300+ Questions to ask a guy

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You really like a guy but don’t know how to talk so we have a list of questions to ask a guy. It’s not a rapid fire round that you would play with him. I would give you a list of 300 questions to ask a guy by framing them in a conversation so that it would be easy for you to go ahead with your conversation. 

questions to ask a guy

Personal questions to ask a guy

Questions to ask a guy related to himself :

1 What your friends love to call you? 

Everyone has that one embarrassing name that our friends love to call out in public or private regardless of how embarrassing you would feel. You can tell more than one name. 

2 One crazy memory you would recall from your childhood

Childhood memories are the most loved memories we have. You must have tons of crazy memories, so would you like to share one memory from your crazy childhood. 

3 When you used to be sad as a kid what was your go to place? 

As a kid we get sad even on the smallest thing but sometimes we get so offended that we want some private space. Every kid has that one secret space that no one other than them knows, where they can hide, cry or play alone. 

4 What kind of a kid you were? 

Kids have mixed emotions and it’s not easy to tell what mood they will have a whole day. So what kind of kid were you ? Crying baby, happy kid, mischievous kid, smart kid, shy kid or boss baby. 

5 How often you cried? 

Kids cry most of the time. They cry when they want something, they cry when they need something or when they are hungry or angry but as a grown up, how often do you cry or you are good at hiding your emotions? 

6 Did you ever bunk from your school or tution? 

Bunking a class is a dream and right of every student and most important when it’s a maths class. Have you ever bunked a class or did you ever get caught? Or had fun watching movies and moving in and out in a city. 

7 Are you a maths lover? 

Boom! Maths is a good subject till high school. Once you opt for maths, your life is all about differentiation and integration. Jokes apart, are you a maths lover? 

8 Do you want to go back to your childhood? 

Now as we grow up, some part of us wants to go back to our childhood to relieve those beautiful memories. Memorise of only happiness, love and carefree life. 

9 Have you ever had a crush on your teacher? 

Crushing your teacher in school or college is every guy’s weakness. Were you of that category of guys who go school just to see their crush and day dream a beautiful date with them. 

10 What differences do you see in life now and then as a kid? 

Kids are happy as they are carefree. As we grow life changes our priorities change but what exactly the major difference you see and miss the fact that you are no longer a child. 

11 Do you think kids are god’s favorite? 

A kid can bring happiness in anyone’s life. There is no single person who would not smile watching a kid or play with them. Do you think the same or you are not a kid lover? 

12 What was your favorite cartoon? 

Childhood was amazing because they were cartoons to watch. Nothing is comparable to watching your favorite cartoon while eating your favorite snack served to you by your lovely mom.

13 Have you ever stolen money from your parent’s purse? 

Kids are stubborn and they want everything in their hands and when they don’t get it they can do things which are not good. 

14 Is there any day which you want to remove from your life? 

Everyone has that one bad day that they want to remove or vanish from their lives. As you never want to relive or re-experience those memories in your life again. 

15 Do you think grandparents are much cooler than our parents? 

It’s a saying that when grandparents see their grandchildren, they try to relive all the moments with them and so never say no to them. Grandparents play a vital role in spoiling a kid in a good way. 

16 Have you ever been to any fight in childhood? 

If kids play, they fight too. Most of the fights are among siblings but some serious ones can happen once you start making friends in school or neighborhood. Everyone has that one big fight about which their parents don’t know. 

17 How would you react if your kids behave the same way as you used to behave? 

Our parents always say this one line on repeat ‘you will know when you will have your own kids’

Would you like to put some light on this. 

18 Most embarrassing moment in school. 

It’s up to you, you can share as much as you can as I know you have a bucket filled with memories. 

19 How mischievous you were then and now? 

Every kid is mischievous, at least in front of their mother. Even the smile on your face tells everything. I’m ready to listen to all the goofy stories. 

20 Do you still miss that little version of you? 

Does a part of you want a part of you (as a kid) in your life? It’s amazing how old we grew and still wanting more. How do you feel wanting a version of you back in life? 

Questions to ask a guy related to his family :

21 Would you like to tell me about members of your family

Knowing about your family is equally important to knowing about you. 

22 Do you have any pets? 

Are you a dog lover or a cat lover? Do you have any pets? Do you think they like to live this way? 

Don’t you feel bad when they would demise? 

23 How grateful you think you are to have your parents by your side? 

Kids are proud of their parents and they would do anything for them. Are you grateful to have them by your side? Do you say I love you to them or like me secretly pray for them? 

24 Do you think Dad’s love is a little underrated? 

We all know when it will be mother’s day but few would remember father’s day. Dad’s are the one who won’t say no to anything, who will himself cut off his expenses but won’t ask you to do it. 

25 How can you define mother’s love

Mother is not only a part of our life but our life. How beautifully can you explain mother’s love? 

26 How much time do you take out to spend with your family? 

We often stay busy with our friends and gf/bf that we find less time for family so how much time do you spend and what do you all do in that fun meeting. 

27 Who is your go to person (Mom or Dad)? 

No doubt we all have a mind set to ask whom for which thing. So who is your go to person for different things like asking for money, taking pieces of advice or anything more you would like to add. 

28 Do you find siblings are a bit annoying? 

Ask him how many siblings does he have and how is there bond? Who annoys whom? What was their favorite game as a kid and things related to childhood. 

29 Do you still take permission from them to go out? 

You will always remain kids for your parents. Do you still ask them before going out or doing something or going to do something big like decisions of life? 

30 Does your parents know everything about you? 

Nowadays kids are smarter, they tell what needs to be told. What about you, how much you tell them or you are like a good kid you spit out everything. 

Questions to ask a guy related to his friends :

31 How close you are to your friends? 

Friends are an important part of everyone’s life. Ask him to know how close he is to know how good he is at maintaining a relationship. 

32 Do you think childhood friendship lasts forever? 

Childhood friendship is rare to have and if he is in contact with some of his childhood buddies so girl he is really good at long distance relationships. 

33 Tell me about that one friend for whom you can do anything? 

He is the one he always relies on. To be in his good books love his friends. Girlfriends tend to always push her bf from his friends which is the biggest reason for any relationship to fall. 

34 Will you prefer friendship over love

That would be any tricky question to ask. If he chooses love then he is lying as friendship plays an important part in life or if he chooses friendship then he doesn’t want a serious relationship. In case he chooses both he is playing smart but best answer to give as these two things are not comparable. 

