Last updated on October 5th, 2019 at 09:00 pm

Do you know how to strike a meaningful conversation or build camaraderie with people around you?

It might be your boyfriend, girlfriend, kids, partner, spouse, or even an unknown person at a party.

It could be anyone.

The following are 251 good questions to ask people, and these will probably help you in breaking the ice.

It’s broken down into 8 categories/segments so that you can tailor your question(s) to the right audience or individuals;

  • Guys
  • Girls
  • Friends
  • Random person
  • Kids
  • Couples
  • Girlfriend
  • Boyfriend

Are you ready?

If so, let’s get started!

What Will I Learn?

Questions to Ask

Good Questions To Ask A Guy

Girl asking a guy questions

1) After you wake up all of a sudden in the middle of the night, what’s that sound that can scare you like hell?

You can give him some time to find out what he is actually scared of. You can also discuss what fears you have in common.

2) Tell me something about who or what you feel is your nemesis.

There are people or things that we dislike and it’s a given fact that he too gets annoyed by something or someone.

This question is a great conversation starter and makes things comfortable for the guy.

3) Do you think you can lie and grab a high-level job of your choice without having prior experience and still go unnoticed?

Discuss what possible ways would you apply in order to stop people from finding out the truth.

Undoubtedly, this one is total fun.

4) If you get the chance to learn a magic spell, but it only has the ability to execute something quite mundane, what would you want the spell to do?

This is one of those funny questions and the answer to this can stir up some really creative replies and be rest assured that you will be completely engrossed discussing the options.

5) What’s the best and the worst thing that you have realized being a male?

You will get to know how it feels to be a guy and you would surely be in for a surprise. Try to shift towards some really annoying things that a guy can face.

Replying to this question is fun and you would probably unearth a few unknown facts.

6) What’s that childish thing that you still fancy doing?

We all have some really fond memories of our childhood and there are things that we still love doing.

This question is bound to receive some really cute answers and even some innovative ones.

7) What is that movie that you can watch repeatedly without getting tired?

He would love to discuss his favorite movie and you would get to know about his taste in films.

This might seem to be an endless discussion as there are a bunch of television shows and films that he might like, rather love.

8) What long shot that you took has reaped huge benefits for you?

He might have never faced such a question before and you ought to give him some time to ponder.

In all probability, you would get to hear quite an interesting reply.

9) What is that movie that you wish your life should resemble?

There are many movies that perfectly reflects how we want our lives to resemble.

This question will definitely help you take a little sneak peek into the life of a guy.

10) What’s the most intriguing piece of trivia that you might be aware of?

This is a fantastic question and for sure it’s going to arouse the interest of the guy.

We all have that piece that when we look back at, it just makes us want to smile for nothing.

11) Who’s that celebrity you think would be the worst leader of a nation?


This is a funny question to ask and I’m very sure that there is this celebrity that no one would ever vote for when he/she wants to contest for a political position or as the president of the nation.

This question will definitely bring out the comedy-side of the guy.

It’s indeed a fantastic question to ask.

12) What’s that thing you used to get involved in and now think it was rather silly?

It usually happens when we are as little as a kid.

We usually get involved in something we thought was great and interesting but now, it is more like garbage and a complete waste of time.

This question will definitely make the guy want to reminisce about his past and tell you fantastic stories of his childhood life.

13) Which historical personality in your opinion shouldn’t have been as venerated as they are today?

This is going to back to history and it’s kinda cool to see the guy’s opinion about history.

Some guys do love history and others don’t.

So, this question will help know if the history of love or not.

14) Have you ever been in a high-pressure situation? What did you do in order to handle it?

We’ve all been in a situation where sometimes go nuts because of pressure.

This question will indeed bring out the inner-side of the guy and you’ll be able to find out how the guy reacts to intense pressure.

15) What was that thing that used to stress you out before, but isn’t a big deal now?

I could remember when I was little, traffic stresses the hell out in me. But when I grew up, I realized there was absolutely nothing I can do about and it’s out of my control.

Although it still stresses me a little today, but not as much like when I was growing up.

So this question will indeed help you know more about the guy’s life – what stressed him a lot in the past and how he has managed to overcome it.

16) Which two events have changed your life forever?

Events do change a life.

So get to know what event has actually shaped his life.

You will surely love his response to this question.

17) What’s that thing that the majority of people don’t get right?


  • School
  • Housing
  • Life in general
  • Conversation
  • Children
  • etc

This question will help you get to know his feelings about people and humankind in general.

18) What’s that thing you are not ready to do even for 5 million dollars?

I read this a lot on Facebook.

Such as;

  • Can you hit your friend’s leg for $5 million dollars?
  • Can you blow your friend’s head for $5 million dollars?

And he likes it.

This is will be a fantastic time to know what he values the most.

19) In your opinion, what do you think you are an expert at, but probably you are not?

Many people think they are good at something but later realize they are just daydreaming.

It happens to just about everyone on this planet.

So sit back and have fun on this one because it’ll have a really funny answer.

20) What, according to you, is a double standard and must be done away with?

We hate double standard but people have a different definition of what it actually is.

So this is really going to help you understand the guy’s viewpoint about what double standard is to him.

21) Who do you think doesn’t deserve your respect anymore?

