Should I Text Him? Decoding the Dilemma

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All you women out there thinking, “Should I text him first?”, this one’s for you. Dating is a daunting enough experience. On top of that, you have to now figure out who should drive the conversation. What exactly are these hard-and-fast rules for wooing someone?

For instance, it was not until recently that I realized there are texting rules that entail weekday texting or weekend texting. There are implicit rules around the best time of day to text a guy too! The unwritten rules of dating are being upgraded every minute, mostly influenced by pop culture and anything hot at the moment.

As a result, women who are actively dating find themselves wrestling with dilemmas like: Should I text him first or wait for him? But what if he’s waiting for me to text him first? Great, now we’re fighting; should I text him first after a fight? These are common worries that often stop you from acting on your feelings and going with the flow. But we are here to offer you solutions.

Should I Text Him — 15 Things To Consider

Table of Contents

Let me tell you, contrary to what you think, many men do find it hot when women text them first. So, that should give you some reassurance if you tend to text him first sometimes, or are tempted to. But if you’ve been staring at your chat with this guy for far too long, wondering about the right thing to do, and torturing yourself with questions like, “Do I text him first or will that make me appear too clingy?” or “Should I text him or wait for him to text me back?”, then you’ve come to the right place today.

First, let’s be clear there is nothing wrong with women texting first. But to make sure you’re doing it for the right reasons, here are a few things for you to consider:

1. What’s your game plan here?

To you, is he just a booty call, a friendly relationship, or someone that you want to be in a serious, established relationship with? Because sometimes, even the way you craft that one message can determine the tone of the relationship you are trying to have. When texting a guy, be clear about what you want this to be, to avoid any drama or confusion later on. That will help you develop the conversation based on your intention.

2. If you are in this for the long haul, just text him

Texting someone or the talking stage is a rite of passage for most couples in modern relationships. The texting game is almost like an endless cycle when trying to find someone who is your type in the long term. But the only reason you should probably text someone and keep the ball rolling day and night is if you see a future and want to go out with them. If you are just feeling lonely and will forget all about them in two weeks, maybe don’t start this charade in the first place.

Related Reading: He Didn’t Even Reply To My Message After We Made Love But I Didn’t Cry

3. It’s really not that big of a deal

“Should I message him first or wait for him to make a move? Stop plucking those petals, sister. Women texting first when as an expression of interest is nothing out of the ordinary. There is research that shows that women do send more text messages and use more emoticons in their conversations with men. Gone are the days of playing hard to get to impress a guy, women now go straight for the kill if they want to. And men are here for it!

So, if you’re going to text him today, even this Reddit user supports you. He says, “It should become more normalized than it is for women to text first. I really don’t understand how some could think that it’s weird and off-putting. Guys want to be pursued JUST as much as girls.” Women texting men about their romantic or sexual interest is hot.

4. Consider your history with him

Mikayla, a physician I met once at an event, spoke to me about how a guy she was interested in ghosted her at the drop of a hat after the first date. She asked me, “I miss him though and wonder what went wrong, I wish I knew what the problem was. Should I reach out to him?” In such a case where ghosting has already happened, there is probably no chance of a healthy relationship. In such a case, it is best to stop expecting closure and move on.

5. Has he texted you first before?

Women texting men is not a big deal. But you definitely don’t want to incessantly text a guy who gives you no signs of interest as it will make you appear as someone with low value and low self-esteem. Unless this is someone you are speaking to for the first time in your life, do consider how much conversation this person has made with you in the past. So if you’re wondering, “Do I text him?”, think about this: Have their responses been warm or cold to you?

6. It helps men commit to you

Quality men will always be happy when a woman shows real interest in them. “So should I text him first if he hasn’t texted me?” Take it from this Reddit user who says, “The woman who ended up being my wife constantly texted me, so much so that it interfered with my workday. I was actually still playing the field when I met her, I wasn’t sleeping around but I was dating other people to see who I liked. Although it was annoying at times, it did tell me she really liked me, so it probably played a role when deciding who I was going to commit to.”