35 What does friendship mean to you? 

Friendship is the utmost important part of anyone’s life. What a person feels about his friends is his real way of thinking. 

36 Have you ever felt betrayed in a friendship? 

Not all friends are good and not all friendships last. This question would help you know his betrayal and what upsets him the most and how to avoid doing that. 

37 Do you think guys are good in friendship in comparison to girls? 

Somewhere it is true and we all girls know this. Know his reaction if he says no means he doesn’t want to hurt you. If he says yes means he is opening up with you and is okay to be honest with you. 

38 How far can you go in helping your friends? 

Men are known for good friendship. This question will help you know more about his helping nature and how much he cares about people he loves. 

39 What would you do if you came to find out your girlfriend is cheating on you with your best friend? 

This question is one the most difficult questions as it is even difficult to imagine. It would be the worst day of his life and let’s know how he would react to not so good questions. 

40 Would you break your best friend’s leg for a million dollar? 

This is a funny question, this question will tell you more about his humor, how he takes this question and well he answers like it’s an imaginary question so ask to know the level of humor he has. 

Questions related to his love life:

41 How many relationships you had? And a serious one too? 

Men hide past relationships as they think if they tell a big number that would hamper his image in front of you. So in the beginning most of the men lie about their relationships but if you are lucky to have a man you genuinely tell you everything then girl he is your man. 

42 According to you, tell me that one thing that would make any girl fall for you? 

Men exactly know what is that one thing that would attract a girl. Some would say there looks, honesty, nature, smile, personality. So it’s a question to know did you fall for any of it? 

43 What kind of girl attracts you? 

He knows what’s his answer but if he is into you he would ask if you are attracted or not and if he doesn’t ask then he would simply narrate a girl keeping you in mind. Please be smart enough to catch his words. 

44 Do you believe in love at first sight? 

This question has nothing to do with your equation with him but just to know if he is romantic and goes with the flow type or the logical one, like the one who checks everything even before falling for her. 

45 Are you ‘everyday new crush’ or ‘one crush for lifetime’ kind of person? 

This will not show his real personality but would give a glimpse of his everyday love life. This would help to know his crush or type of interest he has in girls. 

46 Did you every day dream about your love life? 

Daydreaming is in the minds of people who are more artistic. They have everything lined up in their mind. They are the people who think a lot before making decisions. 

47 Do you believe in ‘exes can remain good friends’? 

This question would have two answers yes or no. If he says yes means he has ex’s as his friends and if no means he can’t be friends with them and he is not into giving other chances. 

48 What would you do if you get stuck in an elevator with your ex? 

This will give your information about the bond he shares with his ex and how comfortable he is with her. 

49 What would you do if you get stuck in an elevator with me? 

Now you can see what he would say to you when you two would be alone and try to find how differently he treats you from your ex. If he answers the same way as he does in the above question, I would say he is not into you. 

50 Are you a long text type of person or love letters kind of person? 

Men who love letters are the most romantic men in the world and are into doing cute little things for their girl. 

51 How expressive are your feelings

Guys are not expert in telling their feelings. His answer would tell you his real nature and how shy he is or how good he is at hiding them. 

52 Would you mind if your girlfriend earns more than you? 

To know a guy who needs to understand his level of understanding and how he reacts to certain things. No girl wants a relationship where she finds disrespect and jealousy. She wants her man to be proud of her. 

53 What would you prefer – splitting bills or paying full bill by yourself? 

Now this question will explain the way he treats women or his partner. Is he money oriented? Or he believes in equality among a couple and if he is not shy in splitting bills and being real. 

54 Do you believe in ‘keeping your love life private until it’s sure’? 

This thing would tell about his thoughts of society and how much he values his relationship and his privacy rather than just showing off and creating problems. In other ways this would hint that he doesn’t want to show until he is sure he would spend his life as this could ruin up his lined options. 

55 How much are you open about your relationships with your family? 

This would tell alot about his family and his bond with them. How his family thinks about relationships and everything. 

56 Are you afraid of introducing your girlfriend to your parents? 

This answer is for future reference. Keep this mind before getting too serious with him as if he is too afraid of his family so he would end up with you but won’t tell his parents about you. 

57 Are you ‘movie in theaters’ or ‘movie date at home’ kind of person?

People who like going to theaters are more extroverted and people who like movie dates at home are introverted plus they love their comfort and enjoy being home. 

58 What is the most crazy thing you have done for your partner? 

Every one of us has craziness inside us. Questions like this makes him feel like you want to know him both outside and inside. 

59 Would you skip your cricket or football match for a date? 

Guys love sports, when a guy is new into a relationship they would definitely skip their match for a girl as they don’t want to lose her. 

60  Are you good at keeping secrets? 

How good he is at this and try to take out some secrets from his mouth. A good secret keeper is good at hiding emotions and his feelings and are not easy people. 

61 Do you believe in giving second chances in a relationship?

This will tell you about his nature and how he sees people and how easily he could forgive you for your mistake or how serious he gets for small things. 

62 What is the most important aspect of a relationship

If you are looking forward to being in a relationship with this man then this is the important thing to know. What matters to him the most is important for a relationship to grow as it is easy to start a school relationship but difficult to continue it with the same pace and craze. 

Funny questions to ask a guy :

63 How funny you think you are? 

When a guy makes a girl smile he has got extra points from other guys. Girls fall for funny guys, ask him to know what he thinks about himself. 

64 Who is your celebrity crush? 

Just a random question to know his interest and how much can you relate with that. 

65 Have you ever done anything stupid in front of your crush? 

Ask him about his crush and how much he is crushing for her and the level of stupidity he does in front of her. This could be funny but you will come to know how good he is with girls. 

66 What would be one gossip that you would like to spread about yourself? 

Interesting and funny, he could be anything. Be ready to listen to the most weird or cool gossip from him. 

67 How often you pull a ‘push’ door? 

Thing that everyone has done at least once in his lifetime. Questions like this keep your conversation funny and not so boring. 

68 How would you react if one day someone told you about your secret rich ancestors? 

This could be interesting to hear as every single person dreams to be rich. 

69 Have you ever stalked your crush on social media? 

Stalking someone is common as we tend to avoid the talking part. Ask him more about his crush and if he is still into her or not? 

70 How long have you stayed without showering? 

Some men can’t live without showering a day and some can live like days in the same clothes. 

