150+ Questions to Ask a Guy That’ll Bring You Closer Together

A date with a guy you like can be nerve-racking. You must know how to relieve the tension and get past the ordinary chit-chat. How can you steer the conversation straight into a purposeful dialogue to get to know each other better? Few things are more irritating than long, uncomfortable silences while you’re on a date. Trying to make conversations using age-old conventional topics can be a bore. To avoid having to resort to those painfully common topics like the weather, I decided to put together a list of thought-provoking questions to ask a guy. When my husband and I started dating, we made use of a lot of these questions on our date nights. They went a long way in helping us learn about each other and even ourselves. Whenever you have a conversation with someone, keep in mind that the idea is not to impress them, but rather to discover who they are. This is a common misconception which can make dating unbearably stressful. If you are constantly trying to be what you think your date wants you to be, you will be utterly exhausted by the end of the evening. Moreover, your date will have spent an evening with a non-existent personality you created for display. I have compiled a list of questions you can explore with the guy you like. These will put you on track to forge a close relationship and enjoy some great conversations in the process. You will find some weighty queries which will make him share a lot about himself too. This is essentially the basis of deep and lasting connections. Also included are some playfully comical ones to lighten the mood. I elaborate briefly on the first 50 questions to bring out their values. I also tell you what his answer is likely to reveal about him. The rest appear as a continuous list. The first set will tell you something about his likes and dislikes as well as some of his beliefs. The second set sheds light on his past experiences and future goals. The final set forces him into a space of introspective, self-examination. These are not only great for you to get to know him better, but may also lead him to discover a couple of things about himself. This list will pave the way for a genuinely close relationship. There are far too many shallow, pretentious friendships out there, so make this one different. Go ahead, ask away and have fun with him. Don’t forget to take note of the specific queries you like most. You need not get through all of them at once. It is best to pose one question and let the conversation take its course. You don’t want to get into something of a quick-fire session.

50 Fun Questions for a Spell-Binding Date

I. His Likes, Dislikes and Beliefs

  • Question 1: Where’s your ‘happy place’?
Everyone has a ‘happy place’ they retreat into especially after a long, stressful day. His happy place will tell a lot about who he is and what is important to him.
  • Question 2: Which movie character would you marry?
This is obviously a hypothetical question because no man expects to marry a character from a movie. Nevertheless, his answer will give you a picture of what his ideal girl looks like. You might not be able to resist wondering if you look anything like her but nevertheless, it will be fun to learn what his idea of a perfect woman is.
  • Question 3: What is your favorite quote or expression?
In this information age, we encounter a whole lot of information in the course of a typical day. However, we only remember a small selection of it all. A quote or expression that stands out in his mind will tell you something about him. It could be anything from a humorous line to an inspirational phrase he finds comforting.
  • Question 4: Describe your perfect day
When my husband and I were dating, we discussed this question on date number 3. As I described my perfect day, he stared at me with his mouth wide open. We were surprised to find that we shared the exact same idea of a perfect day.
  • Question 5: What is the most unusual pet peeve you have?
We all have that little something that never fails to drive us up the wall. Some are understandable while others are totally irrational. It will be fun to hear what his irrational peeves are. Pay close attention to them all so you know how to avoid irking him.
  • Question 6: Name one habit that makes even the most stunning girl totally unappealing to you.
You can never go wrong with this kind of information at the back of your mind. It may help you avoid doing the one thing he hates.
  • Question 7: What could we all do to make the world a better place?
This will be the start of an interesting conversation. It will bring out what he feels is wrong with society today, as well as his view on what can be done to fix it. You will learn what qualities he deems to be valuable in the process.
  • Question 8: What angers you?
Common wisdom says alcohol, anger, and money are the most effective ways to bring out a person’s true colors. This list contains some money-related questions. As to how he carries himself after one too many drinks, you can only wait for the situation to present itself and observe. Use his answer to this question to probe a bit further. You will get a feel of how easy or hard it is for him to lose his temper.
  • Question 9: What do you deem to be totally inexcusable?
His answer to this question will reveal his boundaries. Personal boundaries tell you a lot about an individual. Be sure to keep his answer in mind so you never accidentally cross his limits.
  • Question 10: What is the one thing you always look forward to and why?
Is he a football fan who can’t wait for football season? Does he love to attend concerts? Perhaps it is warm, loving kisses from a spouse that he longs for. His answer could be absolutely anything. Whatever it is, you will enjoy hearing about it.
  • Question 11: Are you a believer in chance or pre-destination?
Which school of thought does he belong to? Does he believe in destiny or that life is a sequence of random events? His answer will tell you how he views events in his own life. It will tell you something about his worldview and his stance on positive and negative life events.
  • Question 12: Do you believe that there is someone for everyone?
With this one, you will find out if he is a practical, realistic thinker or a hopeless romantic.
  • Question 13: Do you agree with the saying ‘Love conquers all?’
His answer will tell you if he is a romantic idealist or a practical realist.
  • Question 14: What keeps you motivated during tough times?
For some people it is faith in a supreme being, for others, it is an encouraging quote. Some simply maintain a never-say-die attitude. What is his way of staying encouraged when times are hard?

