Connell Barrett [00:00:00]:
like if I could go back and do it over again, sure, I’d make one or two moves, but all I would do is think, how can I make Katie feel comfortable while being me? Welcome back to the How to Get a Girlfriend podcast. I am your host, dating coach Connell Barrett. I’m a dating coach. I help men like you who struggle with flirting know exactly what to say, how to say it, so that you can attract a great girlfriend. And we do this by being authentic, not using sketchy pickup artist tricks. And speaking of sketchy pickup artist tricks and being authentic or inauthentic, today’s episode, I’m going to be really open with you. I want to tell you 5 times I was creepy AF with women. 5 times I creeped women out so that you can avoid making these creepy mistakes that I made in the past.
Connell Barrett [00:00:58]:
My journey with learning how to talk to women, how to approach, how to connect, it goes back 20 years, 21 years actually. So I’ve got a lot of stories. So I’m going to share 5 moments when I creeped women out unintentionally, but it happened. Or I was just weird. And they all have a theme. Every single story I’m about to share with you, I wasn’t really being me. I wasn’t being the true core authentic Connell. I was trying to figure out what works.
Connell Barrett [00:01:33]:
I was trying to do what worked, even if it meant being somebody I wasn’t. And that is a losing proposition. So let’s get to it. Here are some, here are 5 stories I think will be entertaining and also enlightening. So you can learn from my many mistakes because The reason I became a dating coach is I had every problem there was to have. Didn’t know what to say, had approach anxiety, struggled. I just felt like women didn’t want me, so I was trying to figure out what worked. So here we go.
Connell Barrett [00:02:00]:
The first story, I call this my, my be an asshole phase. I worked with a couple different, many different coaches over the years, and I worked with a couple of old school pickup artist guys, and And at one point I was really struggling. I just couldn’t get the kind of approaching success and confidence I wanted. And one of my coaches, who is not an inherently sketchy, creepy person, nevertheless gave me really bad advice. He said, Connell, you’re too nice. Go out for a month and just be a dick. Be a bit of a dick to women. Women like that.
Connell Barrett [00:02:39]:
That kind of made sense. I didn’t like the sound of it, but I said, all right, whatever my coach says, I’m going to do it within reason. So I went out for a couple of weeks, mainly approaching, and I went out one night. I remember these 2 or 3 women were dancing on the dance floor and I said, okay, what is a jerky alpha thing to say? And I said, hey, you, no dancing. This is a no dancing zone. And they looked at me like I was an alien. And a couple nights later, I’m at a different venue and I’m being really a real cocky jerk. Now I have a smartass side.
Connell Barrett [00:03:19]:
I have a cheeky side, but I’m also a pretty big sweetheart, I like to think. Yet I was just going overboard with the cocky badass, you know, fake alpha behavior. And I was just saying jerky things to a group of 3 women. And one of the 3 women, about 5 minutes into my interaction with them, came over and came up from behind me. I was so annoying and so obnoxious that she poured a pitcher of ice water down my shirt, a well-deserved pitcher of ice water down my shirt. And so that was the time I said, you know what, not only does this not work, I felt like I was wearing an ill-fitting suit. I felt like I was not being me. And so the big lesson I learned was being some fake alpha, that’s really creepy to women.
Connell Barrett [00:04:12]:
That’s not attractive. It’s one thing to be confident. It’s one thing to be certain in yourself. But it’s another thing to be an obnoxious jerk. And that’s what I learned. So whoever you are, young woman from the past who poured that ice water down my shirt, I deserved it. Thank you for the lesson. And anyway, I gave up, I gave up the whole fake alpha, be a jerk thing for good at that point.
Connell Barrett [00:04:39]:
And another story for another episode. I had one of the best nights of my life a week later when I just fully leaned into being myself and not putting on that mask. Okay, story number 2, creepy Connell story number 2. I call this the “Does this work?” date. That’s what a woman asked me. So I’m sitting in a lounge and I had a first date with a woman I met from a dating app. I forget her name, but I remember we’re sitting in this cool lounge, low-lit lounge in Hell’s Kitchen neighborhood of Manhattan. And at the time I was really leaning into this idea of, oh, cocky, cocky and funny.
