← How to Get a Girlfriend with Connell Barrett
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)
00:48:56
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...
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- [00:00]
Connell Barrett
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. 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 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.
- [01:08]
Jessamyn
Hi. Thanks for having me.
- [01:11]
Connell Barrett
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.
- [01:21]
Jessamyn
It definitely feels like a first. It's the first date all over again.
- [01:24]
Connell Barrett
A little nervous. How's it going to go? Is she going to like this? Let's see what happens. And by the way, stick around to the end of the episode, because Jessamyn is going to share with you three of the biggest mistakes that men make on first dates that you might be making. And we're also going to talk about how to fix those things. Thanks. So stick around until the very end. Okay? So thank you for being here, Shmoopy. By the way, Shmoopy is our. Is our kind of pet name for each other. So it's annoying, but it's us being cute.
- [01:57]
Jessamyn
It's annoying, but it's us.
- [01:59]
Connell Barrett
Trigger warning for people who don't like Shmoopy.
- [02:03]
Jessamyn
Who don't like Seinfeld.
- [02:05]
Connell Barrett
Exactly. Let's talk about how we met. We met on a dating app called the League. And what. What made you want to match with me? When you think back to first seeing my profile, what made you want to swipe? Right?
- [02:20]
Jessamyn
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 tall ginger. You had 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.
- [03:07]
Connell Barrett
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?
- [03:31]
Jessamyn
I remember they were mostly. They were good photos. They were. I couldn't tell if they were necessarily professional photos. I think a couple of them were, but they were, like, 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. In the policeman's Halloween costume.
- [04:20]
Connell Barrett
Right. Sergeant Dick Utopia, my alter ego Halloween photo.
- [04:27]
Jessamyn
It was a good variety. You weren't taking yourself too seriously, but you were taking dating pretty seriously.
- [04:35]
Connell Barrett
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, these are. Maybe these are professional, but relaxed, genuine.
- [05:11]
Jessamyn
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.
- [05:20]
Connell Barrett
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. And that appealed to me because, sure, she's pretty, but she. She's also got a little bit of an unusual quirky side that's coming out, which is definitely my type.
- [05:57]
Jessamyn
Damn right.
- [05:59]
Connell Barrett
That was proved 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, and 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 or professor type vibe, based on my photos. Am I making that up, or is that something you recall?
- [06:31]
Jessamyn
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, just. And not in, like, a weird way. Literally, just like a very, like, gentle, friendly, open presence. Like, 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 like a very genuine person in front of me.
- [07:02]
Connell Barrett
Yeah, I've heard that before from other people. Like, oh, Connell, 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. 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.
- [08:11]
Jessamyn
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, or maybe the opposites attract, if you're taking that approach, whatever the case may be. Yeah. Definitely tune into what you actually are, not what you maybe want to be or think you should be.
- [08:33]
Connell Barrett
And the other thing you said was, oh, the whole dating coach thing was an unusual hook that was unusual for you, which is. 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 is. Oh, that's different. Is that basically what you're saying?
- [08:56]
Jessamyn
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 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.
- [09:27]
Connell Barrett
Right. It's so easy to look like every other guy.
- [09:30]
Jessamyn
Yeah.
- [09:31]
Connell Barrett
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 not a dating coach, but. 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. Like, for example, I have a client, former client, named Brian, who, when we, 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? He said, oh, I like cold plunges. He does that. That. I forget what it's called. Like the. The polar swim, where you swim five miles and frozen cold water in the winter. He does all. Does all these extreme things. So I said, yeah, let's play it. Let's play that up. Because every other guy's talking about hiking, and as you and I know, hiking sucks.
- [10:50]
Jessamyn
We'll get into that.
- [10:51]
Connell Barrett
Yeah. But if you're into extreme things, play that up. Or if you. 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 sound like every. Seem like everybody else.
- [11:13]
Jessamyn
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. 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 meeting 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, like, 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.
- [12:03]
Connell Barrett
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?
- [12:23]
Jessamyn
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. 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 genuinity, whatever, over text. But being able to have that easy flow, that definitely stood out.
