How To Text A Guy To Keep Him Interested (+ 21 Flirty Examples)
How to text a guy to keep him interested with examples. Discover the new flirty texting rules for dating guys. The ultimate guide that will totally make him take notice and see you as a high value woman worth pursuing.
Knowing the in’s and outs of texting a guy, doesn’t come naturally to most of us. At first glance, understanding how to talk to a guy over text, seems simple enough. But in reality, navigating those waters can be somewhat confusing.
Especially, early on if you want to play it cool. So that you don’t look desperate or come across as annoying.
How To Text A Guy To Keep Him Interested
If you want to keep a guy’s interest over text then it’s vital to always text him in a way that adds value to your relationship. In addition, don’t be afraid to send him flirty texts. Or to initiate a fun conversation by asking him open ended questions. However, it’s also important not to over message him by always being the person to initiate. He should still be taking the lead and texting first most of the time. That way you’ll be able tell if he’s interested in you back.
To find out exactly how to text him in a way that brings value to your conversation and helps to move the relationship forward, then read on. Because, below I’m sharing with you the 21 best text messaging guidelines and rules for texting guys.
Sound good? Let’s dive in!
Showing A Guy You’re Interested Over Text
You’ll discover what to say to him over text. How to start a conversation and how often to text him. As well as find out if it’s ok to text him first or text him again if he hasn’t replied yet. With easy text message examples that you can send him to get his attention and build attraction. And lots more, there are 21+ ways after all!
21 Ways To Text A Guy To Keep Him Interested
How to text a man in a way that keeps his interest and that shows that you’re a woman of value. A woman with the kind of irresistible confidence, that is so very intriguing to quality men.
1. Let Him Initiate (Most of The Time)
One of the major complaints I often hear from women, is that they feel like they’re always the one initiating the conversation over text. If this is you, then it’s time to take a step back.
I know you’re probably super excited about this new guy, and see nothing wrong with hitting him up first. Which of course there isn’t. But in the early stages this should be done in moderation.
Besides, if you’re always the one messaging first. Then you’re actually not even giving him the chance to initiate a conversation with you.
And not to mention, that if you’re always the one messaging him first? It can become problematic. Because, what you’re really doing is setting the tone and framework for your relationship. One, where you’re doing all the work. And him? Not so much.
Of course, if that is what you want, then that’s perfectly ok. However, most women I speak with that have set up this type of relationship end up frustrated. Constantly wondering why he doesn’t make any effort to court them.
That being said, I’m not saying to never initiate. Ideally, you want a relationship that is balanced. Not one that is completely one sided, for either of you.
Part of learning how to be a good texter with a guy to keep him interested, in a way that also moves the relationship forward. Means that you’ll need to pay attention to your communication patterns and tempos. If you want him to pursue you, then this looks like he sends 3 or 4 first messages, then you send one.
This will allow you to maintain the courtship process. While simultaneously allowing you to observe his texting habits. Which will turn, will help you to gauge his level of sincerity and interest in you.
Which brings me to my next point…
2. Yes, It’s Ok To Text Him First (But Do So Sparingly)
Another question that comes up quite often is if it’s ok to text him first. The answer is yes. It’s totally ok, within the context of genuine connection.
When you first start dating someone, you want your communication to feel natural while still letting him come to you. After all, you don’t want him to feel like he’s doing all the work. Because when a man is pursuing you he needs to feel like he’s making progress with you.
So yes, it’s ok to text him first. When in doubt, refer to the general rule of thumb that I mentioned in point #1, let him initiate 3 or 4 times. Then you initiate the next time.
Though please keep in mind this is not a hard and fast rule! Don’t let yourself be paralyzed by specific numbers or thinking that you’re doing something wrong.
If it feels good to you and you feel confident, go ahead and send him that first message anytime. Just beware of your messaging habits and patterns. And if you realize that you need to pull back a bit, then make sure you do so.
Example of What To Message A Guy First
This is an example of a flirty, cute and casual first text to send a guy that can spark a conversation:
“Hey! Finally checked out that show you recommended and now I’m officially #addicted…:) How do you know me so well?”
I go into more details of when to text him first and when not to in my article here.
How To Make A Guy Chase You Over Text
3. Keep His Interest By Sending Him Texts That Add Value To The Relationship
There are texts that add value to a relationship and build connection. Then there are texts that can drain the life out of it.
In the early dating stages, this often looks like some kind of version of, a guy sending a message along the lines of “Hey, what’s up?”. Then you reply “Nothing, I’m bored, what’s going on with you?”.
