As far as I can tell, this is the most comprehensive list of questions to ask a guy on the whole internet.
I spent almost a month brainstorming and interviewing ladies to come up with this exhaustive list.
You don’t need to visit any other site or try to come up with questions to ask a guy (although you do need to be creative sometimes) because I’ve done all the leg-work for you.
I’ve also arranged them in such a way that you can easily skim through.
You can also use the table of content down below to jump to sections that you think are most important to you at the moment.
777+ Questions to Ask a Guy – The Ultimate List
So if you’re ready, grab a cup of coffee, bear, pop-corn, or whatever that kicks that gear in you, and let’s ride out…
100 Interesting Questions About Sports You Can Ask a Guy
1) Who is your greatest sportsperson of all time?
2) What is your favorite sport?
3) Which is your best contact sport?
4) Computer gaming sports or regular live events, which would you rather become active at?
5) Do you have a fantasy team?
6) Which player would you have had in your fantasy team more often and why?
7) What would be your motivation in sports? The money or the records?
8) Three champions league title or one world cup win?
9) Who is the GOAT? Christiano Ronaldo or Leo Messi?
10) What are your top three favorite sports in order from the most favorite?
11) Why do you like your best sport?
12) Can you race in F1 sports if given the chance?
13) What common sports-related thing have you not done before in your entire life?
14) What is your scariest extreme sport ever?
15) Which player have you loved even when they moved to other clubs?
16) Who was the most valuable basketball player in 2018?
17) How much do you know about your best sports?
18) Would you take a random quiz on the sports teams you support?
19) Who is your favorite tennis player?
20) How many titles has your best tennis player won?
21) What does offside mean?
22) Would you rather be the captain of your team or be the best performer without getting the praise you deserve?
23) What is the most interesting thing about football?
24) Why do you spend time watching sports apart from other entertainment?
25) Would you pay more to attend a live sporting event in the stadium while keeping social distance?
26) In soccer does a player score from throw-ins?
27) A little current affairs quiz. Without looking it up, in which year was the first world cup played?
28) Who is the fastest athlete ever?
29) Do you know the story of how the marathon race came about?
30) What position did you play in your favorite team sport?
31) How often do you watch soccer?
32) Do you think Liverpool would have failed to be champions were it not for VAR in their 2019/20 Premier League title win?
33) Do you watch sports videos on YouTube regularly?
34) How much of a football fan are you?
35) How much do you know about football?
36) Which sports can’t you do without?
37) Who is your greatest team sports coach ever and why?
38) “Liverpool” or “VARchester” which is more valid?
39) Which sports league competition is the toughest in the world?
40) What ways can sports teach real-world lessons?
41) Can you withstand these sports trivia without looking them up?
42) What is the diameter of the basketball ring?
43) How wide is the hockey goal post?
44) What is the area of the soccer goalpost?
45) What does FIFA stand for?
46) Who is the best female soccer player in [your country]?
47) Who is the best English footballer ever?
48) Why has your country not won the World Cup?
49) Which factor would change the fortune of your sports team the most?
50) Which athlete would you add to your team that is not so famous but could be a great addition?
51) Which sports can you represent your country in?
52) Given the training, would you like to try extreme sports or it’s too dangerous?
53) Which athlete’s story is more motivating? CR7 or Messi’s?
54) Which female athlete do you want to go out with?
55) Kaka or Giroud, who do you trust most around your girlfriend?
56) Which players would make your ultimate 5-a-side team?
57) Which defeat of your team is the most painful?
58) What margin was your team’s biggest win ever?
59) What would you trade for supporting your best sports team?
60) You can stop following one. Your sports team or a TV show?
61) Which rival team would you prefer to play in a cup final?
62) What is your team slogan?
63) Which foreign team’s jersey have you ever bought?
64) Do you support your local rival team in continental competitions or you don’t care?
65) Which recent match do you think could have been fixed? Why did you think so? This may not be
easy for him to pick especially if he’s not an ardent sports follower.
66) Which mid-table team does your team need to take more seriously if they must win the championship?
67) Which sports do you wish you to know more about?
68) What have you gained from sports generally?
69) Which city would you rather live in because of sports?
70) When a player swap shirt, what do they use it for?
71) What was the most exciting win your club has had away from home?
