Skip to content
Discover the modern way of flirting Download now icon  
Modern Success
  • Home
  • Program
  • Testimonials
  • Masterclass
  • Podcast
  • Blog
WATCH FREE TRAINING
Discover the modern way of flirting Download now icon
Modern Success
  • POSTED ON December 22, 2024
  • CATEGORY Dating Skills, online dating

The 6 Biggest Mistakes Men Make in Texting Women

Jared Laurence

dating coach for men

Discover the modern way of flirting

Book A Free Training Call

Introduction

Texting is the modern-day warzone of dating, and for many men, it’s where things go horribly wrong.

 

This is the most common story I hear from men:
You meet someone amazing, hit it off, exchange numbers, and you message her and then… silence. Or worse, she starts replying with one-word answers, and you’re left staring at your phone wondering, What did I do wrong?

As a dating coach, I’ve seen thousands of men stumble at the texting stage of dating simply because they didn’t understand what were doing wrong time and time again. And it’s not because they’re not smart or they are doing it on purpose. Most men genuinely don’t know the ins and outs of texting and how it differs from the perspective of a man and a woman. 

 

The key factor is attractive women have thousands of men messaging them on online dating apps, Instagram, and their social circle. Her world of texting is very different from your world of texting as a man. If you’ve ever blown a promising date over text, then this blog is for you. Let’s dive into the biggest mistakes men make when texting women and, more importantly, how to fix them

YouTube player

1. Sending Too Many Texts Too Soon

Neediness is the kryptonite of attraction and dating, and nothing screams needy louder than a flood of texts to a woman. If you are sending her multiple texts or even getting mad at her for not replying to your text then it is already game over. Being needy on text is a recipe for disaster. 

 

When you over-text, you’re essentially telling her, “My entire focus is on you, and I have nothing else going on in my life.” I am needy and I can’t get any girls so I am going to smother you with my love and attention in hopes that you like me.

 

And as you can imagine that’s a speedrun to getting ghosted by women and possibily blocked. Women want to be pursued, but they also don’t want to feel overwhelmed. Balance is key. Push pull is the secret. You need to have a abundance mindset in dating. 

The key to avoiding this texting mistake is patience and abundance of women in your life. If you are only talking to a single woman in a week of course you are going to be needy. You need to have be talking to a lot of women when you are developing your dating skills. 

 

Let woman respond on their own time. Your job is to have a awesome life, meet attractive women and keep leveling up as a person. And if she doesn’t respond to your texts then you simply move on. There are 4 billion women on this planet. A few girls not responding to your messages doesn’t change anything. 

2. Being Boring or Predictable

If your texts look like this:

  • “Hey, what’s up?”
  • “How was your day?”
  • “What are you doing?”

… you’re not texting; you’re putting her to sleep. Like I said before women are bombarded with thousands of messages like this, especially if they’re active on dating apps and social media. Do you really think she is going to reply to you with your boring messages?

 

Instead of asking generic questions, share something funny, interesting, or unique. Be creative with the way you speak and text. Makes a world of difference.

You are not there to conduct an interview.

Openers:
●  Always personalize your opener, basing it on the girl’s profile, a specific prompt, or a picture she liked.
●  Situational openers are ideal as they show you’ve taken the time to notice something unique about her.
●  Leverage humor and make it about her, not you. Tease her and be playful about it. 

Examples of situational openers:

●  Based on her prompt: If she mentions wanting a guy with a sense of humor, you could say: “Mind if I shamelessly flirt and hit on you? Just seems more fun than all the typical boring stuff.”
 
●  Based on a liked picture: If she liked your photo with your dog, you could say: “If you like me, my dog comes as a package deal. Can hopefully have more than one type of puppy love if you play your cards right.” 😉

3. Turning Texts into Therapy Sessions

Texting is not the place to unload your emotional baggage or seek validation from women. I am sorry you need a therapist not a girlfriend. Women want a dating partner, not a fixer project. Yes some women do like to listen. But she won’t feel attraction to you if you’re constantly talking about your ex, your childhood trauma or your existential crisis. By you unloading all your trauma on her you’re going to push her away to Narnia and she isn’t coming back.

  • Do you talk about your exes and childhood trauma all the time?
  • Are the topics you choose to talk about always negative?
  • Does she seem hesitant and awkward when she talks to you about the topics you choose?

Messaging Style:

● Start playful, transition to flirty: Start with lighthearted, fun messages and gradually introduce subtle flirting and roleplay.
● Don’t aim for deep connection over text: Texting is for building attraction and setting up a date, not having profound deep conversations. SAVE THAT FOR YOUR DATE
● Maintain Positive vibes: Always make sure you give fun positive vibes when texting. Don’t talk about boring topics. 

 
Playful Flirting Techniques:
 
● Exaggerate and be funny: Take everyday situations and make them humorous by exaggerating, and making fun stories out of it. Be creative. The art of story telling is attractive to women. 

●Be creative and fun: Always make sure you are are creative and different. Don’t be afraid to be silly and bring fun into the conversation.
 