If you’ve been dating awhile, wether it’s been on a dating app like Bumble or Tinder, or a traditional online dating site like Match. You’ve probably received and sent more than your fair share of these conversations. All of which are boring, tedious and lacklustre.
What’s worse is that more often than not. They can take a once promising connection and make it totally fizzle out and die.
Before we go on, I’d like to clarify one thing. Texting in a way that adds value, does not mean that it’s your job to be super entertaining for him or artificial in anyway.
This is more about having something to bring to the conversation that in some way adds value. So that you start to build connection and rapport with him. (1) Rather than engaging in small talk, that goes totally nowhere.
Of course this can take some practice, but it doesn’t have to be complicated.
For example if he sends you a message along the lines of “Hey how are you doing?”. You can send something back that can continue the texting conversation that sparks his curiosity or interest.
For example…“The funniest thing happened at work today, I can’t wait to tell you later…”.
Or even if you really are bored, that doesn’t mean that you have to kill the mood by telling him. Instead you can send him a cute flirty picture or funny photo and simply say “Thoughts?” or “This made me think of you…:)”.
4. Text Him According To His Level of Investment In You
Nowadays many women seem to get caught up with men that are low investment texters. These are the guys that like you, but only enough to keep you as an option.
Like the guy that seemed great at first. But then disappears for weeks, only to pop back up again with a “Heyyy!!”. Or the guy that only seems to send texts late a night. Or the one that is really great at messaging you, but never asks you out.
These are the guys that you don’t want to over invest in. I know that it sucks to hear this. Because some of these guys are really great at leading a girl on. Giving you false hopes that this relationship is eventually going to go somewhere.
Men value a woman that they have invested their time and attention into. That means the more effort that he puts into you, such as initiating texts and planning dates etc. Then the more he feels invested in you.
If he’s interested he will make an effort to get to know you. He will reach out to you and text you more than one word replies. He will make plans and follow through. These are the men that you should also be investing in.
And, if he’s not investing in you. Then he’s more than likely not interested in you. And keeping you on the line as an option.
Now does that mean that you shouldn’t reply to him at all? Well it depends. If you really like him you can. But just because he texts you back, doesn’t mean that things are going to change. Most of the time men will text you back regardless of their intentions.
So if he sends you a “How are you??” and it’s been weeks. You can respond, but don’t go over every detail of your life and gush about how great it is to hear from him.
Even if you really like this guy and are excited to get even a crumb of a reply from him. It’s important to see his efforts for what they are.
If he he steps it up and shows you that he’s worthy and deserving of your time and attention then great. If not, well then that means it’s time to move on to someone who will.
5. Wait Until He Responds Before Texting Again
If you’ve just sent him a text, don’t message him again until you hear back from him. Even if, he disappears in the middle of a conversation.
I know that this can be hard to do. Not hearing back from a guy you like immediately can turn minutes into hours. It can feel pretty crappy. Trigger anxiety and fears that you’ve done something wrong. Or that he doesn’t like you anymore. But that couldn’t be farther from the truth.
The truth is you don’t know what’s really going on with him. Response times from guys can vary. Just because he doesn’t text you back right away, does not mean he’s ghosting you. Any number of things could have come up that distracted him from your conversation.
Along the same lines, you also want to avoid rapid fire texting him. Also known as “machine gun texting”. Which is when you fire off one question after the other. Without waiting for his response.
In real life it’s a bit like asking someone a question. Then interrupting them with another question in the middle of their answer. Do this several times and it can be quite frustrating.
Think of texting to be a bit like a tennis match. There needs to be back and forth between two people to make the game work. He texts you, you text him back, then you wait until he responds.
If you just constantly fire off one message after the other, not only can it be overwhelming for the other person. It can also come across as needy or desperate for attention. Which can be a huge turn off for many high quality men.
Though it’s tempting to send a follow up message right away, it’s much more high value to wait. So put your phone down, relax, and hold tight. Then live your life normally until you hear back from him.
6. Don’t Overthink Your Texts (His Or Yours)
Spending ages overanalyzing every message that you send and receive, can be the kiss of death in the early stages of dating. Over analysis = paralysis.
Texting with your guy should be fun. Don’t let anxiety take over and lose the joy in it by getting caught up in trying to send the perfect message. Or tripped up by reading into what every little word or emoji from him means for your future together.
The truth is guys are much more simple and straightforward than you think.
They are often very literal. So if anything, the best thing you can do is use the KISS method. Keep-It-Simple-Sweetie. Focus on clear communication and getting to the next date!
