How To Text A Guy To Keep Him Interested

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How To Text A Guy To Keep Him Interested

Most of us send the usual boring texts every day. How are you? How was your day? Blah blah…

But how do you text that intriguing guy? And not just text. Keep him interested and finally win him over?

If your goal is to make him notice you over texts, the rules must change. Don’t think the standard texts will do the trick. You must put in the work and stand out in his inbox. After all, what makes you special if you are sending the usual basics?

Stick around to learn how to text him to keep him interested. Without further ado, let’s jump right in! 

How Do You Keep a Guy Interested While Texting?

The secret is to stand out. There are so many rules on winning a guy over texts, some of which are not practical in real life. For example, the common rule is, don’t text first. The logic behind it is not to come out too available. Which I totally agree with.

However, can’t you text first and not come out available? I mean, why is the concept of ‘being too available’ based entirely on texting first?

Again, how will a guy be interested in you if he always texts first? Actually, the assumption is you are not interested. He is the one interested more than you are. So instead;

1. Don’t be afraid to text first

Woman thinking whether to send a text message while leaning on a dark wooden table.
Woman thinking whether to send a text message while leaning on a dark wooden table.

Guys love to feel wanted and valued as much as we do. So if you are interested in him, feel free to text first. 

Texting first doesn’t necessarily mean you are too available. It means you like having a conversation with him and you are trying to make one. 

What is portrayed as ‘too available’ is constantly texting throughout the day. Especially when there is no response, so you keep texting until you get one. And if you don’t, you send numerous texts the following day.

It’s nagging, annoying, and a little too much. So go ahead and text first to start that exciting conversation so he is glued to his phone conversing with you. This makes you intrigued and he even texts first next time. In addition, use these tips to make him text first.

How to get a guy to text you first

  • Be engaging in what you talk about and how you present yourself. No man will text you first if you are boring. Instead, he will look for something interesting to do. So be that exciting person he looks forward to texting.
  • Make him want to text you. I don’t mean telling him to text but giving him a reason to text you. I mean, be super special in every conversation you have such that he misses texting you. So on top of being interesting, let him see your value so he wants to keep you for himself.
  • Don’t look desperate. And I don’t just mean by over texting. Get a life so you are busy working and maintaining an active social life such that the moment you two start chatting feels incredible. 
  • Give him space. He also has a busy life. Giving space shows you understand this. Besides, if you text all the time, it becomes monotonous so allow him time to notice you are not texting.

2. Be yourself

I know you are excited and anxious at the same time. Maybe too much that you are tempted to be someone you are not. Probably because you think he would like you in a certain character. Relax! Faking a character is not a wise thing to do. Just be you.

Don’t pretend to like things you don’t. It’s a turn-off. Talk about what you love. This way, you get to express your passion and if he likes you, he likes you for who you are. Besides, it’s hard to talk about things you don’t like and sound convincing. Which means he may figure out you are faking. 

Furthermore, being yourself portrays your confidence. You are bold enough to talk about your interests without fear of coming out as ‘not cool.’ The reason most people fake their personalities is to sound cool and fit in.

Pro tip: Work on your self-esteem so you are confident enough to influence him.

Woman wearing a white tank top and blue jeans confidently typing a text message
Woman wearing a white tank top and blue jeans confidently typing a text message.

3. Avoid bland texts

As much as I agree with you texting first, don’t do it for the sake. Because if you do, you will end up sending bland texts like;

  • Hey
  • What’s up
  • How are you

And there’s nothing as dull as bland texts. They call for short answers, which lead to small talks. You want to keep him interested, so how will you do that with a simple hey? The best you can get is a ‘hey too, how are you?’

Instead, text when you have something to say. This way, the conversation flows perfectly and you don’t have to struggle. So don’t beat yourself up trying to force a conversation. If you don’t have something to say then fine. You can talk next time.

Another tip is to ask more open-ended questions. These are questions that require a detailed answer. For example, instead of asking how his day was, where he answers ‘good or okay,’ ask him what was interesting about his day.

Such a question requires a detailed answer. It might even prompt more questions, therefore, creating conversation.

I also have to say this, don’t make him carry the whole conversation. Whether he initiated or you did. I know women do this;

You: Hey, what’s up?

Him: Just chilling with friends, you?

You: Watching a movie

Him: Cool, how was your weekend?

