20 Dating Lessons That Took Me 20 Years to Master—You’ll Learn Them by Lunch (Special Series!)

not creepy and weird to go for a kiss.

You know what's creepy and weird?

Having a pretty solid, good first date where you're vibing nicely, and then you go in for the hug like you're burping a baby.

That's creepy.

Welcome back to the How to Get a Girlfriend podcast.

It's a very special episode.

I'm your host, dating coach Connell Barrett.

I am here to help you flirt, gain confidence, and get a great girlfriend.

And do it with the power of authenticity.

No sketchy pickup artist moves needed.

And I have a couple quick questions for you.

Let me ask you, do you struggle talking to women?

Do you feel lonely sometimes?

Have you ever settled for a relationship that you just weren't that into, but that was the best you could do?

Or maybe you've wanted to approach women, but you just never can get over the fear, the feeling of freezing up when you see that woman you want to talk to in a coffee shop or a bar or

the gym, but you just don't want to be a creep.

Well, if you struggle with these things, guess what?

I did too.

In fact, exactly 20 years ago in 2005, That was when I first began actively, intentionally working on fixing my dating life

and today's episode is the first in a recurring series I'll be doing here on the feed and I'm calling this recurring series my 20-year dating transformation

and

because I've got 20 years under my belt now 20 years ago exactly literally roughly this time of year in 2005, I was in a relationship with a wonderful woman, but we were not right for each other.

It was the wrong time, wrong relationship.

And essentially, I was settling.

And so was she, frankly.

She was settling with me as well.

And

I became single midway through 2005.

And so this year marks my 20th year,

focusing on dating, studying dating, and essentially...

figuring out cracking the dating code of how the heck do you connect with women and

the reason I asked you that question, do you feel lonely sometimes?

Do you struggle with flirting?

Are you just not sure what to say?

I dealt with all those things too.

It was in 2005 when I was absolutely insecure settling.

I didn't know how to talk to women.

I had stumbled into a couple of relationships, but it was settling every time.

And so, yeah, so to commemorate the 20th anniversary of me getting my dating act together, I'm beginning this new series here on the feed, and I'm going to share with you the best wisdom I can possibly share.

And here's the good news, by the way.

You don't need to spend 20 years.

Trust me on that.

It took me 20 years to get here today, where I am right now in 2025, a dating coach, an author, a podcaster, the world's most incredible girlfriend, in my biased opinion, but I love her so much.

It took me 20 years to get here.

Don't worry.

You don't need 20 years, bro.

Okay.

You don't need 20 years.

You might need

20 months, maybe to find the one.

You might need 20 days to get

20 days to get a couple dates a week.

And you know what?

If you listen to this podcast, and I mean this quite literally, If you listen and take action and do the things that I tell you to do, you can be approaching women and getting phone numbers in 20 minutes.

I'm not exaggerating.

You don't have to wait 20 years.

You might need to wait 20 minutes to go approach a woman confidently.

Or it might take you 20 days to get two or three dates or 20 days to overhaul your online dating profile.

And it might take you 20 months to find love, but you don't need to spend 20 years.

What I'm saying to you is I...

I've been taking action for 20 years so you don't have to.

So you can get results in 20 days, 20 minutes 20 weeks 20 months a lot less time than it took me so let's get to today's episode enough uh enough pre game yeah pre-game today i want to give you 20 of my favorite best most practical power powerful tips from my book dating sucks but you don't dating sucks but you don't came out in 2021 and at the time it was the latest greatest best

dating tips I could muster in a 200 page book.

I'm really proud of it.

So right now, I'm going to give you the 20.

I wouldn't say that they're the 20 best tips, but they're the first 20 tips I thought of that made me say, Yeah, this is how I want to start celebrating my 20-year dating transformation.

20th anniversary of me getting this handled.

So, let's go.

Here are 20 tips from my book.

Dating sucks, but you don't.

And by the way, if you want a free copy of my book, no strings,

no mailing list, no sketchy upsells.

If you want a free copy of my book, email me,

connell at datingtransformation.com, and just write me an email that says free book, and I will zip it to you as soon as I read it.

Okay, let's get to it.

Tip number one, be radically authentic.

You might have heard that message by now.

Be radically authentic.

Stop wearing masks

and don't put on some

persona when you're on a date.

Don't try to be somebody you're not.

Don't say the things you think she wants to hear don't approach a woman and put on some weird facade trying to be a pickup guy or super charismatic if you don't feel that way women are attracted to authenticity because it's rare and it creates trust and it creates genuine connection if you are being your true best self at least with the women who

are attracted to your type.

