How to Get a Girlfriend with Connell Barrett - My Girlfriend Jess Reveals the #1 Secret to Landing Second Dates! (Most Men Make 3 BIG Mistakes)

Episode Date: February 18, 2025

So, you finally get a first date with a smart, attractive woman… only for her to say, “no thanks” to a second. It’s discouraging. Let’s fix that! After last week’s special 4-part Valentine’s Day series on meeting and attracting women IRL, you don’t want to put in all that effort only to hit a first-date roadblock. Connell and his girlfriend, Jess, break down what made their first date a fun, flirty success—and what you can do to get a LOT more second dates. (Originally aired in November.)In this episode, Connell and Jess discuss:3:20: The Profile Photos that Made Her Swipe Right13:05: The Right Way to Text a Woman Before a First Date18:20: Jess’s Top First-Date Tip29:00: What to Talk About So You Never Run Out of Things to Say30:48: How to Avoid Interview Mode and Not Get Friend-Zoned34:15: Jess Called this First Kiss Move “Suave”—You Need to Know It!37:18: How to Ask Women Out for a Second Date39:21: Her Top 3 First-Date Mistakes that Guys Make45:00: Why Women Want Authentic Men, Not Toxic “Alpha Males”Sick of hearing “Let’s just be friends”?Learn how to get more second dates, starting now.BOOK A CONSULTATION CALL TODAY & GET A FREE COPY OF CONNELL’S BESTSELLING DATING GUIDE!Frustrated with dating? Ready to find an amazing girlfriend? Book a FREE call with Connell to see if his coaching is right for you. If you book your call today, you’ll get a free copy of his No. 1 Amazon bestselling book, “Dating Sucks but You Don’t.” Spots are limited, and this deal expires today—don’t miss out. Use this link to book your free call now to see if coaching is right for you.www.datingtransformation.com

That's a great tip. A woman notices if you're rude to the hired help. Yeah. Like I verbally assaulted my butler this morning and I felt so bad afterwards. Welcome back to the How to Get a Girlfriend podcast. I'm your host, dating coach and author Connell Barrett. I help men confidently flirt, get dates, and attract their dream girlfriends all by being authentic. No creepy pickup moves needed. And in this episode, you're about to find out what women want on a first date.

And also you're going to find out what they don't want. This is so that you can have really great dates that lead to second dates and third dates and third dates and eventually finding that dream girlfriend. And today's guest is a woman and she's not just anybody. She's my girlfriend, she's my best friend, she's my soulmate, she's my shmoopy. She's the most important person in my life

and I wanted to have her on to talk about, well, how I got her to be my girlfriend. Welcome to the podcast Jessamyn. Hi thanks for having me. I was about to start chatting with you and all of a sudden I had flashbacks because we've never done a podcast together and I'm like wow this is kind of like a new first date. It definitely feels like a first it's the first date all over again. It definitely feels like a first it's the first date all over again a little nervous. How's it gonna go? Is she gonna like this? Let's see what happens and by the way stick around to the end of the episode because

Jessamyn is gonna share with you three of the biggest mistakes that men make on First dates that you might be making and we're also gonna talk about how to fix those things. So stick around until the very end. OK, so thank you for being here, Shmoopy. By the way, Shmoopy is our kind of pet name for each other. So it's annoying, but it's us being cute. It's annoying, but it's us. Trigger warning for people who don't like Shmoopy. Who don't like Seinfeld. Exactly.

Let's talk about how we met. We met on a dating app called The League. And what made you want to match with me? When you think back to first seeing my profile, what made you want to swipe right? I remember I had just joined The League. I think I was on it for maybe five minutes when I came across your profile. So it didn't take very long.

And I just saw this, Tollal Ginger, I get some really nice photos. I think your tagline or headline was something like the real life hitch. And I was like, okay. And you kind of read further and you're a dating coach. And I'm just like, I wasn't necessarily looking to

have fireworks or have like, you know, jump into a relationship or anything like that. I was just trying to get back into the dating game after being isolated for so long. Yeah, it was mostly curiosity, but good curiosity, maybe a little weird curiosity. So one of the things I teach my clients, and this is in my book too, is think of your online dating profile as a piece of marketing and you want to stand out and be different in a positive way. So I stood out to you because of the dating coach angle.

