What Questions To Ask A Guy When Dating

If you want some questions to ask a guy to know his intentions, you’re in good hands.

I have 5 questions you will ever need in order to know what he wants for sure.

There’s nothing more important when you’re dating than to figure out whether you’re dating a good natured, honest and commitment-friendly guy.

You wouldn’t want to get invested in an avoidant guy or a toxic and manipulative guy if you can help it.

So you need to figure out what kind of guy he is as early as possible.

Here’s a specially crafted quiz we made that will help you figure out how commitment-friendly your guy is.

Plenty of men have perfected their pick up “game”, and you want to be able to figure these guys out, and even better, put them on their back foot.

Some guys know how to prey on women just to get sex from them. They will present themselves as your ideal guy, but secretly they’re anything but.

Of course, there are plenty of guys out there who are the real deal as well (I’m married to one, and so are many other women), so don’t ever lose hope.

One way to suss him out is to have some high value, spontaneous and playful questions to ask a guy to know his intentions.

We believe that you shouldn’t use serious and boring questions when trying to uncover a guy’s intentions.

Let’s talk about why that is right now.

Questions to Ask A Guy to Know His Intentions Should Be Playful

Before we get into them, let me be very clear on why you need playful questions rather than serious, “interview” like questions.

The point of having questions to ask a guy to know his intentions is to create moments of spontaneity, because that creates more fun in romance.

With playful questions, you will find that a good guy will enjoy them and feel more attraction towards you.

However, if you’re dealing with a narcissist or even a psychopath, these playful questions will actually reveal him.

So the benefit is two-fold.

Every toxic guy has a tired old pattern of behaving in dating. This tired old pattern is easy to catch out if you’re smart enough to be playful and to banter.

The all-important intention with playful questions is also to build high value banter with the right guy. 

Here’s the challenge with the more “serious” questions to ask a guy to know his intentions:

You run the risk of creating disconnects with good, high value men when you lead with serious, boring, interview-like questions.

Not all serious questions are bad of course, but there’s huge value in questions that create spontaneity.

Whilst all good, emotionally healthy men want to feel emotional attraction and emotional connection with a woman, manipulative players who have their own game to play will not want to feel these things.

That’s not their goal. 


Because they don’t want to fall in love.

They want what they want (ie: sex) at any cost, and they usually don’t care about you.

So if you lead with questions that create playful banter with a guy, you’ll reveal the low quality guy and excite the high value guy.

High value banter is what creates real romantic tension and triggers emotional attraction as well as emotional connection with the high value guy.


Here are five high value and playful questions that will build spontaneity and emotional attraction with the right guy, whilst revealing the bad intent of the “wrong” guy.

Question #1: “So when do I get to meet your other girlfriends?”

Said with playfulness and a smile of course. Or a smiling emoji if you’re asking it through text message.

The idea here is to put him on the spot and create a moment of playful spontaneity. From that spontaneity, you can get a more accurate picture of his character.

Here’s the thing…

Men who often lie to women are very good at putting on a show. It’s well rehearsed.

Your job is to see past his facade and not get caught up by his “show”.

The way to do this is through playful spontaneity.

Any guy who is actually messing around with many women will have to work extremely hard not to be taken aback when you ask him this question.

Is it mean to ask this question?

No. It’s done through playfulness.

Let me ask you, Is it mean to waste months and years of your life on a player?

Well, yes. It’s mean to yourself.

So be bold, and don’t be afraid to not be boring.

Question #2: “So how long is it going to take for you to murder me in cold blood like many other charming psychopathic serial killers?”

Why is this on the list of questions to ask a guy to know his intentions?

Because it’s unexpected. As such it creates a moment of spontaneity, hopefully a playful one.

From that place of spontaneity, you get to who he really is behind the masks and facades.

And because of the very slight chance that he is in fact a psychopath or (god forbid), a serial killer, you’ll see that look on his face.

Which look? You may ask.

The surprised look of “how did you know my plans??” on his face.

No psychopath expects any woman to be this smart and this playful about such a serious and horrible subject.

So, ask it with one intention: to watch how he responds. There are three possible responses a guy could give you here.

  1. He’ll get defensive (let’s hope not) and perhaps react in anger, accusing you of being a jaded man-hater
  2. He’ll reassure you that he would never have such intent (and perhaps worry that you’ve actually encountered a man like that in the past)
  3. He’ll be attuned enough to see that you’re just bantering with him, and he’ll banter back playfully.

Believe it or not (because honestly it’s hard to believe it as a woman), a lot more men than you think will respond with playful banter when you ask them this.

