How To Start A Conversation Over Text (For Grownups!)

By: Carlos Cavallo
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When you meet a guy or just want to start up a relationship with a man these days, you need to know how to start a conversation over text. Luckily, this isn't hard to do if you know what he is looking for.

Sometimes it's hard to come up with the right thing to say, especially if you're trying to make a good impression. And if you're over the age of 25, you may have a different focus.

dating advice how to start conversation using text messaging How To Start A Conversation Over Text (For Grownups!)

These days our phones are our primary communication tool. Ironically, we mostly use them for everything else but calling friends and other people. Most of the time, we use our phones for texting only.

And, depending if you're an introvert or extrovert, you may find it difficult to think of what to say for that all-important first message. Some people might send a text without a thought but if you're like me you probably agonize over what to send in that text.

  • You don't want to come across as if you're needy or insecure. And you also don't want to embarrass yourself in the process.
  • You also don't want to appear as if you're not interested...
  • You also don't want to appear too interested...

It's no wonder that people go crazy thinking about this stuff.

IMPORTANT: What You Should Think About BEFORE Texting Him!

Consider that before you text the guy you should think about who it is you're really texting here.

  • Who Is he?
  • Is he a friend?
  • Is he a romantic interest?
  • Is he an acquaintance that you would like to turn into something more?

When you know these answers in advance, you will know what to do and what not to do much better.

Another question to ask is:

How Long Have You Known Each Other?

If you barely know the guy, you want to get as much information as you can to work with. This doesn't mean you want to flood him with a thousand text messages. But you do want to give up some information from yourself first.

Guys find it hard enough to text women in the first place, so you want to help them as much as possible.

Chances are he is wondering exactly the same thing you are: What to text you, and what not to text you. And if he doesn't have an answer, he will just not text you at all.

Which means you have the responsibility for getting this thing off the ground.

If you've known him for a while, they should have some familiarity. Which means you can be more playful with your messages.

But even then, it helps him if you offer up some effort into a thoughtful question for him.

What's Your Connection Level?

Another good question is how well-connected are you?

Assuming that this is a guy that you want to date, you should be thinking about how much connection you have with him. Remember that every communication you have with a man is an opportunity to connect deeper with him.

16 How To Start A Conversation Over Text (For Grownups!)

If you want him to invest himself in you, he needs your help in finding that emotional hook.

TIP: DON'T Start Texting Him With This...

There are a few things you definitely don't want to start with. Here are a few of them:

  • "Hey"

This is kind of the default for a lot of our text conversations. It's a simple, no-frills way to start a conversation with very little risk, but the problem is that it gives the other person nothing to work with to keep the text conversation going.

It's not easy to start a conversation with just a one word prompt. And it usually feels like the person who said "hey" is just trying to avoid a little vulnerability.

  • "Hello"

This one is right up there with "Hey." Again it's just too little for the other person to work with. Instead say something that gives them something.

  • "Hey You"

Yup, this is just another variation of "Hey."

  • "What's up?

This one isn't terrible, but it starts right out with an expectation that the other person needs to put the effort in first. Which is a little unfair considering you're starting the conversation. Instead, why not tell them what's up with you, then ask what's up with them.

  • Random Emoji

Some women like to send an emoji to a guy as a playful way to start a conversation. But again if you're not giving him any information, he's left thinking "WTF? What does she want?"

If you're confusing him, you're losing him.

dos donts starting text conversations with men How To Start A Conversation Over Text (For Grownups!)

One of my top bits of advice is to cut down on the amount of emojis you use with men. Guys simply don't use emojis in text all that much, and we sometimes have a hard time understanding what you're trying to communicate with them.

The easiest way to think about this is, if you wouldn't want him to send it to you, don't send it to him.

TIP: Remember to not go into overload

One of most common mistakes women make when they text a man is texting too much at once.

