Become a Magnetic Flirt on First Dates in 3 Simple Moves (Live Coaching with Matthew)

didn't just live in the friend zone.

I owned real estate there.

Welcome back to the How to Get a Girlfriend podcast.

I am your host, dating coach, Connell Barrett.

I'm your podcast dating coach.

If you struggle with what to say to women, I'm here to help.

If you struggle with confidence, I'm here to help.

If you struggle to get second dates, get stuck in the dreaded friend zone, I can definitely help because brother, I didn't just live in the friend zone.

I owned real estate there.

And today we're going to do a really cool episode.

I love doing coaching call episodes where I record an actual coaching call that I had with my client, Matthew.

You're going to hear Matthew.

Matthew, he lives in California.

He's a business owner.

He's about 40, I believe.

And he's a single dad.

And when he first came to me, he was really struggling to get second dates, struggling with the friend zone.

He just was having trouble making those spark, making those sparks happen.

He's about midway through my coaching program right now.

And this is very typical of a one-hour coaching call that I do with my clients.

And you're just going to be able to listen in and hear me help.

Matthew with some of the things he's been working on.

He's doing so great.

I remember there was a moment a couple of weeks ago where he said, Connel, I've got three women in my rotation and tonight I have a date with a Russian-born model.

You've created a monster.

And Matthew struggled with

coming off as a little bit too,

what's the right word?

Fake nice.

He was coming off like a therapist.

He was just listening to women and being like a friend.

And I said to him at some point, look, it's good to be friends.

It's good to be friendly with women, but you can also flirt with her.

You can let her know she's sexy.

You can tease her.

You can give her a really fun, authentic, true experience of what it's like to be with you.

And since he made a couple of flirting and first date shifts, he's really seen some improvement.

So anyway, if you struggle with first dates, not sure what to say, not sure what to talk about, if women friends own you, listen to Matthew's coaching call with me.

And I'll bet you'll be able to use a lot of the same pieces of advice that I give Matthew on your next first date.

So you can start getting second dates, third dates, and soon get a great girlfriend.

All right, let's take it away.

Here is me and Matthew.

All right, Matthew, let's get to it, man.

What's on your mind today?

How can I help you with your dating life?

Connell, cool.

Thanks.

Yeah, no, I got a bunch of questions.

The first one I was thinking about is we've talked a little about this, but it's that man-to-woman communication.

We kind of touched on this a couple sessions ago.

Really wanted to kind of ask, what does the man-to-woman communication look like on a date?

And does that just translate into picking the place or expressing clear opinions?

Or can you kind of dive deeper on some of the things you kind of feel are important?

A good way to think about man-to-woman communication is

have you been on any dates, Matt, where you looked over and saw a couple and you were just like, wow, they're hitting it off.

It's going well.

You ever seen that visually?

And have you ever been, and I know you've been on a lot of dates.

And have you also looked and seen a couple and they're just like, he's sitting on his hands, figuratively, if not literally, and they're both being very safe and polite, but you can just see there's not sort of a chemical vibe happening?

Yes, I guess.

So you want to be moving toward that first pair, which is equal parts, physicality,

eye contact, the way you look at a woman.

There's a way to look at a woman where it's like,

yeah, okay, right.

And then there's a way that you and I would look at each other if we were getting together as a couple of buddies.

Uh-huh.

Oh, yeah, cool, right?

Yeah, the Dodgers, they're good this year, or whatever we'd be talking about.

So, a lot of its vibe, it's eye contact, it's voice.

It's also clear statements of romantic interest.

Probably the easiest way to create, put a man-to-woman card on the table on a date is to say and actually feel

make a statement toward her that lets her know there's something sexy about her.

You know what's really sexy about you, Tracy?

It's the way you bite your lip when you're thinking and you look up and bite your lip.

It's super cute.

Anyway, I just wanted to say that.

So yeah, tell me more about your college experience.

You sort of like throw those little, those, those verbal and non-verbal cues to sort of crank up the romantic tension on a date.

That's essentially how I define man-to-woman communication.

There's really only three ways to communicate with people outside of family.

It's friend to friend.

It's business slash transactional, which is essentially what you and I are doing right now.

Even though we have a friendly coach-client relationship, it is a business one.

So there's friend to friend, there's business, and then there's man to woman.

And man-to-woman is a combination of you just feel it, but it's also how you talk to her, it's what you talk about.

basically it's turbocharged flirting

and do you think that stays pretty consistent through date two three and four or does that kind of change you've noticed throughout the dates i'm several years into dating my girlfriend jess and i still flirt with her and look at her perfect butt

and and banter with her and let her know that I think she's hot and sexy and cool.

Sometimes I tease her, which is one of the ways I flirt.

So yeah, it never ends.

It'll ebb and flow.

And you want to read the room, of course.

But yeah, man-to-woman communication, it's, it never goes away if we do it right.

Okay, interesting.

Another question,

you know, that have come across in my, my dating, dating world lately is that I've obviously, you know, and I'm sure other guys have this and they've brought it up to you, but it's those first.

you know, five to 15 minutes of like kind of like, okay, we've met, you know, you don't know me, I don't know you, this like interesting energy/slash conversation flow.

And I feel like the questions I'm asking might start off sometimes a little too deep, but like, is there a good kind of cadence or a good flow or a good kind of mix of conversations that you're kind of talking about within that first 15 minutes?