I remember I approached a woman one night early in my journey and I just remember thinking, oh, be really real, be genuine.

What's the most honest thing I can say to her?

And I walked up to her and I said, excuse me, I don't usually do this, but I'm actually really shy.

I'm really nervous right now, but I had to meet you.

And she was so into it.

She thought it was vulnerable.

In fact, she thought it was a pickup line.

She thought I was actually playing the part of a nervous guy.

And she thought it was kind of like, nice, nice, nice going, dude.

I see you found an angle, but she really liked me.

Really, it was just me being really radically genuine, vulnerable, and she loved it.

And I remember that moment.

I was like, wait a minute.

That night I got her number.

I'm walking home thinking, wait a minute, you can just walk up to a gorgeous woman who looks like

the girl from Flash Dance, which is why I approached her.

You can get her phone number.

That's amazing.

So.

Number one, be radically authentic because, hey, there's a million guys doing a million cheesy lines.

You're the only one who can walk up to a woman or who can go on that date and be 100% you.

You are not one in a million.

You are one in 8 billion.

So be radically authentic.

It's kind of like, don't be a watered down wine spritzer.

Be a shadow Jameson.

Women who like Jameson are going to catch a buzz off of you.

Tip number two from my book, Dating Sucks, But You Don't.

Use the rule of one in three.

When you're approaching and you get good at it, when you get in the zone, you go to a bar, you go to a venue where there's a lot of single people, you're going to be very attractive to one in three women.

The other two out of three, they're not going to be into you, but they'll be pretty polite.

They'll be pretty chill.

No one's going to throw a drink in your face.

No one's going to call the manager, kick you out, as long as you're normal.

One in three women are going to be really attracted to you.

And two out of three won't.

I want you to be liberated by this rule because now you are allowed to get rejected by two out of three women if you want to.

I mean, not if you want to.

That's actually the way it works.

But it gives you permission to not attract every woman.

Okay.

So the rule of one and three is really powerful.

I remember walking up to three gorgeous women at a bar here in New York City called the Brass Monkey.

This was almost 20 years.

Well, 17, 16 years ago.

I walked up and I said, hey, what's up, you three?

Or what's up, ladies?

I'm Connell.

How's your night?

And

two of the three women just could not give me the time of day.

They were fine.

They were polite, but they weren't interested.

But one of them looked at me like with these wolfish eyes and said, you are cute.

I was like, whoa,

the rule of one and three.

My coach had told me about it and it blew my mind and I actually saw it happen.

Okay.

Tip number three.

Your looks don't matter, but your look matters to women.

Looks are way overrated to women.

They don't, it's a nice bonus.

If you're a good-looking guy, it's kind of like

having a jacuzzi.

Women are like, eh, it's nice to have, but overrated.

Women don't really care if you're Brad Pitt.

They do care if your clothes fit.

If you have a good look, good style.

So good style beats good looks every day.

At least in real life.

approaching dates.

Now on the dating apps, okay, good looks are going to play a larger role.

But man, if you dress well,

nice haircut, fresh haircut, clothes that fit,

you can look like Brad Garrett.

You can have the kind of success that Brad Pitt might have.

So don't get in your head about how you, how attractive you are or aren't in terms of handsomeness.

You can't really control that, but you can control your look, your style.

It's so important.

Tip number four, every approach is a win.

Reframe every approach as a win.

There's no such thing as win-lose.

The reason why guys have approach anxiety is he's like, okay, I'm going to take my shot.

If she likes me, I'm amazing.

If she doesn't, I suck.

I failed.

No, every approach is a win because either you get a number, get a great conversation, you feel amazing,

that'll change your life.

Approach the right woman.

Or even if she's not into it, you're going to put another brick in the wall of the character,

of your cathedral, of your character, of an authentic, courageous man.

So that's how I want you to think of approaching.

Every approach is a win because you either win or you learn.

You win or you grow.

And this helps you also overcome the fear of rejection.

All right, tip number five is make sure you have at least one really good bulletproof dating app, dating app opener.

Something you can can go to.

Here's my favorite go-to.

If I'm not sure what to say to a woman on a dating app, I'll write, hey, name, you seem like you might be my type, dot, dot, dot.

But I'm curious, are you as charming in real life as you are here on Name of App?

Now that's a one-size-fits-all opener, and I generally prefer specific personalized openers, but I do like this one because you can send it to any woman and it brings good vibes.

You're saying she's charming, but you're also subtly screening her to see if she is as cool as you hope she is.