Related Reading: Do I Like Him Or The Attention? Ways To Find Out The Truth

7. Do his intentions match with yours?

Bianca, a distant cousin of mine, was stuck in a situationship with a guy from her yoga class. She said to me once, “He said he will text me to make plans for coffee someday but has not even reached out. Is he going to text? Does he like me? What should I do?”

When texting a guy, try to know his intention with you before you come on too strong. There may not be a point in making so much effort for a man who does not want to reciprocate. Stay strong and reach out if you think he does appreciate you. In Bianca’s instance, she messaged him, “Hey, I am available sometime toward the end of the week on Thursday or Friday for coffee if you want, let me know if you have time then”, to which he politely declined. She made an effort and it was clear that the guy was not thinking of her in the same way. Conversation closed, and Bianca never reached out again.

8. It statistically works

A landmark study has revealed that on dating apps, the odds are often in favor of the brave woman who messages a guy first because 30% of those messages turn into a conversation. Women are 2.5 times more likely to get a response than men if they initiate contact. So if you two are conversing on a dating app and you are interested in this guy, do not hesitate and send him that text message.

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9. Don’t text if you just want a distraction

Don’t worry, a lot of us have been there when a difficult breakup or mental health phase leaves us crippled and we don’t know how to pick up the lost pieces. A lot of us hop onto dating apps or start meaningless conversations by sliding into DMs or texting someone, hoping for a distraction. Even if you are having a hard time, be cognizant and aware of your condition, and do not rope someone else into it. The important question is, are you even ready for a new connection, or even a casual fling at best? If not, then he probably does not deserve it.

10. Is he your ex?

Texting conversations with your ex is probably a bad idea. Even if you two are on decent terms, initiating conversations to create a daily routine of staying connected with an ex-boyfriend may not end well. You can have respect for them, but don’t talk to them every day. Making mistakes every once in a while is okay, but try not to become dependent on them once again like you used to be.

11. Consider what stage your connection is at

“Should I text him if I haven’t heard from him in a week?” To answer this, we first need to ask you: How often have you been conversing with this man in question? If you two have been texting for two weeks or so, then it is normal for you to send him a good morning message and if he replies, then you can try to hold a conversation throughout the day.

However, if he is just someone that you reach out to in your free time occasionally, then perhaps it is best to keep things intermittent and you should attune your texting habits that way. In that case, maybe the safest bet is to leave the ball in his court and see if he shows any interest in you.

Related Reading: 11 Warning Signs Of Lack Of Emotional Connection In Relationships

12. Has there been a long period of silence?

Maybe you two have simply been occupied by other obligations, and are dealing with bad days or are just not interested in each other anymore. Perhaps a month ago, you two engaged in romantic texting frequently, some pretty high-value banter, and were trying to develop emotional intimacy. But all that has fizzled out now.

In such a case, starting a conversation like the old days may not be feasible. But if you want to know if he is still interested in you, no harm in hitting that send button and asking him straight up if he is still available and interested in starting things again.

13. Men want to know if you truly like them

Men can be pretty brutal when it comes to judging who cares for them, and are equally hoping for women to make an effort for them. Take this Quora user, for instance, who thinks that a high-value woman who cares for a man will always show she cares. He says, “If she never texts first, then she’s doing it because either she KNOWS you’ll text first again or she’s not showing interest in you. So test her, and cut her off for like a week. If she doesn’t say anything then at least you know where you stand.”

should i message him
Text him if you truly care about him

14. Are you drunk or not in your senses?

“Do I text him to tell him I like him?” — Not if he thinks you’ll forget all about it the next day. Also, it’s usually not cute to text a guy when drunk, especially when things are very new between you two. While some might be receptive to it and entertain it as pure fun, it does not necessarily set a good precedent for your relationship.

Even if he is the one reaching out to you, in certain situations, the best way is to probably not respond instead of shooting off multiple messages. Consider this one of the primary texting rules.