72) In soccer, a player who scores a hat-trick takes the ball home. What can he take home if he scores five times?
73) What can you promise that you’d do for your girlfriend who does not like sports to watch a game with you?
74) Are you more likely to love a girl more if she is interested in sports as much as you do?
75) What event in sports are you most thankful was possible?
76) What technology introduction in sports has helped your favorite team the most?
77) Has VAR been good for your favorite sports or not? And why?
78) Do you think AI and computer technology will take more control of officiating sports one day?
79) What sports could you watch every day without being bored?
80) Which female wrestler are you attracted to?
81) Can you marry a female boxer who is muscular than you are?
82) Would you rather marry a footballer or a basketball player?
83) Do you think the most popular sports were designed to distract people from more serious matters like politics and economic inequality?
84) Which sports would life not make sense without?
85) Which player has never let you down and why?
86) Which opponent’s team manager do you wish was in charge of your team?
87) Mention a female football player from your favorite team?
88) What is your take on the difference in income between ladies players and men players?
89) How much do you want to see the world’s best women team take on men in a match?
90) How much do you know about the battle of the sexes?
91) How much would you be worth if you were to sign for your team?
92) Would you name your son after a famous athlete?
93) Would you watch a major world tournament or get a PlayStation for free?
94) Who should represent your household in a PES competition?
95) Would you rather win the Fantasy League or your team should win the Champions league?
96) Which is the most difficult team to beat for you?
97) Which Female Tennis star would you like to be your friend now?
98) Will women one day be allowed to compete in male competitions that are more lucrative?
99) Will women ever be better at football than men? For example, can a woman win the Ballon d’ Or someday?
100) Would you trust a woman to be on your team in the Premier League?
34 Questions about Politics and Humanities to Ask Your Man
1) Do you think the government should have more or less control of private information for the common good?
2) Should the government tax the rich more or tax everyone less?
3) Has democracy succeeded better than other forms of governance?
4) Should money be controlled by the government or Blockchain should carry the day?
5) What is your most common difference between modern humans compared to people of old?
6) Is politics affecting the normal process of evolution?
7) Would regulations in politics save the planet?
8) In what ways can social injustice end?
9) Will there ever be equality?
10) Is religion truly the opium of the people?
11) Do you care about social debates?
12) How can society prevail in creating a balance between reason and emotion?
13) Is it possible to have a social view without political bias?
14) Is socialism evil altogether?
15) Will capitalism survive as-is for longer or it will evolve?
16) How do you think capitalism has evolved?
17) Is it possible for activism to be without the perception of being considered as an avenue for opposition politics?
18) Is taking part in politics a waste of time?
19) Assuming I’m a religious person who doesn’t believe in taking part in politics, what would you tell me about politics?
20) Have you ever tried to talk other people into sharing your political views? Why?
21) How do you know someone who is brainwashed?
22) Is there any pressure in taking a political stand in your family?
23) Do you consider yourself to lean on the left, right, or center politically?
24) Did you vote in the last general election?
25) Who did you vote for and do you regret your decision?
26) Do you ever lose faith in the politicians and their policies?
27) What do you call the democracy where family members are appointed into public positions?
28) Would you sacrifice leading a country and become a millionaire or becoming a billionaire and not taking any elected position?
29) Which ministry or government agency would you serve in your country and why?
30) Do you think an e-governance solution has helped your country over the years?
31) How corrupt do you think your government is?
32) Which issue should be given the biggest priority?
33) Do you think your citizens complain too much about the government? His perception may reveal how he thinks about political leaders too.
34) Will racism ever end with the political will or without it?
35 Questions About Science and Technology to Ask Him
1) Who would you consider the most influential scientist ever?
2) Which is the greatest invention?
3) Did China steal 5G technology?
4) Will the cryptocurrency eventually crash?
5) What is the responsibility of scientists to maintaining stability when there is chaos due to political disagreements?
6) Have you ever imagined if science could make blood transfusion avoidable?
7) Is science becoming more and more dogmatic?
8) Is capital a bigger driver of research and development than labor?
9) What science explains why guys don’t do as much makeup as girls?
10) Would you rather be a scientist in the dark ages or a contemporary scientist?
11) Will you be the first to take a COVID-19 vaccine at your house?
12) What technology are you interested in?
13) If you’re not in the current tech industry, where would you rather work?
