5 Texting Mistakes Women HATE! + 5 Ninja Text Moves to Get Her Pursuing You
You’re About to Learn:
03:44: The #1 Texting Mistake that Kills Attraction
13:08: The Texting Cadence that Prevents Canceled Dates
17:33: Why Being Mysterious Is a Dating Dead End
22:23: The “Resurrection Text” that Brings Dead Matches Back to Life
26:58: The Flirty Way to Confirm Dates by Text
35:49: How “Callback Humor” Builds Chemistry and Connection
45:21: Connell Breaks Down His Own Text Thread
DO YOU WANT TO ATTRACT YOUR DREAM GIRLFRIEND? BOOK A FREE CALL WITH CONNELL TO LEARN ABOUT 1-1 COACHING:
http://www.DatingTransformation.com
EMAIL CONNELL FOR A FREE COPY OF HIS NO. 1 AMAZON BESTSELLING BOOK, “DATING SUCKS BUT YOU DON’T”:
Connell@datingtransformation.com
Listen and follow along
Transcript
Getting sexual way too soon.
Some guys
go from zero to sixty-nine in seven seconds.
Not smart.
Little Marvin Gaye.
I think it's a lovely
textual healing.
Singing, Marvin.
Textual healing.
Textual
healing.
Oh, yeah.
Text you wool.
Oh, man, I am so white.
Anyway, that was Marvin Gaye.
Classic, great song.
The unofficial theme song to these last few episodes of the How to Get a Girlfriend podcast.
Welcome back.
I am dating coach and best-selling author Connell Barrett.
I am a dating coach.
I help men flirt with confidence and get great girlfriends, all by being authentic.
No sketchy pickup artist moves needed here.
And this is the last of a multi-part series we've been doing about textual healing.
And I have a lot of great stuff planned for you today.
I'm about to give you five advanced texting moves that will help you stop getting ghosted, get more dates, be funnier, be wittier by text, and women are going to love it.
But first, I'm going to give you five dreaded texting mistakes to avoid.
Because once we remove the mistakes we make when texting women, we'll start having better responses from women.
and help you get more dates.
And stick around until the very end of today's podcast because I'm going to go over, I'm actually going to read word for word, a really good, solid text exchange, very bread and butter text exchange.
I had with a wonderful woman on it on a, we matched on a dating app and we went from the dating app
to setting up a date.
And I'm going to read the entire text exchange for you so that I can help you see the matrix.
of texting women using my framework.
The framework, I call it play, play, play, play, pull the trigger.
When texting women, we mainly want to be playful and light.
And then every so often we pull the trigger and ask for what we want, which is usually a date.
So I'm going to read you an entire text exchange.
You're going to see me go from matching with a woman, playfully flirting with her, and then getting the date lined up.
And that'll be at the end of today's episode.
So let's get right to it.
Let me start with five of the most dreaded texting mistakes you want to avoid.
Here's number one.
You want to avoid very needy,
did you get my text energy?
You want to avoid neediness and only asking for what you want.
I think this is the most common and universally destructive mistake that men make.
Essentially, most text messages can fall into one of two categories.
You're either giving value to her, making her smile or keeping her interested in some way, or you're trying to take.
You're only asking for what you want, and that can come off as insecure and needy.
And we certainly don't want that.
So that's
a big thing we want to remove.
Now, I'll give you the fix for this, or I'll remind you of the fix for this in just a second, but let me first read you a really bad, or sorry, a good example of bad texting.
This is actually from my book, Dating Sucks But You Don't, page 111 in the flirting chapter.
And I'm going to read you a text exchange from my former client, Barry, with a woman he had just met named Rachel.
Here we go.
This is Barry writing Rachel after their very first date.
They're in college, by the way.
So Barry writes at 12.03 a.m.
after their date.
And Barry and Rachel had a pretty good date.
A pretty good date.
And notice how just in a few text messages, she's going to go from really liking him to ghosting him.
Here's how it played out.
First message from Barry at 12.03 a.m.
I'm home.
Hope you had as good of a time as I did and that we can go out again soon.
Rachel replies one minute later at 12.04.
I did have a great time.
Exclamation point.
I hope we do.
Smiley face, she's into it.
She is into it.
She likes Barry.
Barry writes him back at 12.04 a.m.
Less than a minute later,
I'm looking forward to it too.
Three exclamation points.
When is the next day you don't have to get up early for anything?
So he immediately asks for what he wants.
Instead of just letting a good
end-of-date text exchange sit with her and make her smile, he immediately starts to ask.
She does not respond.
Then the next day,
so that, by the way, that was Monday morning at 12.04 a.m.
So basically late Sunday night.
Then no response from her.
Monday night, 9.07 p.m., Barry writes, how was your day?
No response.
Tuesday morning at 10.20 a.m.
Barry writes, come hang out with me.
See, he's asking.
He's not giving anything.
He's asking for what he wants or he's asking questions that fail to offer value.
Again, later, about five hours later at 3.46 p.m.
on Tuesday, Barry writes, did you drop the class or just give up on coming?