Flirty Techniques:

●Role-plays and reversals: Come up with playful role-playing scenarios or reverse typical gender roles in a flirtatious way.

●Introduce fun challenges: Position yourself as a prize to be won, and the guy who needs to be impressed by playfully challenging her and making her work for your attention.

●Be subtly sexually suggestive: Hint at sexual themes without being overtly crude or explicit.

4. Trying Too Hard to Impress

We’ve all been there – trying to craft the perfect text to make her fall in love with you. But the reality is, there is no such perfect message. If you are overthinking every message or trying too hard to be witty and smart, it shows. Women can sense when you’re performing instead of being real, and it’s a major turn-off to women.

 

Even things you were authentic about will feel fake to women if you try too hard. The way to fix this is to be outcome independent. Be fun interesting and have a good conversation with her and don’t put her on a pedestal. Putting women on a pedestal is why nice guys fail with women.

5. Neglecting to Escalate the Conversation

Here’s a common scenario that most men end up with: you’re texting back and forth, the conversation is going good, but then it just… fizzles. Why?

 

Because you didn’t take the next step to actually go on a date with her. The goal of texting is to go on a date with her. Not to be texting partners. 

Or you have the opposite situation where it’s a texting marathon where you are both sharing your life stories on text but now she is not interested in meeting in real life. 

 

Understand something my friend, you cannot have a relationship only over text. You need to meet her in person. The idea is to go forward and have a date. Stop getting caught up in the little things and focus on the goal. 

When the time feels right, suggest something specific: “This has been fun—want to continue this over at the new gameshow/arcade/coffee shop on Saturday?”

 

Women appreciate men to take the lead and give her a fun experience. Mystery and space create attraction, which keeps her interested. There is no need to text her daily.

Recognize clear interest:

When you sense she’s attracted to you and reciprocating your flirting, go for the date.

● Suggest a date and be a bit direct: Propose a date idea and then confidently ask for her number. Don’t overthink it. If you are talking to multiple women as we suggest in our coaching you should not be dilly dallying for one date. Ask her out on a fun date. 

● FaceTime before the meeting: This weeds out catfishing and other problems you might have in the future and helps establish a more comfortable vibe for the first date.
 
Example of transitioning to the date:

● Her: “I’m bored, there is nothing to do on the weekend”
● You: “What a night of drinks, dancing, and laughter with a cute bearded guy help?”
● Her: “Most likely yes, that would help!”
● You: “Perfect. If tomorrow works for you, shoot me your number. If it doesn’t, then send it anyway.”
 

6. Misreading the Vibe

Sometimes, men get so focused on flirting that they forget to read the room. Understanding what women actually mean on text is harder since you cannot see their body language and tone. If she’s replying with short, polite answers and not asking questions, it’s a sign she’s not that interested. On the other hand she is trying to make conversation even if it is clumsy that’s a very good sign she is interested in you. 

You need to be creative and fun for her to be interested. Also if you are already doing your best and if not she’s into you, she won’t appreciate your effort. If she’s not, it’s better to move on and talk to other girls who will like and appreciate you for who you are. There are plenty of fish in the sea. There is no reason so spend your time on women who are not genuinely interested in you. 

 

Free An upset couple seated on a park bench, expressing frustration during an autumn day. Stock Photo

Final Thoughts:

Texting is a means to a end. You cannot impress women over text. The idea is to be fun and as a introvert it might seem like a easy solution but nope. You have to meet women physically in real life in order to build a connection with her. Using texting to get to know her a bit and ask her out on a date. The biggest mistakes most men make -over-texting, being boring, or trying too hard- stem from one underlying issue: insecurity and neediness. You need to stop being needy as a man. 

If you struggling with these issues I suggest talking to me or one of our coaches to solve your issues. There is no need to reinvent the wheel just take the help of someone who already has one. Use the button below to book a free call with me and my team. 

Ready to transform your texting game and your dating life ? Take action now..!!

Conclusion

Book A Free Training Call

about the author

jared lawrence

Founder and CEO Of Modern Success

Table of Contents

checkout latest articles

dating coach for ceo

Best Dating Coach for CEOs: Top 5 Picks for Leaders

dating coach for lawyers

Best Dating Coach for Lawyers: Top 5

dating coach for bankers

Best Dating Coach for Bankers

BOOK A CALL TO RECEIVE FREE TRAINING CUSTOMIZED TO YOU

THIS IS NOT A SALES CALL.

Keep your wallet in your pants. This is a chance for us to prove ourselves to you by giving you custom training based on your unique challenges and desires.

book now
logo
  • Navigate

  • Home
  • The Program
  • Our Coaches
  • Resources

  • Youtube
  • Blog
  • Socials

© 2025 Modern Success ALL RIGHTS RESERVED
  • Privacy Policy
  • Terms & Conditions
  • Home
  • Program
  • Testimonials
  • Masterclass
  • Podcast
  • Blog
WATCH FREE TRAINING
Facebook Instagram YouTube Linkedin