My Girlfriend Jess Reveals the #1 Secret to Landing Second Dates! (Most Men Make 3 BIG Mistakes)

Speaker 1 a great tip. A woman notices if you're rude to the hired help.

Speaker 1 Yeah.

Speaker 1 Like I verbally assaulted my butler this morning, and I felt so bad afterwards.

Speaker 1 Welcome back to the How to Get a Girlfriend podcast. I'm your host, dating coach and author, Connell Barrett.

Speaker 1 I help men confidently flirt, get dates, and attract their dream girlfriends all by being authentic. No creepy pickup moves needed.

Speaker 1 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.

Speaker 1 This is so that you can have really great dates that lead to second dates and third dates, and eventually finding that dream girlfriend. And

Speaker 1 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 schmoopy. She's the most important person in my life.

Speaker 1 And I wanted to have her on to talk about, well, how I got her to be my girlfriend. Welcome to the podcast, Jessamine.

Speaker 2 Hi, thanks for having me.

Speaker 1 I was about to start chatting with you and all of a sudden I have flashbacks because we've never done a podcast together and I'm like, wow, this is kind of like a new first date.

Speaker 2 It definitely feels like a first, it's the first date all over again.

Speaker 1 A little nervous. How's it going to go?

Speaker 1 Is she going to like this?

Speaker 1 Let's see what happens.

Speaker 1 And by the way, stick around to the end of the episode because Jessamine is going to share with you three of the biggest mistakes that men make on first dates that you might be making.

Speaker 1 And we're also going to talk about how to fix those things. Thanks.
So stick around until the very end.

Speaker 1 Okay, so thank you for being here, Shmoopy. By the way, Shmoopy is our kind of pet name for each other.
So

Speaker 1 it's annoying, but it's us

Speaker 1 being cute.

Speaker 2 It's annoying, but it's us.

Speaker 1 Trigger warning for people who don't like Shmoopy.

Speaker 2 Who don't like Seinfeld.

Speaker 1 Exactly. Let's talk about how we met.
We met on a dating app called The League.

Speaker 1 And

Speaker 1 what made you want to match with me? When you think back to first seeing my profile, what made you want to swipe right?

Speaker 2 I remember I had just joined the league. I think I was on it for maybe

Speaker 2 five minutes when I came across your profile. So it didn't take very long.
And I just saw this tall ginger. You had some really nice photos.

Speaker 2 I think your tagline or headline was something like the real-life hitch. And I was like,

Speaker 2 Okay, and you kind of read further, and you're a dating coach.

Speaker 2 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.

Speaker 2 I was just trying to get back into the dating game after being isolated for so long.

Speaker 2 Yeah, it was mostly curiosity, but good curiosity. Maybe a little bit of curiosity.

Speaker 1 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.

Speaker 1 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.

Speaker 1 What do you remember about the photos?

Speaker 2 I remember they were mostly, they were good photos. They were, I don't, I couldn't tell if they were necessarily professional photos.
I think a couple of them were, but they were like well framed.

Speaker 2 It was just you.

Speaker 2 I think there was one of like you and your niece. There was one of you with a dog.

Speaker 2 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.

Speaker 2 Like there, 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

Speaker 2 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 in the policeman's halloween costume right there's a whole movie sergeant dick utopia

Speaker 1 My altered ego, Halloween photo.

Speaker 2 So

Speaker 2 it was a good variety. You weren't taking yourself yourself too seriously, but you were taking dating pretty seriously.

Speaker 1 That's good to know.

Speaker 1 I've 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.

Speaker 1 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,

Speaker 1 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 these are 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

Speaker 1 I liked your profile because

Speaker 1 well you're super pretty obviously

Speaker 1 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.

Speaker 1 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, a quirky type.

Speaker 1 And 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.

Speaker 1 Damn right.

Speaker 1 That was pretty right.

Speaker 1 I was thinking before that we got on to record today, I was thinking of something I remember you telling me that you, that you liked about my profile.

Speaker 1 And this is something that I think the listener can

Speaker 1 find

Speaker 1 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

Speaker 1 professor type vibe based on my photos. Am I making that up or is that something you recall?