And that's a great signal to send women.

So give that one a try.

It's a really good one size fits all opener.

And you're going to be surprised how many women will write you back and they'll say, well, of course I'm as charming in person as I am here on my profile.

And she's actually teeing you up to then say, well, I think I better find out in person if you're as charming as you say you are.

And then you're moving things toward a date.

Okay, speaking of dating apps, number six, use a hook in the first line of your bio.

Use a hook.

What's a hook?

You want to lead with something that breaks her swiping pattern, takes her out of the moment of the boring things she's used to seeing on the dating app and makes her stop and laugh or be surprised.

You want that first line to hook her interest, just like the first line of a BuzzFeed article is going to hook your interest or any clickbait is going to hook your interest.

So a really good hook would be something like, danger, all capped.

My

insert a talent you have.

Danger, my karaoke voice will make you swoon.

Something that's like over-the-top confident.

That can work work really well as a hook.

And, or you might just put the most extreme, unusual, odd thing about you and just say, just a heads up, just so you know, and then boom, fill in the blank.

Like for me, it's just, hey, just so you know, I'm a dating coach

and I have very high standards.

And that really catches a lot of women off guard in a good way.

So use a hook for that first line.

And there's a lot of great hooks in my book.

Number seven, remember this paradox.

In dating, what you think is risky is actually safe and smart.

But what you think is smart and safe is very risky.

I'll say it again.

Risky is safe.

Safe is risky.

My first coach, Owen, a great approaching coach back in the day, a guy named Owen Cook, he taught me this.

Phrase, came from him.

What's risky is safe and what's safe is risky.

It's counterintuitive.

you want to you want to make moves with full commitment go all the way whatever you're going to do you need you need to do it all the way so if you're if you're going to approach that woman you got to walk up to her like you belong there that will feel risky to you but it's safe and smart because that shows confidence

paradoxically

or i should say inversely If you walk over to that woman and you're like hovering,

timid,

trying to decide should i go should i not go i don't know is this the right moment am i going to bother her am i a creep but i like her she's cute if you tiptoe and take a safe approach and just like say hey excuse me hi excuse me miss over here hi if you're playing it quote safe you are massively risking a massive rejection So what's safe is risky and what's risky is safe.

The metaphor Owen used that I loved is he used to say, imagine you're flying in in a plane.

It's your first time flying a jumbo jet and you're afraid because it's your first time flying.

So what do you do?

You fly the plane very close to the earth, the ground, 100 feet above ground.

Guess what?

You're going to smash into buildings and mountains.

You play it safe, very risky.

But if you pull back on the throttle, zoom up to 20,000 feet, that feels scary.

You're way up there, but that's where the clear flying is.

No mountains, no buildings.

You can fly nice and safe.

I always like that metaphor, especially with approaching.

So, if you are approaching a woman, do it in a way that feels risky to you.

I, you know, walk right up, look her in the eye, shoulder to shoulder, post up.

Hey, what's up?

I just saw you.

You are gorgeous, and I wanted to come say hi to you.

What's up?

I'm Connell.

Just don't say you're Connell because that's not your name.

Okay.

Number eight.

Ooh, number eight, master, man-to-woman communication.

Okay, I can't condense this into one minute, but I'll do my best.

Man-to-woman communication is my turbocharged form of flirting.

Man-to-woman communication.

That just means don't talk to her like she's your friend.

Don't talk to her like she's somebody you work with.

This is a woman.

You're a man.

You're on a date or a dating app, or you're approaching her.

Talk to her that way.

Talk to her like a man talks to a woman.

Tease, flirt, give her a cute little nickname a little bit.

Pepper in some flirty moves.

If you talk to her like just a friend, then she's going to see you as just a friend.

So man-to-woman communication.

There are no,

there really are no magic bullets that instantly transform a guy's dating life overnight.

But if there's two,

that are pretty darn close to magic bullets, it would be beginning to be making the shift toward man-to-woman communication.

And also the other shift would be, again, radical authenticity.

If you do nothing else from this episode, or if you never listen to my podcast again, then at least take away these two things.

Be a man.

She's a woman.

Talk to her that way.

And be authentic.

Really lean into who you are.

These two things alone really can change the game for you.

Number nine, use the push-pull.

What's the push-pull?

It's one of my favorite old school flirting moves.

It's where you combine a compliment with a light tease, a playful tease.

It's kind of like a compliment.

It's like a compliment meets a joking, playful tease.

On my first date with my girlfriend Jessamine, I said to her, you know what?