I think, you know, like there's different stages of the date, I like to call it, right?

The first 15 minutes are, how are you, stage?

And the next 30, like, okay, let's talk about us.

Okay, then let's dive a little deeper.

But would love your kind of help and feedback on that?

Cause I feel like those first 15 minutes are really, for me, have been kind kind of like, uh-oh, like everybody's nerves are there and I don't kind of know what to say and how to drive the conversation.

Well, how would you, can you give me some examples of what you do say or questions you do ask in those first 15 minutes?

Yeah.

Because you've been going on a lot of dates, as we both know.

Yeah,

a lot of first dates.

And now second and third dates because of you.

I appreciate it.

So, yeah, so I think, I think the things I was asking, you know, like, how was your day?

How was, you know, what's been the most exciting thing that's happened to you this week other than meeting me?

Just trying to kind of keep it general and kind of like open-ended.

Again, just trying to

feel where they are and what energy they're bringing to the table on the date.

I think those are good options, those first 15 minutes.

Really, you're just trying to not

lose

any points in the first 15 minutes by

trying too hard

or by saying something that's just weird.

I don't think that's a matt problem.

That's not a me problem.

No.

But

yeah, for the first 10, 15 minutes, I am, you know, it's figuratively, if not literally, how about them Dodgers?

Or how is the traffic on your way here?

Basically,

it's okay to ease into a date with some basic small talk because you're just letting...

the two of you get more comfortable in the environment.

And it's okay to make a little small talk.

It's also okay to be a bit vulnerable.

I remember saying this on many dates early on when I was really nervous, getting comfortable going on dates like 20 years ago when I first started really working on my dating life.

I remember, you know, that feeling where you're waiting and you keep looking at the door to see if the next woman who walks in might be her.

Yes.

Because you haven't met her in person yet, you're like, I think that, I don't think that's her, but I'm not sure.

Or I hope that's her.

Whoa, she's hot.

Or, God, I hope that's not her.

Like, you've different people come in.

It's almost like it's like some kind of roulette.

Is that my date?

And I remember I would be vulnerable and say that to my actual date once she arrived.

She would down and after a couple minutes of maybe chit chat and small talk, hey, how's your day?

Where'd you park?

That kind of stuff is fine.

Then I would say, by the way, I got to be honest.

A couple other women came in.

I couldn't tell if it was you or not.

And I'm just really glad that you are you because you look like your

or I was so nervous waiting for you to come in.

So I might admit to being nervous a little bit if it's genuine, not as a move, but if it's genuine because that kind of vulnerability is attractive because hey, it's a first date.

If you're not a little bit nervous, you know, you're probably not,

probably shouldn't be there for some reason or another.

No, that's good.

Okay, you know, it's been interesting.

I have been saying sometimes, oh, I was really nervous to meet you.

And I noticed the energy kind of shifts on the date.

And they like it.

They're like, oh, really?

I was too.

So that's been interesting.

So I appreciate Appreciate that.

No, that's good advice.

And then, you know, kind of even.

Can I throw one more question at you?

I don't know if we've talked about this on previous coaching calls.

A really good question to have in your back pocket for the first 15 minutes to sort of move out of small talk to something a bit more real, but also that totally makes sense.

Have you ever asked a woman about the weirdest first date she had?

No, I was always trying to shy away, which for sure is a question I had in my head is, you know, on the topic of first dates or dating or boyfriends, girlfriends,

you know, on the first dates.

It's a follow-up question, but no, I try to stay away from those topics.

I get it.

In fact, I agree with that.

You don't want to go down a rabbit hole of talking about dating or getting each other's exes, probably on a first date, but there is one exception to every rule.

And I found it really helpful in the first 10, 15 minutes to say something or to ask her something like,

hey, by the way, I'm just curious,

what's the weirdest first date guy you ever met or the weirdest thing that ever happened on a first date?

I found that to be a really good question because it's fun, hopefully fun.

Hopefully it's not something terrible that happened to her, God forbid.

But pretty much every woman has a first date weirdo story.

The guy,

some of the answers I've gotten to that question over the years were

a woman would say, oh, one guy showed up with

plastic vampire fangs in his mouth, and it wasn't Halloween.

It was like Easter.

Another guy showed up, and this is actually in a recent episode.

I mentioned this, and he sat down, and within five minutes, he asked this woman I was on a date with, she's retelling the story to me.

This guy asked her what shape and size her areolas are.

Because he's looking to date a woman with silver dollar-sized nipples, silver dollar-sized areolas.

This is like 10 minutes into her date.

And another woman said this guy's Coke dealer showed up in the middle of a first date and gave him a delivery.

So I like having that as a good back pocket question for the first 15 minutes because the topic, first dates, is totally relevant because you're on one with her.

And it's a fun way to diffuse some tension.

Almost every woman has some weirdo she met.

And then somewhat subtly, I like to think that because she is conveying a story about a guy who just kind of creeped her out,

you're juxtaposing yourself.

You're this cool, chill, well-dressed, spoken guy who's so normal and attractive.

On some level, I feel like that also makes you look extra good because she's almost like comparing the two of you.

And it's just a fun topic.

So even though I don't want to talk about dating for that long, that's one exception to the don't talk about dating rule.