People don’t respect themselves don’t deserve my respect.

And I’m sure you’ll agree with me on this one.

This question you help you get to know the deeper of the guy as to his view towards self-respect, his attitude toward others and what he can tolerate.

Here is a complete list of questions to ask a guy with a comprehensive discussion of each. Enjoy!

Good Questions To Ask A Girl You Like

Guy asking a girl questions

The following are questions to ask a girl that will make her want to fall in love with you and be your bride for life!

So make sure you understand the intent of the questions and use them wisely.

22) Which stranger had influenced you big time?

This indeed is one of the deep questions, and in all probability, she will take a substantial amount of time to ponder over it.

However, the answer can be funny as well as a serious one.

23) What’s that achievement you are proud of?

This simple question can unearth what kind of a person she is, in reality.

Of course, you will get to know and learn something that you never knew before, in case she is a girlfriend.

24) Which historical period had probably the finest fashion sense?

Although not every girl has an inclination towards fashion, a vast number of them are actually into it.

Fashionable or not, girls do have a strong opinion on this topic.

You can elongate the conversation by adding a different angle to it.

25) What funny thing completely freaks you out?

This one can induce some really strong reactions.

There might be some funny stories that she would like to share, but you could also give a serious angle to the conversation, in case you want to dive a little deep.

How fast do you have the tendency to judge people?

This is genuinely one of the best questions to ask and it will give you an insight into what she thinks about other people.

You can also ask what opinion she had about you when she chanced upon you for the first time.

26) Would the world have been a different place if superheroes and supervillains existed?

The answer to this ought to be a creative one for sure, and she can put forth some interesting as well as funny scenarios that might emerge if superheroes and supervillains would have existed.

27) What’s that significant change in the education system of your country needs to go through?

The answer to this question will indeed bring out the girl’s understanding of her education system and you’ll get to know him into the education-style conversation or not.

28) Have you ever done anything for which you might regret in the future?

We’ve all done a thing or two that we later regretted.

I’ve done a handful, believe me.

So sit back and relax and the girl reminisces about her past misdeeds and this will indeed bring out the imperfect nature of her.

29) What significant aspect of your culture are you proud of?

There are so many fantastic and awful aspects of our culture.

So, this question will help you know if she truly understands and values her culture or not.

30) What’s the best and the worst thing about being a woman?

Women are one of the most intelligent and beautiful creatures on earth, in fact, in the whole universe.

So this question is indeed spot on!

You’ll get to know her opinion about women in general.

And this question will help you know if she is a feminist or not.

31) If you had the option of replacing the handshake as a form of greeting, how would you want to replace it?


This is a really funny question.

I love it!

Few people that I know don’t like a handshake.

Yes, it’s true. They don’t.

I don’t know why.

So maybe, she might be one of those that don’t appreciate or want handshake as a form of greeting.

This question will really be an interesting one and the answer will be damn hilarious.

32) Are humans beings different from animals? If yes, what makes us different?

So many people around the world believe that all humans are animals. In fact, we are even worse than animals.

So this question will bring out a lot about the girl’s opinion about humankind.

34) Do you resemble any book or movie character?

Yes, I do.

Ain’t going to tell you.

But the majority do find themselves mimicking movie or book characters.

So, find out if the girl is one of those.

35) Does people’s ignorance about an important fact surprise you?

Yes, it surprises and pisses me off.

This is also true of many people around the world.

So get this going and find out her stance about her attitude towards those people.

36) Which memory continues to haunt you?

We all have that memory that continues to plague us even after decades of the incidence.

The girl may or may not have any memory that plagues her.

But you might not know until you find out.

37) Which is that thing which you can’t stop being passionate about?

People love so many things or hobbies.

This question will help you get to know her hobbies and what she is indeed passionate about.

You never can tell, her hobbies might also be the same as yours.

38) What according to you is the best comeback ever?


This is a very intersection question to ask a girl.

Nothing gets sweeter than coming back strong after a loss or a threat.

This question will lead to an avid discussion of her past.

39) Which is that place you wish to go before you die?

I’d love to visit The Bahamas one day.

It’s my dream destination.

And ladies love traveling a lot!

So this question will open up interesting things about the girl and she’ll pour her heart out to you.

40) Have you ever been incapable of doing something in your life that you now regret?

Yes, I have!

So have you too and many others the world over.

Some girls may not want to tell you about their past lives but some don’t bother at all.

So if you meet one that’s shy about exposing her past life, then you can skip to the next question.

But if otherwise, then enjoy the answer to this question because it’s really going to be an interesting one.

41) Have you been ever annoyed with anything so far? If yes, then what’s that?

We get annoyed almost twice in a day.

Annoyed at how people behave, the country leaders, the political system, education system, drivers, teachers, etc.

This question is indeed the bomb!

I’ll ask this question to a girl any day, anytime.

Here is a complete list of questions to ask a girl with a detailed explanation of each question.

Interesting Read: 101 Romantic Good Morning Text For Her

Interesting Questions To Ask Friends

Friends are like gems to us and that’s why I have gone to great lengths to bring out the best of the best interesting and good questions to ask friends for your perusal.

Friends asking each other questions

42) Who was the first person you fell head over heels for? What was that quality that made you go weak in the knees?