So they were taking a class together in college.
And obviously she did not show up for that class.
Who knows?
Possibly because she didn't want to see Barry, because Barry was getting super needy.
And the next day, Wednesday
night, 10.39 p.m.
I'm sorry, 10.39 a.m., he writes, good morning.
And he follows up with a couple more boring, how are you?
Where are you?
messages.
And basically, Rachel went cold.
So Barry's big mistake was he immediately went into
asking for what he wanted instead of giving her what she wanted, which was
maybe messages that might make her smile, maybe a nice light joke, maybe a good question.
So the biggest mistake that men make is primarily asking for what they want.
The way to fix this is you want to shift away from only asking for what you want and primarily give women value in your text messages.
The framework
I call this is play, play, play, pull the trigger.
You give value to women by sending nice, light, playful text messages that don't ask her for anything.
They're seeking to make her smile.
They're seeking to make her engaged in some way.
Barry did not know how to do this, so that hurt him with Rachel.
This was why Barry came to work with me.
So,
yeah, that's the biggest mistake.
And the fix for this is to shift from only asking for what you want to my play, play, play pull the trigger framework.
So, go back and listen to a few episodes earlier if you haven't listened to my play, play, play pull the trigger episode.
Okay, dreaded texting mistake number two to avoid is assuming that you're getting ghosted
only one unanswered message.
Don't give up too soon.
Don't make an assumption that just because a woman doesn't answer one message, that means you've been ghosted.
That is not the case.
Don't overread one unanswered text message.
If one unanswered text message meant that you were getting ghosted, That would mean that my girlfriend would have ghosted me 47 times since we've been together.
There have been plenty of messages she didn't respond to.
It would mean my sister Colleen ghosted me last week.
She did not answer my text message about a family event.
So I guess my sister doesn't want to be my sister anymore.
No, that's not true.
Look, women are busy.
Everybody's busy, right?
And especially
datable.
good catches, women who have dating options.
She's going to have other things going on in her life.
Don't overread the texting tea leaves and assume that one unanswered message means you're getting ghosted.
The fix for this is do what I call the three times rule.
The three times rule is that you can and should send three messages, good messages, messages that offer playful value before you should assume that you have been ghosted.
Let a woman
Let a woman go quiet for three good messages before you make any assumptions that she is not into you.
It could just be that she's busy.
It could just be that she's,
it could be she's testing you.
Sometimes women are testing you, not because they're trying to be super judgmental or trick you.
It's not game playing.
It's just that a lot of women have a lot of dating options and she can't respond to every message.
Sometimes a woman wants to see if you're going to be persistent.
Some women want to see if you're going to be keep things light, give her space, but they also want to see if you're going to give up too soon.
And that's not a smart proposition or a smart strategy either.
So what I teach is the three times rule, which is if you send one unanswered text message, no worries.
Send a second good playful message or even a third good playful text message.
And then only if you've got three unanswered messages where she has gone very, very quiet should you then make an assumption that she might not be into it.
And then you can move on if you want to.
Because hey, there's a lot of other women out there for you to potentially date.
But don't just assume one unanswered message means that you're not, she's not into you.
I've had multiple women over the years say to me variations of, oh, hey, sorry, I didn't get back to you in time.
I got really busy.
But hey, yeah, let's do drinks on Friday for my second or third message.
And I had a couple women actually say to me, just I just wanted to see how persistent you were going to be.
How about Friday night drinks?
So follow the three times rule.
Three charming, playful text messages that offer value will, I can almost guarantee you that you're going to get dates from following the three times rule that you wouldn't have gotten if you just give up after one unanswered text message.
Okay, the third dreaded texting mistake to avoid is
going silent between setting up the date
and the actual day of the date.
A lot of women will lose interest if you don't have some kind of communication cadence between setting it up and having the date.
For example, my client Nick,
last year I remember reading
his text exchange he sent me.
It hurt so bad because I could see what was happening, but he sent me a text exchange where he had set up a date with a woman from Bumble
and everything was going great.
And then five days passed and he did not send her a single message.
And then on the day of the date, like the morning of, he sent her a text message
saying,
oh, hey, just making sure we're still on for tonight.
And the woman said, you know what?
I got to be honest with you.
I didn't hear from you for five days and I've kind of lost interest.
Sorry.
And she basically gave him some
painful, but helpful feedback.
So you want to keep a texting cadence going.
How often, how many days, how many messages?
It depends on you and her and your texting chemistry and how much you and she like to message.
Some people love to message back and forth a lot.
My girlfriend Jess and I, we sent a few dozen messages between setting setting up our first date and actually going on our first date.
But we both love banter and we love texting banter.
Other people aren't like that.
You might not love texting banter and that's okay.
You still want to have some kind of cadence.
I would say at least one message every other day
between the day of the date being set up and the day of the actual date.
Could be more, could be a lot more, but you want at least one message every other day so that you stay on her mind in a really simple way.
And I think the easiest way to message a woman leading up to a date is just talk about something fun that she and you can both look forward to about that upcoming date.
