21 CRITICAL Questions To Ask A Guy

By: Carlos Cavallo

It can be tricky talking to men when you don't know what to say. You might find yourself stuck in silence wondering what to talk about. The best solution is to have questions to ask a guy that get him interested in you.

If you know what questions to ask, you can make him feel whatever you want. Including attraction for you.

how to build connection intimacy with men ask questions 21 CRITICAL Questions To Ask A Guy

You don't need "1000 questions for every possible situation..."  You only need a few questions that do the job right!

Questions can be conversational magic if you know what you're doing. And if you're a woman dating a man, you better know some of these if you want him to see you as different, and to get his attraction.

First of all - let's review -

Why it's so important to use questions with guys:

  • Men respond to questions - especially from women

Men have a primitive program that makes them almost compelled to answer questions from a woman.  So you never really need to worry about him going silent on you or not responding when you know how to ask questions correctly.

  • Questions awaken his emotions

Many women wonder how to reach a man's emotions so you stir his feelings for you. The easiest way to do this is to ask questions of him.  Questions can arouse his feelings in a way that no other words can.

  • Questions get him to pay attention to you

They engage his attention and keep him focused on YOU. Guys think and communicate linearly, so they will be entranced - IF you know how to ask the right questions.

  • Questions get you secret info...

A good question is like Truth Serum to men. When you ask the right questions, you can find out ANYTHING you ever wanted to know about him.

And the best part is he won't ever feel like you're interrogating him or interviewing him. If you know how to ask him questions right -  And ask the right questions.

As you might imagine, questions are the magic bullet when it comes to getting a man to respond to you. Questions can also be a magic remote control for a man as well.

As we go through this list, keep in mind that having more questions just means more things you want to memorize. And let's be real - NOBODY wants to memorize a bunch of stuff! We did that in public school, but it's not fun anymore.

So I'm going to give you a few questions that you can choose from. Use them to inspire him to open his heart up to you.

You don't want to just be a parrot, either. You want to be able to know WHY these questions work with men so that you can come with your own anytime.

24 21 CRITICAL Questions To Ask A Guy

One question you should never ask a man:

  •  Anything dealing with relationships before the 16th date...

Okay I might be exaggerating a little bit by the 16th date but honestly that's a good limit.  And the reason that I say that is because if you're the one bringing up the relationship, one of two things is probably true:

  1.  You're bringing this talk up too early...
  2.  You're asking about your relationship because you're not getting anywhere with him, and it's likely he's just not interested in a relationship

If a man is ready for a relationship, he will tend to move forward with you. All by himself!

Men don't resist the thing they want in life, any more than you do. If he's not interested in a relationship with you he will drag his feet and stall in the way that you may hear many women complain about.

And there's very little if anything you can do about it. If you have to push a man into a relationship, then you probably made a mistake much earlier that made him decide you are not the one.

(If you want to know why this happened, go read this special report on commitment...)

Let's jump in and review -

21 ESSENTIAL Questions To Ask A Man

I'm going to Run-through some really important questions you need to ask a man.  Each one has a purpose, and I'll explain how to use it as well.

Of course most of these can be used as phone texts or topics of conversation for when you're in person.

Question #1:  Take him back to being a kid...

dos donts how to talk to men ask him questions 21 CRITICAL Questions To Ask A Guy

When you ask a man a question, you should know what state you want him to feel from the question. In other words, you want to elicit a certain emotional reaction. And maybe even awaken some memories.

Here are a few ways of doing that:

  • What is your favorite guilty pleasure?


  • What is your favorite childish fun thing to do?

This question gets him to break past his own internal barriers. Most people are stuck in small talk. If you want this guy to start having feelings for you, you have to be brave and break free of the small talk.

Most women stay in small talk too long, asking questions that are so boring they could put any man to sleep.  In fact it's a common complaint from men that women are too safe with their conversation.

Most women are trying to avoid being confrontational, awakening any negative emotions, or taking any risks when talking to men. This is a huge mistake, because he will very likely lose interest because you played it to safe then if you took a risk.

Question #2:  Break Through the Wall...

One of the most important things to do is to get him to be vulnerable with you. Most women understand this and do their best to open him up.

But if you don't know how men want you to do this, you can very often scare them away.

Here's a great question to get him to start exposing his feelings more:

  • What are you most doubtful/uncertain about right now?


  • What is one of your biggest doubts?

The secret power of this question is that it gets him to talk about an area of his life where he may be struggling with a decision, or deliberating a lot.

21 21 CRITICAL Questions To Ask A Guy

I can't emphasize enough how important it is to get a man out of his casual frame of thinking with you.

Question #3:  The Origami Question...

Here's one that will really stir up some great energy in your conversation:

  • "Can you remember the last time you lost your keys? Or wallet?"


  • "Tell me about the last time you broke your phone screen..."

There are a lot of different questions in this particular vein. What you're trying to do is to ask a question about a seemingly small event that has a lot of emotional punch. I call it the origami question because asking it will open up and unfold a whole bunch of stories.