71 Have you stolen something from hotel rooms? 

Hotel rooms have those picky things that you don’t want to have but don’t want to purchase. So does that ever happen to you and you just stole it. 

72 Do you do ‘cheat day’ or ‘everyday is a cheat day’? 

How often you do cheat day or everyday is your cheat day and you enjoy having your favorite dishes by your side all the time. You will get to know how foodie he’s and what sort of food he enjoys the most. 

73 Have you done anything weird in front of your crush? 

Your friends are teasing you and you got caught while watching your crush. Millions of incidents could be there to share about your weird conversations or meetings. This will show how courageous he is in front of girls he likes. 

74 Did you ever mistakenly like someone’s one year old picture? 

Nightmare for anyone living on this planet. Stalking is now part of our lives but what if you mistakenly Liked someone’s old picture. What would you do and how less you would panic. 

75 What is your go to dance move in every party? 

Whether you are a pro dancer or a noob dancer. That one step that makes you look cooler, more happening and your go to dance move at any party and on any song. 

76 Did you ever sneak out of your room to party late at night? 

As a teenager some daring people have done stuff like this. Were you a part of this kind of gang or part of a boring gang like I was in? 

77 How you tackle a person with whom you’re having a boring conversation? 

Are you a straightforward person and say directly you don’t want to talk or you are kind who resist in saying no as you don’t want to hurt another person and listen to his talk till he ends. 

78 What’s that one weird thing you have in your room? 

This could be anything like a collection or weird toy or weird gift or any weird thing you have picked up from somewhere. It’s there in your room, sitting quietly at one corner and is of no use. 

79 Most useless app on your phone? 

We get excited knowing about a new app from any YouTube recommendation or any friend’s recommendation and after some time it’s there lying in your phone and used like years ago. 

80 How crazy you and your friends are? 

As a kid, teenage or adult, we don’t stop from doing crazy things with our friends. Show some light on those crazy moments and memories you have with them. 

81 Do you have a bad habit of laughing at the serious moment? 

Are you of this category who couldn’t control their laughter at serious moments. Tell me some of those times. 

82 How much credit you would like to give to yourself for spoiling your friends? 

Are you the one who spoiled your friends or there is someone else who did it? 

83 The most epic excuse you told to your parents. 

We all have said tons of lies till date. But the excuses we used to made as a kid are bit stupid and funny. What were those excuses? 

84 Tell me something about your secret talent. 

It ranks good in the list of questions to ask a guy. You will get to know a lot about him and his secret talent and something you would adore about him. 

85 Are you a bathroom dancer or singer? 

It’s an extended version of the above question. It’s a funny question to ask a guy to know his interests and how he enjoys little things in his life. 

86 Who is your partner in crime? 

Partner in crime is not necessarily to be a girlfriend. It can be his buddy or sibling who is always ready to do some crazy and out of the world stuff. 

87 What do you do in your freetime? 

Free time is the time when a person actually thinks about himself and does the stuff he really wants to do and loves to do. This question will help you know about his interests. 

88 Your favorite meme page on Instagram? 

If you’re on Instagram you are always scrolling and laughing on memes. Meme world plays a major role in the lives of teenagers as they bring a smile to our faces. 

89 What’s that one movie or tv series you can watch everyday? 

Everybody has that one favorite movie or tv series that they can watch at any time and at any place at any cost. Such questions to ask a guy would help girls know his interests in series and to know if you both have common interests or not. 

90 What is the most funny and annoying thing about you? 

The funniest thing about you which charms everyone around you and that one thing of you which is annoying others but is ok for you. 

91 Any weirdest eating combo you would like to share. 

As we grow we all have our choices in terms of food, places we go, our clothes we wear. Would you like to share some of the weird combos which you have invented and so far is in love with them. 

92 How bad are you at taking criticism? 

No one likes to receive criticism but it’s a gift you will get without asking. You can’t ignore but simply have to accept it. How about your experiences in terms of taking criticism. 

93 What’s the one body part you find unnecessary? 

Each body part has their specific functions but some are not that important so which body part you find unnecessary and you want to remove it from your body. It could be anything. 

94 Have you ever made fun of someone and later felt sorry about it.

Are you of that type who speaks out without thinking much that it might affect the other person but later feel sorry about it. What do you do after that and how you say sorry for what you said(if you do so) 

95 Can you make someone laugh? 

Happiness is a key to any relationship. The one who can make others laugh has my heart. Those people are the gems. How can you make someone rather me laugh? How about trying it right away. 

Deep questions ask a guy

96 How can you describe ‘life’ in one line? 

Questions like these will make you understand the way he thinks. Is he like you or something different from you? 

97 What morals you follow in life? 

Deep questions to ask a guy like these have different meanings. These will help you understand him and his way of thinking and his upbringing and nature. 

98 Do you feel bad seeing poor people around you? 

If you are that person who whenever sees a poor, shares their food with them then you definitely need to ask this question to him to see if you both are on the same page. 

99 What makes a man rich? 

Ask him about his thoughts on this and does he dream the same? What would he need to do to achieve his dream to be rich in life. 

100 Do you want a rich life or satisfactory life? 

This will tell you about his complete nature and how he sees life and career. Rich life is the dream of everyone but if you don’t have satisfaction in whatever you do, how would you be happy? Just ask him what is happiness according to him. 

101 Have you ever helped someone in need? 

Kindness towards needy one is a sign of humanity. Whether you help them with just a penny, it counts. Humanity counts. 

102 Do you love going outside or sitting inside? 

Just to check if he will be vibing with you or not. As most of the fights among couples is the one is not going out or he is not taking me out somewhere. 

103 Are you comfortable with people intriguing in your private space? 

Some people are really private. Till now you have already intrigued in his life and if he still says yes then girl he is okay with you being so close to him and lying in his private space. 

104 Does anyone ever break your hurt? 

Break ups are difficult. If it has ever happened ask him how he stopped thinking about her. What did you do to forget her? 

105 How can someone be happy? 

The way he would answer is the way he thinks about happiness. Is he relying on others for his happiness or does he know the real meaning of happiness. Happiness is an inside job. 

106 According to you, what’s the rule of the universe? 

Universe works and it works in it’s own way. Everyone has a different way of understanding it. How intellectual he is would be known by this question from questions to ask a guy. 

