Questions To Ask A Guy Over Text

By: Carlos Cavallo

If you've ever found yourself wanting to flirt or just reconnect with a guy, you probably wish you knew some questions to ask a guy over text.

This article is going to be different, though. Instead of giving you a bunch of careless questions, I'm going to give you the kinds of questions you MUST ask him - along with some examples.

questions to ask men using texts Questions To Ask A Guy Over Text

Don't mistake Quantity for Quality.

If you don't ask him the right questions, you could push him away and totally ruin the vibe between you and him. You don't need 100 questions - you need just a few that you can remember and USE!

Remember, the most important thing your man needs to feel for you is that you GET him. That you understand him like no other woman does - or could.

And the only way you can make him feel that way is to ask him the questions that have power.

This is how you get him to fall in love with you. Through the power of text questions.

Using text messages is one of the best ways to get a man thinking about you, too. You can delight his imagination and infatuate him all at the same time. It's kind of like remote control that way!

Really quick, let's cover a few of the questions you should never ask first:

NEVER #1: Never ask him about your relationship directly

This one is tempting for many women. If you haven't seen him in a while or you're in a long distance relationship, you may find yourself panicking and wanting to talk about your relationship through texts.

Don't do it!

If there's one thing a man doesn't want to do it's discuss your relationship through text messages.


  1. He won't be in an emotional state where he feels the same love for you that he would if you were together - in person
  2. It's too easy for him to draw the wrong conclusion about your relationship if you're not there - present with him
  3. His emotions will not be properly focused on you. He could be doing anything when you text, and thinking about your relationship feels like a really bad advertisement shoved in the middle of a television program. It just doesn't feel like it belongs there. And you won't get an accurate response.

There are a bunch more reasons, but these should be enough to caution you.

NEVER #2: Never Ask A Guy 'Blue Sky' Text Questions

Blue Sky questions are the ones that are wide open for answers.

Here are a few examples:

  • "What are you thinking?"
  • "What should we do this weekend?"
  • "How do you feel about me?"

09 Questions To Ask A Guy Over Text

These questions are too wide open for him to answer accurately. Guys panic when we hear a question like this because it doesn't give us anything to hold onto. No good starting place to even begin answering it “correctly.”

And keep in mind, that's what he is thinking about when you ask him a question.

“How do I answer this correctly so that I can keep sleeping with her? And I won't make her mad?”

A man never wants to feel like he's guessing. He wants to have the right answer to avoid any hassles and keep the peace.

So even if you're not texting, you should never ask a guy a question that is this wide open. You have to know how to steer him for the answer you want.

I'll show you more about this in a little bit.

NEVER #3: Never Ask Him About His Ex

Trust me on this one: You probably don't really want to know, and he really doesn't want to talk about her.

If there is anything to learn about his ex it's that she's not around anymore.

If you're feeling adventurous you may want to ask him why they broke up. That's about the best info you can get about her.

Trust me that you want to avoid going there. You probably already know this.

NEVER #4: Never ask him about his salary

If you are just getting to know him, you should wait to discuss anything related to money. If you need to know, just take a look at his lifestyle.

And then maybe peek at one of his credit card statements later on if you really need to know if he's pulling down the wampum.

dating relationship advice best questions to ask guy using texting Questions To Ask A Guy Over Text

Guys are very sensitive to women looking at him as a source of support - or that she might be a "gold digger." So you want to avoid questions that look like you're interviewing him for your next "sugar daddy."

Besides, the truth is that so many people live beyond their means, you really can't tell much anyway. Just bide your time.

Now let's talk about those questions you can ask a guy in text.

Keep in mind that these rules apply to conversation with him anywhere and anytime. Not just texting!

Obviously talking to him in person is much better than just texting. But if you want to stay in touch and stay connected with him, you do have to use texting from time to time.

The key to using these texts is simply to slip them in as if they are something you're curious about.