And if you have a weird first date story, you can certainly share yours as well.

I don't have one directly.

I have a friend.

We talk about dating.

He told me an interesting one.

He went out with a girl and he got there and she brought her a six-month-old

son.

Okay.

She didn't know.

She didn't know.

And he just kind of this child slept through the date.

And then

he kind of like started a question, like, hey, so you have a kid?

And she was like, yeah, I probably should have told you that earlier.

And they ended up walking.

They're actually now dating full time, but full-time.

But they're dating long term.

But yeah, it was an interesting thing.

He's like, hey, that's a good one.

Meet her, meet her child.

That's a good one.

I know it didn't happen to you.

You could share that as an anecdote you heard from a friend.

Anyway, feel free to use the,

what's the weirdest first date

you've met question in your back pocket in those first 15 minutes as a perfectly good way to kind of ease into a date.

Yeah.

Okay.

And then kind of, from there, how deep are you going?

How deep of like questions are you asking?

Or should I be asking, I guess?

The better question is how deep of questions should I be asking on a first date?

Like, are you going deep into topics or is it kind of surface level?

Depends on the date.

I mean, it's going to change depending on your vibe, her vibe, who the two of you are.

But as a general rule, I would say keep it light.

Keep it fairly light, fun.

Think.

Think you can have a deep, you can have an in-depth conversation about stupid shit.

That's always been my sweet spot.

My first date with my girlfriend now, Jess, we talked for 30 minutes about ketchup and why she hates ketchup and why I hate mushrooms and why she loves Italian food and roller coasters and TV shows.

We were all over the map in a nice, fun, bantery way.

Very light topics.

So I'm generally going to keep the first date topics light.

If I'm going to get deep about anything, it's probably going to be more like,

I remember on my first date with Jess, I remember thinking we were about 45 minutes in, it was very fun and bantery and light, a lot of jokes back and forth because she's very funny.

And then I remember thinking, well, I want it to be a little bit more deep.

So

I said to myself, Yeah, who are you closest to in your family?

And all of a sudden, not all of a sudden, but she opened up a bit and she told me about her brother Aaron, how close they are.

And then I talked about my big sister, Kelly, who was the sister I was closest to.

And I say was because she passed away last year, but at the time she was still with us.

And I talked about that.

All of a sudden, we went from banter, fun, light,

talking about why we love dogs and

love cats and hate jogging and she hates ketchup to, all right, let's talk about some real stuff.

Now,

is that a deep topic?

I guess it depends on your definition of deep, but I do like to find out who matters to her in her life, who's important to her.

I want to know.

I'm curious about who really matters to her.

And I also want to share with her who matters to me in my life.

So we start getting to know each other

in a slightly way,

if not deep, deep.

Did I answer your questions or your question about depth?

No, no, no, no.

No, that did.

What kind of deep questions or topics have you found yourself talking with women about?

I've been trying to keep the first dates light.

So I kind of was trying to, you know, trying to keep it more on, hey, you know, tell me about travel, tell me about uh food, tell me about, um, you know, some past experiences you've had as a child, trying to keep it kind of light.

But some of the deeper topics I've been kind of going into, um, family has been one.

Um, obviously,

um,

even

do you like to cook?

What do you like to cook?

Again, just trying to keep it light, but some of the deeper ones, you know, would love to know about past childhood, family, brothers, siblings, things like that.

But again, keeping it certain level, I feel like it depends on the woman.

It depends on the woman.

That's a great roadmap for you.

I usually think about a first date more about,

let's get on the same kind of flirting vibe, right?

I love Jess.

Again, I use my girlfriend for obvious reasons, but there have been many other first dates I've had.

If you have a nice, light, bantery, jokey vibe with a woman, the topics almost don't matter.

You're connecting in terms of how you're talking to each other.

Other women

I've had dates with where it was a lot more about emotional connection, kind of being vulnerable and opening up about fears and hopes and dreams.

And

we are on a more emotional connection wavelength.

I've had some women, they don't want to talk about their family members.

They just want to talk about, they just want to laugh and have raunchy, fun,

even sexually charged conversations because she's a bit more edgy.

So I'm looking more to try to match her flirting vibe than getting too bogged down in the actual topics.

You can talk about almost any topic.

It's more about the tone, the

tone of how you're talking about that topic.

Does that make sense?

No, that makes sense.

Okay.

No, that makes sense.

Yeah.

And I know we've talked about this before,

this sort of topic, but that helps.

Okay.

And then kind of in regards to the dates, you know, I know we had talked and was a huge help for me was, hey, you got to turn the

flirting energy and the,

you have to turn up where you're going on the second date.

So kind of want to kind of flow into logistics.

Wanted to talk about that.

So like second, third dates, you know, I can't thank you enough.

I was having a hard time getting second and third dates.

And now I have, you know, women calling me like, hey, when are we going out again?

So I wanted to ask.

Hold your question.

I want to answer it.

It's the whole point of me talking to you.

But can you, just for the audience today, can you share any quick stories from recent

successes, moments, moments of connection?

As I recall a few weeks ago, you and I were going back and forth, and you started being a bit more direct with women, or just literally being more silly, playful.

Didn't you grab food off or pretend you were going to take food off of somebody's plate?

I don't remember the story, but share any aha moments you've had on dates, if you would.

