How to Get a Girlfriend with Connell Barrett - “His Coke Dealer Came to the Date!” 5 Funny Dating Disasters to Keep YOU from Being Her Horror Story

Episode Date: September 11, 2025

Want to know what NOT to do on a date? Dating coach and bestselling author Connell Barrett shares five cringe-worthy dating disasters. From the investment banker whose cocaine dealer made a surprise appearance, to Connell’s double-decker bus ride straight to the Friend Zone, these cautionary tales will help you avoid becoming her next dating nightmare.Highlights—Err, Lowlights?—of this Episode:05:34: MURDER, SHE WATCHED: Maybe Don’t Show Her Your Student Film Where You “Kill” Someone12:03: BUS RIDE TO THE FRIEND ZONE: Why Grand Gestures Just Don’t Work20:54: AREOLA GRANDE: Because There’s No Good Time to Ask Her Nipple Size25:50: FIRST DATE, LAST RITES: “Here Are Pics from My Grandma’s Funeral. So How About a Second Date?”31:25: COKE-BLOCKED! Meet the Banker Who Brought His Coke Dealer as a Plus-OneBOOK A FREE CONSULTATION WITH CONNELL TO LEARN ABOUT 1-ON-1 COACHING:http://www.DatingTransformation.comEMAIL CONNELL FOR A FREE COPY OF HIS BESTSELLING BOOK, “DATING SUCKS BUT YOU DON’T”: [e-mail]

You know, there's a lot of people who are better wing men than a cocaine dealer. I'm just saying. Welcome back to the How to Get a Girlfriend podcast. I'm your host, Dating Coach Connell Barrett. I am your podcast, dating coach. I'm here to help you flirt with confidence, get more dates, and attract an incredible girlfriend into your life. And do it all by being authentic. No sketchy pickup artist moves needed.

This is about being the best true, real you, what I call being radically authentic. My question for you today is, have you ever had a disastrous first date? I don't mean a disappointing date where it was just okay. There wasn't chemistry and you went your separate ways. That happens often. That's just dating. I'm talking about a full-blown disaster. I'm talking about an iceberg hits the hull of your date and you sink.

Well, I have. And so have many women I've met over the years. And so have a handful of my clients as well. And so I've been a dating coach now for 13 years and I've been studying dating for 20 years. And I've heard some pretty amazing horror stories from women. I've got a few cringe-worthy stories myself. and today I'm going to share five of the most spine-tingling, cringe-inducing first date disasters that I can share with you.

And I also want to give you some lessons that you can use along the way so that if you have made some mistakes like I have or like a couple of the men mentioned in these stories, you can fix them and correct them so that you don't have dates that go down in flames. And if you do have a date that ends in a bad way or ends in a lack of connection, hey, at least you can learn a lesson from it. So let me start with a first date disaster from my own dating history that still gives me chills. I was once on a double date with my good friend Cameron. He had set me up with a lovely, stylish, wonderful woman of Chinese descent.

Beautiful and smart and wonderful to be around. However, this was at a phase in my dating path. before I was a coach, when I was still learning how to be confident as myself, I wasn't really being authentic. I was working with these pickup artists guys. And one of them had said to me, Connell, just be a dick. Just be a bit of a dick with women. Women like bad boys. Don't be too nice. You're too nice. And I said, okay, I guess if you say so, it didn't feel like great advice, but I wanted to do what my coach at the time told me. So I tried to turn up the dial on my jerk side.

And I'm on this double date with Cameron, and it's Cameron and his first date, and maybe their second date, actually. And it's my first date with this woman, who I will call Anne of Chinese descent. And we're on this double date. We're at a fancy lounge in Manhattan, and I'm just trying to say,

I'm trying to say bold out there things just to show her that I'm a bad boy. And I crack a quote unquote joke that included an epithet for Asians. And it was so unfunny. I don't even remember the joke. I just remembered I used a term that is essentially an epithet for Asian people. I was just trying to be funny. and my unfunny joke was meant by Arctic silence and dropped jaws. And it was, oh, I felt awful instantly in the moment.