14) What tech invention is the most awesome for you?
15) Technology has impacted art so much and this makes us wonder if creativity is dying. What do you think? Is creativity dying because of technology?
16) Will AI technology ever be good enough as a judge in civil matters?
17) What invention do you know that was discovered by accident?
18) Which science and technology topics are the hardest to understand?
19) Do you love watching Da Vinci TV programs?
20) Which science and technology TV shows do you find most interesting?
21) Are you more of an art person and you like to do science stuff?
22) When do you think more about technologies?
23) Do you sometimes think about what could be invented from time to time?
24) Do you sometimes imagine being in the past trying to make things?
25) Which characters from science fiction films do you like the most?
26) Have you ever had an idea of a science fiction story before?
27) Can you take the challenge of writing a sci-fi novel?
28) What if practicing science and technology were as interesting as TV and game shows entertainments?
29) Will virtualization give people more power in computing of the future?
30) Do you think encryption will not be required as a way to secure data in the future?
31) Simulation and virtual learning technologies can help students to learn better but what could be the disadvantages?
32) How far ago do you think 3D web technologies were imagined?
33) What is the best idea you’ve picked up from the science class?
34) What principles have taught you the best lessons from the sciences?
35) What was the most annoying science class lesson you’ll never use in your life?
35 Current Affairs Questions to Ask a Guy
1) What is the capital of Bangkok?
2) When was the United Nations formed? If he’s the civic person, asking questions like this can make him have conversations about world history.
3) What do you think was the most important factor that ended the world second world war?
4) Out of the seven wonders of the world, which one is the most awesome?
5) How many Chinese holidays do you know about?
6) Which foreign country do you know much about?
7) Would you take a quiz on a particular country?
8) Who should study what is seen when someone is suddenly given a heavy slap in the face? Sorry, this is playful but fun trivia can lighten the mood sometimes.
9) Which popular person do you like to make your role model?
10) Which person challenges you to try to be your best?
11) If you were to choose a famous billionaire to travel around the world with, who would it be?
12) Which popular celebrity would you go on a date with?
13) How did your current affairs go? This may be funny but it should make him think.
14) How many percent playful would you say you are?
15) How many percent serious would you say you are generally?
16) What motivates you more? When people say “you can’t do it”, or when you are cheered on?
17) What would you do to make me happy now?
18) What’s on your mind right now?
19) What skill would you learn that you never want to use?
20) Would you learn how to smoke for acting a role or it will make you choke? You may learn about his tolerance for smoking from this question.
21) Are you the big picture guy or the devil is in the details?
22) What is your biggest personal struggle?
23) When you’re happy which impulse comes first? Have a drink or a dance?
24) What do you do when you’re pissed off?
25) Do you know how to ride a bicycle?
26) How long did it take you to learn how to ride a bicycle?
27) What story has made you have hope in humanity?
28) What motivates you to control your anger?
29) How often do you relish the old memories?
30) Who will you never forgive?
31) What is the center of attraction that you must be in the picture?
32) What picture of the future from films scares you the most?
33) Do you think it’s unwise to disregard all the conspiracy theories?
34) Apart from money, what makes the world go round?
35) What would you like to change in your next life that you cannot change now?
47 Personal and Interpersonal Relationship Questions to Ask a Guy
1) What is your purpose in life?
2) What are you born into your family?
3) Would you marry a very religious person or the less churchy the better?
4) Does empathy mean you cannot hate people?
5) What personal struggles did you overcome in your family?
6) What could make you cry?
7) Would you cry if you lost someone special?
8) If it was legal and you had the means, how many wives would you marry?
9) How many children would you like to have?
10) What soundtrack will fit the story of your life?
11) Who would be the supporting character if you were to write a story about your life?
12) What social responsibility do you think you should be in the forefront of?
13) Who will be the antagonist in a possible story about you?
14) What do you think of when you’re all by yourself?
15) Why do guys love entertainment so much?
16) How much do you think girls like femininity in guys?
17) Do you know if you’ve ever sleep-talked before?
18) Who is your best motivational speaker?
19) Do you listen to audiotapes on personal improvement?
20) Have you spent on a personal development book recently?
21) What aspect of your life is most important to improve on?
22) Who is your ideal person between John C Maxwell and Robert Kiyosaki?
23) What makes you love someone?