And in terms of the photos, do you remember anything about the photos that made you say, okay, I like what that photo is saying about him? What do you remember about the photos? I remember they were mostly, they were good photos. I couldn't tell if they were necessarily professional photos. I think a couple of them were, but they were well-framed. It was just you. I think there was one of like you and your niece, there was one of you with a dog, but the pitfalls that you see a lot are like,

you know, guys that have like a clearly cropped photo, like group photo and it's like blurry, or they just take a bunch of selfies. Like there needs to be some sort of effort put into it. And there was obviously some effort in there. And then you also had a photo, your head was cut off, which was a little concerning, but it was like the last one and I'd seen your face, I didn't care. But it was you in the policeman's Halloween costume.

Right. I was a hot cop, Sergeant Dick Utopia. My alter ego. Halloween photo. It was a good variety. You weren't taking yourself too seriously, but you were taking dating pretty seriously. That's good to know. I found that the best, most effective photos for a single guy, one or two really good portraits that probably were taken by a professional or a good photographer, but that don't feel super editorial, that your smile is authentic,

it's genuine, you're caught in a moment of feeling good as opposed to here's my LinkedIn headshot cheese, which is exactly the wrong way to try to get a match. So it sounds like that got your attention when you saw mine and thought, okay, maybe these are professional, but relaxed, genuine. Yeah. Yeah. I put effort into my profile. I do expect the guys I'm matching with, the guys I'm seeing on there to do the same. I liked your profile because, well, you're super pretty, obviously. And I thought, wow, super cute girl. There's a big check for me. And there was a sense of kind of quirkiness that came

out. You're making a funny face in one of your photos, like an intentionally ugly face. And that seemed weird, the good kind of weird. Like, oh, she's kind of a quirky type. That appealed to me because sure, she's pretty, but she's also got a little bit of an unusual quirky side that's coming out, which is definitely my type. Damn right. That was pretty right. I was thinking before that we got on to record today, I was thinking of something. I remember you telling me that you liked about my profile.

This is something that I think the listener can find his way to do the same thing that I was able to do to get a date with you. I think you said to me I had a school teacher vibe or like a high school or professor type vibe based on my photos. Am I making that up or is that something you recall? I feel like when I've described you to people in the past, I've been like, I don't know any other way to describe it other than like the cool middle school teacher. Yeah.

And not in like a weird way, literally just like a a very gentle, friendly, open presence. That comes out immediately. It definitely came out of your profile, but just even getting to know you, I'm like, there's no scariness or bad weirdness here. It was just a very genuine person in front of me. Yeah, I've heard that before from other people. Like, oh, Conner, you come off like a school teacher, high school teacher, college professor. And I'm not necessarily going for that in my photos.

But what I do try to do is to say, okay, what's like a real, the real but best side of me that a certain person might be attracted to? A type, in other words. And what I like to have my clients do is I say, cool, let's come up with a couple avatars that are genuine to you, that are authentic to you. Because if you had seen me on a motorcycle with a leather jacket trying to look all cool and tough, either that would have seemed really off to you and not seemed like me, or when you met me, you would see that that's not who this guy is.

So it's about, what I teach my guys is, hey, let's come up with an avatar that's authentic, that's genuine, and maybe play up that side of you so that you don't have to be Mr. Six-Pack Abs or male model, but you can, if you are just one of the kinds of types of guy a woman might be into, that's more than enough to get a date. Right, or thinking about what kind of woman you actually want to attract. Do you also want to attract a motorcycle riding babe? I mean, if you do, great. Or maybe the opposite's attractive if you're taking that approach, whatever the case may

be. Yeah, definitely tune into what you actually are and not what you maybe want to be or think you should be. And the other thing you said was, oh, the whole dating coach thing was an unusual hook that was unusual for you, which makes total sense. There's not a lot of dating coaches out there, at least not dating on the league like I was at the time. And so just the fact that that was unusual, that caught your attention as, oh, that's different. Is that basically what you're saying?

Yeah, I mean, anything that's different from any of the other guys. We're in New York City, there's however many million men out there that are, whatever their job is, whatever their interests are, sometimes it all kind of feels the same after a while. I think the league in particular maybe attracts a certain kind. And so being able to say like, hey, this is my job. And not only is it unique, but it's something that I enjoy and that I'm proud of and that

I'm like, you know, poking fun at a little bit. That's really special. Right. It's so easy to look like every other guy. Yeah. Or to get lost in the shuffle of so many people you're swiping on, left or right. And so you were attracted, or at least hooked by the idea of me being a dating coach. You listening to this episode, you're obviously being a dating coach, you listening to this episode,

you're obviously not a dating coach, but a thought I would have for you is ask yourself, what is something that is completely singular about me and unique, that I can either show or mention that's different but cool, different but interesting, or super nerdy. Because by getting specific about what makes you unique, you might jump out at a woman to say, wow, I've never seen that before.