II. His Past and Future

  • Question 1: What have you never been able to do well?
We all have that one thing that we are terrible at, no matter how hard we try. It will be fun to hear what he ‘sucks’ at. Share yours as well and enjoy a good laugh together.
  • Question 2: Describe your happiest childhood memory
For most of us, events and experiences in our early years have molded us into who we are today. Memories of these times remain with us forever, whether they are pleasant or not. Talking about those years never fails to bring out great stories. Answering this question will make him share with you some of the purest, most joyous times of his life. You can be sure he doesn’t get to reminisce like this very often.
  • Question 3: What has been the toughest phase of your life?
This question may require him to divulge some confidential information. It is best not to ask it until you have built a fair level of trust. We have all gone through some difficult phases. For some people, puberty was the most difficult while for others, the post-teen years were the toughest. You may find that all these years went well for him and challenges begun to set in much later. Whichever period of his life it was, it will help you learn something about him.
  • Question 4: What do you take most pride in?
Almost every man has a grand plan and it is from this that he derives goals which he is constantly trying to achieve. If a woman displays a deep understanding and support of this plan, he feels closer to her and will easily share more with her. Through this question, you will learn what he values most.
  • Question 5: What was the most humiliating experience you ever had?
Use this question to find out just how at ease he feels with you. If he likes you, he may not tell an extremely embarrassing story. Instead, he will likely tell of a somewhat embarrassing experience. If he is a bold individual, he will tell it all with no shame or fear of judgment.
  • Question 6: What’s is the biggest mistake you ever made?
They say the most successful people have made the most mistakes. Mistakes develop and shape us into who we are today. But we have all made some bad decisions we would never, ever make again. What is one thing he swears he will never do again? His answer will definitely reveal a lot about him.
  • Question 7: What part of your childhood did you hate the most?
Venture into the subject of childhood with care for you may unearth some deep, long-standing pain and emotional struggles. On the other hand, you may find that he had a wonderfully happy childhood.
  • Question 8: What are your most thankful for this year?
Here is a simple but powerful question. It demonstrates a sincere interest in his life and then gives way for him to share what is probably personal information about something that is very important to him.
  • Question 9: What is the one moment in your life you would live differently and why?
Some people would respond by saying that they would not change a thing in their past because it’s the mistakes that have made them who they are today. Others would re-do a lot, given the opportunity. Where does he fall?
  • Question 10: What will you never let another person do to you?
Personal boundaries define who we are. This question will have him define his limits on certain issues. Boundaries are rarely drawn until an unpleasant experience where someone else crosses them so it will definitely be intriguing to hear a story of how he came to set certain boundaries. Question 11: What has been your life’s most significant disguised blessing? Many people will tell you that life is best understood in hindsight. We have all had experiences where something felt like the worst thing that could happen to us at the moment, but it later turned out to be a huge blessing. It is these experiences which shape and define who we are.
  • Question 12: When did you last have a good cry?
Men rarely open up about their emotions so this question may make him feel a little bit uneasy. The truth is that sometimes emotions have to be let out, whether you are a man or a woman. Let him know that you are willing to listen without being judgmental. Do not do or say anything that would make him feel like a weakling. Sharing this will make him grow fond of you and create a feeling of closeness towards you.
  • Question 13: What experience are you happy to be over and done with?
We have all had difficult experiences which we struggled through, but eventually changed us for the better. What difficult experience is he glad to have gone through, but would never want to endure again? How has this made him a better person? This discussion could elicit some fascinating stories.
  • Question 14: Who was the victim of your biggest lie?
In the unlikely event that he has psychopathic tendencies, this answer will clue you in. It will definitely be an interesting story to hear.
  • Question 15: What do you hope to have achieved by this time next year?
This answer will reveal if you have shared expectations. If you are looking for a committed relationship and he wants to spend the next few years travelling the world, you are probably not a good match. If his answer is that he hopes to grow his career and perhaps settle down with someone, then you may be a great match.