24) How willing are you to sacrifice your comfort for other people?
25) What do you consider before choosing a friend?
26) Do you have a strong religious relationship?
27) Can you argue on doctrinal matters?
28) How do you think you can love yourself more?
29) Do you want to go alone or to carry everyone along?
30) How much influence is too much on your relationship with others?
31) Who is the one person that you think helps to inspire you but you don’t want to be like them?
32) What is your best example of someone who you should do as they say but not as they do?
33) What is the one thing you hate about your best coach?
34) What do you like about the person you hate the most?
35) Do you find out that people trust you so easily?
36) How will you move towards a future that people will trust you more?
37) Do you honestly think you have to do more in life?
38) Do you feel accomplished or there is more to be done?
39) Do you believe it’s hard to work alone or hard work and luck matters?
40) What is too much for you to handle?
41) What personal improvement routine can you follow throughout a day without being tired?
42) What is the longest time you’ve spent reflecting on your life?
43) What lessons from the books have you applied in your everyday living?
44) If you’re to make your rule about life what would it be?
45) If you can choose two other careers for the rest of your life which ones would you choose?
46) What matters most to you when you think about success?
47) What is your worst regret in life that turned out to lead to a better life decision?
40 Unexpected Questions You Can ask a Guy
1) How old were you when you had your first sex?
2) Where did you have sex for the very first time?
3) What do you hate about your parents?
4) Have you ever hated someone?
5) What do you like about the person you hated the most?
6) What was the stupidest thing you did as a child?
7) Have you ever won a sports bet before?
8) What is the highest winning you’ve won from betting on your team?
9) What do you hate about your parent?
10) Which of your parent do you love the most?
11) Why do you prefer your favorite parent
12) Do you like taking selfies?
13) Why do you like taking pictures?
14) What profession would you like to do if you reincarnated?
15) Why was the reason you lied the last time you did?
16) What did you think guys do that girls don’t do?
17) Did you have sex before 14?
18) Were you abused sexually as a child?
19) Would you say you like sex?
20) Who is your go-to person when it comes to financial matters and why?
21) What pressing question do you want to ask a girl?
22) Do you love God?
23) How important is it for people around you to be cool? Should they never swear around you?
24) Do you have fears about a possible apocalypse?
25) What was the most shocking moment of your life?
26) When did you escape a possible mishap that could have led to death?
27) What would you like to master that is not so important?
28) Do you like to bring another angle or one must focus on the main ideas?
29) What was your last house number?
30) Do numbers matter to interpreting life occurrences for you?
31) Should your night dreams be taken seriously?
32) Which game do you have on your phone?
33) What sparks debate for you too easily?
34) One should club once in a while or never?
35) A family should have tough people and calm people in it, which team do you rep?
36) What price of greatness have you paid in your entire life?
37) What is the biggest opportunity you regret failing to take in your life?
38) Are you a natural influencer or you learned to influence people through books?
39) Where does your leadership abilities rely on? Do you prefer leading by showing example or you like leading when you have compelling results for others to follow?
40) Do you hate religion? Which religion do you hate the most?
31 Questions You Can Ask a Guy to Know What He Likes and Dislikes
1) Do you like pets?
2) How much do you hate stress?
3) Would you like to be on TV?
4) Which TV would you like to host?
5) What is most important in your life right now?
6) Would you like to holiday abroad or you’d save the money?
7) Are you a night flyer or an early bird?
8) Do you prefer vampire films or horror films?
9) Do you want a big wedding or a big house?
10) What is your best food?
11) Which food do you least prefer?
12) Do you like sea travel?
13) Would you rather travel by sea or by land?
14) What will make your day change from bad to better?
15) What is your best color?
16) Would you tolerate someone who smokes around you?
17) What sides of you do you like the most?
18) Where will you like to spend the last days of your life?
19) Do you like people around or you want to be alone most of the time?
20) Do you like delegating tasks or if you must do it right you have to do it yourself?
21) Do you like to move fast or you’re the one to take things slowly?
22) Which food would you never try?
23) Which food did you not like before but someone made you like it?
24) What would you like to put your name on soon?
25) What life experience proves to you that change is still possible even in the worst situation?
26) When it comes to decisions how do other people’s opinions matter? Or you often act fast?
27) How do you roll best? Is your passion the drive or the people first?