I had insulted my date. I had said this epithet, and there was like five seconds of silence. It may as well have been five hours. And I embarrassed myself. I felt not only terrible for Anne and how I must have made her feel, but I felt like, oh my God, Cameron had set me up with her. I made him look like an idiot. I made him look bad in front of his date.

It was a quadruple-decker shit sandwich. And I remember texting him that night. I'm so sorry, man. I am so sorry. And I apologized to Ann as well later in the night. Bottom line is that I ruined the date. My main takeaway from that moment was don't try to be somebody or not just to try to create attraction with a woman.

it's not worth it. It didn't work. And even if it had worked, it would be had worked. It would have been such a terrible karma to bring to a date. And so that was actually a turning point moment for me. I remember thinking, no more. I'm not going to be somebody I'm not. I'm really going to lean into being the nice, good, kind guy. A bit of a smart ass at times, sure, but the nice guy that my mom and dad raised. I'm not going to crack jokes. I'm certainly not going to crack race-based jokes. And I'm just going to really express my true self. So even though that story still makes me wince, in a way I'm glad it happened because it allowed me to sort of realize, okay, no more pretending to be somebody I'm not. I'm going to show women the true best, kind, sweet, nice Connell.

And that guy is so much more attractive to women than fake, cocky, nagging, bad boy Connell was. anyway so let me share five more stories with you and i want you to stick around until the end of the episode because at the end i'm going to share with you a story about a guy who made a mistake so outrageous i'll just tell you what it was he brought his cocaine dealer to the date with him i kid you not i know a guy or i know of a guy who brought his coke dealer with him to the date and you're going to shake your head in disbelief when you hear that story at the very end. So stick around for that. Okay, let's go.

Here are five stories. The first one, dating disaster story, number one, I'm calling this story, murder she watched. Murder she watched. Here's the disaster story. A client of mine, I'll call him Raymond. He was a film student at a pretty notable film school out west. And he was on a first date with a woman named Sarah, and they were having a really good conversation.

They were at a wine and tapas bar. And this actually, as bad as this is, this isn't the disaster part of the date. He had forgot some medicine of his. And he started having a little bit of a panic attack, a little bit of an anxiety issue and getting dizzy. And he had forgotten his pills. And he starts to shake a little bit and feel out of him. it almost faint and sarah god bless her she takes his hand she's like patting his hand saying hey are you

okay are you all right and he explains to her oh my god i i left my my medicine at home as bad as that might sound to you that's not the disaster part so they end up going leaving the wine bar going to get his medicine and this was not a move by by the way with him to get her at his place this is just it just happened this way so they go back to his apartment they find his medicine. He takes a couple of pills of whatever his prescription was. And he starts to feel better.

Okay. And now they're at his place. So he says, well, while we're here, he decides to quote unquote impress her by screening a short film that he had written, directed, and starred in, a student film. And that sounds good on paper, right?

But here's the thing. in this movie that he decides to show Sarah, now that he's feeling better, in this movie, he plays the lead character, and in the movie, the character murders his girlfriend in the film. So there is Raymond and Sarah sitting on a couch watching Raymond on this movie screen murdering somebody. Sarah is already giving him a lot of leeway with the whole, issue with his anxiety medication, right?

But she's watching in stunned silence as he's, his character is murdering his girlfriend. Now, I don't know what the tenor was of the movie, if it was like a, it was probably like a Tarantino type of movie, pretty violent. And it got awkward. She got really quiet and basically said, hey, I don't really feel comfortable. I really like to go home now. And she called an Uber and she excused herself politely, but she said, I just need to leave now. And they did talk a couple more times, but they never went out again.