You know, it could be as simple as let's say you and she set up a date at a wine bar and you might say, oh my God, you're going to love this place.
They have fantastic, they have a great selection of both reds and whites and you're going to love it.
Are you more of a white wine woman or a red wine woman?
You could keep the cadence going that way, looking forward to the activity.
Or there's some cheeky things you can do as well, which I'll share shortly.
But basically,
don't worry about making the content amazing.
You just want to stay in touch with her in a way that lets you and she both look forward to that date.
Okay, the fourth dreaded texting mistake to avoid is getting too sexual too soon.
Getting sexual way too soon.
Some guys
go from zero to 69 in seven seconds.
Not smart.
Look, there will be a time,
probably in person,
probably not by text.
There will be a time for you and a woman to get sexy time, right?
But it's probably not going to be when you're texting, and certainly it's not going to be early on in the texting game.
So avoid vulgar or R-rated text messages early early on.
It is a giant red flag to many women, so many women.
So keep it light, keep it PG, keep it GPG, or at most PG-13.
At most.
And that is only if you're reading the room and can feel there's sort of a little bit of a kind of a sexual naughtiness that
she and you are feeling.
But general best practices is keep it G-rated or PG-rated.
Here's what not to do.
I know a woman who matched with a man on Bumble,
and within two or three messages,
he had said to her,
I love your smile, and I just wonder what else you can do with those lips.
Ew,
ew,
instantly turned her off in a big, big way.
By the way, that man was not me.
I'm happy to say.
I'm not covering myself here.
Don't get me wrong.
I've made plenty of dating mistakes, texting mistakes.
I don't think I ever made that mistake, though.
But yeah, so keep it PG, keep it G.
Yeah, you don't have to do sexual, sexy talk.
In fact, there will be, there'll be time to get sexy at some point if you and she hit it off, but don't get too sexual too soon.
And the fifth dreaded texting mistake to avoid is
playing it too cool slash being mysterious.
You know, going quiet,
going quiet, taking a few extra hours to respond,
being all mysterious.
The truth is, you know, hoping she'll chase you because, oh, I'll go quiet.
I won't respond.
I'll make her wonder about me.
You know what?
That That never worked for me.
And I just don't think it works in general in 2025.
Because, hey, I don't know if it ever worked, to be honest, but I don't think it works very well, period.
It also just feels very game-playing.
You don't need to play games.
You don't need to go quiet.
You don't need to be James Bond mysterious because in today's dating market, a woman has, she's the buyer.
She has the market to choose from.
And if you go quiet, then it'll be a case of out of sight, out of mind.
And
women don't chase a guy because he goes quiet.
The only reason anybody chases anybody in dating is because that person sees so much value in the other person as a dating partner.
We chase things we value.
We don't chase things that disappear.
So if you just go out of sight, out of mind, or sorry, if you go out of sight, you'll go out of mind.
And she'll match with and be messaging some other guy.
So don't play it too cool.
Don't be Mr.
Mysterious.
The fix for this is to
give value through the lens of your best, most authentic self,
conveying, expressing your true, real,
genuine, best personality, sense of humor, feelings, thoughts, the power of authenticity, the power of believing in who you are and what you offer women and what you will offer your future girlfriend, the future love of your life.
That is so much more attractive to a woman than some guy going quiet and disappearing.
So don't go quiet.
Rather, the fix for this is to become what I call radically authentic,
where you feature your personality, you put yourself out there, you try to be bold,
you give give value.
You're playful.
You're light.
You are yourself.
And a woman who values your type of guy, she is going to be responsive to you.
She's going to be excited to meet you.
She's going to love messaging with you.
In the dozens of text exchanges that my girlfriend Jess and I had leading up to our very first date, neither of us went quiet.
Neither of us played any silly
manipulation game.
We were just bantering and flirting flirting back and forth and having a blast.
And
we were chasing each other, I guess you could say.
We were chasing each other because she was really excited to meet a dating coach.
She was intrigued by that and also liked my overall vibe and personality.
I was excited to meet a beautiful, witty, intelligent woman who seemed kind of quirky and weird, but in the best way.
And so, yeah, anyway, we didn't need to play games.
We were just
ourselves and
our first date could not have been better.
And now we're together.
Okay, those are the five dreaded texting mistakes to avoid.
Now, I want to give you five advanced texting moves.
These are five moves that I have used or, yeah, used in my, gosh, 20 years now.
I've been working on my dating life.
It was in 20.
It was in 2005.
I became single after a long-term relationship ended.
And I said to myself, 20 years ago, after settling in a relationship I wasn't happy with, I said, I got to figure out this whole dating thing.
So I've literally been working on this for 20 years.
So here are five advanced texting moves that I have seen work really well.
The first one, this advanced texting move, is I call this
the resurrection text.
The resurrection text.
What does that mean?
Well, have you ever matched with a woman?
You messaged back and forth for a few times, but then it just went quiet, kind of fizzled out, and weeks or even months passed.
And you said to yourself, Boy, I'd really like to talk to that woman again.
I never did meet her.
It just kind of fizzled out.
But it's too late now.