15. He never texts first but always replies

If he replies without waiting for too long, clearly, he is interested and does want to talk to you. Women should demand an equal footing in the relationship where the guy also initiates a meaningful conversation. Maybe you can hold off a few times to test him and see if he puts his foot forward in starting a conversation with you.

When Should You Text Him First?

A guy’s perspective on texting is different from a girl’s when the idea of a love interest is on the cards. While a girl feels that texting first might make her look needy, on the contrary, a guy feels that when she hits send, she likes him so much that she is eager to start a conversation with him. He’ll text, but he will be happy to receive texts from you too. So if you are thinking, “I like a guy, should I message him first?”, then just go ahead and do that.

Given that there are so many new unsaid rules of texting while dating, figuring out your next move can leave you crippled with fear. You’ve been thinking and overthinking, “He hasn’t texted me. Should I text him or leave him alone?” But take a moment to remind yourself that perhaps he too may be in throes of similar dilemmas and that’s why he hasn’t reached you yet.

As a result, two people might keep waiting for the other to make a move and send that first text, and let a connection with potential waste away. So, if you want to text first, you definitely should. You don’t need a dating coach to walk you through it. Here are some solid reasons it’s a good idea:

Related Reading: Dating Etiquette – 20 Things You Should Never Ignore On A First Date

1. It shows confidence and men like confident women

Should the guy or girl text first after a date? This is a common question in the modern-day dating world, and frankly, there are no right or wrong answers here. However, if you do decide to text him first, you are sending across the message that you’re not afraid to take the reins of the relationship in your hand.

It indicates that you are confident enough to break away from the norm without caring about coming off as desperate or being seen as clingy girlfriend material. The ability to follow your heart shows that you are sure of yourself. Sometimes, texting first speaks volumes about you as a confident woman.

2. You should take the leap if you don’t wish to play mind games

Isn’t that what a wholesome relationship looks like? No stupid mind games as that is the worst thing for your connection. It’s better to double-text than to withdraw completely. No see-saw of power struggle in the relationship. No gender stereotypes and biases about what a girl or a guy can or should do in a relationship, but a level playing field where both partners are equals. Texting him first shows you are not into playing games but are considering his companionship.

“Should I text him first after no contact?” Why not? If you had been giving each other space and you want to interact now, then shoot him a text; what’s the harm? If he replies cordially or warmly, go ahead and have a conversation. If he doesn’t, forget it and move on. No, you don’t lose your dignity, so don’t feel bad about it.

3. Your date might be waiting for you

While you are out here asking all your friends, “Should I message him?”, he is probably out there staring at his screen 20 times a day hoping that you do. Maybe he’s even more shy and introverted than you are. And in that case, it’s perfectly fine for you to make the first move. Perhaps he thinks you’re out of his league and is unsure of himself. As we said before, there is a good possibility that the guy in question is overthinking this a lot more than you are.

Related Reading: 12 Things To Know When You Are Dating an Introvert

4. Because you want to

Forget all the other things about dating and texting. What if you just really, really want to talk to him? Should you be holding back then? Probably not. Do not torture yourself by trying not to contact him and telling yourself, “If he likes me, he’ll text me.” Don’t let your emotional attraction fizzle away. And if you are wondering, “Is he waiting for me to text him first?”, he probably is.

5. Texting him first after a date could work in your favor

To text or not to text after your date? Sending at least one message to the guy you went out with really can’t hurt, can it? You’ve come home from a date and spent a fair share of your time agonizing over “Should I wait for him to text after the first date or should I message him first?” All the while typing and backspacing a message you’re dying to hit send on.

If you do believe that the guy has true intentions with you and you had a great date with him, then you should consider jumping in with both feet. Even if that means texting him first. If he cares enough, he’ll respond. He will, in fact, value that you had as good of a time as he did.