Speaker 2 I feel like when I've described you to people in the past, they've been like, I don't know any other way to describe it other than like the cool middle school teacher. Yeah.

Speaker 2 Just and not in like a weird way, literally, just like a very like gentle, friendly, open presence. Like that comes out immediately.

Speaker 2 It definitely came out on your profile, but just even getting to know you, I'm like, there's no scariness or bad weirdness here. It was just like a very genuine person in front of me.

Speaker 1 Yeah, I've heard that before from other people. Like, oh, Connor, you come off like a school teacher, high school teacher, college professor.
And I'm not necessarily going for that in my photos.

Speaker 1 But what I do try to do

Speaker 1 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.

Speaker 1 And

Speaker 1 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.

Speaker 1 Because if you had seen me on a motorcycle with a leather jacket trying to look all cool and tough,

Speaker 1 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.

Speaker 1 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.

Speaker 1 Six Pack Abs or male model,

Speaker 1 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.

Speaker 2 Right. Or, you know, thinking about what kind of woman you actually want to attract.
Do you also want to attract a motorcycle riding babe? I mean, you know, if you do, great.

Speaker 2 Or maybe the opposites attract if you're taking that approach, whatever the case may be.

Speaker 2 Yeah, definitely tune into what you actually are, not what you maybe want to be or think you should be.

Speaker 1 And the other thing you said was, oh, the whole dating coach thing was an unusual

Speaker 1 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

Speaker 1 so just the fact that that was unusual, that caught your attention as, oh, that's different. Is that basically what you're saying?

Speaker 2 Yeah. I mean, anything that's different from any of the other guys, you know, we're in New York City.
There's however many million men out there that are,

Speaker 2 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.

Speaker 2 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.

Speaker 2 That's really special.

Speaker 1 Right. It's so easy to look like every other guy.
Yeah.

Speaker 1 Or to

Speaker 1 get lost in the shuffle of so many people you're swiping on, left or right.

Speaker 1 And so

Speaker 1 you were attracted or at least hooked by the idea of me being a dating coach. You listening to this episode, you're obviously not a dating coach.

Speaker 1 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.

Speaker 1 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.

Speaker 1 For example, I have a client, former client named Brian, who...

Speaker 1 When I was coaching him, 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?

Speaker 1 He said, Oh, I like cold plunges. He does that, that

Speaker 1 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 it.

Speaker 1 Let's play that up because every other guy's talking about hiking. And as you and I know, hiking sucks.

Speaker 1 We'll get into that. Yeah, but if you're into extreme things, play that up.
Or if

Speaker 1 you are the expert in, I don't know, iced coffee, and you are, if you're a nerd about something, lean into it.

Speaker 1 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.

Speaker 2 Yeah. And I think that's kind of the beauty of online dating.
I think it's, you know, it's much more accepted now than maybe it was like 10 years ago.

Speaker 2 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.

Speaker 2 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.

Speaker 2 It's great meeting people in public too, and organically through friends, whatever.

Speaker 2 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.

Speaker 2 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.

Speaker 1 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

Speaker 1 leading up to the date? Any memories or any feedback or thoughts?

Speaker 2 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.

Speaker 2 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,

Speaker 2 made a few jokes. You know, it was 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.

Speaker 2 And it's hard to communicate a lot of things over text. It can be really hard to communicate your sense of humor, your genuinity, whatever, over text.
But being able to have that easy flow,

Speaker 2 that definitely stood out.

Speaker 1 I'm just looking at our very first text exchange ever. I have it right here.

Speaker 1 You opened me on the league by saying, hey there, Connell.

Speaker 1 I wrote back with my incredible wit and intelligence, hey Jessamine. I thought that was brilliant.

Speaker 1 But then I really,

Speaker 1 I did something that I want men to do out there, or to at 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?

Speaker 1 And you'd mention about being into running from dinosaurs and scotch swilling.

Speaker 1 I didn't know if you were kidding or not. But I wrote, you had me at scotch swilling.

Speaker 1 And then I followed up with, what's your favorite dinosaur to run from?

Speaker 1 And do you remember what your favorite dinosaur to run from is?

Speaker 2 I mean, my go-to would be the T-Rex. Yeah.
Yeah. T-Rex.
Oh, and pterodactyls.

