two people using gadgets

200+ Questions To Ask A Guy That’ll Bring You Closer

If you have been in a relationship with your boyfriend for a while and want to learn more about him to help you decide if he is right for you, many questions can be either informative or annoying – so proceed with caution.

Instead of simply confronting him with all sorts of questions that you can ask a man, try to approach him with some classic questions to make him feel comfortable and open up a little more.

Getting to know people is more difficult these days

Although we have a lot of access to people through technology, it’s actually more difficult to get to know someone now because we are all so distracted by the same technology that should be bringing us closer.

To get in touch with people on a deeper level sometimes you have to try harder, and asking these questions to someone is a great way to get the information that will help you decide if they are the right person for you.

Questions that you should ask a guy to get to the root of his thoughts

There is no right or wrong way to ask people questions. However, there are a few things you can do to make the most of these questions and get the information you want.

Whether or not he says things you want to hear is another story, but you can certainly work on your questions so that you learn as much as possible.

Don’t just ask a question; be sure to ask follow-up questions to make the best of your conversations.

Once you’ve gone through them, you’ll be best friends in no time!

The first 17 questions you have to ask a guy and why
1) What do you wake up excited about?

This is not only a great way to start a conversation and show someone that you are interested in them, but also a perfect way to find out what they are excited about.

2) What is your unusual hidden talent?

An entertaining way to find out how much someone is willing to talk about themselves, and if you make it to a first date, the question of proof is another great icebreaker.

3) How do you spend a typical Saturday night?

The way someone spends their free evening is a good way to find out what their priorities are.
Whether he’s a party animal or a workhorse, your lifestyle and taste will determine whether he gives the “right” answer.

4) What did you notice about my profile?

This gives more insight into their intentions. A specific, thoughtful answer indicates that they are interested in really getting to know you, a generic copy/paste answer indicates that they just want to have fun.

5) What achievement are you most proud of?

When you encourage someone to praise themselves a little, not only do you learn more about them, but you also show them that you are someone who lifts others up and is worth getting to know.

6) What are your thoughts on religion?

This may be a sensitive topic for some people, but it can also tell you whether your values are in agreement. Which becomes important when you get along well.

7) Where did you study? Why did you choose this school?

If you ask yourself how someone made an important decision, e.g. where to go to school, you will get an insight into the decision-making process and priorities.

8) “Would you rather…” questions.

Questions like “Would you rather jump out of an airplane or swim with sharks?” are a fun way to break the ice, tell some stories and really get to know someone.

9) What is your most embarrassing story?

Not taking yourself too seriously is attractive. Embarrassing stories are hilarious. It’s fun to tell stories with a sense of humour. This question is a gold mine.

10) How often do you see your family? Where do they live?

This is a good way to assess what values they have as a family and whether they match yours. If you get along well, this is something that becomes important.

11) What is the thing you are most passionate about?

Your enthusiasm for the subject will shine through in their words, and you will learn all about something that is truly special to them.

12) What are your interests?

On the same topic, but with a slight deviation from the Passion Question above, it is a great way to learn more about someone. An interest in boat building could mean a trip to the museum from time to time, a passion for it could mean bending over a replica ship in a bottle for hours.

13) Do you describe your drinking habits?

Hopefully you will take this conversation offline and personally, it’s nice to know if you will share a jug, sip wine or cheer with coke.

14) What are your favorite books, TV shows or movies? And why?

A classic question and a good start to the conversation. You may find that your love of the throne game brings you together, or you may receive some great new recommendations.

15) Who is your greatest role model?

Whether you are describing a historical figure or a family member, you will learn about their character from the people they want to emulate.

16) Describe your dream vacation.

This will not only give you the opportunity to share stories from previous vacations, but also let you know if your vacation styles match, if you get along well and plan trips together.

17) What is the best way to earn someone’s respect?

An eye-opening question that explains what they really value in themselves and in others. Do they admire kindness? Or do they show respect when they work hard?

40 Questions of principle and follow-up

Here is a list of 40 questions you can ask a man, and we have included some possible follow-up questions to help you get more out of your conversations.

What was your proudest moment in your life?

1) What made them so special?

2) What is the funniest thing you have ever witnessed?

3) What made it so funny?

4) How do you like to vegetate there?

5) What is your favorite Netflix binge show?

6) What is the most horrible thing you have ever experienced?

7) Did you change anything in your life after that?

8) What is your best memory of growing up?

9) What was your favorite toy?

10) When was the last time you did something nice for someone?

11) What made you do that for that person?

12) What makes life worth living for you?

13) Why is that important to you?