It's been two months, three months.
Well, that's the perfect time to use what I call the resurrection text.
Why do I call it the resurrection text?
Because it'll bring a seemingly dead, dormant messaging, text exchange back from the dead.
So here's how it works.
So let's say you've got this.
Maybe you had
a few messages back and forth with this woman, but then weeks or even months passed and you never even met her.
Then you send this text.
I'll use, let's say her name is Katie.
You write her this, quote, Katie, baby,
I feel like we're growing apart.
We barely talk anymore and we haven't made sweet, sweet love in ages.
But I don't want to give up on us.
Honey?
Have we lost that love and feeling?
Or should we give it one more try?
Winky Face.
So this is an over-the-top romantic role play.
This works because you're being playful.
very silly and playful.
It's certainly not needy.
And you're basically making a joke out of this idea that you and she are
in a long-term relationship and it's not, you've lost some of that love and feeling, but you want to get it back.
So it's a pure role play.
And this is very powerful and effective with women who like this kind of humor.
And it works because it's fun, it's playful, it's not needy.
And also women just love to play.
Women just love to play.
My client Paul used this text with a woman named Oksana.
A woman named Oksana kind of ghosted him after a few text exchanges.
I think they actually had a date, actually.
I think they had one date, come to think of it.
And then they went quiet.
She went quiet.
About
six weeks passed, and he sent her the resurrection text.
And she said, okay, baby, let's give it one more try.
I used this text message once with a woman named Lane, a woman I met many, many years ago.
And
we had been trying to get it together.
Beautiful, beautiful, charming, intelligent woman,
looked like Minnie Driver.
If Minnie Driver, the actress, was blonde, that's what Lane looks like.
And I remember thinking, oh, gosh, Lane was stunning.
She was incredible.
I'd love to meet her.
Let me try.
Let me try something.
So I sent her, you know, hey, Lane, baby, I feel like we're growing apart.
We barely talk anymore.
And we haven't made sweet, sweet love in ages, but I don't want to give up on us.
Honey pie, have we lost that love and feeling?
Or should we give it one more try?
Question mark.
And she wrote back, to my delight, she wrote back, hey, hey, babe.
We'd never even met.
She wrote back, hey, babe, I'm so glad you reached out to me in such a vulnerable way.
Let's give it one more shot, shall we?
How about Tuesday night?
And all of a sudden, I had my first date with a gorgeous, cool, incredible woman.
And we dated for a while.
We didn't become boyfriend, girlfriend, but we had a wonderful kind of six-month, six-month-long, you know, situationship.
And it never would have happened without the resurrection text.
So give that a try.
That's a fun, advancing texting move.
Here's your second advanced texting move.
It's the cheeky first date confirmation.
Cheeky.
Confirm your first dates in a playful, playful, cheeky way.
Don't do it in a business-like way.
One of the biggest, one of the secondary big mistakes I see men make is they confirm a first date like they're confirming a meeting with their accountant.
Hey, just confirming we're still on for Thursday at seven.
Still, still good for you.
No, don't do that.
It's a first date.
It should be light and playful.
So you don't want to confirm your date that way because here's why.
When a woman agrees to a date with you, she's in a great state.
She's in a good mood.
She's excited to meet you.
You are an attractive, cool, awesome, datable guy, right?
And then, you know, three or four days pass.
Maybe all of a sudden it's Thursday night.
She's tired.
She definitely wants to meet you, but also she's had a tough week.
Her boss is being a jerk.
And she's thinking, oh man, I'm kind of not even feeling like going out tonight.
It's not even about you.
It's about her emotional state.
And then she gets your text message that says, hey, are we still on for tonight?
Let me know either way.
And that essentially gives her a
get out of date free card.
Don't give her a get out of date free card.
Okay.
Because you're basically opening the door.
When you try to confirm the date in a business-like, logical way, remember, women don't want logic and
analytical conversation.
They want it light, fun, and flirty.
And so you're not giving her the emotions she wants.
You're also giving her a get out of date card.
And she'll take it, not because she doesn't want to meet you, but because, hey,
it's been a tough week.
She'd rather just stay home maybe and watch some Hulu.
I don't blame her.
So anyway, don't confirm the date that way.
Confirm the date in a fun, cheeky way.
And I like to do it in a couple of ways.
And you can certainly tailor this to fit your personality, but I like to confirm a date
either by roughly lunchtime day of the date or even better about 24 hours in advance.
So maybe the day before.
So I'll send a message something like,
let's say here, let's go with the name Katie.
Hey, Katie, just so you know, I'm at the gym right now.
blasting my pecs.
So I'll look huge for our big date tomorrow night.
And then I'll put like a little weightlifter emoji in there.
That's very much my sense of humor.
So I'm being light and silly, right?
That's my way of confirming the date because all I'm looking for back from her is
some like an LOL.
Ha ha.
Okay, you better, those muscles better be, better be ripped for our date.
So that's now she has just confirmed the date with me by simply responding to my silly little heads up.
Or I like this one.
I've used this one many times.