She basically dropped, lowered the boom and said, hey, I just, I'm not feeling like you and I are a good fit. So here's the fatal mistake, no pun intended. Here's the fatal mistake that Raymond made is he was trying way. too hard to impress her with a risky creative showcase in this case. And there's nothing wrong with trying to impress a woman with something with a piece of art or a piece of work that you put out into the world. But you do want to think about this important lesson. Here's the biggest lesson that I gave Raymond after he told me this story. The big lesson is whenever you're on a date with a woman, first date especially, when she's still getting to know you and just figuring out

how she feels around you, you want to filter the moves you make, the things you do through the lens of, will this make her feel comfortable or might this push her away? It is so important to think about how your behavior is making a woman feel. And he had lost sight of that because he was thinking, I want to impress her and show my student film. Awesome. That's a good intention. It's a good, bold intention. But he lost sight of, gee, might it make her feel uncomfortable to watch me as a character murdering somebody in a movie? Yeah, maybe not the best thing to make her feel comfortable. So that's the big lesson for Raymond and yourself. Now, your move, your dating move going forward

it's totally okay to share something that you're proud of that highlights your strengths in a positive intriguing way maybe it's a song that you love or a song that you wrote maybe it's a piece of art you created on my first date with my now girlfriend jess i gave her a copy of my book because my book had just come out and i was really proud of it and i wanted to be really open and genuine

and basically allow her to see who i am however you want to think about what side of yourself you're showing to a woman and you want to ask yourself is this going to make her feel comfortable or might this make her feel uncomfortable and you to the best of your ability you always want to try to make a woman feel comfortable around you it's not just good dating strategy it's also just good human strategy it's just good to make people feel comfortable or try to. So anyway, that's your tip there. Your winning dating tip is always filter everything through the lens of, am I going to make her feel comfortable or might this push her away? And always err on the side of making that woman feel comfortable.

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 it. 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 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 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. Okay, here is dating disaster story number two. Bus ride to the friend zone. This is my story. Oh boy, this one's on me.

So many years ago, I had a crush on a woman named Laura. I was so into Laura. She looked like Britney Spears, but she had Tina Fey's brain and wit. My wow girl. My dream girl. Beauty brains. I was so smith. with Laura. I was smith-faced. I was basically writing Laura plus Connell inside of a giant

heart on my trapper keeper. I was so smitten. So we had a first date and it went pretty good. Not great, but pretty good. Good enough. Now we had a second date. And I thought, okay, I'm really going to knock her socks off. Now, she'd give me the heads up a few days earlier. We were talking about second date plans. And she said, yeah, let's just keep it pretty chill. You know, maybe watch a movie or something. She had said, let's keep it pretty chill.

But I decided that I wanted our first, I'm sorry, our second date to be epic. So I planned not one, not two, but three elaborate dates. I should say elaborate events all in one date. Here was the plan. Saturday night in New York City. First stop, we meet up at the Empire State Building. I went and bought tickets in advance. Second step, after we go to the top of the Empire State Building together,

then we're going to get on a double-decker bus tour of Manhattan, and we're going to pretend to be tourists from Iowa. I even went and bought buttons that said, I heart New York. And I think I bought us a couple of T-shirts to show that we were like pretending to be Midwestern transplants in New York. That was going to be part two, phase two of a three-phase date. And phase three was I had made us a reservation for to have at a ice cream, a fancy ice cream dessert. place called Serendipity 3, a place where they have these things called frozen hot chocolate. I'm not sure if it's still there or not, but it was many, many years ago. So this

was my big plan, elaborate three-part date. Because in my mind, that's what they did in the movies, right? That's what they did in all those 80s movies, rom-coms. Big grand gestures is what gets a woman into you. And come to think of it. This was exactly 12. 20 years ago. This was in 2005. Anyway, so it was 2005 just to date things. Okay. So the moment the bus pulls up, Laura's arrived, by the way. And because I had said to her, hey, I've got a surprise for us. Meet me at 34th and 5th, 34th Street and 5th Avenue, Empire State Building. She arrives and I sprang the big date on her, the big date idea. And she's like, I don't want to, I don't want to wait in that line, Empire State Building line.

I don't want to do that. And I said, oh, okay. Well, in that case, let's go right to part two. And then I explain the date idea. And this double-decker New York City tourism bus pulls up right on cue. And I lay out my big tourist roleplay date idea to her. And she says, I don't want to get on that thing. I don't want to do that.

