Best deep questions to ask a guy

When you get the opportunity to strike up a conversation with someone you’ve long liked, take advantage of it. Because this is a one time opportunity, this time won’t come back.

You can start the conversation with a generic yet fascinating question. However, if you ask a question that you can’t naturally follow up on, things could soon get awkward and I don’t want that to happen so I will also tell you some follow up questions too.

The guy you want to impress is a hard-to-get person and that is obvious if he wasn’t tough he would have had a girl in his life already.

In this article, I will give you some best deep questions to ask a guy you want you to get in your life. So, without any ado let’s get started.

Best deep questions to ask a guy

  1. Which city would you choose to be born in if you had the option?

It does more than only give details about a person’s birthplace and hometown. It’s a chance to learn about your crush’s background and experiences as a child. She might finish up telling you some personal stories about their early years. 

This would only make the person feel closer to you and more at ease when speaking with you. The question might also reveal a lot about how your crush thinks and sees the world.

It’s possible that you’ll realise you don’t want to date them after all. With this inquiry, you’ll discover a plethora of more natural discussion topics to pursue.

Follow-up questions

Why do you want to be born there?

 Asking this follow-up question will pave your way towards knowing his mindset about things; you will know what he looks up at and is he deserves your time or not.

What makes you think your life would have been better there?

Not all men think about life the way a genuine person thinks. Just like it was showcased in the movie “Joker”, men have a vast mind which has thousands of things going on in their heads which at times they can’t control like us girls. Making a man feel heard and knowing his views simultaneously is one of the best ways to impress a guy (gentlemen).

  1. What has been the most important life lesson you’ve learned?

This question, like the first three, is more than just a fun way to get to know your crush. It’s also an opportunity to learn more about the person you’ve been secretly admiring. If you want her to share her life experiences with you, this is a good question to ask. 

The question will very certainly be returned to you, so be prepared to respond thoughtfully and honestly.

Follow-up questions

Have you been in a situation where you were wrong but you didn’t realise it until the end?

When a person is genuinely interested in you they won’t hesitate in telling you about what they have done and how they have tackled the situations life threw in front. 

Being wrong is not a sin but covering up or not realising or not improving is wrong.

What did you do when you realise you were wrong?

If he says he apologies or improved himself then bro you are with the right person. If not then I would advise you to consider things again.

  1. Which is more important to you: what you say or how you say?

Such questions are meant for both girls and boys but I’m asking you to ask the guy because there is a reason- It will help you understand how careful they are with words and how they can affect the other person’s sentiments. You will come to know about their point of view on conveying something. Especially, how they convey their thing.

Follow-up questions

Have you ever been in a situation when you needed to be very careful with your words?

Men have a lot in their hearts, intact, seeking someone to know it, heal it or help it. This question is a way to ask them about their past without talking about their past. If they are smart enough to understand this then they will surely be impressed.

Do you believe it is vital to avoid hurting the other person when expressing a harsh truth?

If you are looking forward to having a relationship with him then you MUST know if he is good at keeping the other person’s sentiments or is a real harsh person who can’t control his words.

  1. What does a perfect day look like to you?

A person is not known just by his average choice; knowing someone requires knowledge about their day to day life. You will learn whether they’re the sluggish kind or the adventurous type. You’ll see how they approach being productive. If your feelings are strong for that guy then in long term this question will help you.

Follow-up questions

Do you value small victories and moments, or do you solely look forward to bigger goals?


Have you ever noticed how easily we may feel sorry for ourselves? 

We usually have no problems feeling bad about what we consider to be poor performance. Punishing oneself, whether for a major or minor transgression, appears to come effortlessly to many people. When it comes to feeling proud of what we’ve accomplished, however, it’s all too easy to let the moment pass us by. 

Note that, if a person can’t be happy (not overly) then that person can never be happy for you. And I don’t think any of us wants to be with a man who can’t be happy for us.

Is your mind at ease with you?

Having your mind at ease is an advantage for others and obviously ourselves. A person who is not at ease tends to fight a lot. And why would you want to be with someone who is not willing to improve this habit? If the guy says his mind is at ease then well and good.

  1. What are some of your beliefs that the majority of the people disagree with?

Checking your compatibility is as important as knowing about their interests! Now you will say they are one and the same thing but no they aren’t. 

Their response will reveal how firmly they hold their opinions and whether or not how society thinks something important to them.

follow -up questions

Do you frequently compare yourself to others?

Whenever people compare themselves to others, they frequently contrast their best qualities with their own. There’s a biological reason for our tendency to compare ourselves to others. Our brain uses comparison to determine how we compare to others. But if you use this in a positive way then you are a better person. The whole point here is that if the guy isn’t good at it, he will compare you! 

How do you deal with the constant barrage of distractions?

In boys, there is a lot of distraction especially when it comes to girls. If the man you are talking to is the kind of person who gets distracted by every little thing, why would you want to have a conversation with him… 

Asking this question reveals their weak point indirectly.

  1. What is your best quality, according to your best friend? Do you agree with them?

You will come to know how they analyse themselves and if they’re self-obsessed or self-enlightened as a result of this. Do they value themselves and are they aware of their genuine selves or not. A person vaping themselves is the person who values others.

Follow-up questions

Do you seek encouragement from friends or are you self-motivated?

It’s a fun question to let him talking. If he is a shy person who doesn’t usually talk then this question will let you speak.

Do you ever give yourself credit for your efforts?

This question is an ego revealing question. You will get to know if he has a healthy ego or is just too much of a SELF person.

Bonus questions

Do you have an all-time favourite film?

Do you prefer the sunrise or the sunset?

What’s the strangest dream you’ve had?

What do you think it means to be committed?

When is the best time to contact you?

How do you deal with issues?

What kind of date night do you want to go on?

What are some of the things on your bucket list?

What is the most important lesson you’ve learned so far?

Which of your guilty pleasures is the most important to you?

Where would you travel if you could go anyplace in the world?

What’s the one thing you wish you could go back and change?

When was the last time you truly pushed yourself outside of your comfort zone?

What’s the most important thing you’ve learned from the previous relationship?

The bottom line

Because men and women think in diverse manners, you must be smart in your questions and sophisticated in how you ask them. 

A healthy relationship relies on effective communication. It would be good if you could just ask a question and receive a straightforward response.

Use these questions and don’t forget to let me know how effective these were.

I’ll be will be waiting for you. 

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