14) What is your favourite animal species?

15) Which animal would you be?

16) What is your favorite movie?

17) What makes it your favorite movie?

18) What is one thing you have never told anyone?

19) Why have you never told anybody this before?

20) What are you afraid of in life?

21) Do you think this is based on a previous experience?

22) If you had to leave your home, what is the one thing without which you could not leave?

23) What would you leave behind in any case?

24) Who is your favorite family member?

25) Who is your least favorite family member?

26) What does Thanksgiving dinner look like in your family?

27) What do you eat on Thanksgiving?

28) What is the best worst joke you ever heard?

29) Who told it to you?

30) What is your favorite kind of ice cream?

31) What kind of topping do you like?

32) What do you like about yourself?

33) Why do you like that about yourself?

34) What is one thing you would change in your life if you could?

35) Have you ever thought about how you could achieve this change?

36) What is one thing you would not change in your life?

37) Why is this so special to you?

38) If you had to eat the same food for a month, what would it be?

39) What would you have for dessert?

40) What is your favourite drink and why?

50 questions you can ask a person that reveal his true personality

1) Which fictional character would you marry if you had the chance?

2) Where would you live if money and work were not factors?

3) What was the worst book you ever read?

4) What was the best book you ever read?

5) Who is your favorite avenger?

6) Batman or Superman: Who is your favorite DC character?

7) What are the three words you would use to describe yourself in an online dating profile?

8) Do you prefer to listen to your heart or brain when making important life decisions?

9) Would you say that you are a spiritual person?

10) Who is a person that you wish you could be?

11) Who is a person you looked up to as a child?

12) Are you asking for permission or asking for forgiveness?

13) What is the best advice you would give someone?

14) What is the best advice you’ve ever received from anyone in your life?

15) What is your biggest nuisance for your pet, and when was the last time someone around you did it?

16) Who is your dream woman, dead or alive?

17) Which fictional character do you think you are most similar to?

18) Who would play you in a film about your life?

19) How much money would you like to earn in your profession?

20) What would you do for a living if you could do anything?

21) What is the best advice your mother ever gave you?

22) What is the worst movie you have ever seen?

23) In which film would you have liked to have the leading role?

24) Which fictitious lawyer would you wish to have representing you if you ever got into trouble with the law?

25) Do you keep up to date with current events?

26) What do you think is the most significant event in the history of mankind?

27) Do you believe BigFoot is real?

28) Would you ever climb Mount Everest?

29) What is one thing on your bucket list?

30) Who is on your fantasy soccer team?

31) Would you rather be smart or attractive?

32) Do you like hot dogs or hamburgers?

33) If you could eat just one food for the rest of your life, what would it be?

34) If you could work for any company, what would it be?

35) Which movie did you watch where you wished you could make a living from?

36) Would you swim with sharks?

37) If you could have a superpower, what would it be and why?

38) Would you ever give up your job to live in the forest?

39) What is the worst job you ever had?

40) What is one thing you regret not doing in your life?

41) What is your favorite TV show, now or in the past?

42) Did you ever have an idea for your own movie?

43) Have you ever tried to write a book?

44) What is the funniest thing that has ever happened to you?

45) What would you wish for if people knew nothing about you?

46) Which music or song do you like to listen to most?

47) If you had to repeat a song forever, what would it be?

48) Do you believe in love at first sight?

49) Do you believe in reincarnation?

50) Have you ever experienced Deja Vu?

30 funny questions you can ask a man

Humor can help you go a long way with a man. Men like to laugh because it lightens the mood and makes them happy.

So if you think you are funny, this can be a good opportunity to make a good impression on your man.

Make him understand that you can make him laugh and giggle.

Here are a few fun questions to lighten the mood:

1) If you were a girl for one day, what would you do?

2) What is the strangest celebrity crush you’ve ever had?

3) Do you find nerds sexy?

4) If you were a vegetable, what would you be and why?

5) If you could have a superpower, what would it be?

6) What would you do if we were in zero gravity?

7) What would your dream villa look like?

8) What is the strangest conversation you have ever heard?

9) What is something you believe in that most people do not believe?

10) What is something you can’t believe that people actually enjoy?

11) What is the funniest failure you’ve ever seen in social media?

12) Who do you think is the hottest celebrity?

13) What would you do if a guy asked for your number?

14) Do you think older women are sexy?

15) What kind of ice cream describes you best?

16) If your life were a movie, what would it be called?

17) Would you still like a girl if she was a foot taller than you?

18) Which alcoholic beverage best describes your personality?

19) If you could make out with a fictional cartoon character, who would it be?

