40 Questions To Ask A Guy To Get To Know Him Deeper

It might be a little tricky to figure out how to get to know a guy. Saying the wrong thing is the last thing you want to do.
Peeling someone’s layers and getting to know them better takes time, but this list can speed up the process for you. Men typically like to hide behind their intimidating exteriors and don’t reveal too much about themselves. They prefer to express their emotions through their actions rather than their words, and the majority feel uncomfortable expressing their emotions in a sentimental way.
You may accomplish just that by helping him by asking the correct questions. You don’t want to frighten him away, so avoid having a rapid-fire discussion about this over coffee one day. Spread them out across multiple occasions, and your partner will show you an entirely different side of him!
These 40 questions for men can help you connect more deeply, which is the cornerstone of successful relationships.


Also check – Best paranoia questions / Things girls like about guys

Questions To Ask A Guy To Get To Know Him Deeper

Who do you go to when you feel like you have no one?

You can learn more about a man’s true special people and closest friends by asking him this insightful question. Make this one of your primary questions for the man you’re interested in, so you can ensure that you and the people he values and trusts will get along.

How Would You Describe Your Family?

Knowing more about his family might provide you with additional insight into how he was raised and his current connection with them. This is an important question to ask if you want to find out more about him than what’s on the surface.

What Do You Remember Most About Childhood?

Childhood experiences frequently mold the person you become now, so asking your partner about his priorities will help you learn more about him and what he really values. This question will let you know what he values, whether it’s time spent with his grandma or a vacation to Europe.

What do you regret most?

One of the finest things to ask a guy you’re dating is this. It will support more emotional connection and vulnerability in your relationship.

Which Song Is Your Favorite?

Asking about a guy’s favorite music may help you learn more about his likes and dislikes while also giving you the chance to connect with him over your mutual love of bands and learn about new musical genres.

How do you picture your future self in five years?

It’s crucial to assess and get a sense of what the future holds for the two of you as a pair when a new guy enters your life. Your objectives need not be the same, but they must cross paths.
Asking a man about his aspirations, plans, and ideas for the future may both bring you closer to him and reveal whether your desires are similar.

Do you think marriage is a good idea?

This is a serious as well as a flirtatious question. Everyone does not adhere to the idea of marriage. Knowing how your guy thinks about marriage and commitment might be important if you’re serious about doing so.

Do you want to have kids?

Whether you want to have kids one day or not, you have to ask him if he wants to have kids later. It is better to know now if this is a must-have for you.

What is your most contentious viewpoint?

One of the typical and well-known questions to ask him while dating online is this.
We’re not trying to create a controversy, but having a topic to discuss that gets people thinking is always beneficial to a couple’s relationship.

What superpower would you choose if you could have only one?

This question is a terrific icebreaker to determine where a guy stands on the superhero spectrum and to bring out his fun side. It doesn’t matter which superpower he chooses—super strength, super speed, or the ability to fly—this amazing question will almost always result in some good chuckles and lighthearted banter.

What drives you to work hard?

Everybody experiences days when it is difficult for them to get out of bed. Knowing what motivates your boyfriend on those days is a smart idea.

What Aspect of Your Job Do You Like Best?

By learning more about his daily activities through this inquiry about his job, you may become closer to him while also learning more about his priorities. This can assist you discover what he is most enthusiastic about in his profession, regardless of what aspect of the job he likes the most.

What would you change about your life if you could go back in time?

There is not a single person in the world who is regret-free. This is the reason why it’s one of the more serious questions to ask a person to learn more about him. You might be able to make him feel better.

What Place Would You Visit If You Could Go Anywhere?

It’s not just that questions about travel are great for kicking off a lively discussion; it’s also possible that discussions about travel and vacations could ultimately lead to a trip for the couple.

What Kind of Relationship Do You Want?

To determine whether you and a guy are on the same page, you must ask him this crucial question. It’s better to openly and honestly address this so that you don’t waste your time if you want a serious relationship and he’s more interested in friends with benefits.

Do you think love can be found at first sight?

There are two types of people: those who believe in, and those who don’t believe in, love at first sight. Which of them is your guy?

Do you have faith in God?

Asking about someone’s perception of a higher power is a crucial and personal way to learn more about them. especially if either of you considers spirituality to be significant.

Which would you choose: winning the lottery or landing your ideal job? Why?