I'm sure you can think of a few more just like this.

Question #4:  Research The Other Side Question...

If you want to have some fun conversation, there's no better topic than gender. Specifically, the experience the other side has.

If you want to start up some really great conversation, ask him something like this:

  • "What's the best thing about being a guy?"


  • "What's the worst thing about being a guy?"


  • "Who do you think has it better, women or men?"

Now, obviously this question is very charged. There's a whole bunch of emotional triggers that could come up, so make sure you are fairly comfortable talking about this kind of topic with him.

But if you listen closely, you will hear very insightful information about how men perceive women. And some insights into how men think and feel too.

Question #5:  Test Their Limits Question...

things men do when falling in love 21 CRITICAL Questions To Ask A Guy

I personally love to ask moral dilemma questions. They always tease out the most interesting perspectives from the other person.

One great way to do this is to ask them what they would NOT do for money.

  • "So what would you NEVER do for $1 million?"

You can also play around with the amount a little bit to find out the threshold they have for certain things. Once you find out, you can then start to play with the question a little bit:

  • "Would you eat a snail sandwich for $50? For $100??"

Play with the situations, and the amount of money. When you find a threshold, ask them this:

  • "So what would you do with that money anyway?"

This way you find out how they value money and experience.

Question #6:  Secret Insider Question...

This question is designed to bring out interesting details about him so you can learn more about him.

It's another fun question:

  • "What job do you think YOU could get with no experience and no references?"


  • "What job do you think you could BS your way into?"

Question #7:  Awaken The Dreams Question...

what men look for in a woman 21 CRITICAL Questions To Ask A Guy

Asking hypothetical questions is a great way to get him engaged in the conversation.

Like this one:

  • "What's your dream job?"

We all have a dream job we wish we could be doing and getting paid for.  This question is easy to remember, too.

There's something enjoyable about entertaining our dreams in conversation like this.

Question #8:  Absurdly Fun Question...

Here's one that can evoke some stronger feelings, but it's worth it when you're ready:

  • "What do you think is the most ridiculous thing about life today?"


  • "What do you think aliens think is the most absurd part of human culture?

Focusing in on the absurd and the ridiculous starts to sketch how this guy thinks about the world. Which of course is great information for you to know.

Question #9:  Words To Live By...

You can also find out about his direction in life by asking about the wisdom he's heard. You can ask him:

  • "Are there any sayings that you think you live your life by?"


  • "What are the most powerful words of wisdom you've ever heard?"

And then pay attention to what he thinks is wisdom. It will probably point towards an area of his life that is important to him. And then you can explore that.

Question #10:  Wake Up The Elephant...

what about women turns off men the most 21 CRITICAL Questions To Ask A Guy

One topic that we don't talk much about but influences us all the time is technology.

Throw this question in and you'll definitely get into some deeper conversation about communication - and life in general.

  • "Do you think that technology is bringing us closer together? or pushing us further apart?"

This will definitely bring up a bit of his views and perhaps his philosophy surrounding our modern age of technology.

Question #11:  Would you rather...?

Perhaps the hands-down winner of fun questions to ask are the "Would you rather...?" questions. My son loves these in particular. So you know most guys probably will.

And the best part is that you can think these up on the spot.

  • "Would you rather eat 1 pound of your least favorite vegetable, or exercise for two hours straight?"
  • "Would you rather lose your car keys or your cell phone?"
  • "Would you rather have nosy neighbors or noisy neighbors?"
  • "Would you rather work in a group or work alone?" (Great for finding out if he's extroverted or introverted)

Question #12:  Marvel At His Answers...

Most people have seen a superhero movie at this point. And you can bet if he's a guy he has, too.

Ask him this one:

  • "If you could be any superhero from the movies or comics, which one would you be?"

Of course you can also ask him the tried but true:

  • "If you could pick any superhero superpower, which one would you want the most?"

10 21 CRITICAL Questions To Ask A Guy

Digging into what kind of power a man values tells you a lot about his personality. Listen closely to his answer!

Question #13:  Open Up The Vulnerability...

A great question you can ask a guy is this one:

  • "What is the most embarrassing thing that's ever happened to you?"

If you're not feeling that you have the right level of rapport yet, you can change it to a softer version:

  • "What's the most embarrassing thing that ever happened to you as a kid?"

This is especially good at breaking down all the barriers that we normally have on the first date. Use it to move faster when you know you like the guy.

Bringing out his vulnerability to you will actually make him feel more connected to you.

Question #14:  Figure Him Out Quick Question...

signs youre in relationship with no future 21 CRITICAL Questions To Ask A Guy

If you're meeting a guy that you met online or on a dating app, you want to know where you stand with him as quickly as possible. When it comes to online dating, you can't know too much too soon.

Ask him this:

  • "So what was it about me that intrigued you the most?"


  • "What did you find most interesting about my profile?"

You don't want this to sound like a test, but you want to listen close and hear what he says. (Warning: This could be a potentially embarrassing moment.)

