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)
Tue, 18 Feb 2025
So, you finally get a first date with a smart, attractive woman… only for her to say, “no thanks” to a second. It’s discouraging. Let’s fix that! After last week’s special 4-part Valentine’s Day series on meeting and attracting women IRL, you don’t want to put in all that effort only to hit a first-date roadblock. Connell and his girlfriend, Jess, break down what made their first date a fun, flirty success—and what you can do to get a LOT more second dates. (Originally aired in November.)In this episode, Connell and Jess discuss:3:20: The Profile Photos that Made Her Swipe Right13:05: The Right Way to Text a Woman Before a First Date18:20: Jess’s Top First-Date Tip29:00: What to Talk About So You Never Run Out of Things to Say30:48: How to Avoid Interview Mode and Not Get Friend-Zoned34:15: Jess Called this First Kiss Move “Suave”—You Need to Know It!37:18: How to Ask Women Out for a Second Date39:21: Her Top 3 First-Date Mistakes that Guys Make45:00: Why Women Want Authentic Men, Not Toxic “Alpha Males”Sick of hearing “Let’s just be friends”?Learn how to get more second dates, starting now.BOOK A CONSULTATION CALL TODAY & GET A FREE COPY OF CONNELL’S BESTSELLING DATING GUIDE!Frustrated with dating? Ready to find an amazing girlfriend? Book a FREE call with Connell to see if his coaching is right for you. If you book your call today, you’ll get a free copy of his No. 1 Amazon bestselling book, “Dating Sucks but You Don’t.” Spots are limited, and this deal expires today—don’t miss out. Use this link to book your free call now to see if coaching is right for you.www.datingtransformation.com
Chapter 1: What makes a dating profile stand out?
She's the most important person in my life, and I wanted to have her on to talk about, well, how I got her to be my girlfriend. Welcome to the podcast, Jessamyn.
Hi. Thanks for having me.
I was about to start chatting with you and all of a sudden I had flashbacks because we've never done a podcast together. And I'm like, wow, this is kind of like a new first date.
It definitely feels like it's the first date all over again.
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. So stick around until the very end.
Okay, so thank you for being here, Shmoopy. By the way, Shmoopy is our kind of pet name for each other. So it's annoying, but it's us being cute.
It's annoying, but it's us.
Trigger warning for people who don't like Shmoopy.
Who don't like Seinfeld.
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Chapter 2: How did Connell and Jessamyn start their relationship?
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. He 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 it 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 um yeah it was mostly curiosity but good curiosity maybe a little curiosity
So one of the things I teach my clients, and this is in my book too, is think of your online dating profile as a piece of marketing, and you want to stand out and be different in a positive way. So I stood out to you because of the dating coach angle. And in terms of the photos, do you remember anything about the photos that made you say, okay, I like what that photo is saying about him?
What do you remember about the photos?
I remember they were mostly, they were good photos. They were, I don't, I couldn't tell if they were necessarily professional photos. I think a couple of them were, but they were like well-framed. 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, um, Or they just take a bunch of selfies. Like there needs to be some sort of effort put into it. And there was obviously some effort in there. And then you also had a photo.
Your head was cut off, which was a little concerning. But it was like the last one. And I'd seen your face. I didn't care. But it was you in the policeman's Halloween costume.
Right. I was a hot cop. Sergeant Dick Utopia. My alter ego. Halloween photo. Yeah.
So it was a good variety. You weren't taking yourself too seriously, but you were taking dating pretty seriously.
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Chapter 3: What texting strategies lead to successful dates?
Right. It's so easy to look like every other guy. Yeah. Or to get lost in the shuffle of so many people you're swiping on left or right. And so you were attracted or at least hooked by the idea of me being a dating coach.
you listening to this episode, you're obviously not a dating coach, but a thought I would have for you is ask yourself, what is something that is completely singular about me and unique that I can either show or mention that's different but cool, different but interesting, or super nerdy? Because by getting specific about what makes you unique,
you might jump out at a woman to say, wow, I've never seen that before. That's really interesting. For example, I have a former client named Brian who, when I was coaching him, I said, what's something really unusual about you? What is something completely unique? He said, I like really extreme things. I said, what do you mean? He said, oh, I like cold plunges.
He does that, I forget what it's called, like the polar swim where you swim five miles in frozen cold water in the winter. He does all these extreme things. So I said, yeah, let's play that up. Because every other guy is talking about hiking. And as you and I know, hiking sucks.
We'll get into that.
Yeah. But if you're into extreme things, play that up. Or if you are the expert in, I don't know, iced coffee, and if you're a nerd about something, lean into it. That could be that one unique thing that's your version of being a dating coach. Because you just don't want to blend in and seem like everybody else.
Yeah. And I think that's kind of the beauty of online dating.
I think it's, 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 being people in public too and organically through friends, whatever, but Um, 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.
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Chapter 4: What are common texting mistakes men make?
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 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. You can ask her what her favorite TV show is, and she might tell you, and then you can say, oh, well, my favorite show is XYZ. And that's a way to find something to say.
Basically, interview yourself.
Yeah, I like that.
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 when you approach a
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. To get your copy of the Flirty 30, it's totally free. Just go to datingtransformation.com slash flirty30. That's F-L-I-R-T-Y 3-0. Datingtransformation.com slash 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 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.
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Chapter 5: How can photos enhance your dating profile and conversations?
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 family. I remember making a little mental note.
OK, 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. Uh, 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.
Yeah. I mean, very straightforward. Um, yeah, I think, I think families, it's not always easy for people to talk about their families.
Right.
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 or maybe tension there or whatever the case. There's always other, you talk about friends, talk about coworkers. I'm sure I talked about like my coworkers and bosses a little bit too. Yeah. Yeah.
So we had a really good couple drinks at this bar in New York City. And then we went to the back room. We went to a different part of the bar just to change the scene.
We went to the other room of the other room.
We were in a bar called the other room.
Right.
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Chapter 6: How did Connell perform on their first date?
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?
Hmm. I mean, honestly, it's, it's a terrible thing, but like everyone's different. Every woman is going to have a different expectation. I know with, I'm thinking of like our first kiss, maybe some other first kisses that I've had, not that I've had a million, but you know, I think
I remember with us, it was, we were sitting next to each other and there was just like, we've been talking for at least an hour at that point. Right. We'd have like a drink or two, no more than two.
And, um, 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 has said, like, I'm going to kiss you now. And I feel like out of context it sounds super weird, but it definitely works. It's the moments, right, if you have that same kind of will in the conversation. Yeah. You can also ask, too. Consent is sexy. You can always ask.
Yeah, consent is really sexy. I love the idea of saying, hey, I want to kiss you, or I'm going to kiss you now, as a way to get sort of a soft consent so you can know it's coming. That way you can say, oh, I don't kiss on the first date. Great. That's great. I would much rather a woman said that to me. Then I just lurch out of nowhere and go to kiss her and she's blah.
So I like that move that guy used saying, I'm going to kiss you now.
Yeah.
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 got to walk the walk.
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