How to Get a Girlfriend with Connell Barrett
‘I Sent a Voice Note About Her Boobs…to HER! Can I Recover?’ Dating Coach Connell Barrett Breaks It Down
18 Dec 2025
Chapter 1: What embarrassing dating disaster does the episode start with?
When you make a mistake on a date, it's not so much the mistake, but how you bounce back from it that women are going to notice. How to Get a Girlfriend podcast. I'm your host, dating coach Connell Barrett, here to help you attract your dream girlfriend by being authentic. No sketchy pickup artist moves needed. And today we're going to do another installment of Ask the Dating Coach.
Chapter 2: How can a dating disaster potentially lead to attraction?
Ask Coach Connell.
Chapter 3: What is the 3-step framework for recovering from dating mistakes?
I get a lot of great questions from guys and my clients. But I hear from you on Instagram. I hear from you on my email. If you have any dating questions, I will answer them as best I can when I get them. You can email me at connell at datingtransformation.com. That's C-O-N-N-E-L-L. Or you can also find me on Instagram at datingtransformation. All right, let's get to it.
And I have a doozy of a question to start with today. This comes to me from a man who I dubbed Connell.
Chapter 4: What are the do's and don'ts of sexting?
vexed by voice note here's his question hey connell i just had a great first date with a total knockout and i was so excited about my date that i recorded an audio message for my trainer that said bro her boobs are ridiculous i just want to nom nom nom on them like a toddler But then I accidentally sent a voice note to her. I am mortified. How do I apologize and not lose her?
I would still like to get a second date with her if I can. Signed, his name.
Chapter 5: How many texts should you send before asking for a date?
And then I'm calling him vexed by voice note. Oh, man. So you know how you can unsend a text message? I think Apple needs to add a reclaim your dignity button to the iPhone. That might help you, vexed. But the good news is sometimes a fuck up is a gift. Sometimes a goof turns into a gift. Here's a quick story from my dating past.
Chapter 6: How can humor help in apologizing after a dating blunder?
I was once on a first date, a sushi date, with an incredible, attractive, witty, stylish, blonde woman named Laura. And I was so into Laura. This was our second date, I believe. And she was way out of my league at the time, so I thought. So for me, the stakes were high. So the sushi date starts well. I excuse myself to the men's room.
We're sitting in these booths, by the way, the sushi place here in Manhattan. And I came back from the men's room, and I returned to what I thought was our booth. I slide in. Because there's a pretty blonde woman sitting in that booth. And I say, hey, I'm back, hotness. Only to look up and see a baffled blonde sitting across from me who is not my date.
I had sat in the wrong booth, catty corner to the actual booth with Laura. And I just saw, oh, pretty blonde. I'll sit there. And my face turns red. And she's looking baffled. And I'm embarrassed. And then seconds later, her boyfriend appears at the booth. He probably just got back from the bar. And he gives me a look that says, what the fuck? What's going on here? So I apologized.
I said, oh, my God, I'm so sorry. I sat in the wrong booth. And I go back. Meanwhile, Laura is at our actual table, gleefully watching this disaster movie unfold. She may as well have been sitting there eating popcorn in the front row of a movie. She loved it. And Laura has a very sardonic sense of humor, my memory of her anyway. And I got back, and she was laughing.
She's like, you're as smooth as sandpaper, Connell. She was laughing, and I just kind of slunk into the correct booth. Now, to my surprise, that screw up didn't sink me with her. I thought it might, but actually it didn't hurt me. In fact, I think it helped me. I know it helped me because about a date later, we really connected. We became intimate.
And she later confessed to me that that moment she said to me, and I quote, that actually made me want you. That was when I really wanted you. Can you imagine? It was only when I screwed up and fucked up that Laura got extra attracted to me. And I said, why? What are you talking about? She said, well, the way you owned it and laughed it off, it was so impressive.
You were like the most confident guy in the room. And We dated for several months. We didn't become boyfriend-girlfriend. We weren't really a good long-term romantic fit. But we did connect in a way that I feel good about, and I think she did as well. So back to you, dear vexed letter writer.
So your embarrassing voice note is not the issue here, or not something that you really need to think about or worry about. How you handle it from here is everything. So here's your three-step plan to give you a really good chance of salvaging it with this woman. Tip number one is remember, it's not the mistake, it's the recovery.
