How to Get a Girlfriend with Connell Barrett - 7 Texting Mistakes that Make Women Flake Before the First Date (and 7 Easy Fixes)

Episode Date: September 18, 2026

You know what’s frustrating? Getting first dates lined up with women you’re into—then they cancel, or ghost you. It can leave a guy feeling rejected and confused. In this episode of “How to Get a Girlfriend,” dating coach and bestselling author Connell Barrett breaks down 7 texting mistakes men make that lead to women flaking on dates. You’ll also learn 7 fixes so you can stop the flaking and get a lot more dates.STRUGGLING WITH TEXTING AND GETTING DATES? BOOK A FREE CONSULTATION WITH CONNELL: DatingTransformation.comGET A FREE COPY OF CONNELL’S BESTSELLING BOOK, “DATING SUCKS BUT YOU DON’T”: Email: [e-mail] (Write “Book” in Subject Line)

So keep it G-rated, keep it innocent. In other words, don't go from zero to 69 in seven seconds. Welcome back to the How to Get a Girlfriend podcast. I'm your host, dating coach Connell Barrett, helping you get more dates, helping you flirt with authenticity, and do it all by being yourself. No pickup artist tactics. It's about being what I call radically authentic.

I want to help you solve some of your biggest dating problems. And one of the more common problems I get from guys when they reach out to work with me is they say, I get dates lined up, but so many women flake on me. They disappear. In fact, I'm thinking of a client I had a couple years back. His name is Arthur. And on my first coaching call with guys, when we start working together one-on-one, where I help a guy go from zero dates to three or four dates a month or a couple dates a week, I always say, let's focus on the thing you want to fix more than anything else. And Arthur said, women keep canceling on me for dates. They flake, and I don't know why. And he was

blaming women. He was like, yeah, women are so unpredictable. They're flaky. They're flighty. And I said, okay, well, let's take a look at a few things. And I went through the last two or three text exchanges he had with two or three different women from Hinge. And I'm looking at his messaging. And there was, there were two commonalities. He was not texting women between the day he set up the date and the actual day of the date. He went radio silent for four or five days. And then when he would text the woman, it was never something flirtatious. He would send a message the day before saying, hey, just confirming we're still on for tomorrow night at eight. And so often women either didn't respond to that message or they said, oh,

actually, I can't make it anymore. I was wondering if we could rain check. And then that rain check never was cashed in because when women say let's rain check, they usually mean let's never meet. And I realized, oh, well, this is your problem, Arthur. All you're doing is you're falling prey to two of the seven most common mistakes men make that cause women to flake, that cause women to cancel. And he was doing two of the seven, which I'm about to get to. One of them is he was confirming the date like it's a business meeting. He was confirming dates like it's a dentist appointment. Hey, just confirming our date for tomorrow night, just confirming our business lunch. And women weren't enjoying that. And plus he was going quiet. He was just letting four,

five, six days pass with total silence. And women were losing that sense of, excitement about meeting him. And then they would go quiet. And that was the only thing getting in the way. It wasn't about him. It's not that he's not attractive or not a great datable guy. And so it was really just all about how he was messaging women or the way he was or wasn't messaging them. So today's episode, let's get to it. Seven mistakes that are costing you first dates that are getting women to flake and cancel on you. Let's get right to it. And, And we'll go with texting mistake. Hold on. My cat is meowing. What is it, sweetie? What is it? My cat, parmi.

Mews like it's the end of times just because nobody will pet her. I'm sorry, him. Okay, here we go. Texting mistake number one that gets women to flake. Texting boring questions. They just text boring questions. Most guys send boring text messages in the days leading up to a date. Things like, you know, what did you do this weekend? How is your day? What are you up to? What's going on tonight? And what happens is a woman, a woman will read these text messages. And a lot of women like a little fun, flirty lead up to the date. And what can happen is women just don't want dull boring dates.