Connell Barrett [00:05:28]:
That’s the secret. Cocky and funny is the magic potion. I don’t know how far back your dating content history goes, but back in the day, there was a guy who went by the name of David DeAngelo, and his whole thing was be cocky funny, cocky funny, be cocky funny. And actually, for me, that was good advice up to a point, because I’m a natural born smartass. I love to bust balls. I love to tease. But I, I didn’t just take a couple pills of cocky funny, I took the whole bottle on this date. And I’m sitting on the date and I’m saying, I don’t know if I can date you.
Connell Barrett [00:06:04]:
You’re not XYZ enough for me. Oh, what you just said didn’t work. You’re gonna have to try harder to impress me. And I just had this veneer of oozing fake cool boredom. Completely fake bullshit. And about 15, 20 minutes into the date, she looked me in the eye and she said, can I ask you a question? Does this work for you, what you’re doing right now? And I said, what do you mean? She said, this, whatever this is, like, what is this? She couldn’t even articulate it. But what she was saying was this fake weird persona you’re wearing. She was probably trying to say, can you just be normal? ‘Can you just be yourself and see if we like each other? I’m on a date with you.
Connell Barrett [00:06:53]:
I matched with you.’ And she called it out. And it was a real killer moment. And the lesson here is don’t perform. Just express yourself. Think expression, genuineness. One of my catchphrases, philosophies I teach my clients is what I’m thinking and feeling, genuinely thinking and feeling, is what I’m saying and doing. And I wasn’t doing that. Quite the opposite.
Connell Barrett [00:07:19]:
I was thinking, what do I have to say and do to get her to like me? And up to that point, being cocky and funny seemed to be the answer. And she basically said, dude, stop performing, just be you. So that was a big moment for me as well. I never made that mistake again. By the way, you might want to avoid these creepy awkward moments, and I hope you do. But if you ever have a date where you just mess up, you, you fuck up, those are some of the best moments in dating that can lead to bigger breakthroughs and better outcomes for you. So don’t be afraid of making mistakes. I don’t want you to be tentative and walking on eggshells around women.
Connell Barrett [00:07:59]:
I don’t want you to creep anybody out. But if you do make a mistake on a date, know that on a date or an interaction with a woman, either you win or you learn. And all of these creepy stories, creepy Connell stories, were moments where I learned. I learned something. And the theme that you might be noticing is not that I was creepy per se, although I was in different ways. What was causing this was every single story I’m sharing with you, I was trying to be somebody I wasn’t. I wasn’t really dating from a place of the real, true, best Connell. I was either trying to be somebody I wasn’t, or I was I had my eye off the ball of, of what does work with women.
Connell Barrett [00:08:44]:
Here’s creepy story number 3, the crass joke. The crass joke. So I was once set up on a double date. A friend of mine at the time, I’ll call him Kevin. Kevin set me up on a double date. It was Kevin, his date, and a lovely woman who was friends with Kevin’s date. And this woman is a woman of, as I recall, Chinese ancestry, very pretty, Chinese American. And we were on a first date at a rooftop bar in New York City at a place called the Jane Hotel.
Connell Barrett [00:09:22]:
I remember it vividly. And the four of us are seated together. And I, again, I was trying so hard to impress be shocking, be, I guess, negging might be the term we would have used back then, that I cracked a terrible racially insensitive or ethnically insensitive joke. I don’t want to say the word here, but suffice it to say, I made a joke and I use an epithet that is commonly used in when talking about people of Asian ancestry. I didn’t call her this word. I cracked a joke. And as the word left my mouth, there was an Arctic silence. 4 of us are sitting there, Kevin, his date, my date, me.
Connell Barrett [00:10:16]:
Oh, hey, Connell being funny. Hahaha. Epithet leaves mouth. Foot enters mouth. There was Arctic silence. Kevin looked at me like, Dude, what the fuck did you just say that for? Awkward silence that seemed to last a month. And of course, and I felt awful the instant the word left my mouth. It felt so awful, not just because I was not being me, which is true, but because I made my date uncomfortable.