Speaker 1 Right, and a few pterodactyls.

Speaker 2 Also, because I could show off that I could spell pterodactyl.

Speaker 1 Nice.

Speaker 2 Yeah.

Speaker 1 Nice.

Speaker 1 And what I love about our texting, and the takeaway here for guys out there is I want them to realize that your texting

Speaker 1 can, and I think should be very light. It can be about nothing.
It's kind of like Seinfeld, the show about nothing.

Speaker 1 Texting, when you can get on the same bantery wavelength with that woman,

Speaker 1 you can text about the stupidest stuff.

Speaker 1 We're not really texting about anything real. We're just cracking.

Speaker 1 I don't even know if these are jokes. We're just texting about silly, dumb things.

Speaker 1 You loving scotch, you running from pterodactyls. I compared you to Don Draper for some reason.

Speaker 1 And

Speaker 1 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.

Speaker 1 I'm not even all that flirtatious, but just because it's light and playful, I hoped that that's the vibe that you enjoyed.

Speaker 1 And I remember a few, a day or two before our first date, you sent me something that just made me smile. It felt so good.

Speaker 1 You kind of broke character a little bit from the playful messaging and you said, by the way, I'm really liking our banter.

Speaker 1 Can you talk about what you liked and maybe any tips on texting for that guy listening right now?

Speaker 2 Yeah,

Speaker 2 I remember just, like I said, it was very easy.

Speaker 2 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.

Speaker 2 If it doesn't match, then it's probably not going to be a good conversation.

Speaker 2 So if you feel like you're not struggling to find the right words to say, you feel like, you know, you're not like worrying about, is this going to be, is she going to take this the wrong way?

Speaker 2 Or is she going to think I'm weird? Like you, you shouldn't be having those kinds of apprehensions if it's a good, genuine connection and a good conversation.

Speaker 2 Yeah, I remember

Speaker 2 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.

Speaker 2 I was like, I know this is going to be an easy conversation. I know I don't have anything to worry about, you know, as of right now.

Speaker 2 It just, it felt really good. And like I said, too, it was my first time kind of on the apps in a really long time talking to anybody.

Speaker 2 So it just, it felt really good to kind of be back in a groove and be excited about meeting new people again.

Speaker 1 Oh, absolutely. I was, 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.

Speaker 1 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.

Speaker 1 And I just thought, okay, great. We're both excited.
We're both looking forward to this. And

Speaker 1 the texting was so, it's so basic, so simple.

Speaker 1 A lot of guys make the mistake of saying,

Speaker 1 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 a good game.

Speaker 1 And all you really need to do is

Speaker 1 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.

Speaker 1 And we just bantered about almost in a way. But it was just that lightness feels good to people as they lead up to a date.

Speaker 1 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.

Speaker 2 Yeah. I think too, like you can, you can take dating seriously.
You can take other people seriously, women seriously, but you don't have to be serious about it.

Speaker 2 You know, like it should be light. It should be fun.
It shouldn't be immediate, like heavy conversations.

Speaker 2 If you find that you're like immediately going into setting boundaries or

Speaker 2 things just aren't flowing in a way that's like, am I actually going to enjoy being with this person?

Speaker 2 Then just, it helps to take a step back and say, like, really evaluate your expectations and make sure that you're finding that balance between like, this is unexpected, but is it good or bad?

Speaker 1 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.

Speaker 1 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.

Speaker 1 But I escaped using the dating philosophy of radical authenticity, which I've used to help thousands of men in 17 countries find love.

Speaker 1 It's what I wrote about in my best-selling book, Dating Sucks But You Don't. And radical authenticity is why Psychology Today called me the best dating coach in America.

Speaker 1 And now I want to personally help you attract your dream girlfriend. So go to datingtransformation.com and book a free call with me.

Speaker 1 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.

Speaker 1 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 a lot of 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

Speaker 1 any any thoughts there what what do women

Speaker 2 want or not want when they're texting with a guy leading up to a date yeah the the 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?

Speaker 2 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.

Speaker 2 Along with the kind of the idea of asking questions, you don't want to fall into like the interview of like you just asking her questions over and over again. Like she knows you're interested.