You're either the coolest girl I've met.

in a long time or the weirdest.

I'm just not sure which one.

And she laughed and said, oh, maybe I'm I'm both.

And she loved it.

I remember another time I approached a girl and she was like 24, 25, gorgeous, cool, but she had these expressions.

She talked like an old person, like a grandma.

She said things like, oh, I got pep in my step today.

And she had these little phrases.

It was just so strange to hear from a 24, 25 year old at a bar in Brooklyn, which is where I was at the time.

And I said,

I got to admit something to you, Heather.

You're really confusing me.

She said, what do you mean?

I said, well, here you are, this gorgeous, cute,

pretty young thing,

but

you talk like my grandma.

I don't know whether to ask you out or play bingo with you.

See how I'm combining a push-pull with a little flirting.

It's really powerful.

And she loved it.

She's laughing and loving it.

So that's called a push-pull.

That's a fun old school dating move that I learned from my old gurus that has aged well.

A lot of the old stuff has not aged well, but this has.

Use the push-pull.

Number 10, escape the friend zone instantly.

How do you do that?

Make

a comment on the, I'm talking about a date, okay?

You're on a date, you feel like you're playing it safe, make a you statement, Y-O-U, and use the word sexy.

Interrupt whatever boring, friendly, safe convo you've been having and say, hey, you know what's really sexy about you?

And then fill in the blank, your laugh, the way you're looking at me, the fact that you backpacked through Europe by yourself, whatever.

Use the word sexy and say, you are sexy.

That is really powerful.

She may or may not want to date you, but she's not going to friend zone you.

You're not going to be seen as just a friend, okay?

Friends don't look at their friends and say, you're sexy.

So do that on your next first date.

Number 11, go for the first kiss.

Don't forget my rule.

You will never lose a woman's interest in you by going for a first kiss on a date

and having her turn the cheek.

You will lose women if you want to go for that first kiss, but you play it safe and don't even try.

You will lose points for this.

Here's a quick amazing story.

My client, I'll call him Brett.

Brett

was really struggling to

go for the kiss on first dates.

He'd actually never done it.

He played it so safe on first dates.

He finally,

finally went for a kiss on the first date.

He and his date, her name was Kara, they leave the bar, they go to the parking lot, and he's like, oh, go for the first kiss.

I promised Connell, go for the first kiss.

And they get to her car and she's jingling her keys.

And

he's like, I got to do it.

I got to do it.

And he finally goes in for the kiss.

She kisses back.

She's into it.

Pretty soon it's getting hot and heavy.

Okay.

And

then he's got her.

They're making out with her like kind of pressed up against the car.

And then then

she says to him, she kind of interrupts the makeout and says, this is their first date, by the way, their first date.

She interrupts the makeout and says, you know,

I wish we could go into my car.

I wish we could get into the backseat of my car, but I've got all these boxes back there.

And he realizes, oh my God, she wants to like.

hook up in the car.

And he says, well, my truck's right over here.

Let's go over to to my truck.

She's like, Okay, great.

And they go over to his truck.

And

let's just say

good times ensued.

On the first date in the parking lot,

he, yeah,

let's just say he put it into fifth gear and did not leave the parking lot.

And all he had to do was go for the kiss.

Now, your mileage may vary, no pun intended, but going for that first kiss, you're going to be rewarded sooner or later, probably sooner.

And again, you're not going going to be a creep.

It's not creepy and weird to go for a kiss.

You know what's creepy and weird?

Having a pretty solid, good first date where you're vibing nicely, and then you go in for the hug like you're burping a baby.

That's creepy.

You struggle with dating, right?

Sure, you have a good job and cool friends, but you just aren't sure how to flirt.

The apps don't work for you.

And sometimes women put you in the friend zone.

It's frustrating.

Hey, I struggled with dating too.

As an introvert and a total nerd, I didn't just live in the friend zone.

I owned real estate there.

But I escaped using the dating philosophy of radical authenticity, which I've used to help thousands of men in 17 countries find love.

It's what I wrote about in my best-selling book, Dating Sucks, But You Don't.

And radical authenticity is why Psychology Today called me the best dating coach in America.

And now I want to personally help you attract your dream girlfriend.

So go to datingtransformation.com and book a free call with me.

On our call, I'll tell you how my one-on-one coaching will help you find your dream girlfriend, and you'll be doing it by flirting with confidence and authenticity.

No creepy pickup tricks needed.

So go to datingtransformation.com, book a free call today, and let my personalized coaching help you get a great girlfriend.

Okay, next, number 12.