Connell Barrett [00:10:48]:
Kevin could not have I’m not saying Kevin’s date dumped him or ghosted him, but it certainly didn’t help him at all. I felt guilty for screwing up my friend’s date. He put his trust in me, setting me up with a woman who his female date knew. I just, I felt awful. I just felt terrible. And so the lesson here, don’t be a dick. There’s a shocking, deep thought. Try not— don’t go for shock, right? Shock is not charm.
Connell Barrett [00:11:26]:
And if I had just been using my head instead of trying filtering the date through the lens of what’s good game, what do the dating experts say? And at the time, everybody was saying, oh, be really shocking. Don’t be boring. Say shocking. Wild things. By the way, people still give this advice, not as much here in 2026 as back when this occurred, but it still happens. You still get that kind of bad advice out there. So the lesson that I learned was trying to shock is not charming. Um, and again, painful lesson, but a lesson that I learned, and I never made that mistake again, at least not the exact kind of mistake.
Connell Barrett [00:12:12]:
And so anyway, Kevin, if you’re out there listening, I’m sorry about that. I really am. Okay. Story number 4, the, the awkward Starbucks note. The I have a crush on you Starbucks note story. Here’s story number 4. This one, this one makes my skin crawl when I think about it. This is a different kind of creepy story.
Connell Barrett [00:12:40]:
Because it wasn’t the kind of creepy where I’m trying to be shocking or polarizing. This is a creepiness that can come out, or an awkwardness that can come out when you’re being really tentative and afraid to make a full move, so you make a half-hearted move. Here’s the story. I used to go to the Starbucks Park Avenue and 30-something here in New York City. And there was a cute lady barista there who I never really talked to her other than ordering the coffee. But she was just dynamite. She had a couple of really cool, edgy, fun tattoos. Like she had tattoos on her right arm and she had this sort of hipster look.
Connell Barrett [00:13:27]:
She had a pierced nose, just a cool, edgy kind of goth chick who at the time maybe was my type. Anyway, I had a crush on her, or at least I thought she was cute. I didn’t even know her name. She didn’t know mine. So I said to myself, all right, here’s what I’ll do. I’m gonna give her a note. So I took my business card. At the time, I worked as a journalist at a golf magazine.
Connell Barrett [00:13:57]:
I took my golf magazine business card, and I wrote like a I have a like, I like you note. I don’t remember what I wrote. What I wrote. I wish I had saved it. But it was something like, hi, I just wanted you to know you’re really cute. And I’ve enjoyed talking to you. And I wanted to know if you would like to have it, you know, have drinks with me. Here’s my number.
Connell Barrett [00:14:23]:
Text me if you, if you want to. And I wrote down my number. Something. It would have been something close to that. And I walked over to her. I was so nervous. I walked up and I just said, hey, this is for you. Handed her the card and I walked away.
Connell Barrett [00:14:39]:
I didn’t just walk away. I, I almost ran away. It’s like, run away, give cute girl card and run away. And I remember looking at my phone that night every 15, 20 minutes. Did she text yet? Did she text yet? Did she text yet? And no, she didn’t. And obviously, there’s no resolution to the story other than I never heard from her. And I since learned from trial and error, but also some of my better coaches, the lesson, the big lesson I learned is that tentative, half-hearted attempts at taking a romantic chance, they just don’t land well with women. It comes off as— women read it as creepy.
Connell Barrett [00:15:34]:
It’s not that you’re being creepy. It’s just that it feels— there’s something off-putting about a guy who doesn’t believe in himself enough to just look the cute barista in the eye and say, hey, by the way, I’m Connell. What’s your name? Nice to meet you. I was curious, would you like to go on a date with me sometime? Maybe get coffee when we’re not— when you’re not working? It’d be nice to get to know you. I just think you’re really charming. Something like that would have been great. I don’t know if it would have worked or not. But avoidance, a half-hearted, non-committed approach, is pretty much a guarantee of a rejection.