You: Good

Him: What did you do?

You: Went out with friends.

It’s so annoying. Let him do the talking, especially if you initiated the conversation. Never do that if you want to keep him interested. Instead, do this;

Send texts that add value and create a connection

Some texts fuel a connection; others drain the life out of whatever you are trying to create. 

As much as being interesting is necessary, send him texts that will add value and fuel that connection to create a strong bond. You want to keep him interested so how about you build or strengthen your bond so he is always interested?

A good way to achieve this is by finding your similarity in terms of interests and text in line with that. For example, if you two are into business, talk about it in a fun way so it doesn’t sound too professional. 

You can also share some ideas and thoughts on how to skyrocket profits or expand your businesses. This way, you are adding value to each other’s lives while bonding over your interests.

4. Understand him as a person

a close-up of the text message screen on a phone
A close-up of the text message screen on a phone.

Through his texting habits, you can understand the kind of person he is. If he responds first and texts a lot, then he might like texting so you can continue with the thread to win him over. But if he takes ages to reply and doesn’t text much, maybe he is not into texting. 

If you understand this, you will only text when it’s convenient for him without coming out as annoying.

Also, pay attention to his interests. You can just ask so you keep the conversation in line with what he likes. 

For example, ask him if he likes pets and which one is his favorite. Assuming the answer is dogs, you can talk about them in detail or use them to spark conversations, e.g. sending a random, “German shepherd or Chihuahua?”

He probably picks one so you ask why not the other. You see, you are building a conversation from his interests, so why would he find you boring?

Another thing, understand his love language. If it’s receiving gifts, find out what he loves as gifts and talk about them. If it’s quality time, give him quality time while chatting. I mean, make his time incredible so he misses chatting with you. 

5. Know when to text

When is he likely to reply and engage in a conversation? Maybe in the evening after work. To know a perfect time, you can ask about his schedule in a way that doesn’t sound possessive. 

Possibly when you are all deep in a conversation on how his day was and what was interesting about it, then you pop out a question like ‘how are your days like in general?’ This way, you get an idea of when he is free, so you don’t text when he is spending time with friends or is swamped with work.

When the timing is right, he concentrates on you and enjoys your conversations, especially if you make them interesting. And if he enjoys talking to you, you are keeping him interested. 

6. Keep it short and sweet

A short message
A short message.

Don’t send too long messages. You also wouldn’t like getting ‘paragraphs’ of messages. We get lost reading a very long text. It appears like a monologue so learn to break your texts even when you have a lot to say.

Besides, short texts are playful. And I don’t mean the bland ones we talked about. Long enough to make conversation and short enough to make the conversation interesting. It gives him time to respond as well as attract his attention.

7. Flirt with him but sparingly

Make things a little spicy by flirting once in a while. Compliment him in a way that makes him feel special now and then. However, do it sparingly. 

If you do it right, he might pick up and start flirting with you too. And before you know it, he is not only interested but is falling for you.

8. Reciprocate the energy he is giving you

All said and done, remember to give him the same vibe he is giving you. If he doesn’t seem interested, try to win him over using the above tips.

However, it’s essential to understand you can’t force him to do anything. And if you do, it will backfire on you in the future.

That’s why you should reciprocate the energy he is giving. I’m saying this because you seem desperate if you try too much, which is a turn-off. It happens that while trying too much to make him interested, you might miss the signals he is giving negative vibes and come out desperate.

Instead, text him according to his level of investment in the conversation. If today he seems out of it, don’t try too much. You might end up spoiling everything. Just give him time and try next time. And again, don’t try too hard.

How Often Should You Text A Guy To Keep Him Interested?

A happy man texting a girl
A happy man texting a girl.

There is no rule on how many texts you should send or how many you shouldn’t. I would say, text him enough to be on his mind but not too much to annoy him.

You are now asking how much is too much. Well, that depends on his schedule, whether he likes texting, and how you text him in general. 

I once asked a couple of my male friends this question, and though the responses were different, they all agreed that you shouldn’t send empty texts for the sake of it. 

One said, ‘If you text daily, I will be thrilled, but the quantity or frequency is a different story.’

According to him, hundreds of texts would be annoying. He implied he would find it obsessive, not interesting.

And I think this applies to almost every guy out there. 

They want you to show initiative by texting often enough but not excessively. This takes us back to texting when you have something to say and knowing when to text.