And if a guy's text messages leading up to that first date are on the boring side and a little bit dull, then she says, well, if this is how he's texting me, this is probably how he's going to show up on the date, and then they cancel. And that's because one of the biggest pet peeves women have about dating is just boring conversations, dull dates. and by sending logical informational text messages, like, what did you do this weekend? How was your day? There's nothing wrong with that inherently as a form of communication in life, but in dating, it's death. Logic is the opposite of flirtation. Information is not what women want. Typically, women want some fun, light, back and forth.

flirty banter. So here's your fix from dating coach Connell. Nothing wrong with questions. Don't be afraid of questions leading up to a date. Be afraid of logical informational questions because that's pretty boring to women. The fix is text playful questions, fun things. Like, you know, hypothetical fun what ifs. It's like, hey, random question. Who should play you in the movie of your life? What actress? That's a fun interesting. question women don't get instead of how's your day ask her the same basic question but do it in a playful way hey how's your day going on a scale of root canal to won the lottery that's a very different question than how is your day than the cliche of how is your day f mary kill could do that

f mary kill harry styles prince harry harry harry potter i remember i did a lot of f mary kill texting. When I was dating a lot, it was back in the Game of Thrones era. Game of Thrones was the hot show. So I would text a random woman, not randomly, but a random first date that she and I had lined up. I would say, okay, F. Mary Kill, Tyrion, Jamie Lanister, or one of the dragons, just being silly and light. And so, yeah, don't worry about texting questions. Questions alone or not bad. Logical informational questions, too many of those can be dull. Let's keep it fun. Let's keep it playful. Okay. Mistake number two that costs you first dates and gets women to flake that compels women to flake or cancel. Number two is sending her the, are we still on text?

This is what Arthur was doing. Too many men, I would argue most men, confirm a date like it's a business meeting like it's your business lunch. Hey, just confirming we're still on for tomorrow at seven. And this opens the door to her flaking. Here's why. You might wonder, well, wait a minute. What's wrong with confirming a date? That's not bad. Well, it isn't. But keep in mind how our emotional states govern our decisions in life. Think of the state a woman is in when she agrees to that date with you. She just matched with you, a little bit of back and forth banter. You're the shiny new thing. She's excited. It's new. And yes, she says yes to the date and she means it. Then maybe a few days pass, she's in a different emotional state. And if you haven't been texting her and keeping

the fires burning, then she might have an out of sight, out of mind situation arising here. where other guys are messaging her, other guys are matching with her if it's online dating. And so she's in a different emotional state. And then when it's time to confirm the date one or two days before, maybe one day before, then she's in a totally different mood and headspace. And people in general and certainly women in dating, they're going to make their decisions based on how they feel in that moment, not on some logical analytical basis.

She's not thinking, well, Michael, accountant, successful, tall, handsome. Yes, I shall go on the date with him. That is my logical choice. Women are really making choices so much from their emotions and feelings. I mean, we all are in life, but I think women are even more in touch with their emotions in the world of dating. So when you send that message the day before, she's saying, oh, you know what? I don't think so. I'm, you know, kind of tired.

I had a long week. why don't we rainjack? And of course, she wants to mean it, but she doesn't really mean it. She's just trying to get out, not get out of something that she doesn't want to do because she wanted to have a date with you. But she's going to make that decision based on her mood. Like, have you ever agreed to something that four or five, six days earlier sounded great? And then when it was time to do it, you're like, oh, sure, I could go out and have that

dinner with friends to go to that party. But man, it would feel a lot better and be more comfortable if I just stayed in and watched Anger Man for the 14th time. I know I've had many of those days and nights. It's not that different when a woman turns down your confirmation. And the thing is, when you're confirming a date by saying, hey, are we still on? You're actually giving her an out. you're opening the door and making it easier for her to say no thanks on second thought i'm not feeling up to it now some women might still say that to you regardless of how you frame things but we want to use persuasion and use smart intelligent communication to make it more likely she'll stick to the date and less likely she'll flake so here's how you do it here's if here's the fix you still want to

