Connell Barrett:
That's a great tip. A woman notices if you're rude to the hired help. Like, I verbally assaulted my butler this morning, and I felt so bad afterwards. Welcome back to the how to get a girlfriend podcast. I'm your host, dating coach and author, Connell Barrett. I help men confidently flirt, get dates, and attract their dream girlfriends all by being authentic. No creepy pickup moves needed. And in this episode, you're about to find out what women want on a first date. And, also, you're gonna find out what they don't want. This is so that you can have really great dates that lead to 2nd dates and third dates and eventually finding that dream girlfriend.

Connell Barrett:
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 schmoopy. 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, Jessamin.

Jessamin:
Hi. Thanks for having me.

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.

Jessamin:
It definitely feels like fur . It's the first date all over again.

Connell Barrett:
I'm a little nervous. How's it gonna go? Is she gonna like this? Let's see what happens. And by the way, stick around to the end of the episode because Jessamine is gonna share with you 3 of the biggest mistakes that men make on first dates that you might be making. And we're also gonna talk about how to fix those things. Thanks. So stick around until the very end. Okay. So thank you for being here, Shmoopy.

Connell Barrett:
By the way, Shmoopy is our kind of pet name for each other. So it's annoying, but that's us being cute.

Jessamin:
It's annoying, but it's us.

Connell Barrett:
Trigger warning for people who don't like Schmoopy.

Jessamin:
Who doesn't like Seinfeld?

Connell Barrett:
Exactly. Let's talk about how we met. We met on a dating app called The League. And what made you want to match with me? When you think back to first seeing my profile, what made you wanna swipe right?

Jessamin:
I remember I had just joined the league. I think I was on it for maybe 5 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.

Jessamin:
It was mostly curiosity, but good curiosity. Maybe a little weird curiosity.

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 wanna 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 was saying about him. What do you remember about the photos?

Jessamin:
I remember they were mostly good photos. They were n't. 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 is one of, like, you and your niece. There is one of you with a dog. But the pitfalls that I see a lot are, like, you know, guys that have, like, a clearly cropped photo, like a 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 is obviously some effort in there.

Jessamin:
And then you also had a photo of your head cut off, which was a little concerning, but it was, like, the last one, and I'd seen your face. I didn't care. But it was you in the policeman's Halloween costume. Right. I was on top.

Connell Barrett:
Sergeant dick utopia. My alter ego, Halloween photo.

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

Connell Barrett:
That's good to know. I found that the best, most effective photos for a single guy, 1 or 2 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 professional, but relaxed, genuine.

Jessamin:
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.

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 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, quirky type, 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.

Jessamin:
Damn right.

Connell Barrett:
That was pretty right. I was thinking before we got on to record today, I was thinking of something. I remember you telling me that you liked 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 or professor type vibe based on my photos. Am I making that up, or is that something you recall?

Jessamin:
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. Just and and not in, like, a weird way. Literally, just like a very, like, gentle, friendly, open presence. Like, that comes out immediately. It doesn't come 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

Connell Barrett:
me. Yeah. I've heard that before from other people. Like, oh, Conner, you come off like a school teacher, high school teacher, college professor. And I'm not necessarily going for that in my photos. But what I do try to do is to say, okay. What's 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.

Connell Barrett:
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 mister 6 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.

Jessamin:
Right. Or, you know, thinking about what kind of woman you actually wanna attract. Do you also wanna 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 in to what you actually are and not what you maybe want to be or think you should be.

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 makes total sense. There's not a lot of dating coaches out there, at least not dating in 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?

Jessamin:
Yeah. I mean, anything that's different from any of the other guys. You know, we're in New York City. Yeah. 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.

Jessamin:
That's really special.

Connell Barrett:
Right. It's so easy to look like every other guy Yeah. Or to get lost in the shuffle of so many people you're swiping on left or right. And so you were attracted or at least hooked by the idea of me being a dating coach. You're listening to this episode, you're obviously not a dating coach, but a thought I would have for you is to ask yourself, what is something that is completely singular about me and unique that I can either show or mention that's different but cool, different but interesting, or super nerdy? Because by getting specific about what makes you unique, you might jump out at a woman to say, wow. I've never seen that before. That's really interesting. For example, I have a former client named Brian who when I was coaching him, I said, what's something really unusual about you? What is something completely unique? And he said, I like really extreme things.

Connell Barrett:
I said, what do you mean? He said, oh, I like cold plunges. He does that so that I forget what it's called. Like, the polar swim where you swim 5 miles in frozen cold water in the winter. He 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.