I just wanted to watch a movie. What's with all the stuff you've planned? And oh, my God, I felt so stupid. I felt so rejected. I felt like, wow, this is not going well. So we just go right to phase three. And we go and we have the ice cream, frozen hot chocolate. And the date goes okay, but really it was pretty awkward the whole time.

Because, you know, she was obviously disappointed that I had not listened to her, that I had gone off and planned all these things. At the time, I was annoyed at her. I was annoyed at her thinking, oh my gosh, how could she take for granted all the effort I put into this? What a waste of money. I bought Empire State tickets. I bought tickets for this bus. I bought all these trinkets. And man, this date is not going well. And it kind of fizzled out. We had a awkward couple of chocolatey drinks at this ice cream place, and that was pretty much the end of it for us at that point friend's own city baby she clearly did not want to see me again she i should i should say she made that clear soon thereafter and a little time passed and i realized oh my god i made a huge

mistake i overplanned i i tried to make a grand gesture i overplanned and the biggest mistake i made is i just didn't listen to her she even said hey why don't we do something chill why don't we just watch a movie she was big into battle star galactic at the tv show that was back when i think battle star was a big show she's like why don't we just watch um some battle star do something chill i ignored that think about how stupid i was she was basically saying why don't we just watch a movie which is probably code for and then we can hook up but no i have to plan a three-phase date and didn't listen to her. And not only did I not listen to her, but also when you plan a big elaborate date, and this is the big lesson I want to share for you, first dates

are in this case a second date. Those early dates are not about impressing her with a big spectacle. They're about creating a fun, playful connection, vibe, and creating like a fun space for two people to connect. I wasn't, I hadn't gotten that yet because I was brand new to dating. I thought, oh, I'll just plan something amazing. The bigger I plan, the more she'll be attracted to me, right? Wrong. Totally wrong. So that was a huge lesson for me. Also, any guy who's got to try that hard to impress a woman that sends the worst message to her. It says to her, I'm not enough. I'm not enough in who I am. So I'm going to have to impress you and liking me. I think that's really why she friends owned me. So don't make my mistake. Your

dating move to learn from my mistake is keep first dates. In this case, it was a second date. But those first one, two or three dates, keep things easy, low key. Think it could be cocktails. It could be, it could be going to, you know, do a fun, a fun event. a fun little gimmick like going on a fun bus ride i'm not saying that's a bad idea i'm saying that's not what laura wanted and she told me what she wanted and i ignored her so i think your winning dating move is listen to your date plan the date with her keep her up to date on what you want to do and just make sure you're on the same page because a really great date is is about her experience with you, not your grand gestures in production value.

Okay, dating disaster number three. This one's called Areola Grande. Areola Grande. So here's the disaster story. I have met a lot of women over the years, and one of my favorite questions to ask a woman on a date is I'll say, hey, you must have some really crazy first date horror stories, right? like just got clueless guys and a woman i asked this i asked this of relayed this story to me one woman told me about a date we're out of nowhere the guy sits down they're five 10 minutes

into the date they're literally still just sip taking the first few sips of their beverage and he says to her so what shape are your nipples and she says what he says what he says i'm curious what shape are your nipples? What size? Specifically, I want to know, what size are your ariolas? And he went on to tell her that he wanted a woman who had very specific ariola shapes. He wanted, or size, he wanted larger ariolas, silver dollars or larger. She was shocked.

She ended up getting through one drawing. drink and made a reason why she had to leave. And that was it for Mr. Ariola Grande. And she never spoke to him again, obviously. So what is the fatal mistake that this guy made? Well, he sexualized her way, way, way, way too soon. Let me rephrase that. You should never sexualize a woman, but you should not sexualize the language, the atmosphere, or try to.