The answer to this question would give you an insight into what exactly your friend likes and dislikes in a person and what qualities is he or she looking for in an individual.

43) What is that one thing you regret you should have done at least once in your lifetime?

This question can throw up some really interesting answers, and you would get to know what intrigues your friend to the core. You can get some creative replies as well.

44) Who are you closest to, your mom or your dad?

That may be a tough question to answer since we love our parents equally.

However, there are instances when we feel we love one a little more than the other and it all depends on who we are close to, emotionally.

45) If you ever get the chance to alter your first name, what would you like it to be?

The answer will display the creative side of your friend, and he or she can give some exciting options.

Do join in the conversation and make it enjoyable by offering a few names from your side too.

46) Which place, according to you, is the most beautiful in the world?

An excellent question that should invite some wonderful answers.

We all have visited some places or the other, that seemed to have caught our imagination.

The beauty of that place has enthralled us time and again and we can’t wait to make our way back there.

47) Which is that song that makes you sad every time you hear it?

There is always that one song that makes our heart weep, and we feel like crying.

In all probability, it reminds us of some sad incidents that we have encountered in the past.

Your friend’s reply might even bring you two closer.

48) What lies under your bed? Is there any secret that you have been hiding?

This is a very funny question.

The most likely answer to this question is a resounding NO!

The intent is actually to get to know some secrets about your friend.

But some friends may not want to give away their secrets especially if they are deep ones.

49) Have you made prank calls to anyone till now?

I’ve made so many prank calls and I believe you might have too.

This is a funny question to ask too and the answers will almost always be hilarious.

50) Do ghosts exist? Have you ever witnessed anything?

This is actually a religiously segmented question and I know a few of my friends who wouldn’t like to be asked religious-specific questions.

So don’t expect to get a positive answer to this question.

But it’s still a great question to ask because it’ll bring out the spirituality of the individual and you’ll be able to know his religious stance on such matter.

For example, Jehovah’s Witnesses believe that there is no such thing as Ghost and it’s a lie but other religions teach differently.

So be ready to get different answers to this question.

51) Have you done justice to your time and feelings in life?

So many have not.

This is a really good question to throw in.

You’ll be able to discern if your friend uses his time correctly or not.

It’ll also show the priorities of your friends.

52) Is there anything in life you are embarrassed about?

There are so many things in life we are embarrassed about.

This is an emotionally charged question because it will bring in the emotional side of your friends.

53) At what age did your mother conceive?


As lovely as it seems, not so many of your friends would be willing to give you a direct answer.

But it is a nice question though and it’s good you ask them.

54) What’s that incident which brought tears to your eyes?

The loss of a loved one or a painful incidence can make us weep profusely.

This is also an emotionally charged question and gets ready to be in a sympathetic mood as the answers pour in.

55) What seems to comfort you at a time when you are feeling down and out?

I love this question so much because it makes us reveal a part of us that is usually hidden from people who are not our friends.

It’s a question that’ll make your friends reveal their HOPE and dreams in life.

It could also get religious because so many people turn to God for comfort when they are feeling down and out.

56) What opinion do you have regarding adopting a child?

Some people like it, others don’t

So it’s an excellent question to ask, nonetheless.

57) Which is the most valuable possession you have in your kitty?

This question will definitely bring a smile to your friends’ faces.

You can even go further by asking them ‘Why is the possession so valuable more than the others?’

Questions like that would lead to an even more fruitful conversation.

58) Did you ever feel that saying sorry for something would have mended things, but eventually you didn’t?

We all have been in a situation whereby saying sorry alone would have straightened a lot of things.

Sometimes you look back and thought you would have things differently.

So get this going with your friends and get epic responses.

59) Is there anything that can be done to make your life run a bit smoother?

There are a lot of ‘wants’ or even ‘needs’ we all yearn for.

So this question will definitely get interesting answers, trust me.

And this might even lead to reminiscing or daydreaming by some of your friends.

60) Which is the most significant memory that you have ever had till now?

We all have those memorable events we’d never ever forget and wouldn’t it be lovely to hear your friends’ most memorable events or stories.

61) What is that food item that you prefer not to eat all in life?


This is indeed a very funny question to ask your friends and I’m definitely sure the answers will be so damn hilarious.

Good Questions To Ask To Get To Know Someone

Guy asking a stranger questions

62) Is there anything that doesn’t allow you to sleep?

This is one of the best questions to ask if you want to know someone from close angles.

Replies can reflect what lingers in his or her subconscious mind.

63) What would you do to make your room look perfect?

This invites for some rather interesting answers.

Aside from that, they would also reflect the creativity of the person sitting in front of you.

65) How regularly do you indulge in sports?

Being active and fit is the order of the day and the more you indulge in any sports, the better will you be, healthwise.

Choosing a particular sport depends on your psychology.

66) What’s your favorite color?

This one, too, would reveal one’s psychology.

For example, if someone chooses white, you can quickly assess that the person loves peace.

67) What’s that job that you dread doing?

There are some jobs we dread doing and would rather die than to do the job.

This question will definitely arouse the interest of the person about your personal welfare.

68) Which is that skill that you want to be an expert at?

There are so many skills in the world today.

People enjoy graphics, baking, cooking, etc.

