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

Episode Date: December 18, 2025

Ever had a jaw-dropping dating disaster? Wait until you hear about the guy who sent a cringe-worthy voice note about his date’s breasts… directly to her! But what if a screwup like that gets her MORE into him? In this episode of “How to Get a Girlfriend,” dating coach and bestselling author Connell Barrett answers listener questions, reveals why dating disasters happen, and shares how to recover with confidence and class.Episode Highlights:00:54: The Vexing Voice Note: How Screwing Up Can Actually Help You02:35: Whoops! Connell “Hits On” a Stranger—in Front of His Date05:40: The 3-Step Framework to Recover from a Dating Disaster16:47: The Do’s and Don’ts of Sexting21:58: Exactly How Many Texts to Send to Get a First DateBOOK A FREE CONSULTATION WITH CONNELL TO LEARN HOW HIS 1-ON-1 COACHING CAN HELP YOU ATTRACT YOUR DREAM WOMAN: www.DatingTransformation.com

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. Ask Coach Connell. 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 at C-O-N-N-E-L. Or you can also find me on Instagram at Dating Transformation.

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 vexed by voice note. Here's this 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 a 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. And then I'm calling him vexed by voice note. Oh, man. So you know how you can unsend a text messages, unsend a text message? I think Apple needs to add a reclaim your dignity button to the iPhone. That might help you, faxed. 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. 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 is 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 might 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 said, she was laughing. She's like, you're as smooth as sandpaper, Connell. She was laughing. And I just kind of slunk, 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 I did, 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 you're, 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 a nom, nom, nom, nom on them like a toddler. Nom, nom, nom, nom, nom. There's nothing, that's embarrassing.

It's absurd, but it's not vulgar. Now, you did home in on her body, right? You did make it about her body. And I'll talk about that in a second. but you were just making guy talk and expressing your physical attraction for a woman. 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. And women judge men based on how that desire is expressed. And yours came off as dorky, almost innocent. I mean, nom, nom, nam? 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, vexed, is that it was about her breasts. her boobs, nom, numb, 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 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. Send her this text. Quote, well, That was meant for my trainer, not for you. I am embarrassed.

I am sorry for the screw up. Yes, I'm attracted to you, but I also know there is much more to you than just your body. So I hope you're still up for date number two. And I promise no more voice memos of me making baby talk. End quote. Then stop. Send it.

Stop. Don't follow up with, hey, did you get my text? 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 see 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, I don't hate the guy, but they hate it when a guy tries to be somebody he's not, or pretent, 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, find. 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 be 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 mele-cunis sort of look to her that was super attractive. And I remember thinking, okay, she's over there with the oranges. Wow, 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. 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 clotsiness and i think i actually my actual opening line became yep i'm that cool guy at whole foods right so much

more, so much simpler and more spontaneous than the scripted, planned thing I was going to say, perfectly imperfect. And it went amazingly well. She and I laughed. We talked, we chatted, we picked up the oranges together. She helped me. And I recovered in terms of my comfort level. And I became, I didn't over-apologize, but I did. I was very self-effacing. And I got her number. And we ended up going on the date. And on our first date, she said that that was the moment that made her basically want to go out with me. Not the oranges falling, but how I recovered from it and just how real it was. She said, oh, that was like something out of a rom-com.

She told four of her girlfriends, or not maybe not four, she told a couple of girlfriends about our meat cute, our meat awkward at Whole Foods. so yeah that's a different apples to oranges no pun intended vexed i didn't send her a voice note but the bottom line is i screwed up and so it's the recovery that got me the girl not some cool perfection so if a woman likes you she's not going to ghost you over a small blunder she may even find it charming the men who succeed in dating aren't the guys who never make mistakes. The men who succeed are the guys who handle messy, human, flawed moments with honesty and a steady hand. The recovery is so much more important than the screw up. Women are noticing how we recover. They don't care about perfection. There's no such thing as perfection

in dating. They care about how we bounce back from imperfection. So if the two of you do end up going on a second date and maybe even beyond becoming a couple or a thing, an item, You're going to laugh about this story, potentially for years if you become a couple. And even if you don't see her again, it's not going to be because of the voice note. It will be because the two of you just aren't a match. Maybe you're not a match. Maybe you are. I don't know.

Now, if she ends up not seeing you again, that might sting, but you're going to be fine. And hey, at least you didn't send the voicemail to your mother. Nom, nom, nom, nom, nom. 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 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, next question comes from Instagram. This is a guy named David. David asks, hey, Connell, I was messaging a woman from a dating app. Things got flirty. Oh, gosh, talk about embarrassment. Clearly this is the theme of today's podcast. I was messaging a woman from the dating apps. Things got flirty.