Connell Barrett [00:16:11]:
And If you want to go back and check out an episode, I talked about this framework I came up with called the 6 icks. All the ways that a man can be creepy to a woman, they all fall into one of 6 categories. There’s 6 ways to give women the ick. And one of the most common ways to give women the ick that you might have committed in your past, I know I did, is half-hearted attempt at a move. You know, you tentatively go in for the kiss, but then you kiss her cheek, or you want to hold her hand, but you just sort of touch her hand with one finger, which is weird, or you want to approach, but instead of approaching, you just stand near here and near her and stare at her. Those halfhearted moves read as creepy and off-putting to women. That doesn’t mean you’re creepy. It means your energy is being perceived that way.
Connell Barrett [00:17:16]:
And this Starbucks note, mash note, I have a I heart you note is an example of me. You know, it’s all about commitment, right? You commit to the move. So if, if a scale, if, if commitment on a scale of 10 out of 10 would be me just looking her in the eye saying, hey, I like you, you’re charming. Would you like to go on a date with me? That would be a 10 out of 10 commitment. What I did with the business card is a 2 out of 10, and that just does not work with women. It just reads as low in confidence. So anyway, that’s a great lesson for you, I hope, to learn. Whatever move you’re going to make, make it, commit to it all the way.
Connell Barrett [00:18:00]:
Doesn’t mean it’ll always work, but if you do it half-heartedly, it never works. This is true in life beyond dating moves. I think if you go on a job interview, you gotta go, you gotta really commit to the interview. You gotta really commit to saying, I want this job. Here’s why you should hire me. As opposed to, oh, I don’t know, you know, it’d be nice to work here, I guess, but I don’t know, what do you think? One’s committed and one isn’t. So you wanna be fully committed. Or else you’re gonna end up being committed because you’re never gonna find a girlfriend.
Connell Barrett [00:18:36]:
So something I learned from one of my coaches that I still quote him and tell my clients these days is what you think is risky in terms of making a romantic move, if it feels risky, then it’s actually safe and smart ’cause you’re really going for it. But playing it safe is highly risky. I was playing it safe by giving her my Starbucks, or sorry, my Starbucks card, my business card. I was— you play it safe by, by just asking women boring questions when you approach instead of really telling her why you want to talk to her. So what’s risky is safe and what’s safe is risky in terms of making moves. And one of the icks, one of the ways we make women feel icky is to do a half-hearted move like I did. Okay, here’s story number 5. This one, I want to, I want to give the nuance here because this involves sex, or at least the hope of sex.
Connell Barrett [00:19:35]:
I approached a woman once, really pretty brunette. I remember very confident, very my, very much my type, bantery, witty. She was funny. We had a pretty good chemistry. I approached her at a club here in New York City. We exchanged numbers. We texted for a while. And I asked her out.
Connell Barrett [00:19:56]:
She said, instead of, instead of, um, us going out, why don’t I just come over to your place with a bottle of wine? All right, that sounds awesome. I was like, hell yeah, it’s a done deal. Or I thought it might be. And so she comes over. I don’t remember her name, but I’ll call her Katie. That’s not her name, but I’ll call her Katie. So Katie, the cute brunette, comes over with a bottle of wine. And I’m trying to say this the right way because I want to be careful here.
Connell Barrett [00:20:27]:
I want to be honest, but, but nuanced. I overescalated. I moved too quickly to— it’s not that I moved too quickly to try to have sex or to make the physical move, but I made the move. We kissed for a while. Then she pulled back, which is fine. And then I escalated again 10 or 15 minutes later. And then she said, hey, I’m not, you know, let’s take our time. I’m like, cool, no problem.
Connell Barrett [00:20:55]:
And then I escalated again, maybe half hour, hour later. I would say 3 or 4 times over the course of our being together, I quote unquote escalated. And that’s the big insight I’m having here as I’m sort of working this out right now on the on this podcast is I just, I think the word, the very word, the very idea of escalation is creepy. Now call it what you will. Men need to lead the dating dance generally, and women like to follow. Men lead and women follow typically. At the same time, the big lesson for me from this night is Stop focusing on what you want, Connell. Focus on making her feel comfortable and just enjoying you.