This a fantastic question to ask and it surely impresses on the mind of the person how interested you are in their welfare.

69) What is your favorite song and why?

This is one of the most interesting questions to ask people to get to know them well.

Maybe one of their favorite songs might just be one of yours too.

70) Which pets did you spend your childhood with?

We all have that lovely childhood pet that we can never forget.

This question will bring out their childhood memories and they’ll be more than happy to share it with you.

71) How many people have asked you for help and what help do they generally ask for?


I love this question so much and the truth is, humans, love help.

We just want to help out but sometimes our imperfection might just draw us out from giving a helping hand.

72) Which activity do you have to spend maximum time on in a day?

This question will bring out the funny side of the person.

And they’ll also share with you their best hobbies/activities for life.

Also, ask follow-up questions to take the conversation to another level.

73) What is that thing you wish you had more knowledge on?

Truth is, we cannot have full knowledge of everything under the heavens.

That’s why specificity is the key to mastery.

But there are a couple of things we’d all love get more knowledge on.

This question will help you discern some of the goals of the recipient.

74) What are those small but significant things that lift your mood?

We all feel down and out many times.

But there are a couple of things that can help us lift our moods and we are more than happy to share those with anyone.

So this question will definitely get interesting answers.

75) Who has impressed you the most in your life? And what is the reason?

My mother is the first person that crossed my mind almost instantly.

And I’m sure you will definitely say the same thing.

This question will bring in the emotional side of the person in question and the conversation will be both glowing and flowing.

76) Which television show or film you utterly refuse to watch?

That is a great question to ask someone.

I’ve asked this question to so many people and the answers are always very interesting.

So get this going today!

77) What has been the best day of the last calendar?

Pretty much everyone on the planet has their best days that they’ll always remember.

So this question will make the person pour out their hearts about the days they’ll always remember not just on the last calendar.

78) How do you like to unwind after toiling through the day?

Some days can’t excruciatingly stressful and we all have different ways to unwind.

A fantastic question to ask because it’ll show that you value them and show personal interest.

79) How far have you ever traveled from your home and where have you been?

This could be more of a personal question and not so many people would be willing to give you straightforward answers.

But the fact is the majority wouldn’t mind giving the answers straight away.

80) What’s the best novel you have watched and what’s the best thing about it?

The majority of us love reading novels.

And I tell you, novels are simply fun to read when they are in line with our goals or personalities.

So, this question is indeed an interesting one and the answers would even more interesting to hear.

81) Which question annoys you big time? Why?

There some questions that we hate so much!

Some questions are just condescending downright rude.

The answers to this question will both be interesting and funny.

82) What’s that thing which warms your heart the most?

We have so many things that warm our heart but there are few that warms it the most.

So the goal here is to try and find out what makes their day complete.


Good Questions To Ask Kids

Girl asking a kid questions

83) Which nursery rhyme is your favorite?

Kids are cute, and the way they recite their nursery rhymes is just lovable.

By asking them to recite their favorite nursery rhyme is a genuine way to interact with them.

84) What is your favorite color?

Colors too are the best way to express your feelings.

A kid’s favorite color would reveal what often goes on in his mind.

85) Which is your favorite animal?

This is undoubtedly among those genuine ones in the list of questions and is a great way to interact with a kid.

Of course, a kid would open up a bit more.

86) What does your mom do?

A reply to this would divulge whether a kid is aware of what his loved ones due to run the family.

87) How old are you?

The answer to this question, trust me, will almost always be quick and straightforward.

One thing I like about kids is that they go straight to the point with their answers.

88) What did you have for lunch today?

You’ll always have a straightforward answer to this question all the time.

But some kids can things to another level by divulging the different types of food served at lunch for the past year.

89) What is your brother’s and sister’s age?

Not all kids might be willing to reveal that to you but the majority will.

And also some kids may not even know their siblings’ age.

90) Which food item does your dad love?

This is really an interesting question to ask.

Many kids wouldn’t mind telling you every food item their parents love and even the ones they hate.

91) How fast do you have your dinner?

You’ll get pretty straightforward answers to this one too.

No beating about the bush.

92) How would your favorite house look like?

O what a lovely question this is.

Kids will definitely love this question and are ready to pour out their hearts until you tell them to stop.

They’d be giving description upon description until you get tired.

93) What is the name of your best friend?

Kids love to make friends and they’ll be more than happy to tell you who their best friends are; what he/she likes or dislikes and so many positive and negative things about their friends.

A really lovely question to ask.

94) What does your dad love to eat?

I’m not sure there is any kid on earth who doesn’t know what their dad loves to eat.

So this question is indeed spot on!

You are definitely going to get funny and interesting answers.

95) If you were to teach something to your pet, what would it be?


Kids love pets so much!

And they are willing to teach them just about anything teachable.

This will really get the conversation flowing because the kid will pour out his or her hearts to you.

95) What makes you sad and makes you cry?

Kids get upset over little things and they’ll more than willing to share it with you anytime.

Get ready to burst into laughter on some of the answers.

And also some answers can be quite emotional too.

97) What is your favorite dish?

The answer to this question will be an exciting one to hear.

One thing to note is that some kids usually don’t have one dish that they love the most and they like to jump on two opinions when it comes to selecting their favorite dishes.