107 Do you believe in saying ‘ family is everything’? 

How important his family is to him and how much he values them in his life and how much they play their part in his life. This is important to know him better. 

108 What if one day you have to make the most difficult choice between your career and family? What would you choose? 

How about your college in a different country or your job which you really wanna do but your parents don’t want you to leave them in a different country. What would you choose? How would you make them understand your decision? 

109 Tell me about that one thing you learnt from your mom? 

Our parents are our biggest teacher. Mother is the one who teaches us the very first lesson of our lives but there is always that one saying or lesson that you will never forget in life. 

110 Tell me that one thing you learnt from your dad? 

Dad’s are the one with lots and lots of experience in life. The things that you would learn from him are priceless and no one other than him can teach you that better. Tell me that one lesson he taught you and you would keep that in mind forever. 

111 How close you are with your parents? 

Parents are family. There is nothing greater than the love of your parents. Whatever you do they will always be by your side. But some of us don’t share that bond with them. What about you, how close do you think you are with them? 

112 Do you share everything with them? 

Being close doesn’t mean sharing every inside out. Sometimes there are things that you resist from sharing as you know how they would react. How are you bonding with them and how much do you share with them? Do you share with them only what you want to share? 

113 Do you believe parents can be ‘good friends’? 

In our generation, parents are trying to be friends with their kids so as to end a generation gap. Some succeed and some fail miserably. But doesn’t mean they didn’t try. What’s your terms with your parents in this context? 

114 Tell me some of the silly excuses you made to skip school? 

No one likes to get up early and go to school. Every kid’s dream is to sit at home, eat some candies and watch their favorite cartoon. But all kids are not lucky, what are those silly excuses you ever made to skip classes. 

115 How bad were you in your academics? 

This question has big double standards. You can’t directly ask him about his marks. Ask him the way he tells you his real remarks from school. 

116 Do you think we teenagers take our parents for granted? 

When we were kids our parents were our best friends but as we grew up our friends took that place and we slowly slowly started taking our parents for granted as we know they won’t say to us and will do anything for us. 

117 Does your heart ache seeing some homeless kid? 

How generous and kindhearted he is will truly be depicted by this question. Questions like these from my list of questions to ask a guy are just to know how he feels for people he doesn’t know and are in bad condition. 

118 Do you ever wished to help someone but couldn’t because of less money? 

Helping someone is not what everyone does. Some people have money but won’t give it too poor and some don’t have it but want to help. What do you think about helping the poor with money? Is it a good deed? 

119 What do you want more ‘money’ or ‘fame’? 

Logical people want both. Who in the world wants only one but a smart one would say money as money can bring fame but fame won’t bring enough money. 

120 Do you feel okay having a kid as domestic help in home? 

Domestic help is not legal plus it’s not right to have minors as a domestic help. It would directly impact his mind and future. Ask me about his thoughts on this and should this practice stop or not? 

121 What is the value of money in your life? 

Some people are just money oriented. For them money is the most precious thing of life. I would say money is important and is not above your life and people in life. Listen to his interesting answer. 

122 Will be satisfied in a job with less income ? 

In life where everything is related to money you will be satisfied with a job with less income as you are doing what you always wanted to do. Is comfort above money? Is self-satisfaction above money? 

123 Do you feel love is above all? 

Love is an emotion. In today’s world it’s difficult to find true love. Will you keep your love and lover above everything. Above means above family, career and your life. 

124 Do you spend time with yourself? 

Life is so busy nowadays that we don’t have enough time to even spend with ourselves. Give time to yourself like do meditation, sit quietly and listen to some songs or you can read a book of your choice. Ask him this question from questions to ask a guy to know he likes to spend time with himself and does he really do that or not? 

125 Do you believe in ‘god-ghost’ or ‘positive-negative energies’? 

God-ghost or energies. How would you start a conversation like this. Every person in this world has different opinions on this and has their own myths and stories related to it. 

126 Have you ever faced karma in life? How hard did it hit you? 

Karma is the reward of your deeds. Sometimes it’s good if you did something good and bad if you did something bad. Have you ever faced it and how good or bad it was. How did you tackle that situation? 

127 Do you believe this hell and heaven is on earth only? 

We say karma hits bad. Even our ancestors say you will pay for all your sins in this life only. Do you believe in all of these and what are your thoughts on it and do you even believe there is any hell or heaven? 

128 Do you hold grudges? 

How often you speak out everything you have in your mind and heart. Did you ever forgive someone and had grudges against him in heart? What was the reason for forgiving him? Why didn’t you speak right away and holding grudges? Why can’t you just go and confront him? 

129 What would you choose ‘true love’ or ‘money’? 

Money and love are the ones that have big importance in our lives. People say they can live without money but not love. What you believe is true according to you and why do you choose it? 

130 Do you believe I love you is overused? 

‘I love you’ is not a phrase but emotion. But nowadays it’s getting too polluted. People don’t know the real value of this phrase and use it to just say but don’t mean it. People say it so frequently as it loses its original and pure meaning. What are your thoughts on it? 

131 Have you ever felt like crying for no reason? 

Sometimes we have things in our heart and when we are in our worst mood, it comes out. Crying without a reason means you have some deep sorrows which you didn’t share with anyone. 

132 Do you believe in fact ‘men don’t cry’? 

We have images of men in our heads that they don’t cry. They are strongest but being Strongest doesn’t mean they are emotionless. How much you agree and disagree with the most used statement for boys. 

133 What do you do when you get hurt? 

Hurt in sense hurt in love, relationship and life. How you overcome that situation of hurt and sadness. What do you do to feel good and get over with whatsoever happened. 

134 Have you ever got dumped by someone? 

One sided or unrequited love is the most painful kind of love. It’s all about giving when you know you won’t get anything in return. How you manage to forget or get over someone you loved so much. 

135 What is the most important thing in a relationship? 

As you earlier was in some relationship. So will you shower some light about important things to keep in mind in relationships. What are the common mistakes that every couple make and what’s the secret mantra to have a successful long relationship? 

136 Are you possessive type or okay with whatever your girlfriend does? 

In the above question from the very list of questions to ask a guy. If a man tells he is okay with whatever his girl does then he is not serious for her as jealousy is a factor that is important in a relationship. This thing should matter to you but possessiveness is what bit over. You should trust your partner but also should keep a silent eye on her for the sake of a relationship. 