confirm, yes, but you want to confirm with a fun question that doesn't give her an easy way out. Something like this. Let's say you have a date lined up for a cool Mexican restaurant. You might text her this the day before. Hey, this Mexican place is supposed to be awesome. I think we're going to love it. I'm curious, are you more into red sangria or white sangria? And then when she replies, oh, well, I like red sangria, of course, or whatever she says, guess what? She just confirmed the date. In part because you didn't give her, are we still on yes or no binary choice? The binary choice you gave her was, hey, which of the kind of sangria are we going to be drinking, catching a buzz, having fun, eating Mexican food? And this keeps her focused on the enticing

fun date idea that I hope you've come up with. And also it just makes it a little bit easier for her to say yes. There's a thing called the law of commitment and consistency in human psychology. There's a wonderful book by a guy named Robert Chiodini called Influence. It's like 30 years old or more. I read it way back in college back in Stone Ages. Stone ages. And essentially, we all want to be consistent with what we commit to do. So when a woman agrees to a date with you, you can use the law of commitment and consistency as a way to persuade her and remind her not logically, but emotionally, hey, I know we're on for tomorrow night. Are you going to have red or white sangria? And that makes it harder for her to say, oh, well, on second thought, I really don't feel like it. Some women might still do that,

but it's harder to do that if you close the door of the, are we still on? So anyway, do not confirm dates like it's a business lunch. Confirm them this way instead. Or here's another way to confirm it. If you don't know, if you can't think of a red or white sangria version of your date, you could do it this way. It's not quite as effective, but it's still better than the confirming it like it's a business meeting.

You could literally move the date back 15 minutes, just 15 minutes. Oh, hey, by the way, I'm running about, let's say, day of. Oh, hey, I'm running a little bit late tonight. I know we're supposed to meet at 8. How about 815? Is that cool with you? And that's a way to confirm the date without it making it a binary yes or no. I do want you to confirm the date. It sucks to get there. And then she cancels right then and there. That's no fun. I was on a date once. I was of two, two-thirds of a draft of Guinness in when the woman texted me, hey, I'm running late at the office. Oh, my God, things are crazy.

Can we reschedule? So I don't want you to have to make the whole trek and not have the date. So we do want to confirm. Okay. Number three. Third mistake guys make that lead to women flaking. Going radio silent. This is probably the most prevalent one.

Going radio silent. You go quiet until the day of the date, several days from. the moment you set it up, and then she cancels because you've gone quiet. So I have a client named Nick, who was running into this problem when he started to first work with me. I remember he showed me a text exchange with a woman from Bumble. He set up the date on Monday. Everything looked great.

Nice fun back and forth banter with this woman from Bumble named Katie. And then radio silence, though, until Saturday. And then Saturday, late morning, Nick says, hey, I'm really psyched for tonight. See you at 8, question mark. And she replied, oh, well, I didn't hear from you. So I made other plans. And she had a little emoji, like a sorry emoji. Wamp, womp.

And Katie was genuinely sorry. She didn't mean to feel that way. But again, women make their dating decisions based on emotion. And Katie lost the good emotion. because Nick went quiet. Here's your dating coach fix. Text her every other day, minimum, to keep her interest and do it with a playful, light flirtatiousness,

not logical analytical messages. What might this look like? Let's say it's a couple days out from the date. You've decided on karaoke, which is a great first date. You might say, hey, just two more days until I show you what karaoke domination looks like. like microphone emoji. Back in my single days, I used to like to text her sometimes literally at the gym.