7. Be Original With How You Initiate A Text
No one wants to be a boring texter, or receive a boring text. One way to avoid this, is to send an interesting conversation starter. Something that’s more than just a simple “Hi!” to your man.
Besides being just plain dull, it’s also super lazy. Remember the analogy that texting is kind of like a tennis match? There should be some back and forth to keep the conversation fun and interesting.
Think original and engaging. With your goal being, that whatever message you send, gives him something he can easily respond to and take your conversation to a deeper level.
Example Of A Good Conversation Starter
“Just got some amazing news and guess what? You were the first person I wanted to tell…:)”
8. Do Ask Him Open Ended Questions
If you want to keep the conversation flowing, then asking open ended questions is key. Open ended questions are questions that can’t be answered by a “yes’ or a “no” or one word answer.
They are questions that will spark conversation and allow him to share details about his life with you. Which in turn, helps you get to know him better and vice-versa.
On the other hand, closed ended questions feel dull and stale. Which can quickly dampen the mood of any text conversation.
Example of a closed ended question: “Did you have a good day?” Closed answer responses: “Good”, “Ok”, “Yes” or “No”.
Instead text him an open ended question for example: “What was the best part of your day?”
This question prompts him to elaborate on a special detail about his day. Which helps move your conversion forward. In a positive and natural way.
9. Don’t Play Games With Him
Healthy relationships are built on communication and authenticity. While it’s important to understand the natural flow of texting. Basic guidelines and rules of thumb. There can also be a fine line between guidelines that show him that you have standards and those that are just you playing games.
I also know it can be confusing. Because you probably heard all kinds of things like if he texts you, then you should wait 3 hours to reply. Or tell him that you’re out doing something amazing with your friends, rather than just sitting at home by yourself binging Netflix.
Buying into these types of scenarios actually comes from a place of fear. With the underlying meaning translating to “I will lose him or he will lose interest if I don’t do X”.
Which is simply not true. If you use your judgement and message him as authentically as possible, you can’t chase away the right guy.
At the end of the day, not playing games, means you don’t turn yourself upside down to appear a certain way to a man. It means being comfortable in your own skin and confident in how you’re living your life.
So if you’re actually busy hanging out with friends when he texts you. Feel free to respond when you are more free. Same goes if you’re just puttering around the house doing nothing at all. If you want to text him back right away then do so. You don’t have to play games or wait a few hours just so you appear busy.
When in doubt consider this: high quality, emotionally intelligent men, don’t play games. And they aren’t looking for a woman who does.
Related – Should I Text A Guy “Thank You” After A First Date?
10. Keep Your Texts Short and Sweet
Texts are not emails. When it comes down to it, texts are primarily for logistics and a bit of playful banter. Anything beyond that – like sending a guy your life story. Or every detail of your day in one long text, is just way too much.
Think of it this way….in real life would you walk up to a guy that you barely knew and give him a 10-minute monologue about your day?
How would you feel if the tables were turned, and a guy did that to you?
This is basically the equivalent of sending him a 3 scroll text. Not such a turn on.
Ideally texts should be brief. Of course, there’s such a thing as too short. I’m not talking about 3 word texts here.
So what is the ideal length of a text? I recommend the “rule of thumb”. If the text is longer than the first top section of your thumb – then it’s too long.
Keeping it short, is also a good way of keeping the conversation flowing. As it creates an opportunity for playful banter. But, if for some reason you have a lot to say, then think about how you can break it up more.
Or even better? Get on a phone call or meet him in person.
11. Focus On Logistics And Being Specific
While texting can be fun, in the end the whole point of messaging each other is to get to the date.
This is especially important if you are texting a guy you just met. When the bulk of your texts should mainly be focused around logistics and meeting up in person.
This looks like sending texts that are about making or clarifying plans. As well as, last minute updates to the plan. All of which will ultimately will help move the relationship forward.
You want to avoid endless back and forth texting. As it can lead to the dreaded “textationship”. Which goes absolutely nowhere beyond your phone.
If you do get into a situation where he’s not making plans or calling you. It’s ok to suggest that if he would like to plan something, you would love to meet up in person. Then send him the days and times you are free.
Texting Example – What to Say To a Guy You Like
“It’s been lovely texting with you. I’d like to get to know you more but I find texting isn’t the best way. If you’d like to plan something I’d love to meet up in person. This week I’m free Wednesday or Thursday night after 7PM. Smiley face emoji”
This approach eliminates the back and forth messages, that can curb ongoing interest.