III. Introspective Queries

  • Question 1. What do you always procrastinate on?
Repeatedly putting off a task or activity is a bad habit but we all fall prey to it and most of us end up feeling terrible about it. Use this question to determine if he is a super-efficient perfectionist. Different people procrastinate different things and what an individual puts off will tell you a lot about him. Aggressive, ambitious people tend to put off boring, routine tasks which will not contribute to the achievement of any goal. Laid-back, emotional people, on the other hand, tend to postpone practical every-day tasks.
  • Question 2: What would you do if you suddenly acquired a billion dollars?
For many of us, our lives revolve around money. We work jobs we don’t like because we have to pay bills and just about every aspect of our lives is determined by how much money we have. We eat food we can afford to buy, reside where we can afford to live and wear clothes within our budget. A popular quote by former US president Barack Obama says ‘Money is not the only answer but it makes a difference’. What if you had access to unlimited amounts of money and never had to worry about what anything costs? How different would life be? His answer will tell you what he values most. Would he live a life of pleasure and self-gratification? Or perhaps he would be the next world-renowned philanthropic change agent.
  • Question 3: Describe one thing that calls for patience but never disappoints.
Patience is the companion of wisdom. His ability and willingness to wait for something he wants is an indication of his emotional maturity. What does he value enough to work for and wait patiently for?
  • Question 4: Describe yourself in 3 words
Some people get a little bit sheepish when they have to talk about themselves. Is he one of those or does he enjoy answering the question? Does he describe himself positively or does he de-value himself? Listen carefully to his response. Remember that our self-image is often a good pointer to how we would like others to see and treat us.
  • Question 5: What would you be quick to change if no one would judge you?
Anxiety arising from fear of being scrutinized or embarrassed is very common in the information age we live in. We hold back on so many things that we would like to do or say and we are constantly trying to conform to social standards. What would he do if he were immune to any form of judgment? This will definitely set you up for an interesting conversation.
  • Question 6: What makes you feel completely in touch with your true self?
This is a deep and powerful question. It is sure to give you a very clear picture of who he really is. You also get to hear how he creatively taps into his inner being.
  • Question 7: Which actor would you like to play you in the movie of your life?
Go ahead and have fun with this one. Find out how he views himself by how high he aims at the Hollywood names. Does he see himself as a George Clooney or a Will Smith kind of guy? Whoever he picks, you will enjoy the conversation.
  • Question 8: What would you do first if you suddenly had no fear?
We all live our lives restrained by fear of something. It could be a fear of failure, pain, rejection, poverty or just an intense fear of making a mistake. What does he fear most? What would his life be like if he were able to release every ounce of fear and live free?
  • Question 9: If you had to give up one of your five senses which one would you choose and why?
This will be a tough one if he considers the consequences of his choice. Whatever he settles on, it will tell you what activities are most important to him. If he is a music lover, he will want to keep his hearing. If he loves to travel and take in magnificent views, his sight will be important. Is he a foodie who delights in luscious cuisine? If so, he will not want to give up his sense of taste. It will be interesting to hear what he would be willing to lose.
  • Question 10: If you had one wish, sure to come true, what would you wish for?
This answer will tell you a lot about him. Will he go the benevolent way and wish for world peace and an end to poverty? Maybe he will take the worldlier path and wish for a billion dollars with all the trappings of wealth and comfort.
  • Question 11: If you could switch roles with someone for a day, who would it be and why?
Find out whose life he admires. Get to learn what kind of life he aspires to live one day. The people he admires say a lot about him.