If he's very general with his answer and doesn't come up with anything specific, there's a good chance he doesn't even remember your profile at all. He's just winging it - or he just wants to have fun.

On the other hand, if he's very specific, there's a good chance he's very interested.

Either way you will know where you stand.

Just a side note: just because he doesn't remember your profile doesn't mean he isn't a good candidate. A lot of guys just don't have a good memory for the details of an online profile. ( I was one of them).

Question #15: Unleash the Power Question...

One of the best questions you can ask is about what it is that really motivates him. This is especially good for you looking at him as a prospective boyfriend, mate, whatever.

20 21 CRITICAL Questions To Ask A Guy

The best way to do this is to ask him a question about his passions.

  • "What are you most passionate about?"

Then sit back and listen to what he says.

A man's passions reveal his character. And it will tell you a lot about whether or not you are compatible with him.

Question #16:  Go for the Jugular...!

Here's one that will tell you everything that you need to know -  if you have the guts to ask it:

  • "What do you find attractive in a woman?"

Most women won't ask this because she's too afraid to hear him say something that she isn't.

Put your fear aside, and ask him. He will tell you everything you need to know in order to win his heart if you listen closely enough.

And if what he says isn't you, then move on to the next candidate.

Question #17:  Peek Into The Crystal Ball...

dating relationship advice questions to ask a man 21 CRITICAL Questions To Ask A Guy

This one is great because you find out about his goals, and even where he sees himself in a relationship:

  • "Where do you see yourself 10 years from now?"

This is probably one of the best questions to ask to find out if he's really interested in a relationship or if he's just a clown winging it through life.


If he can't come up with anything very specific or interesting sounding, he's probably not very ambitious and not goal oriented. And you should move on.

Because if you're not careful, his answer could be your life 10 years from now.

Question #18:  Friends First Question...?

Here's one that will tell you a little bit about how he sees the Platonic part of your relationship:

  • "What makes a good friend to you?"


  • "What do you think a good friendship should be like?"

Most couples understand that a romantic relationship is also a very deep friendship. So find out early on what he thinks you two should be as friends!

Question #19:  Get Tricky...

Here's a great question to ask a guy that will tell you more about his character:

  • "Tell me about something you're putting off right now..."


  • "Tell me about something you're procrastinating on right now..."

This question is great to find out what his motivations are, and his DE-motivations.

Of course the next question to ask is: "Why do you think you aren't you getting that done?"

Don't sound like you're accusing him, just sound curious.

Question #20: The Big Prize question...

what men over 40 want in women 21 CRITICAL Questions To Ask A Guy

Here is a good old standard that works every time:

  • "If somebody dropped $100 million in your lap, what would you do with it?"

This is probably one of the best ways to find out all kinds of things about him...

  • How he values money
  • If he's really doing what he wants to in life right now
  • Is he charitable?

You can learn a whole bunch with one little question!

Question #21: Get Philosophical...

Every so often it's a good idea to throw out a deep think question, too.  This one is especially good because it's wide open - after he answers yes/no.

  • "Do you believe everything happens for a reason?"

It's also very hard to answer this question with just a yes or no. He'll probably launch into a very long explanation of his answer.

Listen to him! You're getting a bunch of juicy detail about him.

Question #:  And For The Big Kahuna...

Once you've established some rapport with other questions in this list, it's time to bring out the big guns.

Ask this whopper when you feel the time is right:

  • "What do you think the biggest thing you've done with your life so far is?"

Yes this is a big whopper of a question. But you shouldn't be afraid to ask it!

You may not want to pop it on the first date, but I would suggest you ask him AT LEAST on the second date.  Some women go their entire lives without ever asking their man something as revealing as this question.

You want to ask this question and then close your mouth and listen to his answer...

  • Let him ramble on for as long as he wants!
  • Listen in between the lines - listen to what he says - and what he DOESN'T say...

And one more thing -

Let me tell you a SECRET about these questions that you probably didn't know...

When he tells you his answer, you may be tempted to answer similar to his. But that would be a big mistake.

One thing most women don't know is that a man will respect you MORE if you answer from your heart. He will know the difference.

And it's actually better if you don't always agree with him completely. Men are more intrigued when you have your own opinions and answers that don't reflect his.

There are a lot of little tricks to understanding how men think about attraction... AND how they choose one woman over another to be with - and commit to!

If you don't know how men connect with you, you're probably going to make a lot of mistakes.

And I don't want you to make those mistakes anymore!

If you could find out what men think, and find out what you may have been doing wrong all this time, would you want to?

how to know you have found the one 21 CRITICAL Questions To Ask A Guy

If you want to fix your mistakes once and for all - with the man in your life right now or the next one - you need to know what his CONNECTION CODE is!

Go find out here...


Carlos Cavallo's Dating Advice Guru Relationship Tips For Women
Carlos Cavallo - Dating Advice For Women

Carlos Cavallo Dating and Relationship Guru

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