Speaker 2 You don't need to show that you're interested by only asking questions. You can share things about yourself.
If you're going to ask questions, make them interesting.

Speaker 2 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

Speaker 2 what was it it was like if you're gonna if you were gonna cook for me what would you make or because I had mentioned something about cooking on my profile like

Speaker 2 again just like really leaning into like what you're able to see about her

Speaker 2 you can use those as conversation starters as questions

Speaker 1 Yeah, and you did something that was fantastic that any guy can do. You sent me a photo of yourself taken in a park.

Speaker 1 I think you were doing some kind of, I don't know if it was a SAS class dance class photo or some other acting class you were taking, but it was you like in the middle of some kind of,

Speaker 1 I don't know,

Speaker 1 was it a medieval outfit or some kind of

Speaker 1 posed battle? Do you remember what that photo was?

Speaker 2 I do remember that photo. I think that was like, that was before,

Speaker 2 that was like the day of our third date. That was a little bit later.
Okay. And yeah, it was a SAS class video shoot.

Speaker 2 And it was, the song was

Speaker 2 S and M. It was the Rihanna and Britney Spears remix.

Speaker 1 Okay.

Speaker 2 And it was just like a funny photo that someone had taken while we were filming that was just completely out of context and looked completely insane. So I was like, hey, so this is what I did today.

Speaker 2 See you later.

Speaker 2 Yeah. Because you knew I had danced and like done some sort of whatever.

Speaker 2 I just thought that one photo was like particularly funny.

Speaker 1 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.

Speaker 1 And you could send that along with one of your text messages. And that helps her see who you are.

Speaker 1 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.

Speaker 1 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.

Speaker 2 Yeah.

Speaker 1 Yeah.

Speaker 1 Okay, let's talk about our date.

Speaker 1 How'd I do?

Speaker 1 I've been waiting years to ask you this. How'd I do?

Speaker 1 Do you want to keep dating me or not?

Speaker 2 Well, it's only been three years.

Speaker 2 I might need a little more time. No, I mean,

Speaker 2 I knew I was going on a date with a dating coach.

Speaker 1 That's going to be weird, right?

Speaker 2 I just, I didn't 100% know what it meant. And I don't think I did any like,

Speaker 2 I didn't do the super sleuth deep dive internet search on you. I I don't think.
I don't remember doing any of that simply because it was like,

Speaker 2 it just isn't like instinct for me. I know it's instinct for a lot of people.
Right.

Speaker 2 So yeah, pro tip. Make sure you know what's out there on you about you on the internet

Speaker 1 before you

Speaker 1 go out there.

Speaker 2 But I just, I didn't want to have any expectations

Speaker 2 because that just didn't feel fair. I assumed there might be some like

Speaker 2 tip, like, you know, little like games or lines. Like, I kind of had like moves.

Speaker 2 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.

Speaker 2 It just felt like I was going on a date with a good guy.

Speaker 1 Aww.

Speaker 1 You're Schmoopy, by the way.

Speaker 2 Ah, not this argument. Do we need to explain Schmoopy and how to do that?

Speaker 1 So you and I are 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

Speaker 1 everybody's getting kind of grossed icked out by it.

Speaker 1 Alright, so what theater do you want to go to tonight? We got the 61st and 3rd or 84th and Broadway. Which one do you want to go to, Schmoopy? You called me Schmoopy.
You're Schmoopy.

Speaker 1 All right, Shmoopies.

Speaker 1 And you and I started doing it as a joke, and it became real.

Speaker 2 Yes, it quickly became an ironic.

Speaker 1 Which I love that. I love that about us.

Speaker 1 Okay, Shmoopi. Back to our date.

Speaker 1 Oh, here's a good question.

Speaker 1 A client actually wanted me to ask you this.

Speaker 1 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.

Speaker 1 There's a little bit of a mismatch.

Speaker 1 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 did the vibe I gave you on my profile match the me who you met?

Speaker 1 Or did it mismatch or was it a little bit of both?

Speaker 2 It was definitely a match. I think with the league specifically, it's not a particularly detailed profile,

Speaker 2 right? It was kind of like you put a few of your interests, you put like a tagline, your age.

Speaker 2 And I think that was kind of it.