Related Reading: Can A Man Sleep With A Woman Without Developing Feelings

6. Texting him first after sex could be a turn-on

Texting after sex is yet another gray area that sends people into an overthinking spiral, especially if you’ve just begun dating, are in a casual dating scenario, or have ended up in bed without talking about what it means. But let us tell you that it helps you keep the ball rolling, to develop more interest and an emotional connection.

“Should I message him first or does that reek of desperation?” You may find yourself mulling this question over and over again while also checking your phone every two minutes to see if he has said anything. But texting a guy isn’t supposed to be all that hard. If you want to take things further with this person, then that send button is your new friend, it is as simple as that.

7. Texting him first for no reason can make him feel desired

“Should I text a guy first to talk to him?” Well, as long as you’re not sending too many messages and bothering him, it really cannot be a bad idea. Quality men appreciate a woman who shows interest in them. A simple “Hey!” is enough to let him know that he’s been on your mind, and that ought to make him feel all warm and fuzzy about you, allowing you to fortify your connection.

When you text a guy first, you’re also in a better position to steer the conversation in a direction you like. If you take it a step further and choose to flirt with your guy over text, it’s sure to send sparks flying, and how!

Related Reading: How Do Guys Feel About Girls Making The First Move?

8. Texting him first can get you a second date

In the early stages of dating, many men are sometimes coy about coming off as too strong or aggressive. This is why they might not initiate going out too much, but keep double-texting you throughout the day. While we are not asking you to take up all the burden of initiating dates, texting him first now and then can lead to a great opportunity for him to show more interest. It’ll help him feel more comfortable opening up to you. Reaching out first is the right move after your first date, as it may just grant you a second date!

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When should a girl text a guy first?

9. “Should I text him first if he hasn’t texted me?” Yes, if it helps resolve a fight

Who should text first after an argument? The answer to this question shouldn’t be gender-specific. There is no reason that you should let issues between you fester. If you’ve had a falling out with your boyfriend or romantic interest and have something to say to him, by all means, pick up the phone and shoot him a text.

Related Reading: 13 Examples Of Mixed Signals From Guys

What Are The Rules Of Texting For Girls?

Now that we’ve addressed the “should I text him first?” question, let’s take a look at another important aspect of texting about dating: how to text a guy the right way so that you get the desired response from him. For instance, even if you decide to text him first, you need to address the when and what. And that’s where these tips come in:

1. Don’t start with just “Hey” or “Hi”

The casual “hey” does not sound sincere enough in the first place. It seems like you are trying too hard to keep it cool and casual. Starting a conversation with monosyllabic words is not okay. So, try to add to the “hey” or “hi” with something interesting that will carry the conversation forward. Perhaps you found a hardcover copy of Catcher in the Rye that he has been looking for, or you tried the beer he recommended. Keep the conversation open-ended so there’s plenty of scope for his reply.

Related Reading: Sending The First Message On A Dating App – 23 Texts For That Perfect Start

2. Playing hard to get is really not cool

Is not texting first your idea of playing hard to get? If so, then it’s not cool. The rules of texting are different now. Men don’t have to be the pursuer here. Frankly speaking, texting first means you are ready to take the reins in the relationship, and who doesn’t like a woman who can take charge? If you two have not been talking and think this tactic is going to solve problems, then you are wrong. It is best to just talk about it then.

Related Reading: 7 Bad Dating Habits You Need To Break Right Now

3. No texting while you are drunk

Waiting around for a man to text you can be tiring. Three shots of tequila, two daiquiris, and five beers might make it seem that it’s okay to drunk text your date, but it really isn’t. Your present beau might not like it. There can be some regrettable drunk confessions that would not play well if you have just started hanging out. Text only when you are sober.

4. No angry texting

Put your phone away if you are mad. This is one of the most important rules of texting. He doesn’t need to hear you rant and vent a lot. You’ve only just started knowing him, so texting, while you are too emotional or sad or upset, is a big no-no. Sharing too much before you’ve developed a certain level of comfort and intimacy can border on emotional dumping, which can leave him feeling drained and might push him away. Or you might end up saying things that you regret later.