This is a simple one.

I like this.

Ask every woman you approach at a bar this question.

Tip number 12.

Ask her,

who are you here with?

Guys, never do this.

When you approach a woman at a bar, you need to understand the dynamics, who she's with, the logistics.

Is she with her family, her friends, her mom and dad?

You've got to ask who she's here with or

if she's with one other person, how do you know each other or she's with two or three people how do you know each other so ask how do you know each other or who are you here with here's why this is so important my client james and i were once out at a bar rooftop bar in new york city called the broken shaker and we're approaching women and we see this gorgeous woman in a red dress I believe she's a Latina, very stylish, really classy, and she's with a very handsome guy.

But we're talking to everybody.

James approaches.

We're chatting, not expecting anything.

And he asks the magic question.

So how do you know each other?

And she says, oh, this is my brother.

So I talk to the brother.

James talks to, I believe her name was Isabella or Annabella.

And they hit it off like crazy.

Here's what I mean.

So I'm talking to her brother, who's a Gulf War vet.

I'm talking to him about his service, trying to distract him from the fact that his sister and my client, James, are hitting it off like crazy.

And then I hear, I actually see and hear these words.

I hear Isabella say to James,

yes, they're real.

Here, touch them.

And she takes his hands and places them on her chest.

And her brother is right there, albeit

her brother's back is to what's going on.

His back is to them.

He doesn't know what's up.

So anyway, let's just

and pretty soon Isabella and James are making out.

And I'm talking to the brother, basically learning all about his service.

The brother might have been totally cool with her sister, his sister being, you know, flirty, but I was trying to distract him anyway.

Okay, next question.

Number 13.

Next question.

Next tip.

Number 13.

When you approach lead with power compliments, I love approaching a woman this way.

Just walking up, giving her a very sincere, specific compliment about nothing about her physical appearance, or at least not about her body parts, but something about her style.

You know, hey, excuse me, that's a great t-shirt.

I love that ACDC t-shirt.

That's so cool.

You have nice taste in music.

I love to just lead with a nice, specific compliment.

Here's the secret to a good, what I call a power compliment.

A power compliment, compliment, it's genuine.

You're not just saying something randomly.

You mean it.

It's genuine.

It's specific.

And you tell her why you like it.

For example, I was at a bar once and I saw this really cute girl.

She had a nose ring in.

And I walked up and said, hey, really cool nose ring.

And I told her why I liked it.

I like it because it's very retro.

It's very early 90s.

It's kind of like grungy.

Is that what you're going for?

And she wasn't.

She was just like, no, I didn't know that, but I love it.

Thanks.

We start talking about music.

And, you know, five minutes later, getting your phone number.

And all I did was I said, hey, cool nose ring.

Cool retro nose ring.

Great style.

That's all.

So lead with a power compliment.

Women love a sincere, specific compliment.

Just mean it, make it specific.

Don't just say, I like your style.

Choose something about her style, her tattoo, her shoes, her t-shirt, her earrings.

I was in a bar in San Diego once with my client, Jason, and he walked up to this woman and just said, hey, I love your glasses.

Those are really cool, nerdy glasses.

And she was wearing these like Lisa Loeb type of nerdy cat eyeglasses.

She lit up.

And all of a sudden, they're like canoodling at the bar.

And all he did was say, hey, I like your glasses.

You have.

you have cute eyeglasses.

That's all you have to say.

Okay.

Tip number 14 from my best-selling book, Dating Sucks, but You Don't.

14 out of 20 here.

Here's a good way to text women.

Think about it this way.

Text her as if she's already your girlfriend.

A lot of guys say to me, what do I write?

How do I text?

And then I say, well, if she was already your girlfriend, what would you write her?

All of a sudden, the pressure would be off, right?

The bar would be lower because you wouldn't be thinking, what do I have to say to impress her?

And by lowering the bar for how impressive you need to be, you'll relax and you'll become expressive.

Instead of trying to impress,

we're trying to express.

And expressing that authentic self is going to help you let the floodgates just open.

I gave this tip to one of my new clients.

Harrison.

And Harrison was like, Connel, I love how just like I'm being so weird and quirky with women.

And I said, what do you mean?

And he told me about how he's texting with a woman on a dating app.

And he said that

he's a little bit on the spectrum.

He's on the autism spectrum.

And some woman had

a comment on her profile about being on the spectrum.

And he was like, cracking jokes about that.

But not, he wasn't making fun of her.

He was being really vulnerable and saying, hey, what's up?

I'm kind of on the spectrum too.