137 What would you choose ‘candle light dinner with girlfriend’ or ‘night out with friends’? 

This question is a fun question. Never ask him to make you as his first choice. Life is incomplete without both friends and girlfriend. But the answer to this question would be interesting to hear. 

138 Do you think after some time a relationship turns boring? 

I have heard lots of couples complaining about less topics to talk about after a few years as a couple. Some say we are tired of the same fights everyday and some say what is left to talk about. What are your thoughts on this? 

139 What is your biggest turn off? 

That one thing that could turn off your happy mood. Anything you would like to tell that could change your mood in seconds. 

140 Do you think girls need makeup or natural beauty is everything? 

Girls look beautiful in both. Makeup is meant for girls so they use it. There is nothing wrong in applying it. But it’s interesting to know his interest in this question. 

141 Why do you think girls wear makeup? 

Makeup is an art. Some girls love to do it and some do it as a part of work but what he thinks is the reason you asked him this question. What he says to say about girls in makeup and without makeup. Ask him about any 5 makeup products. 

142 What is that one thing you hate about yourself? 

We all know that one thing we hate about ourselves and want to change it but couldn’t do it instantly. Tell me about that one thing you are trying to change about yourself or want to change about yourself. 

143 Why do girls like bad boys? 

Some say good men stand no chance in front of bad guys. Do you anyway agree to it? If you do , tell me about some reasons to justify the statement. 

144 What is the biggest surprise you have given to someone? 

Were you in a relationship where you pushed your limit and did something big and surprising to your partner. I want to know every basic detail of that surprise as I also do surprises for the people I love. 

145 What is the most useless thing you have? 

One thing you have with you right now and you find it useless for now but can be useful later in life. 

146 Are you still on talking terms with your ex-girlfriend? 

Ex’s are those undue payments that irritates you the most. Are you still talking to her? If yes then this means two things m, first you are in love with her. Second, you both were never in love with one another. 

147 What is that one word you would like to say to your ex

If you are not in talking terms with her but still have something in heart then open your heart and pour out or spill out everything related to her and one forward you would like to say. 

148 Do you believe ‘Girls run behind money’? 

Some girls do run behind money. As nowadays it’s not easy to earn money and when you are getting free of cost, you go.

149 How important your phone is to you? 

Phones are now an important part of our lives. Nowadays people live mostly on social media and less in the real world. That virtual world created by phone and things inside is an easy escape from the real world. 

150 Who is your crush right now? 

She can be anyone. You always wanted to know who is his crush, so ask him directly as men don’t understand our indirect talks. Ask me right away to know who is in his heart and how serious he is for her. 

151 If you have just one chance to talk to your crush, what would you say to her? 

Another fun question to know how good he is in expressing feelings. It’s that one question you would be looking at.

Important questions to ask a guy

152 What’s your dream date looks like? 

You must have that one perfect date planned in your mind. Tell me something about that dream date you always want to live. 

153 Would you rather go on ‘date on beach’ or ‘date at home’? 

Both are romantic in it’s own way. But it’s a question to know if he has the same thinking as you have. So it would be easy for you to plan your future dates. 

154 Have you ever cheated in a relationship? 

Cheating or lying in a relationship are common nowadays. So have you ever cheated on someone or cheated by someone in a relationship you have invested your everything. How was that feeling? 

155 How good you are at lying? 

People lie so often that it’s not easy to distinguish between the truth or a lie. So how much do you lie? And why do you prefer to lie than speak the truth? 

156 Why do girls cheat or lie in a relationship

Do you know why girls cheat? It would be easy to answer if he had any bad experience or know friends who did that.

157 What do girls desire in a relationship? 

What according to him girl desires in a relationship. This will tell you about his thinking related to girls and also tell us about his past experiences with girls. 

158 What is the best way to avoid any fight? 

Do you know how to avoid those silly fights in a relationship? Every man comes to that stage of a relationship where they don’t want to fight on useless topics and find ways to avoid such situations which could lead them. What is your mantra to avoid fights? 

159 If you ever cheated on your partner, would you tell her

Mistakes happen. And this happens by humans only. So have you ever cheated on your partner intentionally or unintentionally? Would you dare to tell her? If not then why?

160 Do you think long distance relationships work? 

Long distance relationships can work. If both partners give utmost importance to their relationship. With this question you will get to know his point of view and also easy to know what could happen if you both went into a long distance relationship. 

161 Are you happy being single? 

Single life is chill life. Questions to ask a guy must have this question as you want to know is she even interested in getting into a relationship or he just wants to be single and enjoy his singlehood. 

162 What are the disadvantages of being single?

Singles can be boring sometimes. Like when you need someone to share your feelings and needs someone when you are sad. Ask him what are the disadvantages of being single who have felt? 

163 What are the advantages of being single? 

Every guy would give plenty of logical reasons for being single and how happy they are being single. You just need to sit back and listen to the list of reasons now he is going to give you. 

164 What is the biggest turn off in a relationship?

Turn off means things according to him that could hurt him and changes his mood. This question is very important to know what things you should avoid to not upset him. 

165 Whom do you listen to the most? 

When a person is in confusion and could decide what to do they obviously seek help. Ask him about his go to person and whom he listens the most. If you wanna reach his heart you gotta have a good impression in front of that person. 

166 Will you compromise in a relationship? 

Are you of that kind who compromise for the sake of relationship or of you kind who could let go of a relationship for his ego. Do you think only one should compromise in a relationship? 

167 In your free time ‘think about future’ or ‘past? 

To know him well you should know about his plans and about him. People who think about their future or past are the ones who take a lot of stress and are always running behind a good future. Hope his answer is he believes in living in the moment. 

168 What is self-love to you? 

If a person doesn’t love himself or doesn’t respect himself he can’t love someone. To a person to be happy he should know the importance of self love. Ask him what he knows about self love and you could read about it here. 

169 Do you believe in mythology? 

Our mythology is our pride. We all should believe in it and if not believe, at least know about it. Ask him about his knowledge in this topic. 

170 Are you satisfied with your life? 

To know if he is happy in life this question is for you. A man can never be fully satisfied but a person should have a piece of satisfaction in whatever they do. 

171 Do you believe in giving second chances? 

Second chance in love or relationship. Does he believe in it or did he give someone a chance and regret it later? 

172 Will you ever go back to your ex? 

This question is important as you will get to know if he is still into his ex girlfriend or not. 