When you make a mistake on a date, it's not so much the mistake, but how you bounce back from it that women are going to notice. Keep in mind, your audio note did not say anything vulgar. Let me go back and restate the audio note. Again, here's what his voice note said to her. Bro, her boobs are ridiculous. I just want to nom, nom, nom on them like a toddler. Nom, nom, nom, nom, nom.
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Chapter 7: What are the key elements to successful sexting?
That's okay. That's very human. It's very normal. Can you imagine the kinds of conversations that women have about us? Everything from G-rated to R-rated to X-rated. It is okay. And what I want you to know is that women don't judge men like us for having sexual desire, at least not negatively judge us. It's called being human. Women judge men based on how that desire is expressed.
And yours came off as dorky, almost innocent. I mean, nom, nom, nom. Dude, you sounded less like a creep and more like Cookie Monster let loose in a bakery. Okay, tip number two to bounce back from this and keep her interested and get a second date. Own it with humor and then shut up. Own it with humor, but then shut up about it. Don't grovel. Just own the mistake with good humor.
A man who can laugh at himself and take responsibility is so attractive to women. So my advice is send her a self-effacing, lighthearted message. And it's really important that in your message, you mention that you like her for more than her body. The only thing about this message that could trip you up, Bext, is that it was about her breasts, her boobs, nom, nom, nom. And that's okay.
Beautiful, attractive women pretty much know they're physically attractive, but women generally don't want to be objectified. They don't want to be seen as just their body. And it's, it's fine to be attracted to somebody, but you don't want a person, a woman to feel reduced to her body parts. So you want to write something like this. Here's your message. I'll give it to you.
Word for word, center this text quote, End quote. Then, stop. Send it and stop. Don't follow up. Hey, did you get my text?
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Chapter 8: How do you know when to ask a woman out on a date?
Just circling back. Don't send a PowerPoint, a seven-part PowerPoint explaining yourself. Just send one text message and see how or if she replies. And your third tip is cheer up. This may actually help you with her. I really mean that. I don't think it's going to hurt you. If anything, it could help you. So hear me out on this.
The accidental audio that you sent, it shows her that you're genuinely into her. You're not trying to seem mysterious or feign indifference. And those are two tactics, two ploys that women just hate. They hate that. Women hate to be objectified just for their attractive bodies. They hate a guy, you know, hate the guy, but they hate it when a guy tries to be somebody he's not.
or tries to play it cool, make her wonder if I like her, fuck that. My number one dating rule, other than be authentic, my number one flirting rule is clarity. Be clear. I never teach my clients to pretend to be mysterious. I wouldn't know the first thing about pretending to be somebody I'm not. I'm not mysterious. You're not mysterious. If you're James Bond, fine. Maybe he's mysterious.
But my first rule of showing romantic interest is clarity. Let her know that you like her. Clear romantic interest. And brother, this woman knows. Nom, nom, nom. And by the way, dumb dating mistakes like this, they're awkward. But they're real. They're human. And because of that, it can actually create more sparks than it would if you were straining to be perfect. Be perfectly imperfect.
Or at least allow yourself to be perfectly imperfect. Here's another story from my dating past. Once at Whole Foods, I saw a woman in the citrus section. She was looking at oranges. And She had a leather jacket on. She had this kind of Mila Kunis sort of look to her that was super attractive. And I remember thinking, okay, she's over there with the oranges. What's my opener?
What's the perfect opener? And I looked at the situation. All these oranges were stacked in pyramids. I thought of a good, funny line, and I had it in my head. I came up with this. It took me like two minutes standing there looking at her or looking at the scene. And I said, okay, I'm going to walk over to her. I'm going to say, hey, you know what?
They finally found a word that rhymes with oranges. And that word is gorgeous, which is you. So as I say that to you now, that's making me cringe. But that's what I was planning on because I thought your opener had to be perfect and witty and amazing.
So I walk over to her and I grab an orange to say the perfect quote unquote opener and the orange lets loose this whole pyramid of oranges and the pyramid topples and tumbles and 15 oranges fall, tumble at our feet. It was hilarious, hilariously embarrassing. And we both cracked up at my incredible klutziness.
And I think my actual opening line became, yep, I'm that cool guy at Whole Foods, right? So much simpler and more spontaneous. then the scripted planned thing I was going to say perfectly imperfect. And it went amazingly well. She and I laughed. Um, we talked, we chatted, we picked up the oranges together. She helped me and I recovered in terms of my comfort level.
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