- [13:18]
Connell Barrett
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, and. But then I really. I. I did something that I. 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? And you'd mentioned about being into running from dinosaurs and scotch swelling. I didn't know if you were kidding or not, but I. I wrote you had me at scotch swelling. 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 is?
- [14:08]
Jessamyn
I mean, my go to would be the T. Rex.
- [14:11]
Connell Barrett
Yeah.
- [14:12]
Jessamyn
Yeah, T. Rex. Oh, and pterodactyl.
- [14:14]
Connell Barrett
Right? And a few pterodactyls also, because I.
- [14:17]
Jessamyn
Could show off that I could spell pterodactyl.
- [14:19]
Connell Barrett
Nice. Yeah, nice. And what I love about our texting and the takeaway here for guys out there is I want them to realize that your texting can be. 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 bantery 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. And 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 not even 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. It 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?
- [15:42]
Jessamyn
Yeah, I remember. Just like I said, it was very easy. I mean, a big piece of it is, 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, like, worrying about, is this going to be. Is she going to take this the wrong way 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. 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. You know, as of right now, it just. It felt really good. And like I said, too, it was my first time kind of on the app in a really long time talking to anybody. So it just. It felt really good to kind of be back in a groove and be excited about meeting new people again.
- [16:57]
Connell Barrett
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. And the date is the movie, and hopefully the. The trailer is great and exciting, and the date and the movie is. 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. 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 with 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 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.
- [18:13]
Jessamyn
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. You know, like, 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 going to enjoy being with this person? 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?
- [18:55]
Connell Barrett
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 yout 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? 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. Any, any thoughts there? What, what do women want or not want when they're texting with a guy leading up to a date?
- [20:26]
Jessamyn
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? 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 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. 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? Because I mention 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.
- [21:25]
Connell Barrett
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 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. I don't know, as a mid. Was it a medieval outfit or some kind of posed battle? Do you remember what that photo was?
- [21:52]
Jessamyn
I do remember that photo. I think that was like. That was before. That was like the day of our third date. That was a little bit later.
- [22:00]
Connell Barrett
Okay.
- [22:00]
Jessamyn
And yeah, it was a. It was a SAS class video shoot. And it was. The song was S and M. It was the Rihanna and Britney Spears remix.
- [22:13]
Connell Barrett
Okay.
- [22:14]
Jessamyn
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. See.
- [22:24]
Connell Barrett
Right, right. Yeah.
- [22:27]
Jessamyn
Because you knew I'd dance and, like, done some whatever. I just thought that one photo was, like, particularly funny.
- [22:35]
Connell Barrett
Well, what were you. What you were doing that. 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.
- [23:22]
Jessamyn
Yeah. Yeah.
- [23:25]
Connell Barrett
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?
- [23:38]
Jessamyn
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.
- [23:48]
Connell Barrett
That's gotta be weird, right?
- [23:50]
Jessamyn
I just. I didn't 100% know what it meant, and I don't think I did any. Like, I didn't do the super Sleuth 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.
- [24:08]
Connell Barrett
Right?
- [24:08]
Jessamyn
So, yeah, pro tip. Make sure you know what's out there about you on the Internet before you go out there. But I just. I. I didn't want to have any expectations because that just didn't feel fair. I. I assumed there might be some, like. Like, you know, little, like, games or lines, things. Like, I kind of had, like, moves. 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. With a good guy.
- [24:50]
Connell Barrett
A. You're shmoopy, by the way.
- [24:55]
Jessamyn
Not this argument. Do we. Do we need to explain sh. And how.
- [24:59]
Connell Barrett
Backstory. 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 shmoopy, and they're just. Everybody's getting kind of grossed icked out by it. All right, so what theater you want.
- [25:17]
Jessamyn
To go to tonight? We got 61st and 3rd already, 4th and Broadway. Which one you want to go to? Schmoopy? You call me shmoopy. You're shmoop. You're shmoopy.
- [25:27]
Connell Barrett
You're shmoopy. All right. Shmoopies. And you and I started doing it as a joke, and it became real.
- [25:36]
Jessamyn
Yes. It quickly became unironic, which I love that.
- [25:40]
Connell Barrett
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's. 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. But did the vibe I gave you on my profile match the me who you met or did it mismatch or was it a little bit of both?
- [26:21]
Jessamyn
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.