And then we'll get back to the topic, of course yeah yeah no so you know from talking to you i realized you know i really need to be myself authenticity is huge and understanding i am who i am i have a silly kind of fun playful personality and i wasn't showing that on dates and um

i went on a date a first date with somebody we met up for drinks and we were sitting at the bar And

she left to go to the bathroom.

I ended up talking to the people next to us for a bit.

She came back.

She's like, oh, that salad looks good.

And I was like, oh, actually, I'm going to grab a piece.

And I grabbed my fork and went to grab a piece.

And she was like, first, she was like kind of mortified, but also kind of like giggly.

We had a little bit of banter with the couple next to us for a minute.

And I turned my attention back to her.

And I'll never forget that she turned to me and she was like, well, I really like that you did that.

That was really, that was really cool and really authentic.

So, again, that's- You said the word authentic.

She said the word authentic.

And I like she's been reading my marketing.

Yeah, you know, Connell.

um

so but yeah it was it's been nice really to be to be myself and go out on dates and not trying to be prim and proper and it and it changed you know working with you again i you know i can't thank you enough has helped me go from not getting second and third dates to again having people like hey i want to go see you again when can i when can i see you uh so it's been a really nice change and i think it's it's being authentic has been a big big part of it sounds like well that story to me says okay you're giving her a more impactful emotional experience.

Yes.

I think before you were getting stuck in the problem of understandable rut of, oh, let me try to emotionally connect with her.

Let me see if we can find the right emotional connection or let me be a good listener.

Let me kind of like just emotionally connect and feel the same way about things.

I'm not, and by the way, I'm not saying not to do that.

That can be really successful on lots of dates.

But I feel like maybe you were just a little bit buttoned up, so to speak, and holding back.

And just, I think women are really drawn to a fully expressive man who's just unfiltered, amplified, putting it out there, doing silly things, like pretending you're just stealing food off of somebody's plate.

That's, that's hilarious.

And that kind of freedom that gives women a more emotionally impactful experience.

And women make their dating choices not just on, does this guy check the boxes I want for a boyfriend?

On some level, there's that there, but you probably already check those boxes.

If she's on a date with you,

really goes on a first and then also a second date is she wants to feel something.

She wants to feel connection to you.

Yeah, she wants to feel like she's with a man

who goes through the world and is on his own path and he's not afraid to speak honestly, truthfully, let the heavens fall, let the chips.

That's attractive to women because most guys are so guarded and safe.

So the reason why I go on and on and on about being being authentic and just literally speaking your thoughts up to a point is

it's that free expressiveness is very refreshing to women because most men are too focused on what's the right thing to say to get her to like me.

Fuck that.

Say that most honest, deepest thing you can think of.

And as long as it's not vulgar

or disrespectful, boom, let it go, let it fly.

Yeah, and I agree with you on that.

And I think you said this to me, I think in a session we had, you You were like, hey, you know, they're prim and proper at work.

Like, you're very like, okay, hey, this is how this sounds, and this is, and I'm, as I'm fake air typing here, you know, yes, we will be able.

And I realized I was bringing that dating energy to the date, and that just doesn't work, right?

They get, they, when you can get that at work, they need something fun and playful to get their mind off of work and off of the normal day-to-day.

You're also being a bit of a rebel

when you that little pretend, let me take that food move.

You were being a bit of a rebel.

You were

not caring.

You were giving fewer fucks.

Yes.

And that's attractive.

Women want a guy who gives, not gives no fucks, but gives fewer fucks.

That's just more fun and refreshing.

So anyway, okay, back to the

logistics overall question you were asking.

Come back to that, please.

Yeah, so you, you helped me realize that I wasn't bringing this date energy to a second date,

which for sure I realized I wasn't.

Like, hey, like, it needs to be a little romantic.

It needs to be, you know, just different.

Hey, there's, it should be at a restaurant or it should be here.

But again, romantic date vibe feeling.

So the second question now becomes these third and fourth dates.

I've kind of mixed it up and done maybe like mini golf or an activity and then like something romantic.

Logistics wise, would love your take.

That obviously energy from that second date of date needs to be there for the third and fourth fourth date.

Is that correct?

Or is it okay to mix it up and do something like active?

Because I'm an active person, right?

Like, I like to go to the beach, I like to run, to work out.

I'm not going to go work out with her.

I mean, maybe interesting third date.

But what sort of activities are you cool with and are you not okay with that drives and continues that energy, but also doesn't feel super datey?

I'm thinking through the lens

of

how can we keep circling the bases, the bases of romance?

I don't just mean sexually, but that too, I suppose.

If our first date is

emotional, romantically, sexually first base,

then I'm thinking, all right, I want us to try to at least get to second base.

And I work backwards from that, so I'm not thinking one size fits all.

For example, on

you know, a first date might be a quick,

I don't know, a quick drink on a Tuesday night,

90 minutes, two hours.

You both have work the next day, quick,

and you're just sitting up at the bar having a couple glasses of wine.

And maybe, hopefully, it ends with a nice kiss, good night, but you know, you're not all over each other.

Probably hasn't been enough time.

And if I'm thinking, okay, second date, I want to escalate things.

I want to leave that dating dance.

And I might choose, yeah, I might choose a place that is a bit more romantic.

Nothing wrong with that.