173 Does other people’s perspectives about you affect you? 

Some are confident of themselves and some are not. People will judge you whether you do good or bad but that should never affect you. Ask him about his thoughts on this. 

174 Do you love someone? 

Ask him at your own risk. There could be two answers, yes or no. A yes would break your heart but a no could let your hopes stay high. 

175 Do you ever feel worthless? 

In life sometimes things won’t fall into place and you feel disgusted with yourself. That worthless feeling is something no one wants to experience. 

176 Have you ever faced some sort of criticism? 

Criticism can never be good unless you take it in a good way. Ask him how he handles criticism and who stands with him in his tough times. 

177 Are you close to your sibling? 

One thing that remains permanent in our lives are siblings. They will never stop annoying us. Tell me about your bond with your siblings. 

178 Do you ever want to go back to your past and correct everything and then restart your life? 

At one point of life every person has given a thought to it. When we are stuck somewhere in our life and losing everything, this common and unrealistic thought crosses our mind. 

179 Do you regret some of your decisions? 

Not every decision you make will go right. Some decisions could let you go into that regret zone. 

180 What is that one piece of advice you always have in your mind? 

We always keep in mind one advice that we have learnt from someone. We may not remember the person but never forgets the advice. 

181 Is there anyone from whom you can’t remain angry for a longer duration? 

First tell me how long you can remain upset with someone. And is there anyone from who can’t remain upset for the long run? 

182 How often you fight with your sibling? 

It’s their birth right to fight in every little thing. What’s your bond with your siblings? 

183 Do you believe marriages last forever? 

What is the reason why marriages last? Marriage is a big part of anyone’s life so how could you maintain a marriage? 

184 Have you ever been into a bad relationship? 

Unhappy relationships or bad relationships should be avoided. No one should live in an unhappy relationship as these will hurt you only. Have you ever been into any bad relationship? 

185 Are you still in touch with your childhood friends? 

Childhood buddies are the ones we make with pure heart. That friendship is without any jealousy and a true friendship. If he is still in touch with any of them then he is luckiest. 

186 How productive do you feel your day was? 

Are you that energetic or of that type who needs to have a productive day every day. Some people have that enthusiasm to do something productive everyday. 

187 Do you believe in quality or quantity? 

Quality or quantity in terms of everything. This would tell or clear a lot about his choices in life. 

188 Choose a rich girl but average looks or good looks but a poor girl? 

Looks matter or money matters. Just a fun questions to ask a guy, don’t take it seriously if he says something annoying. 

189 What is your biggest fear in life? 

There could be a list of fears you have in mind but tell me that biggest fear and which you will never try to overcome even if you have given million dollars. 

190 To whom you want to give credit for whatever you have in your life? 

Achievements you have till now it’s your hard work. But there are people behind your achievement who have motivated you to reach upto this level. 

191 What is the most unpredictable thing that has happened to you? 

Unpredictable means things you never expected to happen to you. This could be anything like a surprise or something you dreamed of and happened. 

192 How’s your dream girl looks like? 

Question every girl wants to ask a man she likes. Listen to him carefully, if he depicts a virtual girl just like you then baby you have a chance. 

193 Is there any difference between love or like? 

Before questioning him you should know the real meaning of love and like. Ask him about his prospective and know if he is lovey dovey types or not? 

194 If you see a homeless kid, how would you help him? 

I guess one should help with providing him some books and money to study Andy further links him to any NGO. 

195 Are you connected to any NGO? 

People with kind heart and soul know what is right to do for society. We people always complain of poverty but don’t do anything for that, ask him about his views on these. 

196 Which one is your favorite sport and you are a pro in it? 

Whether digital gaming or any sports, men love playing all sorts of games. Know about his interests and do have a little bit knowledge about them to have a good conversation. 

197 What are those 5 things which you would like to change in the world? 

You might have things that you like to change about the world. How interesting it would be to know his 5 things to see the level of understanding you have. 

198 Choose ‘bike ride with friends’ or car ride with girlfriend? 

Difficult one for couples but easy for single guys. No one wants to miss both. 

199 Have you ever felt like saying something to someone but something from inside stops you? 

When you are having an argument and you really want to say those harsh things coming to your mind but couldn’t say. Does that happen to you? 

Good questions to ask a guy

200 What is your go to song when you are sad? 

201 Do you ever feel like leaving your home and living your life to fullest? 

You do have restrictions in family and once in lifetime we do wonder what if you live alone and live it on your terms. 

202 How do you like to spend your weekend? 

Weekends could be enjoyed as a chill day at home or happening somewhere out in the city. 

203 What’s your favorite web series? 

YouTube is such a huge market. What is your favorite web series and how many times have you watched it? 

204 How much do you think a man contributes to his country? 

Does a common person contribute to a country and in which way does he? Does he only contribute in the form of tax or there are some moral values that could contribute? 

205 Don’t you feel nostalgic seeing your old friends or school? 

Nostalgia is a feeling of happiness and that throwback you want to relive. How about that feeling? 

206 How will you explain your feelings for someone? 

Are you someone who would go and directly tell his feelings or the one who took hell a long time to even talk! 

207 What are your thoughts on feminism? 

Feminism means equality. What he thought about women will depict his mentality towards this growing topic. 

208 Do you think men are taken for granted

Men are said to take care of family, not to cry, be strong and have responsibilities. We all ask men to behave, to give us to earn for us and take them for granted. 

209 Do you support any feminist group? 

It’s not supporting a feminist. It’s supporting what is right and standing by people who feel it’s right. 

210 Do you believe in life after death? 

Life after death is still a big question. Know his views on science and life. 

211 What are your thoughts about a destination wedding? 

Destination wedding is a dream of girls. Men usually don’t think about it that much. Listen if he is into the future or not. 

212 Would you go out on a solo trip? 

Trips with friends and family are interesting but a solo trip is worth an experience. 

213 What’s your dream destination? 

Dream destination is the place where you want to go and will definitely go once in lifetime. 

214 What would you prefer, skydiving or scuba diving? 

This question will tell you how adventurous he is. 

215 Do you have any interest in modern science? 

Modern is knowing about science, missions, earth and about our solar. Ask him if you have some interest in this. 

216 Do you have any idea how earth would destroy

If he has interest in science then this question is important for your conversation to continue. 

217 Would you rather go to a museum or watch a movie? 

This will tell you about his interests related to museums and antic things. 