All you have to do is start off the text like this:

  • “So I was just curious…”
  • Or
  • “I was just wondering…”
  • Or
  • “Just had the coolest conversation with my friend…”

It's that easy to just ask any question you want, and then ask him in a text.

QUESTION 1: Thoughtful questions

When it comes right down to it, you can't go wrong asking a guy something that makes him think a little bit. You'll impress him that you must be smart, and that he needs to step up and match your intellect.

You don't have to be Einstein or anything. But you should try to tickle his brain cells from time to time.

questions to ask a guy over text Questions To Ask A Guy Over Text

Here's a few good examples of thoughtful questions:

  • What’s one good time you put someone in their place in a conversation?
  • What’s the hardest thing about being a guy?
  • Would you do __________ for 5 Million dollars?
  • What do you think is the one most important event that shaped Who You Are?
  • If you were to die tomorrow, what is your greatest achievement?
  • What's the best decision you've ever made?
  • If you could level up like in a video game, where would you put your next skill point?
  • What's your next goal you're going to accomplish?

That last one is an excellent way to figure out whether or not he's goal-oriented or not.

I'm presuming you want a guy that wants to do something and be something in life. No better way to find out than asking this question.

QUESTION 2: Emotional Questions Texts

You may have been told that you don't want to get into emotions with a guy. But the truth is that if you know what text questions to ask, you can ask him about emotions all night long.

But you do want to be clever about it so you don't seem like a therapist.

16 Questions To Ask A Guy Over Text

That's where these questions come in. If you ask him a smart text question about how he feels about something, you can learn a lot.

Try these texts on for size:

  • Who do you respect the most?
  • Who has lost your respect in the last year?
  • When you're really frustrated, how do you handle it?
  • What do you think the most important part of friendship is?
  • Who are your closest friends and why?
  • What game do you suck at the most? (This one is good because it makes him own his shortcomings - and admit them)
  • What was the last movie that made you cry? Or at least got choked up about…
  • What’s the best compliment you ever got?
  • What are you most passionate about?
  • What's the smallest thing that makes you really happy?

You can come up with a bunch more on your own. Just find an emotional topic and texting him a few questions to start finding out how he feels about it.

QUESTION 3: Dark Side Text Questions

If there's one thing we don't like to admit, it's that we have a dark side. There's always this part of us that's just a little bit evil.

And we LOVE that dark side of us, even if we’d never admit it!

And guess which one makes much more fun in conversation? - Asking about his Dark side or asking about the goody-goody side?

dos donts asking a guy questions using texting Questions To Ask A Guy Over Text

We ALL have a shadow side. Bring out a little bit of his "dark side" to get him interested in the conversation, and fascinated with you.

Ask him a few of these questions to find out more about his dark side of the force:

  • Who is the one person you’d most like to get revenge on?
  • What was the worst thing you did in high school?
  • If you were James Bond, who would be your evil nemesis?
  • What famous person in history do you think is really overrated? (Watch out this one can get political)
  • What is the most annoying food?
  • What celebrity would you like to beat up?
  • If you were a ghost, how would you haunt? (Great way to find out about his dark side)
  • Do you think you'd ever agree to be a vampire?
  • If you could pick any superpower…? (We’ve all used this one, but it’s still a great question for finding out about his dark desires.)

Sure, you might think these texts are a bit dark. But that's the point. You want him to dig into his shadow from time to time.

QUESTION 4: Fun Text Questions

Of course ALL of these texts I'm showing you are fun. But every so often you really want to stomp on the gas when it comes to fun texting.

To be honest, most men experience texting as a game of “How long will the fun last?”

Inevitably, men are just watching and waiting for the text messages to turn serious and heavy. The more you can avoid this the better.

how to attract men using text messaging Questions To Ask A Guy Over Text

Send him a quick fun text message every couple of days to keep things light and interesting.