- [26:56]
Connell Barrett
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.
- [27:10]
Jessamyn
Yes. The middle school. The middle school history teacher that I was expecting to meet on the date was definitely there having drinks.
- [27:18]
Connell Barrett
Remember when I helped you with your times tables on our first date? So romantic, so good, so normal. You were. 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. Mid to late 20s. She's probably, you know, pardon the cliche, the a manic pixie dream girl type. Just. 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. And we talked about your family and your brother and your mom and dad, and we kind of opened 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.
- [28:30]
Jessamyn
Yeah. I mean, honestly, kind of sort of same. I had no interest really in like diving into a relationship, especially coming out of the 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 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. @ 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 because 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 was obviously a lot more than that.
- [29:44]
Connell Barrett
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 is a woman just wants you to continue. She wants to feel like she's meeting the guy from the profile and then everything just, 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. 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 really they're really excited about?
- [30:41]
Jessamyn
I think, you know, it's tricky. 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.
- [31:03]
Connell Barrett
Yeah.
- [31:04]
Jessamyn
You know, you want to ask questions, but you don't want to just ask questions. Questions that are like, that have like a single answer. The typical, like, how many siblings do you have? Do you have any pets? Whatever. Whatever questions you have. 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, you 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.
- [31:44]
Connell Barrett
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 the country, and it's just a funny first date story. So you can have a back pocket story. You can have back pocket topics. 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. 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, but basically interview yourself.
- [32:57]
Jessamyn
Yeah, I like that.
- [32:59]
Connell Barrett
Yeah. Don't fast forward. This is not an ad. It's a free thing that's going to help you flirt with confidence because I'll bet that you struggle with what to say to women and how to flirt. Right? Well, let's fix that. I'm going to give you what I call the Flirty 30. These are 30 flirty questions to ask women on the apps or on dates or. Or when you approach so that you can Confidently connect with cool, sexy women. Starting today, it's time to stop running out of things to say and start asking them flirty questions that are going to make them want to date you. So to get your copy of the Flirty 30, it's totally free, just go to datingtransformation.com Flirty 30 and that's F L I R T Y 30 datingtransformation.com Flirty30. You're about to start confidently flirting with women, going on dates, and soon getting a great girlfriend. Go get your flirty 30. 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. 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 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, 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 story, a couple stories about my family, too. So we connected about. I think we connected about each other's families, among other things.
- [35:04]
Jessamyn
Yeah. I mean, very straightforward. You know, I think, I think families. It's not always easy for people to talk about their families.
- [35:14]
Connell Barrett
Right.
- [35:15]
Jessamyn
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. There might be 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.
- [35:41]
Connell Barrett
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.
- [35:53]
Jessamyn
We went to the other room of the other room.
- [35:55]
Connell Barrett
We went. We were in a bar called the other Room.
- [35:57]
Jessamyn
Right.
- [35:57]
Connell Barrett
And then we went to the other room. And then we went and watched the room. The movie. No, we didn't.
- [36:03]
Jessamyn
No, we didn't.
- [36:04]
Connell Barrett
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 the. 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?
- [36:40]
Jessamyn
I mean, honest, 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. But, you know, I think I remember with us, it was. We were sitting next to each other and there was just like, we'd been talking for at least an hour at that point, right. We 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 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 sounds super weird, but it definitely works if the moment's right. If you have that same kind of lull in the conversation, you can also ask, too. Consent is sexy. You can always ask.
- [37:58]
Connell Barrett
Yeah, consent is really sexy. 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. That way you can say, oh, I don't kiss on the first date.
- [38:12]
Jessamyn
Great.
- [38:12]
Connell Barrett
That's great. I would much rather a woman said that to me. Then I just lurch out of nowhere and go to kiss her. And she's so. I like that move that guy used, saying, I'm gonna kiss you now.
- [38:26]
Jessamyn
Yeah.
- [38:26]
Connell Barrett
So, 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 gotta 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 do you. 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 point of view? What's the woman's take on that?
- [39:29]
Jessamyn
Yeah, there's that antiquated, like, three days rule kind of thing. 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, text her the next day, maybe later that night. Just be like, hey, I had a great time. But definitely communicate what you want and what you're interested in, because how else is she gonna know? Women are very intuitive, but we're not mind readers, right?