Look at us, a couple of spectrum people.

Why don't we meet up and have you know drinks and talk about being on the spectrum?

Which you wouldn't think would be good game, quote unquote, but it was just so genuine, and they were clicking about this topic that they shared.

He was just he wasn't trying to impress her, he was just really kind of leaning into something genuine, and boom, that worked for him.

So, again, if she was already your girlfriend, what would you write her?

That's my question for you.

Slash tip.

Okay, number 15 out of 20, tips from dating sucks, but you don't.

Every morning, do a daily confidence kickoff.

Spend 15 minutes every morning, and you want to get yourself in the state of gratitude.

You want to remind yourself how incredibly wordy and attractive you are to women.

And you also want to focus on very clear, specific dating outcomes.

So you want to do a daily confidence kickoff.

Tony Robbins calls it an hour of power.

I love that term.

There's a book called Miracle Morning.

Others have thought of this.

I'm hardly the first one.

But man, there's something so powerful about taking about 15 to 20 minutes at least every morning and say, why am I worthy of women?

Oh, it's because

of my heart and my intelligence and my sense of humor and blah, blah, blah, whatever works for you.

And then

focus on how grateful all the things you have in the world, how you're already rich in so many ways, if not in dating, at least rich in other ways, rich in health, I hope, rich in money, I hope, rich in friends, rich in all sorts of things.

Get in touch with gratitude and then tell yourself, what is my dating goal?

What can I get excited about?

Think about your dream girl.

Think about how amazing it will be to sleep in, snuggling her, giggling with her, spooning for 15 more minutes, like my girlfriend Jess and I did today.

And you basically every morning, get yourself in a good state.

And then it's going to be easier for you to approach women.

It'll be easier to take action toward getting your dating goals.

So do a confidence kickoff every morning.

And again, I go into much detail.

about this in my book.

And again, email me, connell at datingtransformation.com for a free copy of my book i'll send it to you right away okay tip number 16

um

you oh this is a good one find oh this is really good i love this tip find your home field advantage

find your home field advantage

find a place that is like a bar slash restaurant probably that you can make your place where you take first dates.

Have your first date home field advantage.

When you find one or two places where you know the manager, you know the waitresses, you know the bartender, you just know the people there.

When you walk in on that date and you're with

Clarissa from Hinge

and she sees the manager say, hey, what's up, Doug?

Good to see you, bro.

And she sees how other people like you.

And you're just going to feel really comfortable there, then it just makes it so much easier for you to feel in the zone.

I had

the,

it was five or six years ago, last time I was, not, it's not the last time I was single, but it's a time when I was single and having a lot of fun.

There was a spot where

I was on a date once with an incredible woman named Catherine.

It's our first date, Kat.

And Kat and I were on the date.

And this place was right next to my improv theater where I did improv a lot.

And I just knew everybody in the bar.

And three different people came up to Kat and myself on our first date.

And basically,

they all knew me.

They were like, hey, watch out for this guy.

He's trouble.

And toward the end of our date, Kat looked at me and said, everybody likes you,

which is not true, but that's how it felt that night.

And I could not have...

planned that night any better if I had paid those people to come up and make me look good.

But they just did because they knew me, because that was my home base spot.

So find a home base.

There's something called social proof

where a woman sees other people socially approving of you, and that makes helps a woman to become even more attracted to you.

So anyway, use social proof to your advantage by creating a home base where you can go on first dates.

And don't worry, the bartender is not going to, you're not going to get busted going on multiple dates at the same place um

i had another bar i had as my home base and uh my date different woman excuse yourself briefly went to the ladies room and while i was sitting at the bar by myself waiting for my date to come back the bartender who was kind of new there her name's christy christy leaned over and said hey are you that guy who brings women here all the time and just makes out with like a different woman

i was like yeah you caught me

Anyway, but never did I ever have like a bartender say that to my date.

They always said it to me.

Okay.

Tip number 17,

give her the boyfriend experience.

No, that is not a special offer that I give

because I'm a male prostitute.

The boyfriend experience is a name I came up with for

When you meet a woman you really like, after one or two dates, if you see her as girlfriend material, give her the boyfriend experience.

What that means is instead of going on another drinks date or another dinner date, once you get to like date three or four, do couple, couples types of activities.

Go grocery shopping and then make dinner at your place.

Take a yoga class together.

Or in the case of Donna,

on our, it was actually just our second date with Donna, who became my girlfriend.

Donna came to my pub trivia night and met my entire pub trivia team who were also my improv friends.