218 Are you by any chance Artist? 

Artistic people think differently. They see everything with their artistic eyes. 

219 Do you feel big weddings are just a waste of money? 

In weddings a family spends about money which they have earned in 3-4years don’t you think marriage at such a large scale is just a waste of money? 

220 Do you believe people sometimes take advantage of your weaknesses? 

Are you too good to people? Differentiating between good and bad people is not everyone’s cup of tea. Do people take advantage of your good nature? 

221 Have you ever seen any mishappening in front of you? 

Mishappening could be anything. Anything that hurts him, it’s just a question to know him deeply. 

222 Are you ‘one episode per day’ or ‘one season per day’? 

In this digital world, our comfort zone is not going outside but just sitting at home and binge watching our favorite tv series. What kind of person did he do? 

223 What’s that one thing that you haven’t told to anyone? 

This question he might not answer. If there is something he doesn’t want to tell to anyone so that simply means he won’t tell you. But in case he told you, then you must be special to him and he trusts you. 

224 Whom should we respect? 

In today’s time, we say we should respect girls or women or elders. But don’t you think a person should be given respect on the basis of his nature and work and not a gender. What are your thoughts? 

225 What’s the sweetest Christmas gift you have ever got? 

Christmas is all about happiness. Tell me about the sweetest gift you have ever received and who was your secret Santa. 

226 How would you like to spend your Sundays? 

Some people left all their work to do on Sundays like cleaning and dusting or arranging books and some wait for Sunday just to sleep all day. 

227 Can you give me some cooking classes? 

It’s a good question to indirectly ask him if he could give you some cooking classes. If he knows anything related to cooking he won’t say no. 

228 Do you think there is a career other than in studies? 

YouTube, acting, social media and sports there are various fields nowadays. Do you think you would have opted for something else if you were aware of it? 

229 How about marrying your ex? 

What if your parents fix your arranged marriage with one of your ex. How are you going to react and what will you do to stop that marriage? 

230 What’s your favorite book? 

Till now you don’t know whether he reads or not. It’s a good way to ask him to know if he likes reading or not and what sort of genre he reads. 

231 What if one day your ex says she loves you and wants you back? How would you react? 

So the situation would be like your ex wants to come back to you and you also love her but now you’re with someone else. What would you do? 

232 What’s the worst movie you have ever seen?

Tell me about that one movie that you regret watching. I will never watch it. 

233 What was your childhood dream to become in future? Will you ever try to accomplish it? 

Every kid has that super fantasy dream to become one in the future. Have you achieved it yet? Or will I try to accomplish it? 

234 Would you rather be rich or handsome? 

Rich or handsome. Girls want both but what if you have only one thing, what would that be and why? 

235 According to you what attracts women the most ? 

You have met and been with a lot of women in life so on the basis of your experiences tell me what attracts women the most. How can men impress them and what are your tactics? 

236 Imagine you became the president of your country, what changes would you like to make? 

Before answering this question I hope you know about the rights president of our country have and who is our current president. It’s just a general knowledge question, answer it if you know. 

237 What would you do if for one day you have all the money in the world? 

You have all the money in the world, what would you do with that amount of money? 

238 Who is the most important person in your life? 

Name that most important person in your life apart from your parents and siblings. That one person without whom you can’t live. 

239 If for one day you have given a chance to live a life of celebrity, so who’s life do you want to choose? 

It’s a dream come true opportunity. Imagine the celebrity and tell me what exactly you would do if you had to live up to their life. 

240 What would you choose, relive your past or see the future? 

It’s an interesting question to ask a guy. Ask him to give reason for both and think will it ever be possible to time travel. 

241 Do you feel unhappy marriage affects children in a bad way? 

You never know how his family is. To know more about their family and life. You have to sneak in with this question. If they are a happy family he would say a simple yes but if they are not a happy family, he would send you a long paragraph. 

242 What would you do if you have a serious fight with your girlfriend? 

Boys don’t know how to convince their partner. They lack this skill of comforting her and saying sorry. 

243 According to you, what’s a perfect relationship looks like? 

When you have experienced some bad relationships, you exactly know what you want from a relationship and how a perfect relationship looks like. 

244 Do you have the courage to ride the scariest ride in an amusement park? 

If you love to ride the craziest and scariest ride in an amusement park then you definitely want to know if you’re going to be better half loves it or not. Of course you don’t want to enjoy rides alone. 

245 What’s the most romantic thing someone has done for you? 

Girls are good at doing romantic stuff. So with a heavy heart be ready to listen to some stories of date night or movie date. 

246 Will you spare your sleep for your partner? 

Boys are usually less into texting and they definitely love their sleep. Actually everyone loves their sleep and if a guy is ready to spare his sleep for you then trust me you are special for him. 

247 Do you want a big fat wedding or destination wedding with few relatives? 

As asked earlier ask him to have a big fat wedding or have a low key destination wedding with loved ones. Things which are private lasts longer. 

248 What do you think, I think about you? 

Important question for you. Don’t let this opportunity go into vain. Ask him what he thinks, you think about him and why he thinks this way. If he says you like him and he knows that then he is also into you. 

249 Will you accept a girl with a bad past? 

Everyone has a bad past. But a good guy is the one who accepts her with all her flaws. Let’s not judge the guy by this answer but hope he says right. 

250 Can you date a woman double your age? 

This question is interesting to ask. There is nothing harmful in dating a woman double your age. 

251 What will you do if your girl is not answering your phone calls? 

Will you panic or wait for some time to text or call back. What if she is angry and not picking up a clue and big problem is she is angry and you don’t know why 

252 Will you get jealous if your girlfriend goes too close to her best friend? 

Are you open minded or possessive type? Does your girlfriend’s closeness to her best friend affect you and why? What would you do to stop it? 

253 What matters more to you, looks or nature? 

Nature is the personality and is what stays with a person forever whereas looks are external beauty which would fade away with time. 

254 Will you ever go on a blind date? 

Is he so single that he could go on a blind date or would he like to do that? Does he think blind dates can lead to long relationships? 

255 Have you ever used any dating apps

When a person is single for a long time he uses dating apps as they could arrange a date easily or sometimes men use it to get over someone. Have you ever used it and why? Did you find someone good in it? 

256 Would you rather live alone or live with your family? 

You need privacy to grow. Family is important but ask him what he would choose and what he would do, so as to hurt no one. 