Never text a man more than:

  • -  one question
  • -  one statement
  • -  one idea

It's not because men are stupid and can't handle more than this. It's that he's linear in his thinking. He won't take your text of three questions and answer all three questions. He'll just answer the last question he sees.

And then you'll be frustrated wondering why he won't answer your other questions.

The reason is that it's an overload for men because we take things one at a time. Women tend to multitask.

So keep each text message simple, and send only one thing at a time.

And remember that when you send too much information at once, in one text, it makes you look like a try hard.

A try hard is someone who's trying way too hard because of their uncertainty or insecurity. Which can be endearing, but it can also push him away.

TIP: Make sure you time your text conversation right

You don't want to send them a text when either he can't respond or when you can't respond.

You also don't want to send them a text on Friday night at 9:30 PM when you should be out on a date. There is value in you looking unavailable as well.

In fact, you don't want to even look at your phone during prime dating hours on the weekend. Not only will this motivate you to get out and meet more guys, but it will make him think you are every bit as valuable as you think you are!

You also don't want to text him first thing in the morning. Guys aren't that into text conversations before work, or even before coffee for that matter.

And you definitely don't want to wake him up with a text. Unless you're lying right next to him...

Before you text him, consider the timing - and the time of day.

TIP: Make Sure You Stand Out

This is a tricky balance for many women to achieve, but you want to stand out to him without blending into the crowd.

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Most women are used to not standing out when they're with a group of other women. Ever since you were in grade school this was frowned upon by other girls.

Now, I won't go into a bunch of evolutionary psychology here, but just keep in mind that your natural instincts will be to blend in more than stand out. But that will hinder you when it comes to guys.

A guy needs you to stand out.

You have to find a way to make yourself look different enough to capture his attention.

An easy way to do that in a text conversation is to ask him unique questions. The questions that other girls wouldn't even think of.

Stuff like:

  • Where would you live if you could live anywhere?
  • What game show do you think you could be a champion on?
  • What's your spirit animal?

You have to challenge him out of his mindset. And in so doing get him to see you as being unique.

TIP: What if you're texting him after an argument?

This is one of those tricky situations where you want to know how to start a text conversation with a man, but it's going to be a little emotionally awkward.

The best way to do this is to not try too hard to seek validation or approval from him. It's only natural that you want to return to normal with your relationship. And you're very likely to send him a "Are we okay?" text to find out.

dos donts using text messaging to start conversations with men How To Start A Conversation Over Text (For Grownups!)

But the best thing to do is to simply pick up right where you left off. It's the confident thing to do, and it's probably where he just wants to pick it up from anyway.

If the subject of your argument comes up again in your text conversation, don't deny it or pretend it didn't happen. But don't Make your argument the focal point of your relationship.  Just keep moving forward.

Just send them a him that has the maximum potential to start him talking.

Definitely do not send a text that is looking to confirm a future date, or asking him something like: "Are we still going over to Wendy's on Saturday?"

These are messages that guys get all the time from women, and it frustrates him. Yes, even a text like that will feel needy and insecure to him.

If you feel you may need to apologize, that's a great thing to throw into that text. Just go light and assume that he's going to accept it.

And there is a time for sending him this text: "Are we okay?"  But only if you can be okay with it not being okay for a little while.

TIP: Starting a text conversation after a long break

Another situation where you may need to restart the excitement and fun is when there's been a long break in your communication. Typically this happens after you've taken a break in your relationship.

Again, you don't want to make it seem like you're walking on eggshells around him. The best thing to do is to jump right in with a warm, fun, friendly text that lets him know nothing has really changed in your feelings.

08 How To Start A Conversation Over Text (For Grownups!)

That's one of the things that guys are actually a little insecure about. He doesn't know how to ask or figure out if you still feel the same way as you did. And he doesn't want to ask. (Men hate it when the woman in his life is angry. Guys are driven to make women happy.)

If it's been a few weeks, there's nothing wrong with acknowledging the time gap at the very start.