Sometimes it was just a joke. But I would text, hey, I'm at the gym getting my pecks and biceps swall. So I'll be huge for our date tonight. And then I throw in a parenthetical joke, nervously twiddling thumbs. A little weightlifter emoji. That's very conal. You don't need to use that if that's not you. But a lot of women would laugh go, ha, ha, ha, that's very funny. I can't wait to see how big and swall your arms are. It's a bit of a joke because my arms are not big and swall ever. And the bottom line is you want to keep

messaging women, at least about once. Well, you can do more than once a day. You can do 10 times a day if she and you have an equal cadence going back and forth, but at minimum, at least one message a day, roughly every other day at minimum. This keeps you on her mind. I like to think of texting leading up to a date like the, can you hear my cat? Oh, of course, as soon as I stop talking,

Parmy stops meowing. I like to think of the text messages leading up to a date like movie trailers. You can use them like movie trailers. They keep her and you excited about the date. And the date is the movie itself. So think of it that way. I think that can be really effective to not only not get ghosted or flaked canceled on, but it can also dial up actual steamy, fun, romantic vibes so that the date goes even better.

Okay. Mistake number four that guys make. that causes flaking and canceling on first dates. A boring date idea. You know, asking her out for coffee, a walk, grabbing drinks. These are cliche date ideas that are just really easy for women to flake on, to cancel on. Or to agree to, and then they lose the interest a couple days later, and then they cancel. Yeah, coffee.

Look, I'm fine with a coffee date. If she suggests it or if there's a way to make it sexy, like, hey, you know what? You love coffee. I'm a cappuccino addict. Let's get the best cappuccino in the entire city. I know this amazing, cool little grungy coffee shop. You could sex it up a little bit. But basically asking a woman out for boring date ideas, like grabbing drinks, a walk, coffee.

it comes off as boring and dull to a lot of women, or even worse, it can come off as really cheap and not try hard, but not trying at all, showing a lack of seriousness about dating. Now, what's your dating coach fix for this? Well, pick a fun date idea that she rarely hears, something that shows a little bit of thought and effort, but that's fun for both of you. arcade date can be fun, going to a comedy show, karaoke night, if you and she are both into it.

My client Mike did axe throwing. He was a big axe throwing guy. He lives in the Pacific Northwest. And he took a woman on an axe throwing date. It led to some fun, flirty trash talking about who is better. So think like an activity date, mini golf, axe throwing. Yeah, these are all good ideas. Now, if you're going to do a drinks date, that's cool. That's okay. But you still want to have some specific reason you're there. It's the best margarita in town. Or I used to go on a lot of, a lot of, or I used to sort of, how should I put this?

I used to pitch it like, oh, hey, I really love dive bars. I was a big dive bar guy back in my single slash drinking days. So I love to take women to dive bars and say, hey, I know an amazing dive bar. We'll get a shot and a beer. And there's only a 33% chance we're going to get stabbed. A lot of women liked that kind of like low, sort of trashy first date. So you just want to make it enticing. And coffee, walk, grabbing drinks.

That's not enticing. And that can get you canceled on. All right. Number five, the fifth mistake guys make. is failing to lead, failing to lead. Banish this sentence from your dating life. So what do you want to do? Women want a guy who plans the date.

She doesn't want homework. She doesn't want to have to do the heavy lifting. I'm not saying don't check in with her, but basically have an idea. Here's my dating coach suggestion. Use the word let's. I love that word, let's. L-E-T-a-pastrophe S, as in let's go to the coolest dive bar in town.

Or, oh, you like baked goods, right? Let's get this amazing piece of cheesecake at XYZ restaurant. Or let's play minigolf. I love the word let's because it's a positive, confident way to lead, but not bossy. You know, let's, let us. Let us do this. to get really nerdy on you, it's an Abraham Lincoln technique. Lincoln, if you look at his speeches and read how he was governing during the Civil War,

which of course was his entire term, he would say, let's let us together come together as a nation. There's something inclusive and collaborative about the word let's. And then if she agrees, she'll say, great, that sounds great. If she doesn't, she'll push back and say, well, I don't really. like mini golf. Let's do something different. Fine. At least you're getting feedback. But I don't like, I loathe saying, what do you want to do? As I write in my book, women don't flake on a man with a plan. Oh, by the way, before we get to the last two mistakes here, if you want to talk with me, have a free consultation about how my coaching works, then all you need to do is go to datingtransformation.com.

