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90% of Men Make This Massive Mistake When Talking To Women

I’ve worked with thousands of guys over the last six years. Yep, 6 years. I started when I was 23. Just kidding , but you get the point…

CYNTHIA UK GIRL · 2026-08-13 03:15 · 59 claps · 5.1 min read paywalled
#realtionships #love #dating #men #women
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90% of Men Make This Massive Mistake When Talking To Women

I’ve worked with thousands of guys over the last six years. Yep, 6 years. I started when I was 23. Just kidding , but you get the point. I’ve been around the block when it comes to dating advice. And here’s something I see over and over again. About 90% of men blow their chance with a woman within the first 60 seconds of meeting her. And it’s all because of one simple, innocent mistake they make in the conversation.

In this article, I’m going to tell you exactly what that mistake is. I’ll give you a real-life example so you can see it in action. Then I’ll show you the simple shift you can make to avoid it, so women actually get interested in you when you first meet. And stick around till the end of this article because a lot to expose in this writing to you guys.

I’m Cynthia, Every day, I’ll give you the no-BS insider truth about what women really want, not what they say they want and the most effective ways to win over any woman you like. So if that sounds good, make sure you hit that follow button so you don’t miss anything.

image Credit: istockphoto

image Credit: istockphoto

Now let me get into it. What’s this innocent mistake men make? I call it the interview mistake. Here’s how it usually goes. After breaking the ice, most guys start firing off questions. One after another after another. I’m repeating that on purpose so you can really feel how it comes across from a woman’s perspective.

It’s overwhelming. It’s exhausting. And honestly, it’s boring.

Interview mode is when a guy asks question after question but never seems to actually hear the answer or care about it. He just gets her reply, then moves right on to the next thing without going deeper or reacting to what she just shared. That creates an imbalance for the woman. She starts feeling drained, like, why am I even answering your questions if you don’t care what I have to say? Now I know that’s not what you’re trying to do. But to her, that’s exactly how it feels.

Let me give you an example so you can really see what I mean. And be honest, tell me if you’ve done this before. Just the other day, a guy came up to me at my gym and said, “Hi, I’ve never seen you before. Are you new?” I said, “No, I come here often, just usually at a different time.” Then he goes, “Oh okay, where are you from?” I said, “I’m from Toronto, but I’ve been in LA for almost 20 years.” And he goes, “Oh okay, what do you do?” I said, “I have my own business.” And right away he hits me with, “What kind of business?”

At that point, I was done. I just wanted to get back to my workout. So I politely told him, “It’s an online coaching business. Anyway, sorry to cut this short but I really need to get going. Nice meeting you though.” And that was it. I was bored. And trust me, that’s the kind of response you’ll get from women when you fall into interview mode. It’s hard for us to emotionally connect if all you’re doing is rattling off questions.

So what should you do instead? You don’t have to stop asking questions altogether. You need questions to get information. Even the boring get-to-know-you ones. You’ve got to start somewhere. Asking a question isn’t a crime. But here’s what I want you to do from now on. Any time you’re talking to a woman and you ask a question, follow up her answer with a statement instead of just moving to the next question.

This shows you’re actually listening, and it usually helps the conversation drift toward more fun or interesting topics. More importantly, it stops things from turning into a boring job interview.

Here’s how that plays out. You ask, “So where are you from?” She says, “I’m from Toronto, but I moved here 20 years ago. I live in LA now.” Instead of jumping to the next question, you say, “Interesting. I’ve been to Toronto. The people are really nice, but I went in winter and it was freezing cold.” Now she might respond with something like, “Oh yeah, the winters there can be brutal. Where are you from?” And just like that, you’ve got a natural back-and-forth going.

If you want to take it up a notch, you can use her answer to tease her a little. Here’s how that might sound. She says, “I’m from Toronto, but I moved to LA when I was 20.” You say, “Interesting. I’ve been to Toronto. People are friendly, but you… you seem a little suspicious. I haven’t decided yet.” She might smile and say, “Really? What makes you say that?” Or she might laugh it off. Or maybe she’ll say, “I don’t think I’m like a typical Canadian.” And just like that, you’ve added fun and flirtation to the conversation. You’ve added a layer.

Here’s another example. You ask, “So, do you have any pets?” She says, “Yeah, I have two cats.” You say, “Oh, so you’re one of those cat ladies. Interesting.” And you give her a cheeky smirk. She’ll know you’re joking. She’ll probably say, “Stop it, I’m not a crazy cat lady. I just love cats.”

Now you can keep teasing her or share something about yourself. “Well, I’m a dog guy myself. I have a 12-year-old poodle. How old are your cats?” And just like that, the conversation keeps flowing. See how that works? You ask a question, she answers, you actually listen, then you follow up with something playful or a comment about what she said. Now I know some of you are wondering, “ Cynthia, do I have to do this with every single question? How many questions can I ask in a row?” Or maybe you’re thinking, “What if I can’t think of anything to say and only another question comes to mind?”

I get it. Some questions naturally lead to other questions. I hear this all the time when I’m talking to guys. But instead of answering those one by one, I want to give you a practical exercise to try.

I want you to do this for two weeks. And I promise, it will break your habit of falling into interview mode. And it’ll answer all those questions on its own.

I call this exercise “three strikes and you’re out.”

Here’s how it works. For the next two weeks, talk to as many women as you can. It doesn’t matter if you want to date them or not. Just talk to women you don’t know. And when you’re talking, remember this: you are not allowed to ask more than three questions in a row. If you ask three questions in a row, you’re out. You have to end the interaction right there and walk away.

This forces you to focus on what she’s saying and respond with a comment, story, tease, or joke. There’s no pressure to say something witty every time. And sure, sometimes you might follow up with a question or a combination of a comment and a question. That’s all fine. The only rule is this: no three questions in a row. It doesn’t matter how great or average your replies are. Your only job is to avoid the three-question streak. If you take this seriously for two weeks, I guarantee you’ll become a more attractive talker than 90% of men out there. Hope you found this useful. And as always, I’ll see you next article.

cheers

Cynthia.


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