Or if I, but, but if on the date, if I, if I discover on the first date that she loves karaoke and I love karaoke, well, guess what I'm going to suggest?

Date number two, be going to a fun dive karaoke bar because that's what both she and I like.

And it might be a Friday night.

And that'll give us, and maybe we'll go to a second place after the karaoke place.

So

the actual thing you do on a date isn't all that important.

It's just a vehicle for two people to get closer.

And I'm thinking about this through the lens of, oh, well, what's different than what we did on the first date?

Because people like variety.

You don't want to do the exact same thing on a second date, probably.

I'm also thinking, how do we keep moving this romantic dance forward?

And so I'll probably suggest something that's just different,

maybe a bit more romantic or more sexy, depends.

or at the very least gives us the opportunity to keep getting closer.

So any of the things you mentioned are all on the table.

I think a bit more about, oh, what would she and both enjoy doing together and also what would be conducive to this further romantic connection slash escalation

okay no it's good to know okay so it's not what we do it's that we're together and that the energy is continuing and that we're doing something that is moving this romantic dance to the next space yeah i once dated a woman i'll call her jennifer and our my first date with jennifer was a brunch date i didn't i didn't do that often but it was like a sunday afternoon brunch date 90 minutes, we did kiss, but you know, it was a 92-hour Sunday afternoon brunch date.

And then she had to go off and do something with her people.

And then our second date, I'm thinking, okay, how can Jennifer and I get closer?

How can I set this up in a way that gives us a chance to just take it one base further?

And our second date, rooftop bar.

Friday night,

a more expansive night, you know, and more of a date night than a Sunday brunch.

And then the second thing I planned was I had a second place in mind to go to.

So one of my favorite dating, first date strategies, or in this case, a second date strategy, is have a second place you can go to if you both want to.

That's easy to get to.

So I planned out Friday night at this cool rooftop bar.

And

it was a five-block walk from this fun little dive-y second spot, which, oh, what a nice coincidence was only a few blocks from my apartment.

Yay.

So I had the second date logistics planned out so that if she and I continued to hit it off as well as I wanted, then it would be really easy for her to then come back to my place and we could do something, hang out at my place, not necessarily have sex, but to just be alone for the first time, which is a further

of things.

So that would be an example of how I'm sort of planning out a couple dates and just making it logistically easy for us to get closer.

Yeah, and I agree with you.

It's interesting.

I was on a date and we went to like one, we were meeting for drinks at a bar and I knew there was another bread down the street that has like this amazing cocktail and I was like, hey, we should go here next.

And, you know, obviously I drove the date trying to do that, you know, man-to-woman communication.

And we got to the second place, had our drink.

And at the end of the night, just like hey, I really liked that you drove the date.

and had a second place in mind and just wasn't like, okay, we're just going to sit here and have drinks.

Yeah.

Be a man with a plan.

You're a man with a plan.

yes women love a man with a plan my girlfriend to this day still says oh i love it when you plan yeah boyfriend girlfriend dates my then different woman many many many years ago 20 years ago actually one of the first absolute stunning wow women i dated as i started to figure all this out 20 years ago her name is lorraine

She said to me two or three dates in, she said, I love what a good planner you are.

You just always have, you have it planned out.

You tell me where to go.

I mean, I tell, not in a jerk, but like, you know, hey, here's what we're doing.

Does this work for you?

And women just love that.

So, yeah, being a man with a plan, it's such a simple thing to do.

Yeah.

And I've noticed,

and I don't know if

this is common, or you hear this from your other, you know, people you're working with, but I've noticed a lot of women, like, I've been lately like, hey, like, it's second date, I'll pick you up.

And like, oh, you'll pick me up.

I really like that.

A lot of these women have been asking for like old school, like, pick me up, open the door.

And look, maybe it's these women I'm going out with, but it's been an interesting thing to hear is like, come pick me up and drive me somewhere for a date.

Yeah.

You should rent a handsome carriage and a horse and just treat it like it's 1890.

If you're lucky, she might show you some ankle.

All right.

Lucky.

And you can finally have sex on your wedding night three years later.

All right.

No,

there's a, look, I'm the most progressive.

feminist men and women are so equal guy in the world.

Even me, Mr.

Progressive Liberal New Yorker, I'm still old school in a dating sense.

I think it's just sort of the way the masculine and the feminine are wired.

Men lead, women like to follow, and they like a man who leads.

And I think there's that old school aspect that still is very present in who we are.

And so, yeah, be that leader.

Yeah.

I want to change topics completely here.

I'm sure, like, I'm sure you hear this a lot.

Dating apps.

Dating apps.

So one of the things I've been noticing is that I'll have some good banter with somebody on a dating app.

We'll have some good conversation and then they go dark.

And I've been kind of, you know, asking some people I'm going out with, hey, you know, I'm interested, you know, to hear about like the dating apps, what you think, how that, you know, again, obviously not first date, but second, third date, stuff like that.

And they all say the same thing, which I'm hearing, I'm overwhelmed.

There's a lot of choices.

There's a lot of people.

Like, I get a lot of messages.

So I've noticed that some of the people I've been messaging obviously go dark and would love some tips or tricks on how to like, is it, do I need to say something?

Should I move those people to the bottom of my list?

Right.

How many messages do you send?

Like, what do I say?

I've been trying to like add some humor.

Like, what's kind of worked for me is like, hey, I haven't heard from you.