And I wanted her to meet my social circle because I wanted her to get a feeling for, oh, this is what it would be like to be Connell's girlfriend.

Not because I knew she would like them.

I didn't know if she would.

I just wanted to lean in authentically to who I am.

Basically, I was saying, Donna, this is me.

I'm a trivia nerd.

I'm an improv nerd.

I got my cool, awesomely dorky, nerdy friends.

And I mean that only in a good way.

And this is me.

Maybe you'll like it.

Maybe you won't.

Turns out she really liked it.

I wanted her to give her a sense of what it would be like to be my girlfriend.

And she apparently liked it because

she became my girlfriend.

So yeah, give her the boyfriend experience.

And starting with maybe date three, date four.

Okay.

Tip number 18 of 20 from dating sucks, but you don't.

This is so important.

Always get verbal consent for sex.

Always do that for obvious reasons, not just to protect yourself, but it's just the right thing to do.

But here's the thing about getting verbal consent for sex.

You don't have to make it something that

ruins the mood.

You can ask for consent in a sexy way.

You can dirty talk getting consent.

You can say to her with that breath, you know, in a moment of passion, things are getting hot and heavy.

And you just say to her, hey,

I really want you.

I want to take you in my bedroom.

Is that okay?

Should I take you in my bedroom and put a condom on?

But you say it with sexiness.

It's not going to ruin the mood.

If she's ready, she'll say, yeah, let's go.

Boom.

You've got sexy turned on consent.

And if she says, oh, that's a little fast for me, all good.

You asked, she answered, and you can just stick to making out, stay on first base, and there's nothing wrong with that.

Maybe next time, maybe the time after that.

But consent is not only right and moral, it's sexy.

It really is.

I remember the first time Kat and I were intimate.

It was so cute.

I turned it into almost like a little bit of a comedy act.

I was joking.

I said, hey, could you sign some documents?

I need to know before this goes further that I have your absolute consent for anything that may or may not happen in my bedroom.

My attorney is faxing over some papers.

And we were in the middle of a hot makeout session.

And

she pulled back or she sat up straight,

put her right hand in the air and said, I,

cat, last name, do solemnly consent to intercourse with Connell Barrett.

So cute.

And yeah, then the night continued.

So you can get consent.

You can.

You should get consent always.

But you can do it in a fun way, a playful way, a sexy way.

It builds trust.

It's just, yeah.

You don't need to do stupid freaking games and try to manipulate women into sex like so many of those sketchy, toxic, crappy, awful male pickup dudes teach.

I know because some of them coached me.

I know exactly what they teach.

You can do it as a gentleman.

You really can and should and will.

Okay, two more.

Number 19.

The 19th tip from my book I'm sharing with you.

What is this one?

What am I?

What did I write here?

Oh, this is a good one.

Express your passion,

not your paycheck, to impress women.

Some guys

try to impress a woman with their money.

They might talk about their cool boat or their new watch or the big raise they got.

And you know what?

That's really not going to help you.

What you want to do is talk about your job, your career,

and through the lens of, well, here's what my money or here's what my job allows me to do to help other people, or here's why I'm passionate about what I do.

So there's a really, one of my favorite, actually chapter two of my book opens with a really compelling story.

I was out one night in LA with my client, Jake.

And Jake is a big time,

very successful, wealthy plastic surgeon in Beverly Hills.

He's not messing around.

And he walks up to these two women.

And by the way, I'm there watching him for the very first time as his coach.

He wanted me to help him approach women.

And I'm like, all right, dude, walk up to some women.

We were at a place called EPLP in Hollywood.

And he walks up to two gorgeous women.

And I'm ready for him to say whatever he's going to say.

He takes out his business card, this golden black card, and he hands it to them.

And he says, I'm a plastic surgeon from Beverly Hills and gives these two women his card.

That was his pickup line.

They were confused.

They thought he was trying to get business.

They're like, is there something wrong with our nose?

Do we need a plastic surgeon?

And then they realized, oh, you're trying to impress us with money and your job.

And they like almost laughed at him as they walked away

and i was like dude come here no no no no none of that

don't try to impress women with your money when you do that

if if you do it you just come off as somebody who feels like he doesn't have what women lack or that he that he lacks what women want uh

We made some course corrections.

Jake and I did that night.

And I said, dude, why don't you tell women about how amazing your job is?

I asked him, what lights you up about your job?

What do you love about it?

And Jake told me, oh, well, my favorite thing about my job is not the money.

It's the way I feel when I can really change somebody's confidence,

give them a nose job that makes them feel beautiful again.