Hey, Katie, just so you know, I got a fresh new haircut and I look, I'm going to look extra handsome
tomorrow night.
So you better bring your A game, okay?
Winky face.
Again, cheeky, right?
It's cheeky.
It's playful.
And so
if she is on the fence about going on the date, because it's just been a long weekend day for her, guess what?
I've just given her a little emotional booster shot, a fun, jokey silliness, almost like a sneak preview of what our date's going to be like.
And hopefully I've made her giggle and smile and think, okay, yeah, I was kind of on the fence about this Connell guy, but that's funny.
Okay, yeah, haha.
And then she'll write back something like, oh, well, great.
I can't wait to see your new haircut then.
Boom.
Once she says, sounds good, or maybe she'll banter back with me.
She might say, well, it just so happens I've got
a sexy new dress for tomorrow night.
So
I'll bring my A game if you bring your A game.
Now we're flirting.
Now we're pre-date flirting.
And that's a great place to be.
So the cheeky date confirmation, it makes it more likely the date will happen because you're not confirming it like in a logical business sense.
You're confirming it in a fun, flirty way, which women like.
And you're also not giving her a yes or no option.
You're basically assuming the date is on.
So that makes it also more likely she will not
flake on you or cancel on you.
And you're also giving her the opportunity to flirt back with you.
I can't tell you how many dates I had that went better because I did the cheeky date confirmation.
And then she wrote back something equally cheeky.
She added a little fuel to the flirting fire.
And all of a sudden we're bantering back and forth.
And
then she's just super excited about meeting me for the date.
So find a cheeky way to confirm the date, or at least a non-logical analytical way.
And if you're not a cheeky, playful person naturally, like I am,
that's okay.
Here's another way you can confirm the date in an effective way.
You could simply play
up
something about the date
and ask her a question
that, when she replies to it, will essentially stand as a confirmation.
So for example, let's go back to the, let's say your first date is going to be Tappas.
Thursday night, Tappas
with
Brooke.
On Wednesday afternoon, you'll write Brooke something like, hey, Brooke, I'm really excited about Tapas with you tomorrow night.
Dot, dot, dot.
I'm curious.
We should get some sangria.
Are you more of a red wine sangria woman or a white wine or a white sangria woman?
So you could ask her a question that has her looking forward to the date in a
positive, fun way.
And then by her saying, Oh, I'm all about red, Sangria, for sure.
Boom, she just confirmed the date with you.
So that's another way you can confirm the date.
That's not so much cheeky, but it's still effective.
And it's way better than, hey, just making sure we're still on for tomorrow.
So don't do that.
Okay.
Advanced texting move number three.
This is, let's call this the
bar banter banter text.
Let's say you're at the bar
and I advise you get to the venue early, 10 to 15 minutes early.
Let's say it's your classic first date drinks situation.
You get to the venue 10 to 15 minutes early.
Make sure you get a good spot, a good seat, a good place for the two of you to get to know each other, especially if it's busy.
That's something I recommend.
And because you're arriving early,
it's fun to shoot her a text message to let her know that you're at the bar waiting for her.
And you can be a bit bantery and cheeky.
For example,
you might text her to say, hey, Emily, just so you know, I just got here a little bit early.
I am the
handsome man.
I am the handsome man standing next to the,
I don't know, fireplace or whatever, wherever you are in the bar.
Or,
and by the way, almost, let's be honest here, so many women are late for a first date.
I have no problem with that.
Women like to cut it close, I've found.
So, if she's running late, she might very well say, Okay, great.
I'll see you soon.
By the way, I'm running a little bit late.
And then you banter back with something like this.
Uh-oh, you're running late.
Just so you know,
you're going to owe me one drink for every minute you're late.
Dot, dot, dot.
And I like the good stuff.
Laughing emoji.
This is a joke, by the way.
You're not going to literally make her buy you a drink for every minute you're late or she's late, but it puts a little bit of fun pressure on her.
Not actual pressure, more like playful teasing pressure on her.
Because let's be honest, she's probably going to be a few minutes late.
So you can say, yeah, well, if you're, no, no problem.
If you're going to be running late, you owe me one drink for every minute you're late you do something like that um
yeah i did that many times on many dates and yeah again the point here is not to actually make her feel pressure it's to make her feel like um you're
you're
putting some flirtatious friction here truth is i mean as long as she's not more than like a 20 or 30 minutes late i don't care i'm happy i'm happy an attractive woman is showing up on a date with me that was always my view.
But yeah, so you can send her some fun banter from the bar, right?
Other bar banter text messages
I've sent.
Maybe you notice something in the environment that's kind of crazy, kind of unusual.
You could say, oh my God, wait till you get here.
You're not going to believe what this couple is doing.
They should just get a room.
You could kind of give her a little sneak preview of what's happening in the bar.
So yeah, consider the bar banter text where you message her when you've arrived.
Okay.
Advanced texting move number four is using callback humor.
You might know the term callback humor.
I've mentioned this before.
Or you might just know it anyway if you're a fan of stand-up comedy or comedy in general.
Callback humor is when you refer back to a joke that you and or she made earlier and you bring it back.