Speaker 2 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.

Speaker 1 But

Speaker 2 yeah, I mean, it was definitely what I would have expected. I didn't feel like I was being catfished.

Speaker 1 Oh, no, I didn't mean that.

Speaker 1 I guess I just meant, was there anything that

Speaker 1 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.

Speaker 2 Yes,

Speaker 2 the middle school history teacher that I was expecting to meet on the street was basically there

Speaker 2 having drinks.

Speaker 1 Remember when I helped you with your times tables on our first date?

Speaker 2 So romantic.

Speaker 1 So good. So normal.

Speaker 1 You were,

Speaker 1 you were what I was expecting, and times 10.

Speaker 1 I thought,

Speaker 1 here's a really pretty girl. There's a lot of quirky, silly, weird humor on her profile.
She's in her

Speaker 1 mid to late 20s. She's probably, well, you know, pardon the cliche, a manic pixie dream girl type.

Speaker 1 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.

Speaker 1 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.

Speaker 1 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.

Speaker 1 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

Speaker 1 100%

Speaker 1 girlfriend material. It's like, wow.

Speaker 1 Uh, so yeah, you more you met and exceeded my expectations in

Speaker 1 every way.

Speaker 2 Yeah. I mean, honestly, kind of sort of same.

Speaker 2 I had no interest really in like diving into a relationship, especially coming out of a year and a half long period of isolation.

Speaker 2 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?

Speaker 2 Am I just excited about this because I've been

Speaker 2 socially restricting myself for 18 months or like is this real because 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

Speaker 2 also hard to take seriously sometimes because there's so many people and it's just very easy to kind of jump to person to person

Speaker 2 so

Speaker 2 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.

Speaker 2 But it is obviously a lot more than that.

Speaker 1 Absolutely. It was fun.

Speaker 1 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 is a woman just wants you to continue.

Speaker 1 She wants to feel like she's meeting the guy from the profile and that everything just,

Speaker 1 you know escalates mutually with organically it's like oh wow it's just like we were on texting together but now we're doing it in person

Speaker 1 and

Speaker 1 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?

Speaker 1 How to show interest, how to not show too much interest? Yeah,

Speaker 1 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 really, they're really excited about?

Speaker 2 I think, you know, it's tricky, it's hard out there.

Speaker 2 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.

Speaker 2 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 do 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 they're ones that three maybe three things or topics that you have in mind that you know 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.

Speaker 2 Just things that you have on tap ready to go that you know will generate conversation. And if they don't generate conversation, then maybe that's a signal.

Speaker 1 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.

Speaker 1 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 hotlight on her.

Speaker 1 And then remember, oh, tell her that story about the funny thing that happened to you in Paris.

Speaker 1 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 the country.

Speaker 1 And it's just a funny first aid story. So you can have a back pocket story.
You can have back pocket topics.

Speaker 1 And 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.

Speaker 1 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.
Basically, interview yourself.

Speaker 2 Yeah, I like that.

Speaker 1 Yeah.

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Speaker 1 So, on our date, I remember, and I don't, 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.

Speaker 1 Plan a great fun place to go. Have a clear, simple plan.
Be that man with a plan. And then, but on the date, be really present.
Just be a real active listener.

Speaker 1 and discover the right things to say on the date.

Speaker 1 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.

Speaker 1 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.

Speaker 1 I wanted to remember this because I wanted to show you that I was listening.

Speaker 1 because that was important to me to understand. I think I shared a story, a couple of stories about my family too.

Speaker 1 So we connected about, I think we connected about each other's families, among other things.

Speaker 2 Yeah, I mean, very straightforward.

Speaker 2 You know, I think, I think families, it's not always easy for people to talk about their families. Right.

Speaker 2 So you can always, you know, if you're asking her like about her parents or siblings, you know, if there's not a lot coming back, it's probably, they may not be super close.

Speaker 2 There might be tension there, whatever the case. There's always other, you talk about friends talk about co-workers i'm sure i talked about like my co-workers and bosses a little bit too

Speaker 1 um

Speaker 2 yeah

Speaker 1 so we had a really good couple drinks at this bar in new york city and then we went to the back room

Speaker 1 we went to a different part of the bar just to we went to the we went to the other room of the other room we went we were in a bar called the other room right and then we went to the other room

Speaker 1 and then we went and watched the room, the movie. No, we didn't.
No, we didn't.