While winning the lottery does feel nice, many people don’t feel fulfilled by the experience. A dream job, on the other hand, can lead you along a professional path that will make you happy virtually indefinitely. What does your man think about this? It may be an intriguing revelation about his personality, objectives, and aspirations.

What Movie Do You Like Best?

Knowing what kinds of movies he enjoys will help you learn more about him and his interests and passions while also assisting you in making future plans for prospective movie dates.

Which is the best gift you’ve ever received?

If you want to know what he truly values, this question is a great way to learn more about what matters to him and what he finds noteworthy.

Which three animals are your favorites, and why?

He compares himself to the first animal’s traits, the second’s to how the rest of the world perceives him, and the third’s to who he really is. It may seem strange, but asking a guy serious questions like these may provide a lot of knowledge.

Which Book Do You Like Best?

Finding out more about a guy’s reading habits is also a fantastic way to discover his interests and pastimes and determine what you have in common.

What Food Do You Like Best?

Talking about food preferences with a guy may be a pleasant way to learn more about him and his while also assisting you in choosing places for your dates.

What would your closest friend say about you?

This question can help you understand a man’s character and the qualities of which he is most proud.

What activities are on your bucket list?

Does he want to visit Europe, skydive, or win a Noble Prize? Asking him about his bucket list is a wonderful way to find out more about what he hopes to accomplish in the future and whether you two have similar objectives.

Are you content with your job?

Sadly, a large number of people continue to hold their current jobs because they can support their lifestyles. But having a job that you enjoy is a very different kind of fulfillment. Is your boyfriend fortunate enough to go through it?

What would ruin a relationship for you?

Before you start dating someone, it’s critical to understand their relationship deal-breakers so you can avoid doing anything that could jeopardize your entire relationship.

What is the one thing about you that people consistently get wrong?

Even those who are closest to us occasionally misjudge us. What is the one thing about which you, as a male, feel misunderstood? By asking him this, you’ll give him the opportunity to open up to you.

What Does the Ideal Date Mean to You?

This is a great approach to finding out what he likes to do while also providing you with ideas for a future date!

What Do You Fear the Most?

Inquiring into his phobias might be a fun way to get to know him better if you want to know more about him than the obvious things.

What one thing about yourself would you change if you could?

A fantastic quality in a man is self-awareness, and this inquiry might show you how he really views himself in that regard.

What are the two most important things you’ve taken away from all your previous relationships?

We may transform via relationships. We are not the same people we were when we entered a relationship. Being conscious of the lessons each connection offers us is a form of self-awareness.

What do you think of as a life wasted?

Every person has a different life purpose. You may learn more about him by asking him this question.

If your parents didn’t approve of your spouse, what would you do?

This is one of the more intriguing questions to ask to learn more about him. You will learn just how important his family is to him by speaking with him.

What stage of your life was the worst?

Sometimes a man makes the struggle; other times, the struggle makes the man. One of the questions to ask someone in order to gain a better understanding of him.

How important are holidays and special events to you?

Men are occasionally accused of worrying over dates, but mostly women are. Better find out before you let him down by missing a crucial event. On the other hand, if he prefers to keep certain occasions under wraps, at least you’d know it’s preferable to keep things under wraps.

Do you let your friend’s opinions to interfere with your relationship?

It seems logical that friends’ opinions are important since they are the family we pick. It’s crucial, though, that they don’t take control of your life for you.

Do you believe that keeping secrets in a relationship is acceptable?

Does your partner think keeping secrets means lying or cheating? Between love and privacy, there are occasions when a line needs to be drawn. You should bring up the subject early in your relationship.

What would be your greatest accomplishment if you passed away today?

One of the most intimate questions to ask a guy He will give this one careful consideration. Depending on the sort of person he is, his response can be witty, sarcastic, or even philosophical.

What Brings You Joy?

Finding out what actually makes him smile can help build your connection and open the door for even more smiles to come if you genuinely want to get to know him better.


It’s essential to get to know your new lover because you’ll need to be completely comfortable with him when things grow serious and it’s time to jump in with both feet. Make sure you actually understand the man you’re with by asking him the correct questions without becoming overly attached. Although it’s lovely to fall in love, it’s best to proceed carefully and get to know your spouse well. Make the most of your relationship by having fun, being flexible, and enjoying it!