He also does,

I guess it's pro bono would be the term.

even though it's not that's a legal term but he does free um skin graphs on little kids who like get burned in fires or who have skin issues

And he does some incredible things.

I said, dude, talk about that in terms of your job.

Don't talk about how much you make or try to impress women with your job.

Make an impression on them based on how passionate you are about it and what it allows you to do.

So fast forward, like two hours later, he clicks with this really wonderful woman and she is just putty in his hands because he's able to share with her, oh my God, I love changing lives and

helping little kids who got burned in fires because I get to help them repair their face and

feel whole again.

And that was all truthful, by the way.

That was genuine.

He was being really real with her.

And I don't know what happened.

I'm not sure they got married or anything, but it was a way better approach than he started off the night.

So, yeah, bottom line is: don't try to impress with your paycheck or your Lambo.

Impress with

your passion for what you do, how it makes you feel, who it allows you to help.

Passion is so attractive to women.

So lean into that authentic passion.

And tip number 20 from dating sucks, but you don't.

Ooh, this is a big one.

I could do, I'm going to do a whole episode about this actually, but I'll just tease you for right now.

Here is your texting framework.

Here's how to text women in four simple parts:

play,

play, play,

and then pull the trigger.

I'll say it again.

Texting comes down to this.

Play, play, play, then pull the trigger.

Most of your text messages should be playful.

Should be you sending a light, playful, no big deal text message.

Hey, check out this video on my cat doing backflips or a playful, sweet little tease

or

a nice light little joke or

asking her a question that you think would make her smile and feel good, talking about a fun topic.

Most of your messages should be light and playful.

And then once you've messaged back and forth a little bit, then you pull the trigger.

You ask her out.

Go for the date.

So play, play, play, pull the trigger.

That's not how most men text.

Most men are very logical, informational.

They ask logical, boring, informational questions.

Where are you from?

What do you do?

How was your weekend?

When did you graduate?

Where were you on the night of January 14th?

They don't play.

And women want to play.

Okay.

So

I'll give you the how on this in a whole separate episode.

But yeah, bottom line is we want to turn dating into something.

that feels playful to women.

Because if you're playing with her, light, playful text messages, then she's going to love it.

I remember I was sitting in the bar waiting for my girlfriend, my now girlfriend, Jess, to arrive.

It was our first date, and she and I had been texting for two or three days, like literally 30, 20, 30 messages, probably.

We were texting like crazy.

And I was just, all I was doing was playing with her, play, play, play.

And Jess is so funny and she's very witty and playful back.

And I got a message from her.

It really made me happy because I was super excited about meeting her.

And she wrote, she kind of broke from the banter

of what we were bantering about.

And she kind of broke character and said, by the way,

I'm really liking our banter.

And then she went back to bantering with me.

And yeah, that's all I did to get the first date with Jess.

And now I'm so lucky.

Anyway, so that's tip number 20 from dating sucks, but you don't.

Play, play, play,

pull the trigger.

That is your whole texting

And frankly, you could bring that same philosophy to first dates.

If you just go on a first date and you get in a playful zone, and then when the moment's right, pull the trigger.

Pull the trigger is different on a first date than texting, right?

Go for that first kiss, make that move, right?

So that's tip number 20.

Okay, we have only just begun

to talk about

some of the wisdom lessons, wins, mistakes that I've

experienced in my 20 years of working on my dating life.

And over these coming episodes throughout the rest of 2025, I'm going to bring a lot of special episodes to you, trying to bring the best of my wisdom.

Because again, I want you to get a great girlfriend.

You don't need 20 years.

You don't even need 20 months, probably.

You can have an amazing girlfriend in two, three, four months if you really put effort into it.

And that's what I do with my coaching.

Basically, it's a two to three month program where guys come, they work with me, and then by two or three months in, they either have an amazing girlfriend or they have lots of dates coming into their dating life and they are beginning to connect with the kinds of wonderful women who one of whom will become his girlfriend.

So you don't need 20 years or even 20 months, 20 weeks, plenty of time to get you a great girlfriend.

Okay, by the way, you can go to my website, datingtransformation.com.

I have a brand new website.

I just relaunched it.

Every podcast episode is on my website.

There's so many great tips.

My column is on my website.

And if you want to talk to me, you can book a free consultation with me to find out if dating coaching is something that can help you.

get a great girlfriend.

Thank you so much for listening.

And

until the next episode, don't forget your dream girlfriend is out there and she is going to love you.

She just has to meet the real authentic you.

Till next time.