Speaker 1 But our first kiss was in the back room of the other room.

Speaker 1 And

Speaker 1 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,

Speaker 1 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.

Speaker 1 A lot of guys never even try just because they're afraid what are what are your thoughts on the do's and don'ts of of the guy going for that first kiss on a first or second date

Speaker 2 I mean honestly it's it's a terrible thing but like everyone's different every woman is gonna have a different expectation I know

Speaker 2 with I'm thinking of like our first kiss

Speaker 2 Maybe some other first kisses that I've had. Not that I've had a million, but you know,

Speaker 2 I think

Speaker 2 I remember with us it was we were sitting next to each other 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

Speaker 2 and

Speaker 2 there was just like a lull in the conversation and we were looking at each other

Speaker 2 and

Speaker 2 you know if you're maintaining good eye contact with her and she keeps it up then that's usually a pretty good sign

Speaker 2 other if you're if you're looking for a more verbal sort of confirmation,

Speaker 2 it can kind of go either way. Definitely depends on the circumstances, but I think

Speaker 2 there have been a couple of times where a guy has 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.

Speaker 2 If you have that same kind of will in the conversation. You can also ask too.
Consent is sexy. You can always ask.

Speaker 1 Yeah.

Speaker 1 Consent is really sexy.

Speaker 1 I like the idea of saying hey I want to 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 yeah 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

Speaker 1 so I like that move that guy used saying I'm gonna kiss you now yeah so

Speaker 1 yeah I think what happened on our date I noticed what I call with my clients, the kiss window opened. There was that lull you mentioned.

Speaker 1 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.

Speaker 1 I gotta walk the walk.

Speaker 1 One last question about first dates and then we'll get to the three mistakes that a lot of guys make. But

Speaker 1 what do you, what's your opinion on asking a woman out for a second date? Do you,

Speaker 1 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.

Speaker 1 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.

Speaker 1 But what's your point of view? What's the woman's take on that?

Speaker 2 Yeah, there's that antiquated, like, three days roll kind of thing.

Speaker 2 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.

Speaker 2 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.

Speaker 2 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. question, you're not, there's no uncertainty,

Speaker 2 you know, you just move on with your life.

Speaker 2 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,

Speaker 2 just say, like, hey, I had a great time.

Speaker 2 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 migrators.

Speaker 1 Right.

Speaker 1 I remember

Speaker 1 the morning after our first date,

Speaker 1 I looked at my phone and I opened my phone

Speaker 1 and

Speaker 1 it's not that you owed me a text, but I thought, I wonder if she wrote me?

Speaker 1 I was like 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.

Speaker 1 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. Like you can't obviously control whether or not somebody wants to see you.

Speaker 1 You go on a date, you're authentic, you're genuine. You try to give them a good, fun experience while being yourself.

Speaker 1 And then so much of this is just chemistry and letting the chips of chemistry fall where they're going to fall. But

Speaker 1 anyway,

Speaker 1 that was, yeah.

Speaker 1 The most important first date of my life. So thank you for making that happen.

Speaker 2 Likewise.

Speaker 1 Let's finish with

Speaker 1 a final three tips from you. So you said you've had two or three thoughts on some things that meant some mistakes that many men make on first dates.

Speaker 1 Fire away. What do you got? All right.

Speaker 2 I mean, the three, I got three don'ts. I have a lot of don'ts, but I think there's good.
Three is good. There are some that are more maybe universal than others.

Speaker 2 I think one of the ones that we've heard time and time again is just,

Speaker 2 you know, 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 you know don't be a dick to the service staff don't don't be rude to anybody but there is that 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

Speaker 2 It there's a power imbalance that's kind of set up there.

Speaker 2 And it just immediately communicates this:

Speaker 2 if someone's going to be this easily dismissive or rude, yeah, a complete stranger, how are they going to treat somebody that they know?

Speaker 1 That's a great tip. A woman notices if you're rude to the hired help,

Speaker 1 yeah.

Speaker 1 Like, I verbally assaulted my butler this morning, and I felt so bad afterwards.