That's really interesting. For example, I have a former client named Brian, who when I was coaching him, I said, what's something really unusual about you? What is something completely unique? He said, I like really extreme things. I said, what's something really unusual about you? What is something completely unique? And he said, I like really extreme things. I said, what do you mean? He said, I like cold plunges.

He does that, I forget what it's called, like the polar swim where you swim five miles in frozen cold water in the winter. He does all these extreme things. So I said, yeah, let's play that up. Because every other guy's talking about hiking, and as you and I know, hiking sucks. We'll get into that. Yeah. But if you're into extreme things, play that up. Or if you are the expert in, I don't know, iced coffee, and you are, if you're a nerd about something, lean into it, that could be that one unique thing

that's your version of being a dating coach. Because you just don't want to blend in and seem like everybody else. Yeah, and I think that's kind of the beauty of online dating. I think it's much more accepted now than maybe it was like 10 years ago, but all the different dating apps that we have,

the way that you are like prompted to design your profile and to like put information about yourself out there, like you should, if you need to maximize that, you need to take advantage of the fact that like this is the first impression that you're making and this is how you're doing it. It's great being people in public too and organically through friends, whatever. But online dating and setting up this profile, it's your time to show off exactly who you are, what those things are that you really want people to know. And then when you get to the first, second date points, it's like we have this whole,

we have all this information already that we're using. Let's talk about, okay, so you and I matched and we decided to go on a date and we're using. Let's talk about... Okay, so you and I matched, and we decided to go on a date, and we're texting and being in contact for several days leading up to the date. What do you remember about our texting leading up to the date? Any memories or any feedback or thoughts? It was very easy. I, you know, I'm someone who likes quick humor, dry humor, and you had that same sense of humor.

So you set me up and I set you up. And it was just like a very easy conversation. I didn't feel like I was trying to like find the right or wrong thing to say or felt like I had to keep the conversation going. We literally just talked for a couple of days kind of back and forth, made a few jokes. You know, it was just very easy. Sometimes you chat with guys or you're having a conversation on the app or texting leading up to it. And it's hard to communicate a lot of things over text. It can be really hard to communicate your sense of humor,

your genuineness, whatever, over text. But being able to have that easy flow, that definitely stood out. I'm just looking at our very first text exchange ever. I have it right here. You opened me on the League by saying, hey, there, Connell. I wrote back with my incredible wit and intelligence, hey, Jessamyn. I thought that was brilliant. But then I really, I did something that I want men to do out there

or to least consider. I looked at your profile and just thought, okay, what does she say? What's on her profile that I can work with? And you'd mention about being into running from dinosaurs and scotch-swilling. I didn't know if you were kidding or not, but I wrote, you had me at scotch-swilling. And then I followed up with, what's your favorite dinosaur to run from? And do you remember what your favorite dinosaur to run from. Do you remember what your favorite dinosaur to run from is? My go-to would be the T. rex. Yeah. Yeah, T. rex. Oh, and pterodactyls.

Right, and a few pterodactyls. Also because I could show off that I could spell pterodactyl. Nice. Yeah. Nice. What I love about our texting, and the takeaway here for guys out there is I want them to realize that your texting can and I think should be very light. It can be about nothing. It's kind of like Seinfeld, the show about nothing.

Texting when you can get on the same banter-y wavelength with that woman, you can text about the stupidest stuff. We're not really texting about anything real. We're just cracking. I don't even know if these are jokes. We're just texting about silly dumb things. You loving scotch, you running from pterodactyls. I compared you to Don Draper for some reason. I mentioned how we're both pale skinny princesses. So we'll probably get along very light very silly. I'm not doing anything sexual I'm not getting all like Sexy, I'm letting her all that flirtatious, but just because it's light and playful I hoped that that's the vibe that you enjoyed and I remember a few a day or two before our first date

You sent me something that just made me smile and felt so good. You kind of broke character a little bit from the playful messaging and you said, by the way, I'm really liking our banter. Can you talk about what you liked and maybe any tips on texting for that guy listening right now? Yeah. I remember just, like I said, it was very easy. I mean, a big

piece of it is like, you know, if your sense of humor matches with the other person, or if your interests match with the other person, that's kind of key. If it doesn't match, then it's probably not going to be a good conversation. So if you feel like you're not struggling to find the right words to say, you feel like, you know, you're not struggling to find the right words to say, you feel like you're not worrying about, is this gonna be, is she gonna take this the wrong way, or is she gonna think I'm weird? You shouldn't be having those kinds of apprehensions if it's a good, genuine connection and a good conversation.