She asked me for a sexy photo. So I sent her one. Hold on. I'm having trouble. Oh, I see. I was messaging a woman from a dating app. Things got flirty. She sent me near topless photos of her, which got me very excited.

She then asked me for a, quote, sexy photo. So I sent her one. Me, smiling, shirtless, with my nipple in the frame. Now she's ghosted. What did I do wrong? And also, how do you sexed without it getting weird? That's from David, who gave himself his own nickname. He said, David, aka digitally confused.

Okay, David, here's your new dating role. If the photo looks like something you would send your dermatologist, don't send it to a woman. Okay? Look, a woman's nipple is a beautiful thing. It's a work of art. man's nipple is unappealing. It's useless, vestigial. Her nipple is Michelangelo. Yours is MySpace. So here's how to get, here's how to get sexting right the next time. Okay. Here are three do's and one don't. Do number one is use words, not body parts. Sexting works best when it's

about what you say, not what you show. So instead of sending her photos of Utopolis, By the way, when she said send me a sexy, send me something sexy, she wasn't necessarily looking for a photo. She just wanted something, a sexy vibe. So use your words. Describe what you would do to her if you were together with her or what you like about her photo. For example, you could say something like, I can't stop thinking about that dress in your

profile pick. Or even better, when a woman does become vulnerable to you and shows you a racy photo like that sounds like, it sounds like a semi. nude, topless photo, or possibly partially topless, then make her feel great about that. Just, I can't stop thinking about that photo. Say something like, you are very distracting to me today. You're making it very difficult for me to think clearly or to clink clearly. Anyway, make it about her and how she is making you feel.

Don't make it about your body. okay uh do number two is if you do send photos keep photos natural if she does ask for a photo keep it casual keep it confident keep it g rated could be your smile women love a smile maybe you in a well-fitted t-shirt um if she wants if she wants if she straight up says hey i want to see what you look like or i want to see you maybe post workout think attractive man not anatomical diagram no extreme close-ups no isolated body parts i never have and never will send a dick pick i the only time i've ever sent a dick pick is the last time i was single pre-pandemic i was i was messaging a girl with a girl and she insisted on me sending a dick-pick

and there was no effing way I'm going to send an actual dick pick. So I googled ginger dickpicks online and found somebody else's junk because in the event she was trying to, this person was going to blackmail me or turn into a scam.

I wanted to be able to say, ha ha, that's not my penis. But anyway, bottom line is don't send any isolated body parts, especially your junk, but also your nipple. And do number three is keep it mutual. Make sure that she's engaged with you as you escalate to sexting. I like to check in

with a woman if I'm sexting and ask things like, hey, are you liking this? Asking, should I, should we do this? Should, can I ask you? Can I ask you something? Can I ask you something that you might be excited by, get permission before you escalate it, I guess is what I'm saying. And if that woman's not sort of giving you that permission or not matching your energy and not giving that consent, pull back. Don't do it. And here's your ultimate don't. Don't send anything that you wouldn't want your mom to see. Okay. Unless you're certain that she wants it. By she, I mean your crush, not your mom but even then i would be i'm just averse to sending any kind of lascivious photo of myself or at least i was when i was single um and by the way if you're unsure what she means by

sexy you could always just ask her she might she was not asking for your nipple if a woman says hey send me something sexy ask oh like what what do you want to see what what kind of sexy are you looking for most women women are not turned down by male body parts the way that we are turned on by female body parts. So you could just say, hey, what kind of photo are you thinking? Or what kind of sexy do you want to see or hear from me? Maybe she wants sexy words. She might say, tell me what you're going to do to me. Or if she does want a photo, then you can proceed there if you and she both sign off on it. Anyway, sexting works when you and she are both on the same page. So don't improvise solo here. Next time, lead with words, keep photos tasteful, and save the

nipples for somebody who's actually seen you naked. Okay? That's when you want to let a woman see your nipples is when you're together, not sending photos. Okay, one more question. This one's a bit more bread and butter. No more embarrassing questions. This is, oh, here's a good one. Hey, Connell, when I'm on the apps, I'm afraid to double or triple text women because I don't want to sound like I'm tryhard. How many messages should I send before asking for a date? Signed, Chris. Okay, Chris, how many messages should you send before asking for a date? Send exactly 11 and 3 fifth messages at alternating times of day, except in the central time zone, in which case it's 9.25 to the 11th power. Did you get all that? The real answer is the number of text.

you send is it's almost irrelevant. Here's what I mean by that. There's not a magic number. Women don't care how often you text. They care how much you bring to their love life. And they gauge that online primarily through your profile, your photos, your bio, and the story that you tell about yourself through your photos, through your profile. So here's a case in point. My client, Ben, came to me for coaching because he was finding it really hard to keep women interested on the dating apps. He would message, but he just couldn't get women out on dates.