- [40:30]
Connell Barrett
I remember the. 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, 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, and I wrote you back. And I Said the same. And. 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. You go on a date, you're authentic, you're genuine, You. You try to give them a good fun experience while being yourself. And then so much of this is just chemistry and letting the, the chips of chemistry fall where they're gonna fall. But. But anyway, that was, yeah, the most important first date of my life. So thank you for making that happen.
- [41:28]
Jessamyn
Likewise.
- [41:29]
Connell Barrett
Let's finish with 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. Fire away. What do you got?
- [41:43]
Jessamyn
All right. I mean, the three. I got three don'ts. I have a lot of don'ts, but I think there's three is good. 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, 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, it's a very specific thing when you are intending 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.
- [42:28]
Connell Barrett
Yeah.
- [42:28]
Jessamyn
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?
- [42:39]
Connell Barrett
That's a great tip. A woman notices if you're rude to the hired help.
- [42:43]
Jessamyn
Yeah.
- [42:44]
Connell Barrett
Like, I verbally assaulted my butler this morning and I felt so bad afterwards.
- [42:49]
Jessamyn
Yeah, your butler.
- [42:52]
Connell Barrett
Anyway.
- [42:55]
Jessamyn
Anyway.
- [42:55]
Connell Barrett
Okay, tip number two, don't do this. What's next?
- [43:01]
Jessamyn
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.
- [43:12]
Connell Barrett
Right.
- [43:13]
Jessamyn
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, 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.
- [43:36]
Connell Barrett
A server, good feedback When I was.
- [43:38]
Jessamyn
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 and it's just a little too familiar. So just avoid it. Best, 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.
- [44:01]
Connell Barrett
I think that's such a good tip, sweet cheeks. No, it really is. But it's weird. It's a little weird to be that familiar with somebody you don't know.
- [44:10]
Jessamyn
Yeah.
- [44:11]
Connell Barrett
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. Okay, do you have a third one?
- [44:24]
Jessamyn
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 rails. So like being like bitter or negative about something. So like I put on my profile pretty clearly I hate hiking.
- [44:44]
Connell Barrett
Yeah, we vibed about that. I loved.
- [44:47]
Jessamyn
Exactly. It was kind of something that I put out there. And you could have said like, oh, I love hiking. Like, I will maybe, you know, I can take that. 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.
- [45:02]
Connell Barrett
Joggers and hikers, we don't hate them, we just hate what they do.
- [45:05]
Jessamyn
Right. Two very different things.
- [45:07]
Connell Barrett
Right.
- [45:08]
Jessamyn
But 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 hate mushrooms. That's something good for me to know.
- [45:23]
Connell Barrett
Yeah.
- [45:23]
Jessamyn
Might 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. Okay. Vegetables are stupid. Like there's a difference between little things like that and just like turning the conversation into this negative.
- [45:42]
Connell Barrett
Right. Okay.
- [45:43]
Jessamyn
You know, speech.
- [45:45]
Connell Barrett
So make anything that you don't like, make it like a glancing blow. Not go down a rabbit hole of negativity.
- [45:52]
Jessamyn
Right. Make it, you know, if it's something interesting, that's one thing. If it's just, just like a vendetta that you have against vegetables and fungi, that's, you know, that's something that we get to on like the fifth or sixth date if we're feeling like we're at that place.
- [46:09]
Connell Barrett
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 gonna 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 for sure. By the way, if tomorrow's pilot is funny, I'm gonna switch airlines.
- [46:58]
Jessamyn
I'm not gonna listen. You were the one that booked the flight. You knew what you were getting into. I don't want to.
- [47:04]
Connell Barrett
We're out of time. We are out of time. 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?
- [47:19]
Jessamyn
I don't know, it might be something if they're avid listeners or readers of yours, that they already know, but it 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.
- [48:07]
Connell Barrett
That's what I loved about you. You were this, 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.
- [48:25]
Jessamyn
Thanks.
- [48:26]
Connell Barrett
I'm so lucky. Thank you very much for listening and remember your dream girlfriend, your shmoopy she's out there. You're not going to call her shmoobie, 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.