Should I send a search party?

And like, they'll reply something kind of like funny and back.

But again, looking for some direction on that.

Well, are you sending those really classy dick pics like I instructed you to?

Like the nice ones.

don't just take a selfie, have like an illustration penis.

That's what works in 2025.

Come on.

No, I know.

I'm kidding.

Yeah,

some of them, no, I know, I know.

So, do me a favor.

Can you kind of walk me through the pattern you're seeing of how many messages are you sending?

And then

when do they go quiet?

Can you give me a quick example?

If there's a, you don't need to use her real name, of course, but kind of walk me through in a minute or so what the pattern you're seeing.

So, you match and you send, you swap how many messages?

We send two or three messages, and usually that's the point I'm like trying to get it off the app, right?

I'm like, okay, two or three messages, and again, maybe I should extend that.

Interested to hear, but so it's usually two or three messages, you know, banter about something.

Look, I'm a big skier, so I'll talk about skiing or

something within their profile.

And then usually it's that fourth or fifth message.

but I notice is there's like a lull, right?

Like they go kind of dark.

And then that's when I'll send a follow-up, like, hey, like, do I send a search party?

But then like, sometimes I'll get a reply back like weeks.

I had one the other day, Connel, that she replied back a month later.

And she's like, hey, I'm sorry, I was on a break from dating, but I got your last message.

It was really funny.

Yes, let's go out.

Right.

But I just don't know,

you know, I'm thinking differently, right?

I think that they probably, probably these women are there but there's just so many choices that how do i get my message to the top but you living in you live in la right so huge population and i've had first dates here where i've said hey here bumble and she's like sure

she shows me and i look and she's got literally four thousand like

four or five thousand likes not i mean an attractive woman but not like a male a female model, like a just a regularly attractive woman.

So women have an insane number of options.

That's part of the battle we're fighting here as men on the dating apps.

I would say my advice here has evolved a bit.

Four or five years ago, when I wrote my book and was talking about this a lot, I would say, you know, a dozen or so messages max, and then make sure you ask her out.

Women don't want a pen pal.

I would cut that down to a third of that today.

I would say, as a general rule, I would say you swap literally one or two messages.

And then I would much prefer you

say, hey, I got to be honest with you, big on

tons of back and forth messages, but you seem interesting and I'd like to meet you in real life.

Would you be up for it?

And B, do that direct, vulnerable communication, which is man-to-woman, clear, direct statement of interest, right?

That's a clear, that's like the first rule of man-to-woman communication is clarity.

I'm a man, you're a woman, and I'm interested in you.

Why would I hide that?

And so after one messages, two or three at the most, you can say, hey, you know what?

I'm actually really not a big banterer back and forth, but I want to meet you.

And if you want to take it to another level, I don't know if you're on Bumble or not, but certain apps allow you to send audio messages.

And sending an audio message takes it up to a higher level of directness.

where you swap one or two quick text and then you might say, hey, Tracy, just so you know, I'm not big on tons of messaging back and forth, but you seem interesting and I want to meet you.

Are you up for it?

She hears your voice.

She hears the confidence you have.

That can take it up to an even higher level.

So I guess

my one two-pronged answer.

One would be to ask her out sooner rather than later, or to put that intention out there sooner rather than later, just because that'll save you both time.

Women are so tired of pen pal as well.

The other thing you can do is read the situation, read the room a little bit.

Don't feel like you have to wait for a certain number of messages.

If your joke or your opener, if she hits you back with like a big lol,

you know, a big hard eye emoji, if you can read that emotional investment in her in that moment, that's when you ask her out because that's when the iron is hottest.

So the iron is always almost always hottest

sooner than later.

Because once you get that brand new match, there's kind of a new excitement.

It's like new match, where might this go?

And then that combined with she gives you a big LOL or three hard eye emojis immediately say, hey, let's meet up.

Let's go on a date.

Basically, because you want to strike while the emotional iron's hot and not feel like you have to wait for a certain number of messages because bottom line is going to have so many other options as well.

Okay.

And then another thing I've been noticing more and more lately is the, again, apps.

You know, look, I came from a, you know, in a company, but I have a sales background, right?

So I'm like, okay, I'm going to send you a message, you know, I, and I'm going to, you know, not, not be crazy persistent, but enough to be like, hey, okay, like I sent a message, you didn't reply, it's been three or four, sometimes five days.

I'll send a cute another follow-up.

I wanted to see your take on like how

three, four messages, they haven't replied, you're sending them like a week apart, and you're like, okay, next.

Or are you just like continually, if you think that's a good match for you, you're going to continually, you know, I don't want to come off, again, I'm not trying to be like creepy, but again, we've talked about how there's 4,000 people, you know, this girl had 4,000 likes, like, which I understand and I've seen that too.

But like, how do you, are you giving it three, four messages and okay, next?

Or are you following up six months later?

Or

you might recall we've talked a little bit about what I call the three times rule, which is I'm going to send three good messages to a woman before I move on and tell myself, okay, she hasn't responded.

She's not interested.

I'll move on.

Three, maybe even four, but it's a nice round number or nice round sounding number.

The three times rule would be send an opener, it's funny, it's good, it's clever, you like it, and no response.

And then this, and then you wait, I wouldn't wait a week, I would wait 24 hours, 48 max, then send the second message.