Yeah, I remember, I just remember feeling like, okay, this is a person that even though we still haven't actually heard each other, we didn't talk in person yet. I was like, I know this is gonna be an easy conversation. I know I don't have anything to worry about, as of right now.

It just, it felt really good. And like I said too, it was my first time on the app in a really long time talking to anybody. It felt really good to be back in a groove and be excited about meeting new people again. Absolutely. I like to think of texting a woman leading up to a date as like a movie trailer, giving each other some coming attractions of what the date might be like. And the date is the movie, and hopefully the trailer is great and exciting, and the date and the movie is great. But I was just so happy that you were enjoying our texting. I felt the same way.

And I just thought, okay, great, we're both excited, we're both looking forward to this. And the texting was so, it's so basic, so simple. It's not, a lot of guys make the mistake of saying, what's the funny, what's the really witty thing to say? What's something really funny? And they put a little too much pressure on themselves to be super funny or flirty or have good game. And all you really need to do is keep it light around themselves to be super funny or flirty or have good game.

And all you really need to do is keep it light about topics that the two of you care about, or at least that they mention on their profile, which in your case was silly topics like pterodactyls and swilling scotch. And we just bantered about almost nothing in a way, but it was just that lightness feels good to people as they lead up to a date. And it just was kind of like we were giving each other a sneak preview of what it was going to be like to meet each other. Yeah.

I think too, like you can take dating seriously. You can take other people seriously, women seriously, but you don't have to be serious about it. It should be light, it should be fun. It shouldn't be immediate, like heavy conversations. If you find that you're like immediately going into setting boundaries or things just aren't flowing in a way that's like, am I actually gonna enjoy being with this person?

Then just, it helps to take a step back and say, really evaluate your expectations and make sure that you're finding that balance between this is unexpected, but is it good or bad? 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 bestselling 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. Are there any pet peeves that you have or that women have about the way men text? I hear a lot of women say things like, oh, I'm so tired of being asked how my day is, how was my weekend? Guys ask too many questions. Any thoughts there?

What do women want or not want when they're texting with a guy leading up to a date? Yeah, the standard, you know, how's your day going? Maybe you like match the day before and he follows up with like, you know, how's your Monday? They're not, it's not like a deal breaker. I think those kinds of questions are fine, but they definitely don't stand out. Along with the kind of the idea of asking questions, you don't wanna fall into like the interview of like you just asking her questions over and over again.

Like she knows you're interested. You don't need to show that you're interested by only asking questions. You can share things about yourself. If you're gonna ask questions, make them interesting. Like I think you had, I don't remember exactly what they were, but there were a couple of times where you said like,

you know, what was it? It was like, if you're gonna, if you were gonna cook for me, what would you make for something? Because I had mentioned something about cooking on my profile. Like, again, just like really leaning into like what you're able to see about her. You can use those as conversation starters as questions. Yeah, and you did something that was fantastic that any guy can do. You sent me a photo of yourself taken in a park. I think you were doing some kind of, I don't know if it was a sass class, dance class photo or some other acting class you were taking, but it was you in the middle of some kind of, I don't know, was it a medieval outfit or some kind of posed battle? Do you remember what that photo was?

I do remember that photo. I think that was before, that was the day of our third date. That was a little bit later. And yeah, it was a SAS class video shoot. And the song was S&M. It was the Rihanna and Britney Spears remix. Okay. And it was just like a funny photo that someone had taken while we were filming that was just completely out of context and was completely insane. So it was like, Hey, so this is what I did today. See you later. Right, right.

Yeah. Because you know I dance and like done some stuff, whatever. I just thought that one photo was like particularly funny. Well, what you were doing that was good, I'm sure you weren't thinking of it probably from dating strategy like I do as a dating coach who's always thinking about this, is have a good G-rated photo of yourself doing something funny, something silly, something cool.