Jessamin:
We'll get into that.

Connell Barrett:
Yeah. But if you're into extreme things, play that up. Or if you are the expert in, I don't know, iced coffee and you are if you're a nerd about something, lean into it. That could be that one unique thing that's your version of being a dating coach because you just don't wanna blend in and sound like everybody else.

Jessamin:
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 who you are, what those things are that you really want people to know.

Jessamin:
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.

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?

Jessamin:
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, and made a few jokes. You know, it was just very easy. Sometimes you can 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 or your genuinity, whatever, over text, but being able to have that easy flow, that definitely stood out.

Connell Barrett:
I'm just looking at our very first text exchange ever. I have it right here. You opened me up to the league by saying, hey there, Connell. I wrote back with my incredible wit and intelligence, hey, Jessamine. I thought that was brilliant. And then I really I I I did something that I want men to do out there or 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 scotchwilling.

Connell Barrett:
I didn't know if you were kidding or not, but I wrote you had me at scotchwilling. 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?

Jessamin:
I mean, my go to would be the T. Rex.

Connell Barrett:
Yeah.

Jessamin:
Yeah. T. Rex. Oh, and pterodactyl.

Connell Barrett:
Right. And a few pterodactyls.

Jessamin:
Also because I could show off that I could spell pterodactyl.

Connell Barrett:
Nice.

Jessamin:
Yeah. Mhmm.

Connell Barrett:
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 kinda like Seinfeld, the show about nothing. Texting when you can get on the same battery wavelength with that woman, it's 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.

Connell Barrett:
We're just texting about silly dumb things. You love Scotch, you run from pterodactyls. I compared you to Don Draper for some reason.

Jessamin:
Mhmm.

Connell Barrett:
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 2 before our first date, you sent me something that just made me smile. It felt so good. You kinda broke character a little bit from the playful messaging, and you said, by the way, I'm really liking our banter.

Connell Barrett:
Can you talk about what you liked and and maybe any tips on texting for that guy listening right now?

Jessamin:
Yeah. I remember just like I said, it was very easy. I mean, the big piece of it is, like, you know, if your sense of humor matches with the other person or if your interest matches with the other person, that's kind of key. If it doesn't match, then it's probably not gonna 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 worrying about is this gonna be, is she gonna take this the wrong way or is she gonna think I'm weird? Like, 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 haven't talked in person yet.

Jessamin:
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 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 felt really good to kind of be back in a groove and be excited about meeting new people again.

Connell Barrett:
Oh, absolutely. I like to think of texting a woman leading up to a date as like a movie trailer, giving each other some coming attractions of what the date might be like. And the date is the movie. And, hopefully, the trailer is great and exciting, and the date and the movie is great. But I was just so happy that you were enjoying our texting. I felt the same way. And I just thought, okay. Great.

Connell Barrett:
We're both excited. We're both looking forward to this. And the texting was so basic, so simple. It's not that a lot of guys make the mistake of saying, what's the funny , what's the really witty thing to say? What's something really funny? And they put a little too much pressure on themselves to be super funny or flirty or have a good game. And all you really need to do is keep it light about topics that the 2 of you care about or at least that they mentioned on their profile, which in your case was silly topics like pterodactyls and swelling 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 kinda like we were giving each other a sneak preview of what it was gonna be like to meet each other.

Jessamin:
Yeah. I think too, like, you can take dating seriously. You can take other people seriously, women seriously, but you don't want 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 immediately going into setting boundaries or things just aren't flowing in a way that's like, am I actually gonna enjoy being with this person? Then just it helps to take a step back and say 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?

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 struggle 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.

Connell Barrett:
It's what I wrote about in my best selling book, Dating Sucks, But You Don't. And radical authenticity is why Psychology Today called me the best dating coach in America. And now I wanna personally help you attract your dream girlfriend. So go to dating transformation.com and book a free call with me. On our call, I'll tell you how my 1 on 1 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 I hear a lot of women say things like, oh, I'm so tired of being asked how my day is.

Connell Barrett:
How was my weekend? Guys ask too many questions. Any thoughts there? What do women want or not want when they're texting with a guy leading up to a date?

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

Jessamin:
I think you have. I don't remember exactly what they were, but there were a couple of times where you said, like, you know what it was? It was like, if you're gonna cook for me, what would you make? Because I had mentioned something about cooking on my profile. Like, again, just, like, really leaning into, like, what you're able to see about her. You can use those as conversation starters as questions.