5. Don’t message when he knows you will be busy

Avoid texting when you have already told him you will be going out for dinner with your sister or a night out with your friends. Give due importance to people other than him and that will define your personality. Hanging out with people suggests you have your own life outside your romantic interests. It is also suggestive of the fact that if you were to get into a relationship, you would have a life beyond him. When you give him space and he has a chance to miss you, he is going to text.

Related Reading: Every Girl Should Do These 5 Things On Their First Date

6. Use GIFs and emojis with caution

Now, this can be tricky. You have to judge if your guy’s perspective on texting allows for GIFs and emojis as an acceptable mode of communication or if he likes words for communication. Send a meme or GIF and see if he gives verbal replies or one-ups you with a better meme. If you can bond over a meme, it opens up avenues to talk about cross-cultural references with a lot of laughter. Perhaps something you could talk about on your next date?

7. Don’t text if you have nothing interesting to say

Craft your words carefully and craft your thoughts carefully too. “Should I text him first?” When you find yourself wrestling with this question, take a moment to assess if you have something interesting to say to him. Sending a “Hi” with nothing interesting to say can dampen his spirit. Before you text, think of some fun conversation starters; something he might have mentioned on your date, a review of a place you have been to — things like that.

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8. “Do I text him at night?”— Not the best idea

Do you want to talk to him? Choose the day time if you’re both just getting to know one another. Like weekend and weekday texting, there’s a rule about not texting too late at night. Yes, there’s a chance he is awake but texting him at bedtime is suggestive of texting him only when there is nothing to do.

It may also seem like an intrusion. And you don’t want that. You might also end up sending the wrong signals if you text him at night. He might think you want something more than just a conversation.

Related Reading: 35 Cute Questions To Ask Your Crush While Texting

9. Grammar check before sending your message

Nothing turns one off more than text messages riddled with typos because they make deciphering the meaning that much harder and a lot of context gets lost in translation. So, avoid texts that read like “wts up w u?” By all means, keep up with the dating lingo and use it to make the communication flow smoothly. But make sure that you’re using the terms and phrases right so that you don’t end up conveying something you don’t want to.

Key Pointers

  • If you are always asking yourself, “Do I come off as needy or desperate if I text him first?” then remember that it is not always bad to be the one making conversation first, but if you do it every single time — then try holding off to see if they do the same for you
  • Texting someone first is a great way to let them know you are thinking of them 
  • When you do text first, say more than just a “Hi” and try to make engaging conversation with them
  • The stage at which your connection is at, should determine how often you should be texting this person
  • Try not to reach out to them when you are too emotional, angry, or drunk

Now that you know the answers to “Should I text him first?” in different possible scenarios, we hope you’ll be able to dial down the overthinking and focus on engaging your man in deep, meaningful conversations. So, let the texting begin! Just don’t bite off your fingernails while you wait for his reply.


1. Does it matter if you text first?

It doesn’t really matter who texts first, and texting first definitely doesn’t mean that you’re desperate, needy, or clingy. If the moment feels right and you have something interesting to say, by all means, go ahead and send that text.

2. Why does he wait for me to initiate contact?

If a guy waits for you to initiate contact, there could be two distinct possibilities — One, he is a shy guy or feels that you’re way out of his league and does not initiate contact due to fear of rejection. Second, withholding contact could be his way of manipulating you and making sure you stay hooked, without him having to make any real effort in building a connection with you. Perhaps he isn’t as emotionally invested as you are and just wants to string you along as long as you take all the initiative.

3. Should I text him first or wait for him to text me?

The answer to this question depends on your circumstances. If you’re genuinely interested in this guy and feel that he, too, may be interested in you, there is no harm in texting him first to break the ice. However, if you’re not sure about how you want to take things forward or his interest in you seems lackluster, perhaps it’s best to wait for him to make the first move.

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