And you could send that along with one of your text messages. And that helps her see who you are. And again, it's kind of like that trailer leading up to a date to get her excited and think, oh, this is what he looks like when he's shooting hoops or on the ski slopes or playing with his dog or what have you. It's like giving women a little window into your world and that can give her the green light

to send photos back toward you and you're both just getting excited about meeting each other. Yeah. Yeah. Okay, let's talk about our date. How'd I do? I've been waiting years to ask you this. How'd I do? Do you want to keep dating me or not?

Well, it's only been three years. I may need a little more time. No, I mean, I knew I was going on a date with a dating coach. That's kind of weird, right? I just, I didn't a hundred percent know what it meant. And I don't think I did any, like, I didn't do the super sleuths deep dive internet search on you. I don't think, I don't remember doing any of that simply because it was like,

it just isn't like instinct for me. I know it's instinct for a lot of people. Right. So yeah, pro tip, make sure you know what's out there about you on the internet. For sure. Before you go out there. But I just, I didn't wanna have any expectations

because that just didn't feel fair. I assume there might be some like, like, you know, little like games or lines, things like I kind of had like moves. So I had my eye out for some dating judo moves, but I don't, I don't remember feeling like, oh, this is forced or oh, this is like a move that he uses. It didn't feel nothing felt inorganic It just felt like I was going on a date with a good guy All Your schmoozie, by the way

Not this argument do we do we need to explain? That story so you and I are big Seinfeld fans and there's a famous episode of Seinfeld where Jerry and his TV girlfriend of the week are calling each other schmoopy and they're just everybody's getting kind of grossed icked out by it. Alright, so what theater you want to go to tonight? We got 61st and 3rd or already 4th and Broadway. Which one you want to go to schmoopy? You called me schmoopy, you're Shmoopy. You're Shmoopy. You're Shmoopy. You're Shmoopy.

All right, Shmoopies. And you and I started doing it as a joke and it became real. Yes, it quickly became unironic. Which I love that, I love that about us. Okay, Shmoopy, back to our date. Oh, here's a good question. My client actually wanted me to ask you this.

Did he, I have a client who came to me because he's having trouble with his first dates because he feels like women aren't getting the same version of him on a date that they're getting on his profile. There's a little bit of a mismatch So when you met me did the vibe of what you were and I know you didn't know exactly what to expect as a dating coach But to divide by gave you on my profile matched the me who you met Or did it mismatch or was it a little bit of both? It was definitely a match. I think with the league specifically It's not a particularly detailed profile, right? It was kind of like you put a few of your interests, you put like a tagline, your age. And I think that was kind of it. But I think, you know, with being

profiles that might be a little more detailed, you do kind of run the risk of there being like a greater room for error. But yeah, I mean, it was definitely what I've expected. I didn't feel like I was being catfished. Oh, no, I didn't mean that. I guess I just meant, was there anything that, if the vibe matched up, which it did, you basically felt like, okay, this is the guy I was expecting to meet and then we discovered more things about each other. Yes. The middle school history teacher that I was expecting to meet on the date is actually

there having drinks. Remember when I helped you with your times tables on our first date? Yes. So romantic. So good. So romantic. So good. So normal. You were what I was expecting and times 10. I thought here's a really pretty girl. There's a lot of quirky, silly, weird humor on her profile. She's in her mid to late 20s. She's probably, pardon the clich cliche, a manic pixie dream girl type.

She's probably just looking for a fun fling. I'm cool with that, if that's where this goes. And then you walk in to the other room, the bar where we met for our first date. And you were exactly what I was expecting in terms of how you looked, and you had that quirky, funny vibe. But you're just so sincere and big hearted. We talked about your family and your brother and your mom and dad and we kind of opened up.

After we did a lot of banter, we really opened up, at least in some ways. And I just remember sitting there thinking, oh my God, this is 100% girlfriend material. It's like, wow. So yeah, you more you met and exceeded my expectations in every way. Yeah, I mean, honestly, kind of sort of same. I had no interest really in like diving into a relationship, especially coming out of a year and a half long period of isolation. And I was careful. I was a little guarded, I think. I wasn't guarded about like how my feelings or anything like that, but I was like, you know, am I just like jumping into this? Am I just excited about this because I've been,

you know, socially restricting myself for 18 months or like, is this real? Cause I had never, you were my first serious boyfriend. Like I just, I had been living in New York city for 10 years ish at that point. And it's, you know, New York city dating scene, say what you will about it. It's fun, but it's also hard to take seriously sometimes cause there's so many people and it's just very easy to kind of jump to person to person.