Connell Barrett:
Yeah. And you did something that was fantastic that any guy can do. You sent me a photo of yourself taken in a park. I think you were doing some kind of I don't know if it was a sass class, dance class photo, or some other acting class you were taking, but it was you, like, in the middle of some kind of, I don't know. Was it mid was it a medieval outfit or some kind of posed battle? Do you remember what that photo was?

Jessamin:
I do remember that photo. I think that was, like, that was before that was, like, the day of our 3rd date. That was a little bit later. Okay. And, yeah, it was a SaaS class video shoot, and it was the song was, s and m. It was the Rihanna and Britney Spears remix.

Connell Barrett:
Okay.

Jessamin:
And it was just, like, a funny photo that someone had taken while we were filming that was just completely out of context and was completely insane. So I was like, hey. So this is what I did today. See you Right. Yeah. Because you knew I danced and, like, done some sort of whatever. I just thought that one photo was, like, particularly funny.

Connell Barrett:
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 to 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 kinda 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.

Jessamin:
Yeah. Yeah.

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 wanna keep dating me or not?

Jessamin:
It's only been 3 years, and I need a little more time. No. I mean, I knew I was going on a date with a dating coach. That's gonna be weird. Right? I just 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 so. 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.

Connell Barrett:
Right.

Jessamin:
So, yeah, pro tip. Make sure you know what's out there on you about you on the Internet, for you.

Connell Barrett:
For sure.

Jessamin:
Go out there. But I just didn't wanna have any expectations because that just didn't feel fair. I assume there might be some, like, tip like, you know, little, like, games or lines. Same like, I kind of had, like moves. So, like, 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 anything inorganic. It just felt like I was going on a date with a good guy.

Connell Barrett:
Aw. You're schmoopy, by the way.

Jessamin:
Not this argument. Do we do we need to explain schmoopy

Connell Barrett:
and how that backstory is. So you and I are big Seinfeld fans. And there's a famous episode of Seinfeld where Jerry and his TV girlfriend of the week are calling each other schmoopy, and they're just everybody's getting kinda gross kicked out by it. Alright. So what theater do you wanna go to tonight? We got 61st and 3rd or 84th on Broadway. Which one do you wanna go to, Schmoopy?

Jessamin:
You called me Schmoopy. You're Schmoopy. You're Schmoopy. You're Schmoopy.

Connell Barrett:
Alright, Schmoopies. And you and I started doing it as a joke, and it became real.

Jessamin:
Yes. It quickly became unironic.

Connell Barrett:
Which I love. 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. I had 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.

Connell Barrett:
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? Or did it mismatch, or was it a little bit of both?

Jessamin:
It was definitely a match. I think with the league specifically, it's not a particularly detailed profile. Right? It was kinda like you put a few of your interests, you put, like, a tag line, your age, and I think that was kinda it. But I think, you know, with dating 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 expected. I didn't feel like I was being catfished. Oh, no.

Connell Barrett:
I didn't mean that.

Jessamin:
I just meant I

Connell Barrett:
guess I just meant was there anything that 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.

Jessamin:
Yes. The middle school history teacher that I was expecting to be down the gate is definitely there, having drinks.

Connell Barrett:
Remember when I helped you with your times tables

Jessamin:
Yeah.

Connell Barrett:
On our first date?

Jessamin:
So romantic.

Connell Barrett:
So good.

Jessamin:
So normal.

Connell Barrett:
You were what I was expecting and times 10. I thought, here's a really pretty girl. There's a lot of quirky, silly, weird humor on her profile. She's in her mid to late twenties. She's probably, you know, pardon the cliche, a manic pixie dream girl type. She's probably just looking for a fun fling. I'm cool with that if that's where this goes. And then you walk into 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.

Connell Barrett:
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 kinda 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% material. It's like, wow. So, yeah, you met and exceeded my expectations in every way.

Jessamin:
Yeah. I mean, honestly, kinda sorta same. I had no interest really in, like, diving into a relationship, especially coming out of a year and a half long period of isolation. And I was careful. I was a little guarded, I think. I wasn't guarded about, like, how my feelings or anything like that, but I was like, you know, am I just, like, jumping into this? Am I just excited about this because I've been, you know, socially restricting myself for 18 months or, like, is this real? Because I never was my first serious boyfriend. Like, I had been living in New York City for 10 years at that point, and it's, you know, the New York City dating scene. Say what you will about it.

Jessamin:
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 kinda jump from person to person. So kinda the same as what you said. I was like, this will be, I'll at least come out of it with an anecdote that I went on a date with a dating coach that I met on a dating app, at the very least. But it is obviously a lot more than that.