Stand-up comedians do this all the time.
They make a joke early in the the set and then they call back to it.
And because
that
comedic
seed has been planted earlier,
it then
pays off later because you're referring back to something that you've already laughed about from that comedian.
The same thing is really powerful in dating and texting.
So callback humor is you simply establish something that the two of you have joked and laughed about, and then
you use it again,
which creates a we have history vibe.
And it can really be a good go-to for texting women.
So for example, I had a first date once with a woman named Jen, and we went to a fancy sushi place in New York City called Nobu.
And Jen is not very good with chopsticks.
She kept dropping pieces of sushi.
And if you know anything about Nobu, that's like $15 $15
per sushi piece or some, or something close to that.
And so she dropped a couple pieces of sushi.
And so
throughout the date, I joked about how bad she is with chopsticks, dropping sushi.
The next day, when I'm texting her, I said, hey, Jen, I just wanted to say I had a really good time.
It was fun last night.
meeting with you or meeting you finally and uh just so you know i'm going to venmo you for the two two pieces of sushi that you dropped um venmo or paypal what's better for you calling back to the joke right
uh so yeah let's say you or it doesn't have to be a date it doesn't it doesn't have to be a first date you've had let's say
in your early
first messages back and forth you're texting about i don't know music right
And she mentions she loves Taylor Swift.
Fine, cool.
She loves Taylor Swift.
So you're messaging about music.
Day or two later, you're texting again.
You might randomly call back to that and say, oh, hey,
I randomly found myself humming shake it off today at the gym.
This is your fault.
I blame you.
And then add a little Taylor Swift meme or gif next to it.
You're calling back to something.
that you and she laughed about or joked about.
And then she will invariably say, hey, don't blame me.
I made your life better by bringing Taylor Swift into your head.
And that creates a nice, fun, bantery vibe.
So, call back humor is very powerful in texting.
Very powerful.
And your fifth advanced texting move, this is a really good move if you are trying to figure out, hey, what do I write to her?
What'll get her engaged with me?
Or,
or it's also really a great tip, number five here.
So I call this fifth tip, this fifth advanced texting move is ask the expert,
where you put her in the role of authority and ask her a very playful question that allows her to
use her expertise in her answer to you.
And this is really helpful if you're not sure what to say, if you're not sure what to text.
Or it's also a really good thing to do if you're
if you're messaging back and forth and you haven't yet met her
and you're just trying to keep things engaged engaged enough so you can get that date.
So here's an example of ask the expert where you make her put her in the role of the expert.
I was once
trying to set up a date with a woman named, I'll call her Jessica.
So Jessica I met on Bumble a long time ago and we're messaging back and forth.
And I'm trying like the devil to get her out on a date, but she's really attractive.
She's a professional artist.
She's a painter.
She's a beautiful, stylish, blonde painter.
Yeah, think like Blake Lively.
Beautiful, but stylish and artistic, a total knockout.
And guess what?
A woman like that has a lot of options, a lot of dating options, a lot of social options.
And she and I were messaging back and forth.
And we could not get our schedules together for a first date.
And it was primarily her not being able to give me time for a first date but she was still responding to me so there was still hope and
i'm walking outside uh i'm in i'm in manhattan one day
and i see an outdoor random art installation it was a cow
uh a sculpt a sculpture of a cow
that was covered in like multicolored newspapers
And it was a work of art.
It was like a random street art that somebody had created, kind of like Banksy does, except it's a cow.
So I took a picture of it and I thought, oh,
let me ask Jessica a question about this because she's a painter and artist.
So I just took a picture of the piece of art
and then I sent her a fun question.
Again, playful, always playful, almost always.
And I said, hey, Jessica, pop quiz for you.
And I sent her the picture.
Is this A
a brilliant work of art?
Or B,
just a fucking cow.
And she wrote back, LOL, oh my God, that's funny.
And then she responded with her artistic opinion.
And I think I even, I think I prefaced the text by saying, hey, question for the, question for the professional painter artist.
So I frame this as her as the expert, which she is.
I'm not an art expert.
I'm not a painting expert.
And everybody loves to be an expert.
So the ask the expert texting move is you simply look at her profile or
ask yourself based on what you know about her, what is a question you can ask her
that she'll want to answer because she's an expert about it.
We all love being experts.
We love being experts.
I love being a dating expert.
That's why I talk so much.
don't shut up sometimes because I love being an expert.
And you probably love being an expert in things that you are an expert in, whether it's movies or music or
training, the gym, all kinds of things you might be an expert in.
Women are the same way.
So ask yourself, what would make her an expert?
Another quick story.
I dated a woman named Maya.
Maya, again, very successful, stylish, New York City professional.
And Maya is a, what's the term, sommelier,
wine expert.
Maya, we matched on a dating app, and early on, I basically said, okay, what is she an expert in?
Obviously, wine.
And I asked her a question.
I think I asked her, okay, you're going to be on a desert island and you can bring a case of only one kind of wine for the rest of your life.
That's the only kind you can drink.
What label would you bring?
So I wanted to use her expertise to engage her.