If you’re worried that this is too bold or direct, it’s really not. You aren’t actually asking him out. You’re just letting him know that you’re interested in meeting in person.
If he’s interested in you, he will plan a date. If he’s just stringing you along, then he will fade away or disappear. And if he does? Then no big deal, you can see him more clearly for what he is – not your guy.
For more on why men disappear read my article here. For what to do when he disappears read my article here.
12. Don’t Be A Complainer
Everyone needs a safe space to vent. Sometimes you just want to dump out our whole day on someone that you’re comfortable with. While doing that may feel like a relief at the time. In the long run, endless complaining can be highly detrimental to any relationship.
It’s also been shown that positive text messages have a positive effect on overall relationship satisfaction (2). Of course everyone has a bad day now and then.
You don’t want to be artificially positive when your day is falling apart. But at the same time, it doesn’t mean that it’s wise to send your new man a long list of how bad things are for you either.
Yes, you can still tell him about the rough day you had. But it will be much easier for him to be there for you, if you save the details to share with him in person.
13. Send Him Flirty Texts, But Keep It Classy
Flirting over text is an art. However there’s a fine line between trashy and classy. Ideally, you want to create a balance of flirty messages that are subtle and playful. Then mix it with a dash of mystery and intrigue. This is not as hard as its sounds, I promise.
All while avoiding sending any messages that could be interpreted as overtly sexual. Which could quickly escalate the conversation into an uncomfortable situation that you never intended. (Unsolicited d*ck pics anyone? Ummm, no thank you!).
Now of course there’s nothing wrong with having an over-the-top sexy texting flirtation. But, if you’re just getting to know a guy. It can send the wrong message (unless that’s what you’re going for then by all means sext away).
For many women who are single and looking for a long term committed relationship, it’s not how you want to start out. It’s best to keep texts more on the subtle playful and sweet flirty banter. And save the hot n’ heavy sexting for when he’s your actual boyfriend.
Flirty Text Examples:
“Watching a movie and the main character looks a lot like you… except, obviously, not nearly as cute…;)”
“You’ve kept me smiling all day….”
“Miss me yet?…. *winky face*”
For more interesting and flirty fun questions to ask him, check out our article here >> 200+ Flirty Questions To Ask A Guy (That He Won’t Be Able To Resist)
14. Always Have A Point To The Conversation
Random conversations and getting little texts back and forth all day can be thrilling. However, when you’re first texting a guy, you want to make sure that you have a purpose for some of your texts.
When deciding what messages to send, consider what kind of outcome you want. Such as, do you want to make weekend plans together? Do you want him to ask you out? Or are you just texting him to touch base and catch up on how his day is going? Etc.
Keeping this in mind, will ensure that your conversation feels fresh. Stays focused, and flows as naturally as possible.
Related – Should I Confirm A Date With A Guy?
15. Be Aware Of The Texts Tone
Texting isn’t like talking to someone in person. Because the subtle clues that we usually rely on to clarify a person’s intention, like tone of voice and body language are all missing. And are really hard to infer over text (3).
Which means that if you don’t factor this in. There’s always a chance that your text could very easily be misinterpreted by the reader. Or vice versa.
For example sending a text that is sarcastic. While the joke may work in real life. Sarcasm will usually fall flat or come across as passive aggressive in a text. Which is probably not what you had in mind.
16. Avoid Texting Him Late At Night
Answering texts from your new guy after 10PM can get you into some tricky territory. While it’s exciting and fun to hear from him. After awhile, it can also start to feel like spending time with you in real life isn’t his priority.
That he’s had his evening out with his friends. And now he’s turning to you because bored and lonely. Not to mention, that late night conversations often veer into some of us experiencing shall we say, less than gentlemanly behavior.
To avoid this, I recommend that my clients have a no texting after a certain time policy. Say around 9 or 10 PM where they stop responding to a new man’s texts.
Doing this helps to set a clear boundary with him that you have certain expectations and standards. As well as, sends a message that you are a high quality woman, and not anyone’s booty call.
17. Text Him Perfectly Placed Emojis (Here and There)
Emojis are the perfect way to add a bit of context and tone to your texts. When used tastefully, Emoji’s can also have a positive effect. In one study by Dr. Monica Riordan, an experimental psychologist, found that messages with emojis had an overall positive effect on the recipient (4).
But there is a fine line. Sending emojis truly is another form of communication. So, when you’re texting a guy, think about how that message will be received by him.