Speaker 2 Yeah, your butler,

Speaker 1 anyway,

Speaker 1 anyway, okay,

Speaker 1 tip number two: don't do this. What's next?

Speaker 2 Um, Pet names. So

Speaker 2 calling, like using like kind of common,

Speaker 2 you know, maybe in like the banter that you have before the date, you can jokingly come up with a nickname like Shmoopy.

Speaker 1 Right.

Speaker 2 But things like hun or sweetie or sweetheart or babe.

Speaker 2 One, it kind of like communicates a familiarity that she might not be ready for, especially considering she's just met you.

Speaker 2 Another thing is like, like sweetie, sweetheart, hun. Like those are things that if I'm getting like cat called on the street, that's what guys call me.
Or like when I was working as a server,

Speaker 2 when I was working 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.

Speaker 2 And it's just a little too familiar. So just avoid it.

Speaker 2 Best 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.

Speaker 1 That's such a good tip, sweet cheeks.

Speaker 1 No, it really is. But it's weird, it's a little weird to be that familiar with somebody you don't know.

Speaker 1 Yeah, or 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.

Speaker 1 Okay, do you have a third one?

Speaker 2 There's there's a difference between like sharing your interests and just like going on like a full-on rant

Speaker 1 or

Speaker 2 going like off the rails. So like being like bitter or negative about something.
So like I put on my profile pretty clearly, I hate hiking.

Speaker 1 Yeah, we vibed about that. I love hiking.

Speaker 2 Exactly. It was kind of something that I put out there.
And you could have said like, oh, I love hiking. Like, well, maybe, you know.

Speaker 2 I can take, like, you could have, if you did like hiking, you could have like spun it and it could have like generated conversation. Yeah.
We connected on like hating hiking, whatever.

Speaker 1 I hate joggers and hikers, we don't hate them, we just hate what they do, right?

Speaker 2 Two very different things, right? But that's different than me saying, like, going on a rant about hiking and nature and how terrible it is. Um, or you know, you don't like mushrooms.

Speaker 2 You can say, like, fun fact, I hate mushrooms. That's something good for me to know.
Yeah, might generate some discourse because I do like mushrooms.

Speaker 2 But for you to then go on a rant about vegetables in general and to go down a hole of vegetables are stupid, like there's a difference between little things like that and just like turning the conversation into this negative

Speaker 2 speech.

Speaker 1 So make anything that you don't like, make it like a glancing blow, not go down a rabbit hole of negativity.

Speaker 2 Right.

Speaker 2 You know, if it's something interesting,

Speaker 2 that's one thing.

Speaker 2 If it's just like a vendetta that you have against vegetables and fungi, that's, you know, that's something we get to on like the fifth or sixth date if we're feeling like we're at that place.

Speaker 1 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.

Speaker 1 Don't go off for five minutes on some negative rant.

Speaker 1 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.

Speaker 1 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.

Speaker 1 Make your things you dislike, make it quick and almost like silly and frivolous because it's just people being human that way.

Speaker 2 For sure.

Speaker 1 By the way, if tomorrow's pilot is funny, I'm going to switch airlines.

Speaker 2 I'm not going to. Listen, you were the one that book the flight you knew what you were getting into

Speaker 1 I don't want to we're out of time we are out of time Shmmippi 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.

Speaker 2 It might be something if they're avid listeners or readers of yours that they already know. But

Speaker 2 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.

Speaker 2 You know,

Speaker 2 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,

Speaker 2 it can skew how you approach, you know, future dates and other women. But

Speaker 2 just really leaning into who you are,

Speaker 2 and

Speaker 2 that should be it. That's really all that matters.
You can't take it personally if she doesn't like who you are.

Speaker 1 That's what I loved about you. You were, in the good way, weird.
Quirky. Very opinionated,

Speaker 1 but also sweet and big-hearted. And I liked 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.

Speaker 2 Thanks.

Speaker 1 I'm so lucky. Thank you very much for listening.
And remember, your dream girlfriend, your schmoopy, she's out there.

Speaker 1 You're not going to call her schmoopy, probably, but she's out there and she already likes you, but she's going to have to meet the real authentic you. So I'll see you next time.