  • Question 12: Who paid you the most gratifying compliment you have ever gotten?
It could be in terms of appearance, ability or a trait. Compliments are a recognition and confirmation from others that we have successfully achieved what we set out to accomplish. It always feels great to receive a compliment and it will be interesting to hear what he likes to hear about himself. The information of who made the compliment and the situation in which it was made will also make for a great story.
  • Question 13: If you had to choose between happiness and success, which would you choose?
This is another one of those that will tell you if he is a type A or type B personality. Type A personalities will probably choose success which means that he will let nothing come between him and his pursuit for success, not even his own well-being. If he is a type B personality, he will likely opt for happiness. Some choose both.
  • Question 14: What always puts a smile on your face?
If you are dating and hope to progress into a long-term relationship, take note of this answer. It would be nice for you to do something to make him smile.
  • Question 15: When making decisions, do you follow your head or your heart?
There are two types of people in the world: thinkers and feelers. There is no clear-cut differentiation but we all reason and make conclusions with either our heads or our hearts. His answer to this question will give you an indication of which side of the divide he falls on. Does he put sense and practicality first, or does he value sensitivity and emotions more than anything else?
  • Question 16: Does spending time with other people make you feel energized or drained?
Is he extroverted or introverted? His answer to this question will tell you which one he is. We generally distinguish extroverts as sociable and gregarious people and introverts as reserved, withdrawn individuals. This is not actually what differentiates the two. The difference lies in how one feels when interacting with people. Extroverts come alive when they are around people. Introverts feel drained and exhausted after interacting with many people.
  • Question 17: What do you do to feel alive?
Every one of us can name one or a few activities that make us feel alive which are actions that make us feel that we are fulfilling our purpose. A few people are fortunate enough to make a living out of these activities such as dancing, sports, painting or writing. Most people have to make time out of their busy schedules to go to their ‘passion place.’ Where is his ‘passion place’? His answer will give you deep insight into who he is.
  • Question 18: Has your perception of right and wrong evolved over time and how?
Hopefully his ideas of good and bad have evolved and he is not holding strong to perceptions he had as an adolescent. We have all grown out of some perceptions which now seem juvenile. We all have memories of regrettable actions in our past. Everyone has at some point struggled to admit wrong-doing, only to learn better later.
  • Question 19: What would you like to have a clearer memory of?
He probably has not thought about this one. We all have some vague memories we would do anything to remember more clearly. Unfortunately, that is all we can recollect. What is his vague memory?
  • Question 20: What gives you a sense of achievement?
The answer to this question could vary widely from one person to another. For some people completing a load of work makes them feel accomplished, while for others it is when they complete routine tasks or errands. Some say they feel most accomplished after they take time to connect with a loved one. What does it for him? Question 21: What do you think is the most likeable thing about you? Unfortunately, many people spend way too much time pondering on what they don’t like about themselves. Therefore, this question may be a little bit of a challenge for some. Will this one be difficult for him, or will he have a quick pre-meditated answer? It will be interesting to hear it.

Bottom Line

Dating can be incredibly fun or excruciatingly strenuous. The truth is that it is up to you. Make a point to listen more than you talk. Next time you go out on a date, try not to pre-create an image of him. Just be yourself, consider him to be a blank page and then let him write in it himself.

106 Extra Questions to Ask a Guy

106 Extra Questions to Ask a Guy 01 106 Extra Questions to Ask a Guy 02 106 Extra Questions to Ask a Guy 03

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