98) Do you go grocery shopping with your mother?

The answer to this question might be straightforward or storytelling type.

Trust kids, they will go on to tell you stories about how their mom behaves inside a shopping mall, what they usually do and how their moms make sure they do not trespass.

99) Which car do you want to have when you grow up?

Get ready to be smoldered with wishes and choices.

Kids can tell you stories of what, when and how they’ll buy their favorites and different places they’ll drive it to.

100) What is that thing that you always hear throughout the day?

This question might be kinda confusing unless the child is a very smart one and actually listens intently to what is going on in his environment.

101) What’s your favorite bedtime story that you love to read over and over again?

O I love to ask this question a lot to the kids in my block.

Kids love bedtime stories a lot!

And they’ll be more than happy to share all the bedtime stories in their memories with you, trust me.

102) Which is that place that you would love to go?

9 out of 10 will tell you straight up: ‘Disney World’.

This is a dream place for almost all the kids in the United States.

But you’ll also get other interesting places you might have thought of.

Good Questions To Ask A Crush

Girl asking crush questions

103) What is that thing that you wouldn’t ever like to repeat?

Wait for your crush to reveal some fantastic experiences that he or she has had in the past.

You would also get to know what the individual is inclined towards.

104) What superpower do you wish you could have?

You can expect all kinds of creative answers here.

A reply here can also reveal what the person wants to be.

You can even expand the conversation by including some more options from your end and make it a funny one.

105) Do you want to be rich or happy?

Ah! That’s a tricky one.

But be rest assured that a reply to this one would make you aware of whether the person values money more than happiness.

106) Which year has been the best in your life until now?

Nostalgia might creep in.

Who wouldn’t want to go back and recall all those fond memories?

This is also a great conversation starter and would allow you to get close to your crush.

107) What do you generally splurge your money on?

Through the replies to this one, you can quickly get a perception of what exactly are the stuff that your crush is attracted to.

You would also get to know what catches his or her fancy.

107) What has been the greatest achievement in your life that you will always be proud of?

We all love telling people about our achievements.

This is really going to be a very interesting question to ask your crush.

108) How would you like to be remembered by your loved ones?

We all love to be remembered in a special way and as someone who has done a lot of good for the family and the community at large.

This answer to this question will definitely require some time and brain processing power because it makes your crush to take a look at his or her past life.

109) What do you mostly shop for and why?

A very fantastic question to ask and rightly so.

We all love shopping and getting new things.

It makes us happy and feels accomplished.

So this question will definitely brighten up the mood of the conversation.

110) Name one experience in your life that has made you strong?

A fantastic question that’ll make your crush reminisce and give you a little motivational speech.

You’ll be pretty motivated by the answer to this question.

111) Who and what has embarrassed you the most until now?

We have mostly been embarrassed publicly by our moms especially when we were still kids.

It’s a good way to know about your crushes’ emotions and how he/she reacts to embarrassment.

112) What is the most ridiculous thing that you have done in your life?

I could remember doing some pretty nasty thing as a young teenager lad that it makes shake my head at the thought of it.

So this would be a nice experience sharing time for both of you.

113) Have you ever found anything hard that others find quite easy?

Yes, we all have.

It’ll really be nice to get to know what it is on his or her end.

114) What’s your favorite dress that you can’t afford to part ways with?

We all have that fantastic dress we can never afford to part ways with.

It’s like a symbol of our elegance and style.

This question will bring out the fashion-life of your crush.

115) How many relationships have you been in previously?

As much as I consider this question a little intimidating and personal, it’s no doubt a fantastic question to ask at this stage.

But you have to very discerning too.

If your crush is not the type that likes personal questions, just skip this and move on to the next to avoid a weird answer.

116) What’s the quality in an individual that attracts you the most and why?

This is it!

One of the most important questions I almost always love to ask.

This question will no doubt draw out some inner farreaching thoughts of your crush.

And he will pour it out to you more than you’d have expected.

And if the qualities your crush mentions align with your personality, then you are a go buddy.

117) What has been the best compliment that you have received so far?

Mine is ‘You are such an Angel, Thank You!’

And who doesn’t love beautiful compliments?

I do and I know you do too.

So get rocking with is one!

118) What skills do you have that can impress anyone around you?

We all have great skills in us.

Some discover early on in life while others, a little later.

But it’d be incredibly exciting to see your crush impress you with his or her skills if any.

119) What’s your idea of a perfect holiday and whom do you want to go on a vacation with?


So many people have their own definition of a ‘Perfect Holiday’.

So wouldn’t it be nice to hear your crushes’ perspective?

Sure it would.

120) What’s your most favorite destination that you have been to several times but can’t get enough?

I’d say the Bahamas!

It’s really a lovely place to visit.

And you’ll surely want to get to know your crush’s most visited place or places he or she will never get tired of visiting.

121) What’s your fashion statement?

A straightforward question that’s asked at the perfect time. It’s indeed a perfect time to know how your crush dress and why he or she dresses in such away.

You can get more interesting questions to ask your crush here.

Good Questions To Ask Your Girlfriend

Guy asking girlfriend questions

122) What should be the role of a woman in a relationship?

Okay, this is obviously one of those deep questions.

You would get to know what role your girlfriend wants to take up after you two decide to settle down.