So kind of the same of what you said, I was like, this will be, I'll at least come out of it with an anecdote that I went on a date with a dating coach that I met on a dating app, at the very least. But it is obviously a lot more than that. Absolutely. It was fun. But it is obviously a lot more than that. Absolutely. It was fun. We continued that banter in person that we had by text,

which is exactly what you want to have happen if you have a nice back and forth going. A woman just wants you to continue. She wants to feel like she's meeting the guy from the profile and that everything just escalates mutually organically. It's like, oh, wow. It's just like we were texting together, escalates mutually organically. It's like, oh wow, it's just like we were on texting together, but now we're doing it in person.

And one question I have for you, because a lot of guys come to me and they say, what do you talk about on a date? What do I say? What if I run out of things to say? Do you have any just general tips for men about what to talk about on a date? How to show interest, how to not show too much interest? Yeah, in terms of what to talk

about and how to talk about it. Any thoughts there for men who are about to go on a first date with someone like you, someone they're really excited about? I think, you know, it's hard out there. They're saying like, there's some sort of answer to find that perfect balance between being chatty, but not too chatty, or like being too quiet, you know. I think it's easy for anybody, guys, girls, whatever, to fall into the trap of like, feeling like you're on an interview. Yeah. You know, you, you want to ask questions, but you don't want to just ask questions that are like, that have like a single answer, the typical, like how many siblings do you have? Have you have any pets, whatever, whatever questions you have. I don't, I don't know if it's good to necessarily be scripted, but make sure

there are ones that three, maybe three things or topics that you have in mind that are going to generate a conversation between the two of you, no matter what her interests are, no matter what her strengths are, what she does for a living, just things that you have on tap, ready to go, that will generate conversation. And if they don't generate conversation, then maybe that's a signal. Right. Yeah, having a back pocket topic or two is great. Having a back pocket personal story that you can share with that person is a good way to break out of potential interview mode.

So you might be on your next first date thinking, oh my god, I've just asked her five straight questions. She probably feels like she's in the back room at the NYPD with a hot light on her. And then remember, oh, tell her that story about the funny thing that happened to you in Paris. They lost your luggage and blah, blah, blah. You got on the wrong, I have a client who has a great story. He got on the wrong plane. He flew to the wrong city, leaving country. This is a funny first date story. So you can have a back pocket story, you can have back pocket topics.

Then one other simple tip if you're a guy who gets stuck in that interview question mode on first dates, is any question you ask your date, feel free to answer that same question as if she asked you, even if she didn't. You can ask her what her favorite TV show is and she might tell you and then you can say, oh, well, my favorite show is XYZ. And that's a way to find something to say.

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So on our date I remember and I don't even though I'm a dating coach, in a weird way when I go on a date or went on dates, and when I have my clients go on dates, I say, do all the preparation in advance. Plan a great fun place to go. Have a clear simple plan, be that man with a plan.

Then, but on the date, be really present. Just be a real active listener and discover the right things to say on the date. So I remember on our date after the first 15, 20, 30 minutes, which was just fun banter talking about nothing like Seinfeld, I remember thinking, I really want to get to know her. And we talked a lot about your family. I remember making a little mental note. Okay, her mom's name is Liz. Got it.

Brother's name is Aaron. Got it. I wanted to remember this because I wanted to show you that I was listening because that was important to me to understand. I think I shared a couple of stories about my family too. So I think we connected about each other's families among other things. Yeah. I mean, very straightforward.

I think families, it's not always easy for people to talk about their families. Right. So you can always, if you're asking her about her parents or siblings, if there's not a lot coming back, it's probably, they may not be super close or maybe tension there whatever the case There's always other talk about friends talk about co-workers. I'm sure I talked about like my co-workers and bosses a little bit, too

Yeah So we had a really good couple drinks at this bar in New York City and then we went to the back room. We went to a different part of the bar just to change the scene. We went to the other room of the other room. We were in a bar called the other room and then we went to the other room. And then we went and watched the room, the movie. No, we didn't. No, we didn't.

But our first kiss was in the back room of the other room. And you can answer this talking about our kiss or you can just speak more generally about the woman's point of view. But in terms of first kisses, men are so nervous about, oh, I want it to be a good first kiss. I don't want to get rejected, but I don't want to not try and get in the friend zone. So some guys get stuck in their heads about even going for a first kiss. A lot of guys never even try just because they're afraid. What are your thoughts on the do's and don'ts of the guy going for that first kiss on a first or second date? I mean, honestly, it's a terrible thing, but like, everyone's different. Every woman is going to have a different expectation.