I do one-on-one coaching, helping guys go from a lack of dates and just a lack of confidence in how they talk to and attract women and helping my clients get a lot of dates, getting really good at flirting, and ultimately getting a great girlfriend, which is why this podcast is called How to Get a Girlfriend. So go to datingtransformation.com. You can book a free consultation with me. It's for guys who are open or considering dating coaching. It's not a free coaching call.

it's a consultation to see if we might want to work together. So you can do that at my website, datingtransformation.com. Okay. Mistake number six, getting sexual too soon. My friend Amy had agreed to a Tinder date with this guy. And then they confirmed the date with each other. Great. Thursday it is.

And then he wrote, Can't wait to see your smile and see what those lips can't. can do. Tongue. Ew. Remove all sexual overtones from texting and messaging up to that first date. A lot of men understandably fear the front zone, but a lot of guys have overcorrected by getting too sexual thinking, well, I don't want to be boring and I don't want to be

Mr. Nice Guy, Mr. Friendly. I don't want to get friend zoned. And they overcorrect in the wrong direction and get too sexual. But the thing about flirting is it can and should be G-rated, at least in terms of those first messages all the way up to the first date. So keep it G-rated. Keep it innocent. In other words, don't go from zero to 69 in seven seconds.

It's way too fast. There'll be a time and place for you two to get sexy, both in your, talk and behavior after a date or two or three, but not when you're texting. Okay. And here is the seventh biggest mistake guys make that leads to women flaking and not getting those first dates. Number seven, the half-assed ask-out. The half-assed ask-out.

Saying something like floating the idea of a date, hey, let's hang out on Saturday. I'll text you. It's not a date until you agree on a time, place, and activity. I work with a client named Martin once, and he said, hey, Connell, Catherine flaked on me, canceled on me. What did I do wrong? What's going on? And I looked at his text exchange.

And he actually never had a date with her because it was like, oh, hey, let's get together this weekend. We might be able to go, you know, check out a cool restaurant. this weekend. I'll text you. And then come the weekend, she went quiet. He felt she was canceling. No, Catherine did not cancel on you, Martin, I said, because you had not solidified a time, place, an activity. Got to have those three elements there. Here's your dating coach fix. Nail those logistics, right? This is not complicated. It could be as simple as, okay, let's do Margarie. read is at roses Saturday at 8 p.m. Sound good? And that last message is important. Sound good

question mark. The last thing you want to mention after you mentioned the time, place, and activity, notice I use the word let's. Hopefully some of these concepts are coming together. But then you say, sounds good. Sound good? Question mark. That's the last thing we want her to read so that her response is hopefully confirming. And if she can't confirm and has another idea or is not available, fine. Let's figure out those logistics. But yeah, no more of this. Let's maybe hang out sometime this weekend. That's not a date. That's nothing. That's just words. That's air. That's nothing. Nail the time, place, and activity. So yeah, something like, hey, margaritas, roses, Saturday night 8 p.m. Sound good to you? That's the last thing you mentioned. Then that makes it easy for her to

respond, hopefully something like, great, I'm in. And then what you want to do to lock it in is then you write this, something like this. Great. It's a date. Those three words, it's a date. Now you've solidified it. And remember how I mentioned the law of commitment and consistency earlier? Now you and she have agreed to a date. She will not flake on you because she's finally meeting a man who knows how to ask a woman out. She is committed. You have committed. And what you're going to do is over the course of those several days is you're not going to text

or boring questions. You're going to keep it playful. You're not going to confirm like it's a business lunch. You're going to confirm with some lightness and light flirtiness. You're not going to go radio silent. You've set up a fun date that's not a boring walk. You've led. You keep it light and g-rated.

fun, playful. And yeah, there's no way she's going to flake on you now. But what do I know? I've only been doing this for 21 years. Anyway, thank you so much for listening until next episode.