There are high chances that there would be a role reversal.

You will also get to match your expectations against hers.

123) What is that one thing that you regret you shouldn’t have done in your previous relationships?

Now, this is one very sensitive aspect in a relationship and can either make someone emotional or even angry.

Going down memory lane and recalling something that makes her uncomfortable isn’t going to be easy.

So, you need to hold on to your patience and give her ample time to relate everything that she wants to.

124) Which relationship was the most serious one? How did it end? Do you still miss those times?

You need to stop being jealous here if you want to know her from close.

She has got ex-boyfriends, and you might also have your ex’s as well.

Even if you don’t, you need to hear her out with full patience just for the sake of your knowledge.

Her likes, as well as her dislikes, will come out in the open.

125) Have you ever cheated on anyone in your previous relationship?

This is a landmine, and you need to be extra cautious on this one.

You can derive a lot of information about what kind of a person your girlfriend has been.

There is a popular saying that ‘once a cheat, always a cheat’ and there is a reason behind that.

However, it’s applied to you as well.

126) Did you give enough time to your ex-boyfriends?

A simple yes or no answer but sometimes it does require some explanation.

This will be a fantastic way to tell if your girlfriend will give you the needed attention you so seek.

127) Have you ever faced any physical abuse in your previous relationships?

This is the real deal!

Some might not admit straightaway but mild persistence will definitely reveal if she had or had not.

128) Which quality/qualities in a man can annoy you? What qualities should a man have to impress you?

A fantastic question to ask no doubt!

Pay close attention to the answer because it might just be the lifeline you’ve been looking for to get the girl of your dreams.

129) What has been the craziest thing that you have done in a relationship?


This is a pretty funny question to ask.

But sometimes the answer might even be a serious one because there are crazy things we did in our past relationships that we wouldn’t want to try ever again.

130) What is the most adventurous thing you have ever done in your life?

I remember traveling to South Africa and walking brutally close to a group of lions.

I’ll never ever forget that day.

So the answer to this will be really funny and it’ll definitely get the conversation lit.

131) Where do you prefer to spend the major part of your day? Is it indoors or outdoors?

Most ladies would say outdoors.

But you can ask to follow up questions too fully understand why she chooses to stay indoors or outdoors for the most part of the day.

Also, remember that it’s not a matter of choice is she’s the 9-5 type.

132) What is the most prized possession in your life that you never wish to lose?

By asking this question, you’ll get to know what she values the most in life and her priorities too.

133) What do you do if a trusted friend starts saying all negative things about you behind your back?

Very excellent and intelligent question.

You’re trying to ascertain if she’s the type that loves revenge more than anything else and can go to any length in making sure she gets one.

I’ll likely run away from such a girl.

134) Which movie and television shows do you like the most? What is the worst movie or television show in your opinion?

Ladies love shows and movies!

I say this with 100% confidence.

So this question will really get her talking.

Also, find out why she loves and hates some movies or television shows and try to find to connect between her personality and the movies she hates or dislikes.

135) How good have you been as far as budgeting finances are concerned? Are you a spendthrift?

This is a very vital question to throw in.

Some girls are so careless about cash and no man would want to such a woman as a wife or girlfriend.

So it’s important to pay close attention to the answer to this question.

136) Is it right for a man to pay for everything? Should a woman also shell out something? When should they divide the expenses between them?

Another great one!

Most women (especially in some parts of Africa, Asia, India) believes that a man should pay for everything and it’s the job of the woman to arrange the home.

White ladies do have a different opinion on that.

So, it’s important to get the perspective of your girlfriend on this so you’ll know how to handle her and the finances too.

137) Do you know anything that you weren’t supposed to know?

A pretty sleeky question that might get confusing sometimes.

But the point here is to know if she can keep or leak out secrets.

138) What has been the most romantic song that you have ever heard?


This is the question I love the most here.

There is no girl on this planet that doesn’t love a particular song or even two.

You can also ask why she loves the music and watch her pour out her hearts.

139) Do you want to erase something from your life?

There is always something we hate to remember and if we have our way, we’ll get rid of it without a second thought.

So this question is pretty nice to ask and it’s also a deep one though.

But you’ll definitely find the answer refreshing.

140) What has been the biggest mistake that you have committed in your life? What lessons have you learned from that?

Not all ladies might be willing to divulge this to you at an early stage of a relationship.

But if you’ve been with her for quite a number of years, then it’ll be more than appropriate to ask the question.

Just be careful to know the right time.

141) Is social media good or bad? What are the positive and negative impacts of social media?

It’s really good to find out her opinion about social media.

And she’ll be more than happy and willing to you about her opinion.

Good Questions To Ask Your Boyfriend

Girl asking boyfriend questions

I’ve selected some of the best of the best questions to ask your boyfriend that will definitely make him never want to leave you.

So get ready to be super-pumped.

142) Which movie has made you teary-eyed and you never wish to watch it again?

This can prove to be one of the best relationship questions as it will disclose a lot of details about how strong they are emotional.

They can be emotionally pretty weak.

They can be devoid of emotions as well.

You would get to witness either of them.

143) What according to you is a perfect day?

This indeed is a perfect conversation starter, and every guy would love to answer this one.

If you can discuss things that he likes, you two would surely a great time together.