Second message might be a PS to the first in a way, or it could just take a different sort of angle, almost like you're reopening.

Oh, by the way, I noticed that you love skiing, Angela.

What's your favorite slope?

Or, you know,

what's the best place you love to just, you know,

crush the powder?

Wait, that sounds like cocaine.

Never mind.

But

second message, right?

No answer for that.

I would wait.

I would send one more.

You know, you could do the dear, you know, dear diary, cute girl who skis is missing.

Send St.

Bernard's search party question mark.

You could do that third little funny one.

And then if three messages go unanswered then I just feel like life's too short you have options bro like when you and I first met talked you had like you know you were just not getting any second dates and you had a big scarcity issue and then I know you're kind of rebooting your dating life right now but there was a while where you had like three or four different women and a little two or three date rotation some really good things were happening so you have an abundance of options if you want them which is great and so my feeling is: all right, three, maybe four messages, and then I'll move on.

And you never know.

Sometimes a month passes and she's back on the app and sees that funny final message you sent.

Hey, Emily, my mom told me that I should ask you out one more time because she thinks I should kiss a girl before I'm 40.

Just wanted to try one more time.

And then bottom line is you're not going to lose anything by sending that message.

A month later, she might

write you back saying, oh my God, that laughed.

I'm sorry, I was off the apps for a while, but that was so funny.

And then all of a sudden, it's back on again.

But yeah, three or four, follow the three or at most four times rule.

And what's what makes it not creepy is that you're not asking for anything.

You're trying to make her smile.

You're trying to make her laugh.

You're expressing Matthew's sense of humor, having fun with it, and going down, swinging if it ends there.

And if it doesn't end, you never know.

Some women do come back

a few weeks or months later, and then you could still bust on them, tease them if you want.

Great.

It was so nice

three months later, Kathy.

Are you free for our first date in October of 2029?

That seems to be the schedule that we're on.

You could still have fun with it.

But anyway, that's my long-winded answer.

My shorter answer is follow up, give it, don't wait a week, 24 to 48 hours, then ping that second or third value text.

And then after three with the max, then move on because,

Matthew, you have options and you don't need to send her 10 messages yeah no I'm not sending 10 messages but you know the three or three or four is what I was okay and are you deleting the match as a whole or are you just like hey because I don't know like some of the apps I'm on like you can delete it then it goes they go back into the queue or like a queue I don't know how it works

or you just like unmatch I don't un I don't unmatch anybody or delete them unless there's some reason that I need to to to free up space to get more matches on a given platform, but I'm not aware of any platforms that work like that.

Okay.

Okay.

Interesting.

And then on kind of that topic of

adding value, we kind of talked, which I agree with.

And I've had, you know, submissions to that in the past.

And it's interesting.

I go out on dates and I hear from women like, yeah, I hate the how are you text or where are you?

or how is your weekend?

And I agree.

I'm the same way, right?

Adding value in a text message.

after a first date,

what any suggestions on that?

Because I notice I'm like, hey, okay, like we've we've planned a second date.

You know, being a single dad, sometimes I can't, you know, meet them for two or three days.

So, you know, I want to keep that energy kind of going.

But, you know, I don't want to send that, hey, how's your week going?

Or, you know, sometimes I'll try to relate it

into like, hey, what do you want to order at this restaurant?

I had a date with somebody.

And I sent her, hey, kind of embarrassed on this, Connel.

I should tell you.

I sent her,

I'm laughing because

I went out with her and before, two days before the date, I didn't know what to send her.

So I was like, hey, I'm really looking forward to going to this restaurant.

I'm looking forward to getting this dish.

And I sent her the menu and she wrote back, I kid you not,

nobody's ever sent me a menu before from a restaurant.

But

so because of that, you get extra brownie points, which they also have brownies we will order.

But I'm looking forward to ordering this.

But, you you know, obviously, like, is there any way, any suggestions or ideas post-first date that I can keep the energy going before the second date?

Because again, it might be three, four days before.

That's adding value as a text message.

It's not just like, how's your week going?

Or.

All right.

Tell me about the last first date you had.

And you don't need to use her name, a real name, if you don't want, although it's fine.

You can use it if it's not identifiable.

Tell me about the last first date you had.

And tell me

two or three, one or two highlight moments of something you and laughed and joked about.

That's a great question.

So the last date I had

went out with somebody.

Sorry, can you ask the question one more time?

Because I was thinking about how to answer it.

Can you ask it one more time?

What are some specific things that you and this woman laughed about, joked about, topics or in-jokes that came up during the date?

Or it doesn't have to be a joke.

It could just be a topic that were little high, little high points of that date.

Moments.

Yeah.

Moments, jokes, topics.

One of them, the last, let's see, I don't want to, I'm not going to give a name,

but I had a date with somebody, and we went to a restaurant

slash bar and were there.

And

we had picked a like high-top table.

and she'd come in these

like

looked like kind of like Cinderella slippers.

They were like kind of like these glass, not glass, but you know, like rhinestone slippers.

Okay.

And

this woman walks by,

two or three women walked by and said, oh, I love your shoes.

I love your shoes.

I love your shoes.

So I made the joke of, hey, maybe we should switch shoes because nobody can see because my back is towards the wall.

I'll wear your shoes.

You can wear my, you know, echo, whatever they were shoes.