way too soon. That comes off as objectification. He objectified her. Very bad. He sexualized her. Very bad. Did it way too soon. Very vulgar. And just, frankly, not even vulgar. It's not even just about vulgar. It's just weird. Weird. A lot of guys ask me, Connell, I just don't want to be a weird, creepy guy. Well, then don't mention her nipple size in the first 15 minutes of a date. There's one tip for that guy. So, yeah, so you don't want to be vulgar or you just don't want to say completely bizarre, odd things so early. Don't forget, first dates are about playfulness, of a light playful connection. That's the ideal win-win here, is you and she get to know each other in a light, playful way. and you don't want to bring up explicit sexual questions or sexual topics in some kind of crow-barred way. Now, it is possible to introduce sex and sexual topics in a more measured, gradual way,

but first we just want to spend the first hour of a date getting comfortable in each other's shoes. goes back to that earlier tip I suggested or shared, which is, which is filter everything through the lens of, is this going to make her feel comfortable or push her away? And Ariel Grande, certainly he didn't get that. So your winning move going forward is, yeah, keep things very light. Don't even worry about. Don't compliment her body parts. Don't talk about her body parts.

don't mention her body parts in any explicit way other than to say, wow, you look fantastic. I love that dress you chose. You have great style. That's fine. That's actually very good. But you want to avoid talking about body parts and allow, don't forget, a lot of men, not a lot, but the occasional man will try to force sexual chemistry. force it or push too hard for it to happen by talking about sexual topics or complimenting her body parts. And that's not really the way to create romantic chemistry on a date. The way to do that is to

allow the two of you to organically start to connect as people first and foremost. And then you can start dialing up some kind of what I call man to woman communication on a date. but doing it about her, commenting and judging her and screening her on this shape and size of her areola is not the right way to do it. Okay, here is dating disaster story number four. This one's called first date, last rites. Now, this disaster story comes from my friend Emily. I put out an email to a few female friends asking for their first date horror stories, and this one came back as worth sharing. with you. Here's what Emily wrote me. Hey, Connell. Okay, I got a story for you. A couple of

years ago, I matched with this guy on Hinge. Now, on paper, he seemed great. He's really seemed smart, funny, he had a good job. So we met up at a little wine bar on the west side, upper west side. The second we sat down, Emily continues, he brought up his grandmother, who had just passed away a few weeks earlier. That's totally understandable. Grief is difficult. We all lose grandparents, but here's the thing. He talked about her nonstop for an hour in 45 minutes, four exclamation points from Emily. I'm not exaggerating, she says. The conversation pretty much never left that topic, and finally I told him I had to go home. I ended the date. At one point, she writes, he started crying right there at the table, calling her.

calling her, calling his grandma, quote, Nana Bird, which was his nickname for her because she loved bird watching. Then he pulls out his phone and shows me a photo of her sitting on her favorite park bench. Then he pulls out other photos from the funeral and shows all the photos of his Nana Bird with her different birds. I didn't know what to do. I felt for him, but it wasn't a date anymore. I felt I was, I had accidentally wandered into a family memorial. Okay.

I'm not laughing at this poor guy. We've all lost parents and grandparents. But, yeah, fatal mistake he made, no pun intended with fatal, was letting grief dominate the date instead of being really present in the moment with her and bringing some positivity. So here's a big lesson for you, the listener. Now, I know you've never said to a woman opened up about the death of a grandparent for an hour and a half, I'm sure.

But a lot of guys say to me, Conall, can you clarify what you mean by being authentic? What if I'm authentically angry? What if I'm authentically depressed? What if I'm authentically this or that? Can I bring different energy to a date and still have my authentic? self be attractive to women. And I'll say, well, no, not every energy is attractive. I don't think anger. I don't think negativity is truly authentic. My metaphor I like to use with authenticity is be an open book, not an open wound. This man was going through some grief. He was clearly

very close to his grandma and he was still grieving. He should not have been on the date. So if you decide to go on a date, make sure you are ready to bring some positivity. Be an open book, not an open wound. If your dog is sick, bottle that up and bring some positivity. If your boss was a jerk to you that day and you're all upset about being passed over for the promotion, don't bring that up on the date. She doesn't give a damn. She's there to have fun. She's there to laugh. She's there to connect with you. Authenticity is essential, but a first date should be about positivity, playfulness, presence, and two people getting to know each other in that light, authentic way. Heavy duty stories belong to a later part of dating, but this is long after intimacy has been established. So no disrespect. to this fellow. He was going through something difficult, but he should not have even been on that date. He brought an open wound. He wasn't an open book. I really like that metaphor, an open book. Why open book? An open book. A book is edited. A book is filtered through the lens of what value