144) What’s that one habit that you possess and a number of people don’t?

People do have some really weird habits, and this is the perfect time that you can learn about him.

Refrain yourself from judging him, since you too have your share of bad habits, don’t you?

145) Do you have a habit that can easily annoy someone?

Now, this is something that you need to know if you are planning a future with him.

Annoying habits, which seem cute in the first place, might drive you mad, once you start spending some time together.

You have all the chances of feeling frustrated.

So, do share some of your habits, while he shares his.

146) Do people overestimate or underestimate you? What can be the reason?

This is interesting as the reply would help you know what your boyfriend thinks about himself, rather then what people think about him.

If he has a misconception, it’s a negative sign, whereas, being humble is indeed a positive trait in an individual’s character.

147) Is there something that you know you need to do, but probably will never do?

Yes, there are so many things in a guy’s mind almost every minute of the day.

But we tend to accomplish less than a quarter.

So this question will no doubt make him talk like never before.

148) What has been the best part of your growing up days?


Guys especially hate been challenged by bullies in school when growing up.

So this will be a pretty nice question to ask you guy and you’ll be amazed at the answers he provides.

149) What do you intend to do the most when you grow old?

O, how I love this question.

Many guys have the dream of retiring and living in dreamland with the love of their life.

I expect your boyfriend’s answer to be the same as the one I’ve provided above.

Because trust me, it’s a man’s thing.

Extra Interesting Questions to Ask

150) What weakness do you see the most in a person? What sign of weakness do you see the most in yourself?

151) Is there anything that you tried to like with all your heart, but somehow was not able to?

152) What is that quality in you that makes you stand apart in a crowd?

153) Is there any mistake you have made, that has ultimately benefited you in the long run?

154) How important is money to you? What would you do if you become a millionaire one day?

155) Who, according to you, is the most harmful person that you have ever come across in your life?

156) Which is your favorite novel? Which character do you like the most in that novel?

157) If you want to put everything aside and go out on a road trip, what would be your destination?

158) Do you love pets? What’s your favorite pet? Do you have a pet at home?

159) What’s that thing you have learned in life and wish you had never learned it? Why?

160) In case of feeling stressed out, which activity brings your peace of mind back?

161) Is there anything that you have done after getting badly drunk and wish you hadn’t done it?

Good Questions To Ask Someone At The Party

Guy asking girl questions at party

162) What’s the hottest thing on the internet today?

Whether you intend to take this discussion seriously or make it a little funny, it’s a good conversation starter either way.

The answers you would get can prove to be rather interesting.

163) Which celebrity, according to you, can be rated as a perfect 10?

This is one of those good questions to see whether your choice matches with that of the others present around you at the party.

Don’t worry if you are not that good with celebrity names. You will get an idea from the replies you get.

164) Among all the purchases that you have made in your life until now, name the best and the worst.?

It goes without saying that we all have made one or more blunders while purchasing something.

Ask people to share theirs.

It’s fun and a good way to gel with people at the party.

164) If you get the opportunity to change your name, what name would you like to give yourself? What would be the reason behind choosing that name?

Another fun way to know people around you.

Many people dislike their original names and wish they got a chance to choose a name for themselves as per their liking.

Let people share their choices and you bet, while some may display their creative side here, some names might sound hilarious as well.

165) If you had the chance to know the real truth to a single question, what question would it be?

It entirely depends on you whether you want to make this funny or a bit serious.

However, it would be really interesting to know what kind of questions usually crop up in people’s minds.

You might find some common questions too.

Extra Good Questions Worth Asking

166) Do you have any talent that has seemed useless to you?

167) Have you been to any such place that has pissed you off completely?

168) Have you ever been tricked into doing any ridiculous stuff? How did you feel after that?

169) What’s the latest thing you have read and felt intrigued?

170) Is there anything that your brain asks you to do and you try hard not to do it?

171) Have you ever come across a messy person in your life? Who is it?

172) Is there any crazy thing that one of your teachers has ever done at school or university?

173) Which exercise do you love doing the most?

174) Which is your favorite day of the year? Is there any specific reason behind it?

175) If you were asked to choose a mentor for yourself, who would that person be?

176) If someone gives you the opportunity to go back in time, which period of history would it be?

177) Suppose, you get the chance to meet someone, either living or dead, who would that individual be?

178) Which are your most favorite quotes? Do you have more than one?

179) Which mode of transportation do you have the least liking for?

180) Do you hate doing anything but still are compelled to do it?


Deep Questions To Ask

Guy asking girl deep questions

181) Will the future be better than the present? What do you think and why?

This is one of those philosophical ones that one needs to ponder on a bit.

It depends on what kind of a past one has had.

If the past has been one that’s worth forgetting, an individual can always hope for a better future.

Humans are still optimistic about a better tomorrow.

182) What is the essential thing that’s required for a perfect relationship?

Being one of the relationship questions, this has the potential to reveal the actual psychology of an individual and what he or she intends to do to make a relationship perfect.

You would also get to know if he or she at all knows the nuances of an ideal relationship.

183) Who is the person you can sacrifice your life for?

People do have that one person in their lives whom they love the most and can do anything for them, even sacrificing their lives for them.

However, with that being said, there are some selfish individuals around for whom, that would be the last thing they would attempt.