Okay.

And she had a good laugh on like okay well this is a good idea and we pretended to start to take them off and trade great that great example perfect so she was wearing very like rhinestone sparkly shoes yeah very like heels very yeah like glamorous heels kind of so do you know that the stand-up comedy concept of callback humor no i don't actually

When a stand-up comedian tells a joke, he gets a big laugh, and then he refers back to that joke punchline 20 minutes later, it creates an even bigger laugh or at least an additional laugh because he's referencing, it's called callback humor.

You can Google callback humor and learn about it on chat or Google or what have you.

And not that we need to go down into the comedy right now, but bottom line is if you if you call back to something that you and she jaffed, laughed and joked about, that's a really great strategy for finding the thing to text her the next day.

So for example, on that date, you could have the next day Googled, you know, gone on Amazon and Googled sparkly rhinestone footwear and found something absurd and over the top, or a whole outfit of rhinestones, taken a screenshot of that and sent it to her saying, Hey, Debbie, or whatever her name was,

I found what you should wear for our next date, totally you.

And it's just like toe rhinestone sparkles or crazy thigh-high boots, maybe, that are all sparkly Rhinestones.

It's not, it doesn't have to be hilariously witty, although I think that's pretty funny.

Just the fact that you're calling back to something that you and she laughed about, you've created a connection,

a playful connection, something that you would not send to any woman because it wouldn't make sense, right?

But you and she now have a little fun, little secret joke.

So that's a really, that's one strategy is ask yourself, what did you and she laugh and joke about?

I briefly dated a woman named Jen many years ago, a different Jen than the Jennifer I mentioned before.

This woman's real name is Jen.

And we had a date at a fancy sushi place in New York City called Nobu.

And a piece of sushi there is like $20, probably.

And she dropped two pieces of sushi on the floor.

And

I teased her about it.

I was just happy to be on a date.

She was stunning and cool and awesome.

But anyway, the next day, I was texting her little jokes like, you know,

did you have any trouble eating your cereal today or did you keep dropping the spoon in your bowl?

You know, or making jokes about how she's,

you know, hey, here's the bill for all the sushi you dropped last night.

I take checks or credit cards, you know, something like that.

So I'm calling back to things we joked about.

That's one thing.

Now, if nothing like that arises in your mind with a given woman,

you can also just ask yourself, what does she care about?

What's relevant to her?

What matters to her?

And you could ask a question about or discuss a topic that she cares about,

whatever that might be.

And again, this is also personalized.

Personalization is almost always the way to go.

What does she care about?

What matters to her?

I dated a woman who was a painter, is a painter, like a professional artistic painter.

And I would text her a picture of a painting or a work of art.

And I would say, let me ask you this.

Is this really a work of art?

Or is this just, you know, a bunch of BS modern stuff?

What do you think?

I dated a woman who was a sommelier, wine expert.

I would ask her wine questions because she cared about those topics.

They were relevant to her.

So I'm always thinking, think, thinking through the lens of, not always, but often thinking, what does she care about?

What matters to her?

If she has a dog or a cat, I might say, okay,

what did Boots do today?

What dumb thing did Boots the Cat do today that just you roll your eyes and think, oh man, I have a cat in the world?

It could be as simple as that.

So that's how I like to text women the next day.

So personalized is what I'm hearing.

Yeah, personalized, ideally.

And,

or you can also, it's ask questions that might even come across a little bit cliche.

We just don't want them to sound cliche.

So yeah, I'm not a fan of how was your day because really, do you care how her day was?

I mean, you don't want her to have a bad day, but you're just trying to find something, right?

So, if you're going to ask, how's your day, ask it in a slightly more,

I don't know,

creative way.

Like, hey, how was your day today on a scale of root canal to won the lottery?

That's basically the same question, but you're using some colorful language to try to make it a little bit more fun for her.

So, you could do things like that.

Okay, that's interesting to know.

Okay, Okay.

Yeah.

Those were all the questions I had.

I mean,

for now, I'm sure as I continue to go out and date and reboot this, I'll have some more.

Okay.

Awesome.

Great stuff.

Well, you got me by text, obviously, as you know.

I'm available by text six days a week for you and all my clients.

And we'll talk again next week.

And not recorded for the pod, but we'll talk next week and keep me posted on how things are going.

But no, I just want to say

how

proud I am of you because you've gone from not getting second dates, having women give you the whole, hey, I'm just not feeling it, to

really seeing some nice wins and having two, three different women on your dance card at any given time.

And yeah, it's just a matter of who ends up being Matthew's amazing girlfriend, not a matter of if or when.

It's a matter of who she is.

And yeah, I'm so glad that the way I coach has helped you.

So thank you.

And I can't thank you enough, Connell.

You have no idea.

Again, it was the had a date last week, or maybe it was a week before, and I'm out with somebody and they were like, I want to see you again.

It was the first time I was like, I'm not really interested in them.

Usually I'm the one that's like, I really want to see you again.

So it's been, you know, the advice you've given me, authenticity and all the other stuff has really helped.

I like that.

I'm sorry that you weren't more into her, but yeah, that's a great feeling.

Once women start saying, hey, when are you asking me out again?

When are we going out again?

That feels so good to be wanted and desired.

I know you're starting to feel that in some real ways.

All right, Matthew, until we speak again.