  • EXAMPLE: "Hey I know it's been a little while since we talked -  I just wanted to connect and..."

And then you simply launch into the conversation.

TIP: Try not to use quirky, awkward tricks in your text messages...

It's best to not fake a "mistake text." A lot of women think about using these as a tricky way to start up a conversation. Especially with a guy they're trying to reconnect with.

An example of a "mistake text" would be sending him this:

"Going to the store, be right back" 

Hoping that he will respond to it and you can say "oopsy" afterwards. ("Oops, that was for my roommate...")

If you're going to get tricky like this, first ask yourself why. Why do you need to play that game?

Chances are you're getting tricky with your texts because you're afraid of putting yourself out there and being vulnerable.

That's fine, but resorting to trick texts is not a good way to work around your fear.

TIP: The Best Way To Start A Text Conversation?

It's simple. Make the focus of your text learning more about him.

rules to follow is there right time to text him How To Start A Conversation Over Text (For Grownups!)

I discussed this with women all the time: It's rare for a man to feel like a woman genuinely wants to get to know him as a person. Guys are used to hearing a lot of nervous talk from women, but not a genuine desire to discover HIM.

You've probably heard a guy spend a good amount of time either bragging or showing off on your dates, too.

The source is the same: insecurity and nervousness.

Hey, we've all been there. We all want to make the best impression possible.

And the same thing is true for that opening text to him. If you can make it about him, he'll be more likely to answer. 

Send him a question about HIM. Everyone loves to talk about themselves. And he will already understand that you're interested in him simply by asking the question. You don't need to overextend yourself to let him know you're interested.

TIP: Never ever forget the power of the question...

Also, if you feel the conversation is stuck too much on you asking him questions, just say this:

"Ok - I've asked you enough questions...  your turn!"

If he struggles, or doesn't ask questions about you, he's not really interested or into you.

This is fairly simple and straightforward, and it's important that you understand.

Let me say it again - if he doesn't ask questions about you, he's not interested in you.

"But Carlos - what if..."

No! There are no exceptions to this rule. If a guy is into you, he will ask questions about you.

Remember my advice: STOP WATERING DEAD PLANTS!

TIP: If You Want A Date With Him...

Once you've gotten the conversation started, inevitably you're going to want to take it somewhere.

I'm assuming you want a date with this guy. Or some opportunity to get closer to him.

But you also don't want to do all the work, because then you'll never know if he's really interested in you.

You want to feel pursued. You want to feel wanted.

So you definitely don't want to do all the work for him.

The best way to do this is this:

Just drop a hint, and keep dropping hints until he gets it.

You should never ask a guy out point blank. I don't care how many "empowered" advisors out there tell you to. 

Again, for the simple reason that you need to know he's actually interested in you and that he would put in the effort to win you over.

There's a reason that fairy tales are so important to women. You know you want him to show his desire for you - just like a Prince performs a quest for the Princess.

After all, if he wouldn't even ask you out, you would never really know if he was interested.  And you wouldn't know if he had the courage to do what he had to in a relationship with you.

how to start a text conversation with men How To Start A Conversation Over Text (For Grownups!)

Would the man you're with now slay a dragon for you?

Let's face it: guys who don't take initiative are duds, not studs. You don't want to date him, and you definitely wouldn't want to marry this kind of guy. 

The best way to start a conversation with a guy you want to date is to tell him about something you're ALREADY going planning to do, then see if he's interested.

EXAMPLE: "Hey, I'm going over to hike in Muir Woods this Sunday... You still up for that walk in nature?"

Just offer him the opportunity, and let him decide.

The real secret is to know what he's going to say BEFORE he even says it. You gotta know how to read him!

And if you'd like to know for sure if he's actually interested , then you really need to read his signals.

Go read this article on how to read men's signals and know what he's thinking...

PRODUCT Read His Signals How To Start A Conversation Over Text (For Grownups!)

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