Connell Barrett [00:21:44]:
If I hadn’t been so focused on trying to get sex or trying to escalate the way my pickup artist coaches were encouraging me to, I don’t know, maybe we would have hooked up. Maybe by trying less, we would have hooked up, or maybe we wouldn’t have. But I would have felt better about myself. By the way, I’m not some hardcore sex-crazed escalation dude. Again, this is another example of her or of me not really being who I actually am. I was doing what I thought I was supposed to do according to my teachers. It’s not my teacher’s fault. But I remember at one point, Katie just said, “Hey, this is moving kind of fast for me.
Connell Barrett [00:22:26]:
Can we just slow down?” And I said, “Sure, no problem.” And then, you know, I tried 10 or 15 minutes later. And she spent the night. I did stop escalating at some point. We just went to sleep. I remember feeling disappointed because I was so focused on me and, hey, must close the deal. Pretty 20-something woman in my apartment. Got to close that deal, right? That’s what my old coaches used to say. Some of them, basically, it was all about sex.
Connell Barrett [00:22:57]:
And so I feel like if I could go back and do it over again, sure, I’d make 1 or 2 moves. But all I would do is think, how can I make Katie feel comfortable while being me? That’s my biggest lesson is I’m not even going to try. I’m not going to— sure, I’ll make a move or two. She came over with a bottle of wine. Maybe she wants a fun, sexy night, but maybe she just wanted to talk first. Maybe she wanted to really connect as people. I don’t know. And I never really gave us the space to make that happen.
Connell Barrett [00:23:27]:
So that would be an example of me definitely coming off as too sex-focused, too focused on what’s in it for me and trying to get out of this what I want. That’s a big lesson. One of the 6 icks, those 6 things, those 6 categories of creepy behavior in the minds of women, one of them is just being focused on what you get regardless of what she gets. Being more focused on you than being just as focused on her, if not more so than you. So that was my ick that night, that I— the sin of ickiness. And she spent the night. Nothing really— nothing obviously happened sexually. Asked her out again.
Connell Barrett [00:24:11]:
Never heard from her. Clearly, she felt like, yeah, this guy’s just trying too hard. Another guy who just wants to get in my pants is probably how she was thinking. Anyway, who knows? But man, that was a painful but valuable lesson. And Katie, or whatever your name is, if you’re out there, I’m sorry that I was so focused on what Connell wanted that I wasn’t thinking, hey, why don’t we just have a Katie-Connell win-win night and see what happens? Something I learned later with a woman who became my girlfriend, became a love of my life, I remember we didn’t have sex and I didn’t even try really the first time she came over and she spent the night. And it just so happens the next day she, this other woman, basically put the moves on me. Things went from there in a very organic, mutual way. And so who knows, maybe that would have happened with Katie.
Connell Barrett [00:25:13]:
Bottom line is the lesson I want you to know, or the lesson I wish I had known back then but I’ve learned it now, is to know that romantic, mutual romantic attraction starts with comfort. Her comfort is so important, not just because it’s good game, but because it’s just being a good person. It starts with letting her, helping her feel comfortable and never feeling never allowing her to feel pressured. And basically, I was making Katie feel pressured. Okay, those are my 5 moments of Connell’s, quote, creepy past or creepy moments. Bottom line is there’s nothing wrong with making mistakes. That’s part of dating. So keep making moves, keep taking chances.
Connell Barrett [00:26:02]:
At the same time, learn from my mistakes, young man, and because I just want you to succeed. Anyway, by the way, if you have any interest in speaking to me or somebody from my team about how my one-on-one coaching works, you are welcome to go to datingtransformation.com. My website has a button where you can book a call with me or my team and do a consultation, a free consultation call to find out how my coaching works and if we might want to work together. So anyway, you can do that at my website. Datingtransformation.com. All right, until next time.