257 According to you what are actual couple goals? 

Do you have any ideals in mind that you find to be the perfect example of couple goals? What are your criterias of couple goals? 

258 How would you describe your childhood? 

Describe your childhood in one line and how much you miss and which part of childhood you miss the most. 

259 What would you do if you feel attracted to some other women being in a relationship? 

Would you reject her or let her be in your life and continue to be with two women at a same time. Do you think it’s the right thing to do? 

260 What’s that one thing you want people to know about you? 

People know you but you know people see what they want to see. So is there anything you want people to see in you and let you judge you on that. 

261 How would you react if one day you got up and got to know you are the richest person in the world

Getting up to news like this is less than a dream. What would be your first reaction to do and tell me about the things you’re gonna do after that? 

262 Tell me the most beautiful compliment you have ever got? 

Men do love compliments. They don’t say it because they love and remember it. Let him say your compliment as the best compliment. 

263 Did you have any clingy girlfriend? How was your experience? 

Clingy girlfriend could be difficult to handle and no one wants to experience it. If unfortunately you are used to having one then share some experience you have got. 

264 What would you like the most in me? 

If he likes you he would give a complete list of things in you and how much he adores you. 

265 Would you rather go partying or camping? 

Is he a travel person or partying person. Ask him how much he loves doing it and would he mind if you join him the next time? 

266 What’s the most expensive gift you have ever received? 

This could be given by any of your friends or girlfriend or family members. Do you still have that gift with you? Did you pay him anything in return of such an expensive gift? 

267 What you prefer more, phone call or texting? 

This would give indication on how to interact with him the next time and what to do and what not to do. 

268 What makes you angry? 

Tell me about things that make you angry. How you control your anger. Do you do any anger management practice? 

269 What is your weirdest habit? 

Habit is developed with time and sometimes we tend to learn some habits which are normal to you but not for others. 

270 Have you ever slept in the middle of a lecture? 

This question has a separate fan. This could be the story of every child. 

271 Does any relationship break because of you? 

Are you a relationship breaker? If yes then how you felt after that and was it intentionally or happened without even realising. 

272 Who’s your favorite, cousins of mother’s side or Dad’s side? 

It’s a cute question to ask a guy. No guy would answer it Dad’s side for Obvious reasons. 

273 If you have a day off, would you rather go out or stay home? 

If you take a day off would you spend outside or inside. 

274 What was your best day ever? 

We all have that one day which we will never forget in our lives. If you would like to share with me you can. 

275 Did any girl proposed to you in public? 

Does something like this ever happen to you? What did you say? And how do you feel about being God’s favorite? 

276 One song that describes you? 

It can be in any language but the one that I know. You can sing it if you want to. 

277 Do you feel awkward with me? 

How comfortable are you with me? Are you okay chilling with me or you feel awkward when I’m around. 

278 Do you judge people on the basis of looks? 

To which level you agree to this statement above. And why do you disagree and what should be that one thing to be used as a criteria to understand someone? 

279 What’s the first thing you see in a girl? 

If a girl is in front you what’s that one thing you notice in her? Are you okay in complimenting her on the very first meeting? 

280 How you like to celebrate your birthday? 

Do you like to celebrate your birthday and how you used to celebrate birthdays as a kid and as an adult? 

281 Are you a morning person or night owl? 

How lazy you are in the morning and how active you’re at night? How do you manage to finish your deadlines by time? 

282 What if one day your girlfriend meets with a tragic accident and ends up losing her legs, would you leave her or stay with her? 

This should not happen with anyone. But what would you do? Will you leave her as she can’t walk or you would be her support for life. 

283 Are you a mama’s boy? 

Do you ask your mom every time before doing anything? Do you accept your are a mama’s boy or ashamed to accept it in front of your friends and girlfriend? 

284 What’s the worst thing you have ever said to someone? 

How rude you can be? Was there any time you said something that you shouldn’t have said? 

285 What you miss the more, school or college? 

School and college have different memories but somewhere deep inside we know exactly which we miss more. 

286 What is your biggest regret in life? 

Would you like to share it with me. Are you okay in talking about things like these? 

287 How about spending your whole life on an island without any internet? 

Will you do in this digitally surrounded world. Let’s change this question to a partner. So now will you live on an island without the internet but with the girl of your dreams? 

288 What is your guilty pleasure? 

What that thing that you would have it any time. 

289 What’s the perfect age to get married? 

Tell me about the perfect age to get married and what are your plans of marriage? Do you think about it? 

290 How career oriented are you? 

What have I achieved till now? Are you satisfied with whatever you have in life or you have bigger dreams than these? Do you believe in pushing yourself to more hard work? 

291 What would you prefer, working out at the gym or at home? 

Do you think home workouts are better or at the gym? Will you try yoga ? 

292 Have you ever ended up dating two sisters? 

Funny questions to ask a guy, I just need to hear some funny answers and if something like this happens then also be real. 

293 What is your go to pick up line? 

You go to pick up lines which have been used since birth. How about trying it on me? 

294 What was your worst date till now? 

Why was that date the worst? Is it bad for you only or for her also? Did you ever talk to her again? 

295 Do you mind doing a part time job along with studies? 

Are you ashamed of your part time job? Do you think status matters more than a person? 

296 What if you got arranged marriage to your crush? 

I guess it would be the happiest day of anyone’s life. 

297 Do you believe life is too unpredictable? 

Is there any incident you would like to share with me? 

298 What are you more thankful for? 

Whom are you more thankful to, to your parents or God? 

299 Is it important to give a name to every relationship

Do you believe a relationship can last only if you have love for each other without any stamp of relationship? 

300 Do you feel good talking to me? 

This will help you know is he interested in you or not? If he says no then I would recommend you to back off. 

301 Have you ever got rejected? 

If yes then how did you manage to handle a rejection

302 Are you the one who always says sorry in a relationship? 

Do you believe saying sorry doesn’t mean you are wrong but it means you value your relationship more than your ego. But does somewhere you fell take you for granted.

303 Are you afraid of losing someone? 

When you are afraid of losing someone it means you have feelings for them. Hope he would say your name

304 Who is your 2am conversation partner? 

Every girl desires to hear her name. 

Hope this article helps you in any way.

Related articles you must read

1. How to stop thinking about a girl you love

2. How to propose a girl on whatsApp

3. How to convince your parents for love marriage

4. Taken for granted in relationship

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