You know, she was engaged by that.
We eventually met up.
And I eventually
met up and dated Jessica as well.
And
so ask the expert that puts her in the role of authority with a playful question.
And the simplest way to do this I found is just look at her profile and notice what she loves to do.
It could be about her career, it could be about a hobby, it could be, you know, if she mentions loving baking, loving to cook, you could ask her a question that you would ask an expert in baking or cooking.
And that's a really good way to keep the conversation flowing because it makes her the expert.
And we all love being an expert.
Okay, so I want to finish up by reading you a text exchange that I had with
a woman named Susie.
Susie and I matched on a dating app once upon a time.
And I'm going to read this to you because what I want, I want to read the entire thing to you.
Because what I'm going to do is sort of take you through a text exchange I had with Susie.
And I'll read pretty pretty much everything.
And
you'll see, hopefully, I'll be able to share with you the play, play, play
pull the trigger framework in action.
Okay, here we go.
So this is a woman named Susie.
We matched on a dating app, and we start with,
she wrote, so you're the real deal dating coach, LOL.
And I had dating coach on my profile back the last time I was single.
I wrote, hey, Susie, yep, I'm an actual dating coach.
Winkyface, you're talking to a professional, ha ha.
And you're the real life Wonder Woman.
And she put,
she had put real life Wonder Woman on her profile.
And then I said, so what are your, what are your superpowers?
Super speed, super strength?
And then she wrote, yes, I'm the real deal Wonder Woman.
I'm a mom, a nurse, a woman's advocate, much more than I can share later.
And then she wrote, hmm, what are my superpowers?
I'm an awesome cook.
My other power is I'm so powerful I can smell bullshit from a mile away.
She wrote L-M-A-O.
Kidding about the last one.
Wish I could, though.
I am a tough yet sweet person.
I think I am.
Okay.
Now, so far, I've kept it pretty light, right?
And I'm always combining authenticity, sincerity with playfulness, but vulnerability too.
So I wrote, wow, you're a mom, a nurse, a woman's advocate.
Those are three of the best things a woman can be.
My family is filled with nurses, my niece Erin, my aunt Colleen, and my sister.
And so I'm being really genuine here.
But at the same time, I'm also thinking, okay, Connell, be genuine, be sincere, but also be playful, right?
So then I wrote, I would love to see how good you are at smelling bullshit.
And then I wrote, okay, I'm going to see how good Susie's BS detector is.
Ready for a test?
Question mark.
And I put a pencil emoji.
She wrote, let's go, exclamation point.
So now I'm going to play a game with her.
Play, play, play.
Pull the trigger.
Remember, I'm being playful.
Here are two truths.
Here are two truths and one lie.
which is bullshit, Wonder Woman.
Number one, I appeared on a reality TV baking show.
Number two, my dad was mayor of my hometown.
Number three, I played golf with a U.S.
president.
So she wrote, number one and two are true.
Three is the lie.
Now, she got that wrong.
She got that 100% wrong.
I have played golf with a U.S.
president.
I was able to play at one point before he was president, but I played golf with our current president.
But I never appeared on a TV baking show.
My dad was not the mayor of my hometown.
Anyway, so she writes back her answer.
I wrote to her, by the way, now we're switching to, now it's Friday.
I wrote, hey, TGIF,
parentheses, which stands for this girl is fire and parentheses, a little flirty line that I really like.
And then I wrote, wrote, sorry, but your BS detector is malfunctioning.
I wish I'd been on a baking show.
Number three is the truth.
So I told her the answer.
And she said, wow, ha ha, that's the first time I've heard something like that.
No way, she wrote to the fact that I played golf with a president.
That's amazing.
Which president?
Now, she's asking me which president.
I did not want to bring in the current president's name because I just didn't want to to get into a whole political conversation.
So I just, I deflected with humor.
So I wrote, which president?
FDR.
Parentheses, I'm a bit older than you, LOL.
And then she wrote, laughing my ass off.
I mean, it could be the bushes.
So now at this point, I've been playful with her.
She's very engaged.
I'm noticing the back and forth is 50-50.
We're both messaging each other the same amount, roughly, which is good.
And then I basically say, okay, now that I've play, play, played with her, now it's time to pull the trigger.
So I wrote, I'd like to find out in person.
Oh, by the way, this is on the dating app.
I'd like to find out in person what other Wonder Woman powers you have.
Do you like fancy drinks with tall, charming gentlemen?
Because I know somebody.
She wrote back,
yes, I can do fancy drinks or fancy water.
Tall, charming gentleman is a huge plus.
Cool.
So she's basically saying yes.
Ba ba ba ba.
And I wrote something about, let's see here.
Oh, I wrote her about how I'm looking for a dog.
I'm looking for a dog, blah, blah, blah.
Oh, and then I wrote to her, by the way, I love your honesty.
I appreciate that.
Maybe that's your superpower.
And then I say, hey, what's your number?
Let's text off of the app.
And she writes me her number.
And then I say, got it.
I'll text you a little bit.
Oh, she wrote back, yes, I'm very honest.