Like these:

  • Do you have any weird tattoos I should know about?
  • What is your most useless talent?
  • If you could have one magic spell to use around the house - but it had to be pretty boring - what would it be? (Like “wash my clothes,” or “do the dishes,” or “find me a good deal on shoes”)
  • What job do you think you could get without any experience? Totally BSing your way into it?
  • What one movie could you watch over and over and never get tired of?
  • Have you ever met a celebrity? Seen one in person?
  • What's the worst thing you've ever bought?
  • What's the weirdest website you love?
  • If you could travel back in time, when would you want to go to?
  • What's your favorite guilty pleasure?
  • What's the most childish thing you still love doing?
  • What’s the furthest you’ve ever been from home?
  • If you had to create events for the “average person” Olympics, what do you think they should be?

The longer you can keep things fun for him with text questions like this, the more engaged and connected he will stay. Save your heavy talks for when you're in person. Guys don't respond well to being probed about his feelings from the other end of a phone - whether talking or texting.

Just sayin'...

QUESTION 5: 'Lead Him' Text Questions

Sometimes you just have to know how to start a good conversation with a good question. The best questions always seem pretty innocent, and then they get really big.

20 Questions To Ask A Guy Over Text

A good "Lead him" text question will also get him to tell you more about HIM.

Here are a few you can use:

  • What’s the one thing you see everybody getting wrong?
  • When was the last time you broke your phone? (Usually there’s a really good story here…)
  • What was your closest close call?
  • What is the best single question you can ask to learn about a person? (Great for you both to explore - and discuss your interpretation.)
  • Who is your favorite author? Why?
  • What's the spookiest thing that's ever happened to you?
  • What's on your “bucket list?” (the things you'd like to do before you die)
  • If someone gave you $100,000 to throw a party, how would you spend it?

The idea with this kind of text is that you want to start off with a light question that has a long shelf life. You can keep digging into it and finding more to talk about.

QUESTION 6: Weird Text Questions

Every so often you want to throw him off with your texts. Be hard to predict.

In fact, the more unpredictable, the better.

RULE: Men are forever infatuated with women that they can't predict or can't control.

how to talk to men asking questions using text Questions To Ask A Guy Over Text

Send him a weird question every once in a while. This will freshen up your text conversations, and get him thinking in new and different ways.

Not to mention it will also give you new insights into his character. Even if you've been dating for a while, these are great text questions to send to him.

  • What movie scene has stuck with you for the longest?
  • What's the farthest you've ever driven?
  • What's the longest you've ever been awake?
  • What’s the worst thing your parents taught you?
  • What's the weirdest thing that's ever happened to you?
  • What's the weirdest subject that you know a ton about?

Questions are important because questions have power.

The most important thing you can do in a conversation is to ask questions.

  • They steer the conversation where you want it to go
  • They tell you things about him you might not find out another way
  • They lead him towards his own emotions - And towards feeling them for you

But in the end, the most important part of all these texts is knowing how to use them to get him to fall in LOVE with you.

Just sending him texts is not going to get him to fall for you - or get you a committed relationship. You have to know what to do with them.

And how to make him infatuated and obsessed with YOU.

Knowing how to talk to a guy is a critical part of dating men. It used to be that mothers would pass this information down to their daughters - but that's not happening anymore.

how to text men asking question Questions To Ask A Guy Over Text

Chances are, you didn't get a lot of guidance from your mom on this topic.

As you might already suspect -

You have to know what to say to a guy to get him to see you as "The One."

If you don't know what words open him up (instead of shutting him down), it's only a matter of time before you find him trying to leave a perfectly good relationship.

It's not that he's "commitment phobic" either!

It's because most women don't know what men are looking for from you. And you're not likely to find out by asking him. (If you've ever tried, you know what I mean.)

I recently put the finishing touches on a program to help you learn the information about men you probably missed out on.

It's all about how to flip a SECRET SWITCH in his heart that makes him see you as his soulmate...

Go see the short video presentation about it here...


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