For example, a perfectly placed emoji like a winky face here and there can be playful and flirty. But overdoing it, like sending angry faces. Or a flood of texts with only emojis can seem immature and be totally off putting.
The top five single emojis for flirting are: the winky face, the winky kiss face, the love heart eyes, the smirking face and the the rosy cheeks smile.
Related – How to Text A Guy First Without Sounding Desperate (+ Examples)
18. Avoid Having Serious Talks With Him Over Text
Sometimes, when you have something that is difficult to talk about in person or more serious to say. Texting can feel a whole lot easier and safer.
Though texting is quick and convenient, some conversations are just better done in person. Like the super serious ones. Or any argument whatsoever. As well as, anything related to the “Where is this relationship going?” conversation.
Because without any real context or tone, it leaves way too much room for misunderstandings and hurt feelings. Resulting in good intentions, quickly spirally out of context and beyond your control.
So, if you really need to talk to him about something that really matters to you? Then pick up the phone and call. Or better yet, meet up with him in person.
Related – 9 Texts To Get Him Chasing You
19. If He Ends The Conversation Ends, Then Let It End
Sometimes you can be in the middle of a great conversation over text. Then he suddenly seems to just vanish. You’re left sitting there alone, wondering where he went. And if he’s ever going to text back.
When your guy, seems to just drop off the face of the earth it can be confusing. Especially when you really like him and are really feeling that good texting flow.
But just like when texting with a friend. Sometimes there’s just a natural ending point to a conversation.
It doesn’t mean something is wrong. But it also doesn’t mean that you should continue to text him either.
It just means that it’s clearly time to end the conversion and to move on. When this happens rather than agonize that he’s no longer interested in you, recognize it for what it is. Just a natural ending point.
Then turn your focus on the other things that matter to you and have going on in your life.
20. Know When It’s Time For You To End The Conversation
Just like you have to recognize when he’s ending the conversion. It’s also important for you to recognize that it might be time for you to end the conversation.
Because, there’s nothing worse than trying to drag out a once fun conversion that is now lagging. Not to mention that it can dampen a man’s interest in you real quick.
Every conversation has a natural ending point. As soon as you start to feel like the conversation is starting to fizzle out, that’s your cue to wrap it up.
Knowing when to make a graceful exit, communicates confidence. And that you also have a life. Both of which are very attractive qualities to a man.
Besides if you’re the one that always ends the conversation first, you’re in a power position. You’re the one in control of the narrative and not sitting around waiting around for him to reply.
21. Don’t Hide Behind Your Phone
Texting is a fantastic platform for touching base with your love interest. But the reality is, it’s not the best for creating the type of deep emotional connection that leads to long-term commitment.
In the early dating stages, it’s important to make sure that you are connecting in other ways too. Such as, speaking on the phone and of course best of all, going on real dates.
Texting Example – How To Get Him To Call You:
“What a great question! You, know, I can talk faster than I can type. Wanna continue this conversation on the phone?…:)”
22. If You Feel Triggered By His Text, Then Take a Moment
Ok one more texting rule for you. Often we are texting so quickly, that you don’t always process the true intent of the sender. Which can end up leading to misunderstandings. Ones that could leave you feeling hurt, angry, upset, insecure or otherwise confused.
So just like you should be aware of tone when texting him. Be aware of context, tone and your own triggers when reading texts that he’s sending you.
If you feel triggered in any way, take a moment before responding to him. Re-read the text and ask yourself what he really means by it.
And if you need clarity, then ask him. In my experience men are always happy to clarify.
Texting A Man To Keep His Interest
Knowing how to text a guy you’re dating is important. There needs to be a good rapport and back and forth flow between you to keep him interested. Especially early on, so that your relationship doesn’t fizzle out before it gets a chance to really thrive.
But equally important, is to pay close attention to the fact that what you text him is only a small part of the dating process.
Rather than focusing only on just what to say to him over text. Make sure that you are also paying attention to what his texting habits towards you are.
Does he initiate conversations with you? Does he respond in a reasonable amount of time? Does he seem genuinely interested in getting to know you? Is he moving the relationship forward with phone calls and dates? Or does he only text and never make actual plans?
His texting habits will be very telling as to whether or not he’s actually serious about you. The courtship process is a dance, he needs to be putting in just as much effort as you are. And if he’s not, then it’s time to take a good look at if this is really the right guy for you.
Because at the end of the day, you’re looking for a man that will be your partner, and not just your texting buddy.
PS. Want to meet a high quality man? Get your complimentary guide 44 Places To Meet A High Quality man Click Here.
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