If you pay attention to these two, you are unlikely to go wrong. Besides, by now you have an idea of his texting pattern and whether or not he likes chatting. 

So, keep him interested by following what he likes. It will be like having a conversation over his favorite meal. Interesting, right?

What To Text A Guy To Keep Him Interested

Now you know how to keep him interested, but what do you say exactly? Do you ask about his work, family, friends, or hobbies?

Your texts should focus on him as a person, on his hobbies, interests, and anything about him in general.

You should know that guys are so simple. 

They are not as emotional as we are, so you can easily please them, provided you play your cards right. And that’s where we go wrong. You will take your time crafting a message you think will interest him because it would catch your attention and forget he is not you.

What I mean is, don’t overthink your texts because if you do, you might ruin things. Be simple yet cute and attractive. 

An innocent compliment is fine. Assuming you are texting on Whatsapp, you can compliment his DP if he has his picture. 

For example, ‘I like your DP; you look great.” It’s simple but does the trick. 

You can also send him random cute videos of what he likes. Let’s go with our previous assumption that he likes dogs. So whenever you come across videos of dogs doing funny things, you can send them. Basically, anything that would make his day, even memes.

Try sending texts that spark curiosity. For example, texts asking him what he thinks of something. He will give his thoughts and he’ll want to know what you think as well. 

This way, you start a conversation and keep him interested. 

Flirty texts are okay. However, be creative around them. Don’t be too straightforward, as it may sound desperate. Flirt in a classy way. Include things that spark imagination and attract attention.

It’s not about what you are texting. It’s what he feels when you text him that matters. 

When you understand this, you will focus more on sending texts that positively affect his feelings—finally winning him over.

What Might Drive Him Away?

What Might Drive Him Away

1. Texting him first and stopping responding when he replies.

You probably have done that. Nothing good comes out of this. 

Women do this, thinking it makes them cool somehow. You want him to think you are busy, and not too available. 

But how would you feel if the tables were turned? What if he texts first and when you respond, he stops replying? 

There you have it, pissed!

2. One-word texts

Have you ever found yourself texting someone who sends one-word texts? If you haven’t, you are lucky. One-word texts kill conversations. So instead of replying with a simple okay, try something like; ‘Okay, that sounds good.’

3. Sending follow-up messages after he takes a while to reply

If he doesn’t respond, assume he is busy and will get back as soon as possible. Don’t send another five follow-up texts asking why he is not responding. 

Do you know what’s worse? Telling him that he doesn’t want to talk to you. That’s one of the things that makes you sound desperate and “too available.”

4. Being straight-up sexual out of nowhere

We said flirt, but don’t get too sexual. It freaks him out, thereby driving him away ultimately. 

However, this doesn’t rule out getting a little naughty if the flirting leads to it. Especially if he follows the lead and gets fully invested, just remember to do it sparingly. 

5. Talking too much about yourself

Ask him questions about him and only talk about yourself when it’s necessary. When he asks something about you, it’s probably better than when you talk about yourself out of the blue. 

Besides, the conversation becomes one-sided.

6. Text speaking

What I mean is using a lot of abbreviations in your texts. For example, ‘OMG’ When you mean ‘Oh my God.’ While some guys might be comfortable with it, most won’t be. Just take your time and text real words. 

Besides, if he is not texting that way, why would you? 

The same goes for punctuation, including question marks and commas. 

7. Bad grammar

Whether it’s an innocent mistake or you are doing it knowingly, bad grammar sucks. Especially when it’s habitual, it’s a complete turn-off. Take your time to correct the slightest grammar mistake. Besides, how do you intend to keep him interested when you can’t communicate clearly with your bad grammar?

Final thoughts

Winning a guy’s interest over texts is not rocket science. You just have to learn a few things, most of which we’ve covered. 

Keep it simple and don’t overdo it. Most of all, relax and be genuine. After all, you can’t force him to like you. You can only do enough to make him notice you, and if he likes you as much, he will reciprocate the vibe. Maybe they will even take over from you and start winning your heart.

And who knows? It might turn out to be something beautiful. All the best!

Photo of author


Over the years, Stephanie has had her fair share of dating experiences. While some turned out great, others weren't so great. She believes that relationships are meant to be fun, exciting, and full of laughter. She wants to help men and women become confident, attractive, and successful in their romantic relationships.