I know with, I'm thinking of like our first kiss, maybe some other first kisses that I've had, not that I've had a million, but you know, I think I remember with us, it was, we were sitting next to each other and And there was just like, we've been talking for at least an hour at that point, right? We'd had like a drink or two, no more than two. And there was just like a lull in the conversation. And we were looking at each other. And, you know, if you're maintaining good eye contact with her and she keeps it up then that's usually a pretty good sign Other if you're if you're looking for a more verbal sort of confirmation It can kind of go either way

Definitely depends on the you know circumstances, but I think There have been a couple of times where like a guy said like I'm going to kiss you now And it's I feel like out of context it a guy said, I'm going to kiss you now. And I feel like out of context it sounds super weird, but it definitely works if the moment's right, if you have that same kind of will in the conversation. You can also ask too. Consent is sexy, you can always ask.

Can I kiss you now? Yeah, consent is really sexy. I love the idea of saying, hey, I wanna kiss you. Or I'm gonna kiss you now, as a way to get sort of a soft consent so you can know it's coming. That way you can say, oh, I don't kiss on the first date. Great.

That's great. I would much rather a woman said that to me than I just lurch out of nowhere and go to kiss her, and she's, wah, wah. So I like that move that guy used, saying, I'm going to kiss you now. Yeah, it was sweet. Yeah, I think what happened on our date is I noticed what I call with my clients, the

kiss window opened. There was that lull you mentioned. We've been vibing nicely and there was a little lull and we were sitting really close to each other and a little window opened in a sense and I just said, all right, dating coach better kiss her or else I need a new job. I got to walk the walk. One last question about first dates and then we'll get to the three mistakes that a lot of guys make.

But what's your opinion on asking a woman out for a second date? Do you, I advise my clients if they want to, they can ask for that second date or say, hey, I'd love to see you again, even before the date's over. I'm a big fan of teaching my guys not to play games, not to play it cool. Just say what you want. If you like somebody, let them know and ask them out whenever you want within reason That's my view but what's your what's your point of view? What's the woman's take on that? Yeah that there's that antiquated like three days role kind of thing we to wait three days before you call her

Or text her or whatever and that's just all that does is cause anxiety for both people. There's no reason to wait There's no reason to play hard to get, especially after you've just met this person for the first time. I think doing it at the end of the day, like you say, like, hey, I had a great time. I'd like to see you again. If she says, no, I'm not feeling it, then everything's set right there. Like, there's no question.

You're not, there's no uncertainty. You know, you just move on with your life. But you also don't have to do it right away, but I think at the very least, you know, text her the next day, maybe later that night, and just say like, hey, I had a great time. But definitely communicate what you want and what you're interested in,

because how else is she going to know? Women are very intuitive, but we're not mind readers. Right. I remember the morning after our first date, I looked at my phone and I opened my phone and it's not that you owed me a text, but I thought, I wonder if she wrote me. I was excited and hopeful, but trying to be zen about the possibility that you didn't write me back. And then there was a nice text waiting for me from you saying, had a good time last night,

and I wrote you back and I said the same. And then we were off. So I try to have a zen approach to that. You can't obviously control whether or not somebody wants to see you. You go on a date, you're authentic, you're genuine, you try to give them a good fun experience while being yourself. And then so much of this is just chemistry and letting the chips of chemistry fall where they're going to fall.

But anyway, that was yeah, the most important first date of my life. So thank you for making that happen. Likewise. Let's finish with a final three tips from you. So you said you've had two or three thoughts on some things that, some mistakes that many men make on first dates. Fire away. What do you got?

All right. I mean, the three, I got three don'ts. I have a lot of don'ts, but I think there are some that are more maybe universal than others. I think one of the ones that we've heard time and time again is just your first date, whatever date it is, it's likely going to be at a bar, at a restaurant, at a coffee shop, whatever. Rule of thumb is, don't be a dick to the service staff. Don't be rude to anybody. But it's a very specific thing when you are intentionally rude or dismissive to somebody that's serving your food or serving your drinks or just working. It, there's a power imbalance that's kind of set up there. And it just immediately communicates this, like if someone's going to be this easily dismissive or rude,

a complete stranger, how are they going to treat somebody that they know? That's a great tip. A woman notices if you're rude to the hired help. Yeah. Like I verbally assaulted my Butler this morning and I felt so bad afterwards. Your butler. Anyway. That's how it goes. Tip number two, don't do this.

