we were sitting on these, you know the kinds of
stools that rotate at a bar? She said something that I didn't like or pretended not to like.
I forget what it was, but let's say she named some band that sucks. I don't know.
She said I love Green Day. And I'm like, I hate Green Day. You know what?
You're on a timeout now.
And I took her stool and I revolved it like 180 degrees away from me.
You're on a 60-second first date timeout.
So that's the kind of stuff I used to do.
Anyway, the date's going great.
We leave the bar.
Go outside.
It's raining.
That sexy summer night kind of rain.
And we have our first kiss outside under the umbrella in the rain.
we make out, she says, I could get used to this.
That's one of the sexiest things I'd ever heard.
I could get used to this.
And she gets in a cab.
I go home and we're texting later that night on the way home.
And she texts me, I have this incredible floaty feeling that you gave me.
Thank you.
And that's the feeling that I want you to give women.
That feeling of I'm a man, I'm authentic, I'm going to give you the feels.
I'm going to make you feel great.
I'm going to lead you on an amazing date.
And that's what I want for you.
So I hope you have your Eileen.
I could get used to this kind of first date, floaty feeling, first date.
That's the end of my short little two-part, how to say out of the friend zone series.
Again, go to datingtransformation.com.
if you would like to talk with me about how my coaching works.
Until next time, adios.