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. If a woman just wants you to continue. She wants to feel like she's meeting the guy from the profile and that everything just, you know, escalates mutually with organically. It's like, oh, wow. It's just like we were 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 should 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.

Connell Barrett:
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?

Jessamin:
I think, you know, it's a trick , 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 in an interview. Yeah. You know, you wanna ask questions, but you don't wanna just ask questions 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 I don't know if it's good to necessarily be scripted, but make sure they're ones that 3 maybe 3 things or topics that you have in mind that, you know, are gonna generate a conversation between 2 of you no matter what her interests are, no matter what her strengths are, what she does for a living. Just things that you have on top ready to go that, you know, will generate conversation. And if they don't generate conversation, then maybe that's a signal.

Connell Barrett:
Right. Yeah. Having a back pocket topic or 2 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 5 straight questions. She probably feels like she's in the backroom at the NYPD with a hot light on. And then remember, oh, tell her that story about the funny thing that happened to you in Paris.

Connell Barrett:
They lost your luggage and blah blah blah. You got on the wrong track . 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 this is 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.

Connell Barrett:
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 x y z. And that's a way to find something to say. Basically, interview yourself.

Jessamin:
Yeah. I like that.

Connell Barrett:
Yeah. Don't fast forward. This is not an ad. It's a free thing that's gonna 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 gonna give you what I call the flirty 30. These are 30 flirty questions to ask women on the apps or on dates 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 gonna make them want to date you.

Connell Barrett:
So to get your copy of the flirty thirty, it's totally free. Just go to dating transformation.com/flirty30. And that's flirty30. 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. Even though I'm a dating coach, in a weird way, when I go on a date or go 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.

Connell Barrett:
Have a clear, simple plan. Be that man with a plan. And then 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 wanna get to know her, and we talked a lot about your family. I remember making a little mental note. Okay. Her mom's name is Liz.

Connell Barrett:
Got it. My 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 of stories about my family too. So we connected about I think we connected about each other's families, among other things.

Jessamin:
Yeah. I mean, very straightforward. You know, I think families, it's not always easy for people to talk about their families.

Connell Barrett:
Right.

Jessamin:
So you can always, you know if you're asking her, like, about her parents, her 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 others we talk about friends, talk about coworkers. I'm sure I talked about, like, my coworkers and bosses a little bit too. Yeah.

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.

Jessamin:
To the other room of the other room.

Connell Barrett:
We went to a bar called The Other Room, and then we went to the other room. And then we went and watched The Room, the movie. No. We didn't.

Jessamin:
No. We didn't.

Connell Barrett:
But our first kiss was in the back room of the other room. And you can answer this by talking about our kiss, or you can just speak more generally about the woman's point of view. But in terms of first kisses, men are so nervous about, oh, I want it to be a good first kiss. I don't wanna get rejected, but I don't wanna 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?

Jessamin:
I mean, honestly, it's a terrible thing. But, like, everyone's different. Every woman is gonna have a different expectation. I know what I'm thinking of, like, our first kiss, maybe some other first kisses that I've had. Not that I've had a million, but, you know, I think I remember with us, it was we were sitting next to each other, and it was just like we'd been talking for at least an hour at that point. Right? We had, like, a drink or 2. No more than 2. And, there was just like a lull in the conversation, and we were looking at each other.

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

Connell Barrett:
Consent is really sexy. I love the idea of saying, hey. I wanna kiss you, or I'm gonna kiss you now as a way to get sort of a soft consent so you can know it's coming. That way you can say, oh, I don't I don't kiss on the first date. Great. That's great. I would much rather a woman say that to me than 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.

Jessamin:
Yeah. So it was sweet.

Connell Barrett:
Yeah. I think what happened on our date is I noticed what I called my clients, and the kiss window opened. There was that lull you mentioned. We vibrated 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, alright. The 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 3 mistakes that a lot of guys make.

Connell Barrett:
But what do you think about asking a woman out for a second date? Do you 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?

Jessamin:
Yeah. That there's that antiquated, like, 3 days rule kind of thing. Wait to wait 3 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 just met this person for the first time. I think doing it at the end of the day, like you said, hey, I had a great time. I'd like to see you again.

Jessamin:
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. Right. 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, Just say, like, hey. I had a great time.

Jessamin:
But yeah. 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.

Connell Barrett:
Right. I remember the morning after our first date, I looked at my phone, and I opened my phone. And it's not that you owed me a text, but I thought, I wonder if she wrote me. I was, 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 brought 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.