What's next? Pet names. So calling, like using like kind of common, you know, maybe in like the banter that you have before the date, you can jokingly come up with a nickname like Shmoopy. But things like hun or sweetie or sweetheart or babe, one it kind of like communicates a familiarity that she might not be ready for, especially considering she's just met you. Another thing is like, like, sweetie, sweetheart, hon. Like, those are things that if I'm getting like catcalled on the street, that's what guys call me. Or like when I was working as a server, as a server a million years ago, they'd be like, hey, sweetheart. Like it just has,

you run the risk of it having this really crappy negative connotation and it's just a little too familiar so just avoid yeah that's that's the option there's a very small chance that she's like oh he didn't call me baby the first time we met so it's a no-go just you're better off just avoiding it I think that's such a good tip sweet cheeks. No it really is. It's weird. It's a little weird to be that familiar with somebody you don't know. Yeah. It's just it shows this person's a little off and if they're a little off with calling me hun when they barely know me what else weird stuff is he gonna reveal so that's a great one. Okay do you have a third one? There's,

there's a difference between like sharing your interests and just like going on like a full on rant or going like off the rail. So like being like bitter or negative about something. So like I put on my profile pretty clearly. I hate hiking. Yeah. We vibed about that. I love that about you. We vibed, exactly. It was kind of something that I put out there and you could have said, oh, I love hiking. Maybe I can take... If you did like hiking, you could have spun it and it could have generated

conversation. We connected on hating hiking, whatever. Hate joggers and hikers. We don't hate them, we just hate what they do right very different things That's different than me saying like going on a rant about hiking and nature and how terrible it is Or you know, you don't like mushrooms You can say like fun fact. I yeah dreams. That's something good for me to know Yeah, I generate some discourse because I do like

mushrooms. But for you to then go on a rant about vegetables in general and to go down a hole of vegetables are stupid, there's a difference between little things like that and just turning the conversation into this negative speech. into this negative speech. So make anything that you don't like, make it like a glancing blow, not go down a rabbit hole of negativity. Right, make it, if it's something interesting, that's one thing.

If it's just like a vendetta that you have against vegetables and fungi, that's something we get to on like the fifth or sixth date If we're feeling like we're at that place Well, that's a good tip, too. I like a guy. I want my guys to be able to be fully expressive One of my little catchphrases is be an open book, but not an open wound Don't go off for five minutes on some negative rant. You might talk about how fucking annoying it is when an airline pilot who should be flying that Spirit plane is cracking jokes and being a stand-up comedian when he should

be flying my plane. I will die on that hill. But I'll just mention it for a minute and then I'll move on. I'm not going to get negative about it. So I guess, yeah, that's a good tip. Make your things you dislike, make it quick and almost like silly and frivolous because it's just people being human that way. By the way if tomorrow's pilot is funny I'm gonna switch airlines. I'm not gonna. Listen you're the one that booked the flight. You knew what you were getting into. We're out of time.

We are out of time. Love of my life. Is into. I don't want to... We're out of time. We are out of time, Shmoopy. Love of my life. Is there anything I didn't ask you that's important for the nice, sweet, probably introverted guy who's listening to this from a beautiful, incredible woman like you that you want to share with him? I don't know. It might be something if they're avid listeners or readers of yours that they already know, but being your authentic self and leaning into who you are is so important. Women are going to pick up on if you're not being yourself. If you're trying to be something you're not, you know, I think that's, I don't know how obvious that is. Maybe it's not obvious. I think there's people have had a lot of whatever experiences you've had it can skew how you approach, you know future dates and other women but

just really leaning into who you are and That should be it that's really all that matters you can't take it personally if she doesn't like who you are. That's what I loved about you. You were in the good way weird, quirky, very opinionated and just but also sweet and big-hearted. And I like that immediately. And now I love it. So anyway, thank you for coming on my podcast. Thank you for being the world's best girlfriend.

Thanks. I'm so lucky. Thank you for being the world's best girlfriend. Thanks. I'm so lucky. Thank you very much for listening and remember your dream girlfriend, your Shmoopy, she's out there. You're not gonna call her Shmoopy, probably, but she's out there and she already likes you but she's gonna have to meet the real authentic you. So I'll see you next time.