I think the East Coast broke my kindness, lol.
I wrote back, got it, meaning got her number.
I'll text you in a little bit, Miss Honesty.
Notice a couple other things I've been doing doing here.
Every so often, I give her a little nickname.
I call her Wonder Woman because she mentions being the real-life Wonder Woman.
And now we've established that she's a very honest person.
So I call her Miss Honesty.
A little nickname like this is a nice little flirting move.
Giving a woman a nickname, it's playful.
It's flirtatious.
And think about it.
We only give nicknames to people who we have a certain rapport with, a certain connection to.
So I'm giving her these little nicknames because it's flirtatious.
Okay, so I tell her I'm going to text her in just a bit.
And then the next message is my first message that I now send to her phone number
from the app.
So I write Susie, dot, dot, dot.
It's Connell from the internet.
Exclamation point.
AKA, the name of the app we were on.
She wrote, lol, hello there.
How is your Friday going?
I wrote, very good.
I took the day off of work and just finished playing tennis.
What are your fun plans this weekend?
She wrote, she wrote, that's awesome.
X, Y, Z plans.
She's got friends coming into town.
Hold on a second.
As I fix my.
As I fix this.
Okay.
Having a little tech issue.
Okay.
Friends are coming over now.
I have a dinner tomorrow.
Then I have a party in Brooklyn.
Blah, blah, blah.
And then I write her, haha, your weekend beats mine.
Then I send her a
little gif
of Seth Meyers
saying, you're very busy.
It's a funny little gif.
It's a funny way to keep it playful, right?
Then I write, well, I better book you while I can.
And then I ask her this question.
Pay attention, please, to my terminology here.
I write, how about a fancy cocktail next week?
What night/slash nights work for you?
This is important.
This is a very simple tip, but it's really important when asking a woman out by text.
I don't say, how about Tuesday?
I don't say, how about Wednesday?
If you throw days of the week at a woman and she's busy or unavailable, she has to shoot down your date offers.
And every time you ask a woman out and she has to say no,
it's almost like you're spending and losing currency.
So I don't like to throw days of the week out at a woman.
I'd rather
simply let her or ask her, hey, what nights work for you?
for fancy cocktails.
She writes back, hmm, next week.
Wednesday is my daughter's birthday.
I can do Tuesday night or Friday night, she writes, Friday early evening.
And she double-checks her calendar and says, Yes, Friday seems best.
And I say,
Great, Friday it is.
It's a date.
I'll find a fun place that serves Wonder Woman.
How about Friday at 7:30?
And
she says yes to that.
And I write, basically, great, it's a Friday date.
And there's a little bit more flirting in here.
If you want me to read everything, I'll read it.
Let's see here.
We're talking about setting up the day.
She writes, as long as I get a glass of wine, to shake off the nerves, you'll have me laughing.
I'm not even kidding, LOL.
It also gives me crazy confidence.
And I write back, bestill my ginger heart.
You're hitting all my pleasure centers.
Crazy confidence plus big nerd, which she calls herself, equals Connell Defenseless.
So I'm letting her know that I really am
being, I'm so charmed by her, that she seems so attractive and charming.
And
she's giving me lots of heart emojis and hahas and thumbs ups.
So I go, great, it's a Friday date.
I'll send you the details.
And
yeah, basically that's how I set it up.
So
I hope that my reading that, I hope you got the main point I was trying to share with you, which is
I was like 60, 75% playful, fun, giving her a fun little quiz, giving her little nicknames, asking her silly questions.
At the same time, I was trying to be, hopefully not trying to be, I was being very genuine.
I took a moment to
be vulnerable, not vulnerable, but sincere, saying, oh my God, that's so cool.
I love that you're a nurse.
You have the best, that's the most important job in the world.
My whole family is nurses, which is true.
And I was being so authentic, so genuine.
And I never met her, by the way.
This was just a test I was doing.
I didn't actually meet Susie.
but had I met Susie, I'd like to think that I'm very confident, pretty darn confident would have went well, in part because she would be meeting the exact same guy from the text exchanges.
She'd be meeting me, except in real life form.
And I think that would have helped the date go really well.
So
this ends the multi-part What is it three now?
Three or four part series called Textual Healing.
In conclusion,
biggest things to keep in mind.
The two biggest things is you want to keep it playful and light.
And the second biggest thing is you want to be genuine.
You want to be authentic.
You don't have to put on a mask.
You don't have to strain to be cool or be somebody you're not.
And please don't play it cool and play games.
Be genuine, be real.
Compliment her
when you're into her.
Like I was complimenting Susie often.
I was also slightly teasing Susie a little bit about her bullshit detector.
And it was a very fun, collaborative text exchange.
And that's the way you text women is play, play, play, pull that trigger when you want the first date and trust that she is going to like you for you.
Okay, that's the end of the textual healing
multi-part series.
Thank you so much for listening.
And I will leave you again with my little end of podcast catchphrase, which is that don't forget, your dream girlfriend, she is out there.
She's going to love you, but she's going to have to meet the real authentic you.
So until next time.