184) Is war inevitable or can it be done away with altogether?

Nobody wants war.

Peace is the motto of every life and the world today strives to achieve that in the most real sense.

If someone wants war, then that reflects an unhealthy mind, to be precise.

Additional Deep Questions to Ask

185) If you had to ask anyone a single question and they had to provide an honest reply, whom and what would it be?

186) How do you want your life to be? Long and boring? Short and adventurous? Why?

187) Have you ever taken anyone or anything for granted? What made you do? Do you continue to do so?

188) Have you been overwhelmed by something or someone? Under what circumstances?

189) Would you give up your life for a stranger? If yes, then why?

190) What’s the most valuable and memorable lesson that your parents have passed down to you? How many times have you applied it in your life?

191) Have you kept your priorities the same as they were five years back? Or has it changed?

192) What’s your definition of an ideal life? Is there anything that you need to do to make your life an ideal one?

193) Which day in your life has been the most memorable one to date? Why is it memorable?

194) What’s more important to you? Money or true love?

195) Is there any hurdle in your life that you have been trying to overcome but without a positive outcome?

196) What is that one thing in your life that you are incredibly proud of?

197) Is your life meaningful? If not, then what have you thought about making it ideal?

199) Is it acceptable to break laws? If yes, then why and how?

200) Who or what has been the most motivating factor in your life?

201) What are the 5 most beautiful things on the planet? What makes them appealing?


Funny Questions To Ask

Guy asking girlfriend funny questions

202) What’s the funniest name that you have ever come across?

One of the funny questions that you can ask someone.

Be ready for a laugh riot as few names can tickle your funny bone.

A great conversation starter indeed.

203) If a necessary amount of alcohol is added to a sport to make it funny, which sport should it be?

Some funny options will crop up, and you might laugh throughout the conversation by just imagining how would the whole thing shape up.

204) What has attained a lot of popularity these days but might seem embarrassing after a few years?

A lot of things rise in popularity in an instant and then gradually die down after some time.

After the hullabaloo decreases, they seem to be funny, and people start wondering what made it famous in the first place.

205) If animals could talk, which animal would prove to be the rudest?

Many of you have pets and imagining them talking is completely hilarious.

However, as far as wild animals are concerned, you have a lot of options.

Extra Interesting Funny Questions

206) What would make people nostalgic some 40 to 50 years down the line?

207) Do you wish an inanimate object wouldn’t have existed?

208) On your visit to someone’s place, what was the weirdest thing you have ever come across?

209) Is there someone you know who reminds you of a movie or a television character? If yes, who is that?

210) Have you ever worn an embarrassing dress?

211) Name a thing, that’s fine if you occasionally do, but not in your best interests, if you repeat it every day?

212) Is there anything that used to be completely trashy, but now has attained a cult status?

213) What’s the most bizarre fact that you have ever known?

214) Have you ever been embarrassed by something in your life? How?

215) What is social media according to you and what are its advantages and disadvantages?

216) Do you have nicknames for your co-workers and customers?

217) What’s the worst name that you can ever give your child?

218) Among all the Wi-Fi names that you have come across till date, what has been the most favorite one? What’s your Wi-Fi name?

219) If you ever get the chance to be a superhero, who would like to be? Why?

220) If there is anything that the Government needs to make legal, what should it be?

221) If you get the opportunity to become invisible, what’s the first thing you wish to do?


Good Relationship Questions To Ask

Happy couple discussing

222) Which habits in other couples that annoy you a lot?

A reply would give a clear indication of which behavior a person finds irritating or annoying.

223) When you become a parent, what kind will you prefer to be?

Irrespective of whether you want to have kids or not, this is one of those relationship questions that reveal her inner thoughts and what kind of a person he or she is.

224) On a bad day, would you want to spend some time alone or would you want someone to perk you up?

This would be a good reminder of what to do next time the person has a bad day. As simple as that.

225) Are you content with the mental and physical aspects of your relationship?

You need to check on him or her time and again to confirm that they are doing well and they are happy with you.

226) How would you prefer to spend your day and what would love doing?

If you want to ask me something and expect an honest reply to that, what would the question be?

Other Great Relationship Questions to Ask

227) What’s your idea of a special day with that special person in your life?

228) Do you recall the first thing you said to your partner?

229) Has anyone given you relationship advice? Which one is the best according to you?

230) Are you on friendly terms with your ex?

231) Which part of the year is your favorite? Any special reason?

232) Have you gone through times you have felt lonely or emotionally down and out?

234) What has been the best moment of your life?

235) How different are you from your partner? Has there been a difference in opinion ever? How many times?

236) Have you ever felt that something is missing from your life?

237) Is your lover your best friend? Or you are not sure enough whether you should confide in them?

238) Do you prefer going out or stay indoors for a date?

239) Do you prefer breakfast in bed or a candlelit dinner?

240) Having a family or Traveling around the world? Which one is more important to you?

241) How would you love your partner to propose? Publicly or in private?

Thank you for reading this article in its entirety.

So go ahead and use as many questions as possible to strike a fruitful conversation with anyone.

Although the numbering says 241, it’s actually 251 with the follow-up questions.

So, let me know your thoughts, please.

Share some very good questions you’d like to ask people.

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