Connell Barrett:
You go on a date. You're authentic. You're genuine. You try to give them a good fun experience while being yourself. And then so much of this is just chemistry and letting the chips of chemistry fall where they're gonna fall. But, but, anyway, that was, yeah, the most important first date of my life. So thank you for making that happen.

Jessamin:
Likewise.

Connell Barrett:
Let's finish with the final three tips from you. So you said you've had 2 or 3 thoughts on some things that meant some mistakes that many men make on first dates. Fire away. What do you get?

Jessamin:
Alright. I mean, the 3 I got 3 don'ts. I have a lot of don'ts, but I think there's some

Connell Barrett:
3 is good.

Jessamin:
There are some that are more 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 gonna 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 be rude to anybody, but there is a very specific thing when you were intentionally rude or dismissive to somebody that's serving your food or serving your drinks or just working. There's a power imbalance that's kinda set up there.

Connell Barrett:
Yeah. And

Jessamin:
it just immediately communicates this, like, if someone's gonna be this easily dismissive or rude Yeah. Or a complete stranger, how are they gonna treat somebody that they know?

Connell Barrett:
That's a great tip. A woman notices if you're rude to the hired help.

Jessamin:
Yeah.

Connell Barrett:
Like, I verbally assaulted my butler this morning, and I felt so bad afterwards.

Jessamin:
Yeah. You're a butler. Anyway, that's my favorite choice.

Connell Barrett:
Tip number 2. Don't do this. What's next?

Jessamin:
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 Schmoobi.

Connell Barrett:
Right.

Jessamin:
But things like hon or sweetie or sweetheart or babe, one, it kind of, like, communicates a familiarity that she might not be ready for, especially considering she's just met you. Another thing is, like, like, sweetie, sweetheart, hon. Like, those are things that if I'm getting, like, catcalled on the street, that's what guys call me. Or, like, when I was working as a

Connell Barrett:
Good feedback.

Jessamin:
When I was working as a server a 1000000 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. You're better off just avoiding it, I think.

Connell Barrett:
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. 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.

Connell Barrett:
Okay. Do you have a third one?

Jessamin:
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.

Connell Barrett:
Yeah. We vibed about that. I love hiking.

Jessamin:
Exactly. It was kinda 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 like, you could've if you did like hiking, you could've, like, spun it and it could've, like, generated conversation. Yeah. We connected on, like, hating hiking, whatever.

Connell Barrett:
I hate joggers and hikers. We don't hate them. We just hate what they do.

Jessamin:
Right. It's 2 very different things.

Connell Barrett:
Right.

Jessamin:
But that's different from me saying, like, going on a rant about hiking in nature and how terrible it is. Or, you know, you don't like mushrooms. You can say, like, fun fact, I eat mushrooms. That's something good for me to know. Yeah. I generate some discourse because I do like mushrooms. But for you to then go on a rant about vegetables in general and to go down a hole of vegetables is stupid, like, there's a difference between little things like that and just, like, turning the conversation into this negative.

Connell Barrett:
Right.

Jessamin:
Okay. You know, speech.

Connell Barrett:
So make anything that you don't like. Make it like a glancing blow, not go down a rabbit hole of negativity.

Jessamin:
Right. Make it you know, if it's something interesting, that's one thing. If it's just like a vendetta that you have against vegetables and fungi, that's, you know, that's something that we get to on, like, 5th or 6th date if we're feeling like we're at that place.

Connell Barrett:
So 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 catch phrases is to be an open book, but not an open wound. Don't go off for 5 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.

Connell Barrett:
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.

Jessamin:
For sure.

Connell Barrett:
By the way, if tomorrow's pilot is funny, I'm gonna switch airlines. I'm not gonna

Jessamin:
Listen. You're the one that booked the flight. You knew what you were getting into. I don't wanna cut

Connell Barrett:
It's like we are out of time. We are out of time, sweetie. 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 wanna share with him?

Jessamin:
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 gonna 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 who 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.

Jessamin:
You can't take it personally if she doesn't like who you are.

Connell Barrett:
That's what I loved about you. You were just in the good way weird. Quirky. Very opinionated and just but also sweet and big hearted. 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.

Jessamin:
Thanks. You're so welcome.

Connell Barrett:
Thank you very much for listening. And remember, your dream girlfriend, your shmoopy, she's out there. You're not gonna call her shmoopy, I probably, but she's out there and she already likes you, but she's gonna have to meet the real authentic you. So I'll see you next time.