can this author bring to the reader. So that's why I like that metaphor of being an open book, not an open wound. Now, your winning dating move is, yes, share yourself. But you want to share yourself in a way that is designed or intended to make her feel good. Or at least to make her see a side of you that is positive, empowering, upbeat, as opposed to grieving over a lost family member. So you want to share funny stories. you want to share your passions, you want to share things about you that light you up.

So you want to save deep grief or pain, for trusted friends, or for the later stages of a relationship, don't bring that to a first date. Okay, let's go with story number five. Here we go. This one is called Coke and Dagger. I love this. Coke and Dagger. So here's your dating disaster story.

My friend Megan had a first date with a seemingly very successful investment banker. They met at a nice cocktail bar. And about 45 minutes in, a guy shows up wearing sunglasses, a baseball cap, and like a dark sweatshirt. And he sort of walks up to the tent, sort of. He walks up to the table, and he hands Megan's date an envelope, like a big, thick white envelope, and Megan thought this might be some kind of a weird prank until he takes the envelope, he thanks the guy, the guy shuffles off, says a quick hello, and Megan realizes what was in the envelope, which was, yes, cocaine.

or it was white powder that he said was cocaine and it was inside apparently it was inside like a plastic zip lock that was tucked into this this big white envelope and he basically he offered her some he said hey do you want to go into the bathroom

and do a little couple lines she said thanks but no thanks I'm good and yeah she made a mental note get out of here as quickly as possible. And she ended the date soon thereafter. Now, she didn't leave without telling him. She came up with an excuse because she didn't want some Coke head getting mad at her.

So the fatal mistake this guy made is obviously flaunting a dangerous red flag in front of his date, actually having his Coke dealer show up to make a delivery, not the best move. you know there's a lot of people who are better wing men than a cocaine dealer i'm just saying so here's the lesson the lesson again i guess we're noticing a theme here which is that first dates should be about making a woman feel safe and at ease and comfortable and sharing anything from your life that signals chaos to her or recklessness That is an instant deal breaker, an automatic deal breaker. So for you, your winning dating move, of course, you're not going to have your Coke dealer show up on a date.

That's an extraordinary, vivid, bizarre, crazy, exaggerated type of story. I mean, it's true story according to her, but it's something that you certainly aren't having going on in your life. But again, you want to filter things through the lens of, I want to be myself. I want you to share vulnerable truths about yourself. But if one of those vulnerable truths is a bad habit, keep that to yourself. Don't mention your, I don't know, your financial struggles from back in the day. Or in this case, this guy was talk about being authentic. He was showing his true self.

but he was revealing something that would say to her, this guy is not ready for a relationship. This guy is not boyfriend material because he has apparently a drug habit, problem slash habit. So you want to remind yourself, how can I show her I'm a grounded, trustworthy guy, but in a way that is real and genuine. Being able to convey that side of you is what makes her want to see you again.

So your winning move is to be vulnerable, but be vulnerable in a way that might show, quote, warts and all, but don't show parts of your life that are in chaos. If they are in chaos, and if they are in chaos, you want to get that shit handled, whatever that might be. Right. So for example, again, the cocaine example is a crazy out of this world story. At the same time, you always want to be putting your best foot forward. You want to put your best foot forward. And so you want to make sure that ideally you have any sort of life issues handled like drinking too much or drug use or if your finances are in a bad place or your career, if you're really struggling in your career, get these areas

of your life handled first, then go out into the dating world. Yeah. Anyway, that's the end of today's episode. Again, thank you so much for listening. And don't forget, your dream girlfriend, she is out there and she's going to love you, but she's going to have to meet the real authentic you. So go out there, be authentic, and catch you next time.