20) If someone had something on their face, would you tell them?

21) If you owned a boat, what would you call it?

22) Which celebrity would be the most boring to meet?

23) What is the worst buy you ever made?

24) Best buy?

25) If you could choose your name, what would it be?

26) What is a compliment you received that was actually an insult?

27) If you had to lose a body part, what would it be?

28) Do you believe in magic? Why do you believe in magic?

29) What is a famous quote that everyone sees as truth but is actually bs?

30) What is the funniest viral video you have ever seen?

30 personal questions that will reveal his soul

Let’s get one thing straight:

You can’t make small talk all the time. It’s boring, it’s pointless, and it won’t spark.

Sometimes you have to go a little deeper.

One way to do that is to ask personal questions.

So here are some questions to get to know someone as they really are:

1) What were the happiest moments of your childhood?

2) What does your perfect relationship look like?

3) What is the main reason why you get out of bed every day?

4) What do you like to do most?

5) What is your most important goal right now?

6) If you were to die in an hour, what would you do?

7) Which book has influenced you most in your life?

8) If you could send a message to the world and they listened, what would you send?

9) Is there anything you are very aware of?

9) What is the most difficult thing in life right now?

10) Are you an adventurous person? Or do you prefer routine?

11) What is the closest relationship you have ever had?

12) What is something you are sure you will NEVER do?

13) Which stereotype describes you best?

14) What is your best character trait?

15) What is your worst character trait?

16) What is the worst advice you have ever received?

17) Without whom could you not live?

18) What lights your light and motivates you?

19) If you could go back 10 years, what would you tell yourself?

20) Do you often say yes or no in life?

21) Which do you prefer to go to an art, history or science museum?

22) What did you feel was the truth when you grew up, but now you know it’s wrong?

23) When was the last time you panicked?

24) What was the strangest conversation you ever had with someone?

25) What is a personality trait of yours that you wish you could get rid of?

26) What do you think about homeless people begging for money?

27) What is your favorite scene in a movie?

28) What is your opinion that is not mainstream?

29) What stresses you?

30) Would you rather be a famous actor or sportsman?

20 romantic questions you should ask

At some point, you probably want to connect on a more romantic level. After all, romance is a beautiful thing.

So if you’re looking for more romance, ask yourself these questions:

1) What is your romantic dream date?

2) What song makes you think of me?

3) What is the most romantic act you have ever heard of?

4) Have you ever been in love?

5) Do you think you could fall in love with me?

6) What nickname/house name would you use to call me lovingly?

7) Do you think that someone can be too much in love?

8) Which trait of mine attracted you to me first?

9) What was your first impression of me?

10) What is something in your life that you have never shared with anyone else?

11) How did you feel when we kissed for the first time?

12) Do you prefer good sex or a good hug?

13) Do you think you will ever settle down and have children?

14) What is the most romantic movie you have ever seen?

15) What is the best thing about being in a relationship?

16) What memories do you hold most between us?

17) Is communication in a relationship more important than sex?

18) Do you want to celebrate a big wedding? Or a small one?

19) What is the sexiest dream you ever had?

20) Guess what I like most about you.

Profound questions

Once you have established a connection, it is time to go deeper. They want to know their life prospects.

Ask these questions to learn how their brain works:

1) For what or for whom would you sacrifice your life?

2) What is something you believe in that most people do not believe?

3) If money was not an issue, what would you do in life?

4) What keeps you up at night?

5) How important is physical attraction in a relationship?

6) Which issue in politics would you like more attention to be paid to?

7) What do you wish people didn’t know about you?

8) Which three words best describe you?

9) How do you want to be remembered?

10) What is the best advice you have ever received?

11) Why are so many people lonely these days?

12) Do you believe in fate?

13) Karma?

14) Are you proud to be part of the human race?

15) How important is money for a good life?

16) What makes life worth living?

17) Can you tell things about a person by their appearance?

18) What was the last book you read?

19) Which film changed your perspective on life?

20) What is your favorite motto in life?


Regardless of where you are in your relationship, it is a great way to ask each other questions, get to know someone, observe where you stand in life, and continue to discover things you may have in common.

Even if you have been with your husband for a long time, you can continue to build a close relationship with him by staying curious about his likes and dislikes and checking from time to time to see if things have changed for your husband.

After all, two days in a row are never the same. So ask questions and listen to the answers, and you and your husband will have a great relationship for years to come.

Was this information helpful?

picture of lovers having fun

This Is What It Means When A Narcissist Says “I Love You”

father and daughter working together

8 Ways To Build A Better Relationship With Your Daughter