Very rarely got phone numbers and barely didn't get matches very many, and it was hard for him to get a date online. And he thought the problem was his texting. He had me look at his texting, and he said, hey, is my texting good enough? Am I not asking them out at the right time? but the problem wasn't his texting. The problem was his profile, especially his photos. His photos were me.

And that's how women saw him as me. And Ben is not a me guy. Ben is an amazing guy. It's just that his profile was not showing that. So we upgraded his photos, including a killer shot of him on the beach. He's a surfer, or I should say he's into surfing. and we took a really cool photo of him surfing or with a surfboard showing off his authentic surfer dude vibe he's also got a really good physique he's a personal trainer and he

just looks really good with his surfboard and within a week boom ben had dozens of new matches and two or three dates lined up and one woman even sent actually more than one but at least one woman sent him her number unprompted in the very first message. She wrote him, hey, I love your profile. We have to get together. Talk surfing. Here's my number. How would you, and she was beautiful. How would you like that for the first message from a woman? Here's my phone number. Text me. How would that feel? It feels incredible. And by the way, Ben did not change his texting strategy. He changed his profile. So he wasn't counting texts. He was counting dates because all of a sudden his profile was getting him all these dates.

So here's a little thought experiment for you, Chris. Imagine that you match with Anna Daarmus and she texts you three times in a row. And they're kind of boring. They're just like, hey, how's your day? How are you? They're kind of meh text. But it's Anna da Armas. Pop quiz.

Pop quiz. Anna de Aramis matches with you and here, and she texts you three boring texts in a row. Do you A, ghost her for being needy? B, play it cool and wait a day to reply. Or C, rent a billboard that screams, Anna de Armas matched with me, texted me. Oh, my God. I don't know about you, but I'm choosing C. And by the way, you would not see her as needy or thirsty. All you would see is the upside of dating her because she is your perfect 10.

And that's the point. When a woman is excited to meet you, just as you would be thrilled to date Anna Daormus, your texting frequency becomes irrelevant, the number of texts. So she'll be excited to hear from you. whether whether once you get a good enough profile and good enough photos she will be so excited to hear from you whether it's one text or 10 so I know I intentionally didn't answer your question just because I want to serve and help you and the number of text messages is not nearly as important is just making sure your profile shows women all that authentic value that you bring to the table

So the question isn't how many texts should you send? The real question is how do you get more women seeing you as their perfect 10, or at least a nice high number? How do you get more women seeing that value, getting excited about you? And once you do that, the number of messages, there's no magic number. All that said, here's a good guideline. Once you are messaging a woman and assuming you have a pretty good profile that she and she's interested in you, which obviously some women are, then here's my, here's my little

guideline. Typically, I'm going to say one or two conversation threads and then ask her out or ask her off the app. So at least one, if not two. So don't count texts. Count conversation threads. Let's say the first conversation thread is about dogs. her dog and your dog. And then the second conversation thread is about Christmas plans. Now you've looked at the messages, say to yourself, oh, we've now talked about two topics, then ask her out. Don't wait any longer than two conversation threads.

Sometimes just one conversation thread is enough. Two max, then ask her out. Another guideline I have about texting is, again, don't count texts, but... focus on her vibe. Is she giving you short, logical answers and not really putting much effort into it? Well, don't ask her out because she's probably not feeling the vibes yet enough. But if she's, if her first or second text message to you, or sorry, you know, dating at message is like three hard-eye emojis and LOL and clear effusive good energy,

ask her out right away. Don't worry about counting text or conversation threads. Read the room and go for the digits, go for the date while the iron's hot. She's basically telling you, ask me out. And one other thing I'll notice other than text messages, other things besides counting texts is I'm more focused. My clients and I are more focused on a mutual, approximately even Stephen balance of texting in terms of the number of my messages and hers. We want the balance to be roughly 50, 50, 40, 60 in either direction. Either

one's good. So whether that's one text a day or 12 texts a day, you want to keep that a nice 40, 60, 50, 50, back and forth cadence. And if you're doing that, then that is going to get you dates. So don't count text messages. Read the room. Count conversation threads. If you're going to count anything, notice the cadence back and forth. And anytime between that first message, you two send through the second conversation thread, anytime you feel like the iron's hot, ask her out. But if you don't feel like the iron ever gets really hot, once you've talked about that second conversation thread, then ask her to get off the app or ask her if she'd like to go on a date with you because it's better to ask her out too soon than to wait too long. All right,

thank you so much for listening. Until next time, bye-bye. You know,