Emotionally mature and healthy men naturally “get” banter, because they’re connection oriented!

And when a man genuinely wants to connect with you, he will easily attune himself to your intentions.

We also cannot forget: banter is the language a lot of men use with each other to communicate.

It comes naturally for securely attached men, and it serves a great purpose for them: to reduce tension and to form connections and trust with one another.

Securely attached women are also more comfortable with banter, though they may have specific tastes about what type of banter they prefer.

By the way, would you like to find out whether you’re securely attached or insecurely attached? You’re in luck, because we have a super quick and easy quiz that will help you find out…

(Why is this important? It is because your core attachment style largely dictates and influences what happens in your relationship. Thus it’s imperative you understand your core attachment style!)

Question #3: “So…what does your wife think about you meeting me?”

I can’t help but laugh at this one myself (haha).

If he really does have a wife, you’ll catch the guilty look or the defensive posture instantly.

If you’re afraid to use this, don’t be!

Most good men will know exactly how to deal with it, and they’ll also find humour in it, because you’ll only be asking the question from a playful place.

Again, we are seeking those moments of spontaneity in order for us to discover more of the truth.

This is also helpful for building emotional attraction because it leads into roleplaying banter, which is extremely important for igniting that romantic tension with a guy.

It can even be useful for those in a relationship or marriage in order to keep the spark alive.

Just as an example, when I approach my husband in an overly affectionate way, it’s not rare for him to say something playful like this to me:

“Um… I have a wife you know…”


“I’m not sure how my wife would feel about this.”

It’s fun and it’s a harmless way to build a solid connection and excitement between the two of you.

If you’d like more examples you can copy and paste, let me invite you to take our free class on high value banter. (My man David runs this free class and I highly recommend you listen to it.)

Question #4: “Are you always this charming towards every girl, or am I just special?”

I once asked a question kind of like this to a guy whom I suspected was a player.

And whether you ask this question seriously or playfully, a player will usually be easy to spot through his response.


Because players usually have tunnel vision. They’re not attuned to you as a woman. They have no idea where you’re really coming from or what you’re feeling.

They are myopic in their approach to women in that they are blinded by desperation and the need to achieve their own goal.

As such, they’ll usually be either very quick to deny that they’re being particularly charming, or they’ll fire off a bunch of compliments, insisting that you’re the special one whom he cannot help but be charming with.

Again, it’s in those moments of spontaneity that you get a glimpse of his truest intentions. Ask yourself, is his response attuned to you and your feelings? Is his response too much or too little?

Does it feel like his response is tainted with avoidance behaviour? Does it feel like he is unnecessarily defensive?

All these little clues help to paint the bigger picture, which is going to help you determine what kind of man this is.

Question #5: “So just let me know when we plan on breaking up because I need to get myself mentally ready to meet [insert celebrity name].”

Again, this is another question that is coming out of left field and thus completely unpredictable.

Of course, this is said out of playfulness as a way to create a moment of playful spontaneity.

It takes a lot of energy and willingness in order to be attuned to spontaneous playfulness.

If a man isn’t willing to stay attuned to that, then he either has ulterior motives or doesn’t care about you enough.

The best kinds of responses from these questions come in the form of playful banter back at you. By banter I mean something that he has come up with spontaneously in response to your question.

Let me give you an example…

He could respond with something like…

“Sure, I’ll make sure to text you the date of our breakup, it will be exactly the morning after I meet [Insert another celebrity name].”

This kind of response shows that he’s willing to play along, and stay attuned to where you are at.

Of course, the larger part of his response is not in his words but his non-verbal communication. Is he congruent with what he’s saying?

Is he playful back? Does he even enjoy playing along with you?

Final Note On The Questions To Ask A Guy To Know His Intentions

Remember, the power here is not merely in these questions themselves.

The true power is really in your ability to bring playful spontaneity to the table and your ability to stay attuned enough to feel his intentions.

People, especially adults tend to be very good at lying, even if they are just little white lies. This is especially true for both men and women in dating.

We all want value for ourselves and we all want to put our perceived best foot forward.

So your job is to see through the facade and the masks that we all wear. Your job is to not fall for the words, but see him as who he is deep down inside.

Author Profile

Sarah Meere
Sarah Meere
Executive Editor

Sarah looks after corporate enquiries and relationships for UKFilmPremieres, CelebEvents, ShowbizGossip, Celeb Management brands for the MarkMeets Group. Sarah works for numerous media brands across the UK.

Email https://markmeets.com/contact-form/

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