28) If you could go back in time would you experience a bad day again just to change the outcome of events for your friends?
29) Generally, do you like debates or not?
30) Do you like to go solo or you like a big team?
31) Would you like to see your future first before living it or you want to take one day at a time?
42 Questions To Ask A Guy That You Like And Needs His Attention
1) What attracts you the most to the girl you like?
2) What is your favorite dress code?
3) What do you mostly derive pleasure in doing even when bored?
4) Do you like working in an established company or you prefer a small scale business owned by you?
5) What are your plans for yourself that you want to tell only me?
6) Would you love to have many kids? How many?
7) What type of women do you feel free to relate to?
8) Do you like ladies that dress seductively or modesty is perfect?
9) Do you feel free to talk with all the ladies you meet and express your feelings to them or only the
ones you think you like?
10) Would you travel abroad or invest if you are given a million dollars today?
11) Do you like anything special about me? What is it you like most?
12) What’s the greatest height you wish to attain in your career?
13) Do you think it is okay having many female friends?
14) Are you a sex addict or your game is more important?
15) What was your favorite game as a child?
16) Are you good at giving a lady your full attention or you’re better at keeping her interested?
17) How would you feel if a lady cries for you?
18) Do you love ladies that are sex addicts or you’re not man enough?
19) Would you love a motivational quiz or I should ask more about you?
20) Do you like showing off your girlfriend to your friends or keeping it a secret until the feeling is stronger?
21) Is there anything you don’t like about me?
22) What do I need to change about myself to become your best girl?
23) Do you like ladies that express their feelings to a guy?
24) Are you a university graduate?
25) Would you do anything to keep your relationship strong if you are in love?
26) Do you think I am a good match for you?
27) What do you hate about me and you’d like it if I change?
28) Who’s your favorite celebrity and why do you like her?
29) Do you like sport? If yes what type?
30) Do you like ladies that act nasty or the quieter the better?
31) Why are you still single when I’m single?
32) Would you have sex with a woman even if you’re not in love with her?
33) Are you good at flirting with women or it’s got to be serious to play with a girl?
34) Do you get shy when a woman that you are not familiar with starts a conversation with you?
35) Dis you regret not giving in to a woman who flirted with you and you thought you would have had a chance with her?
36) What is the line between being outspoken or talking too much for a lady?
37) If I was your fiancé what pet name would you like to call me?
38) Do you prefer highly intelligent ladies or very romantic ladies matter most?
39) How far have you planned your future? Are you a long term planner or a short term planner?
40) What have you been wishing to become when you grow up as a child?
41) Do you easily trust people or they have to work harder to earn your trust?
42) What type of life do you want your future kids to live?
30 Truth or Dare Questions to ask a Guy
1) Who is your crush?
2) If you’re a bisexual which boy would you make out with?
3) What part of your body is the most sensitive?
4) Would you send your nudes now?
5) Who is the girl you have a crush on?
6) What are your top three turn-ons?
7) How did feel about your first kiss?
8) Where was the strangest place you’ve had sex?
9) What was the most embarrassing public fails you’ve experienced?
10) What was your biggest steal?
11) What is your worst moment that you wish to delete from your memory?
12) Why did you cheat on her?
13) What habit will you never stop?
14) Which of your friends is the most facially beautiful?
15) What was your most embarrassing sex moment?
16) When was the last time you peed in bed?
17) What was the biggest crime that you’ve denied?
18) What were you guilty of but you denied?
19) What would you do if you were a girl for a year?
20) What retaliation did you make that you don’t regret?
21) What lie have you told that hurt someone?
22) Who would you save first now in case of an accident?
23) What’s the most embarrassing thing you were caught red-handed doing?
24) What have you done already and wish could be undone?
25) What was the wickedest thought that has ever crossed your mind?
26) Which supervillain would you become?
27) What was the standout moment that you cheated to attain?
28) What would you like to change about your family?
29) Which country do you dislike the most and why?
30) What was the busy body moment that you cannot forget?
21 Questions to Ask a Guy to Get to Know Him Better
1) What single factor would make the world a better place?
2) How do you recover from a bad day?
3) Have you ever gone to the night clubs before?
4) Would you adopt a child?
5) How many kids would you like to have?
6) What is the best virtue you want in a woman?
7) Do you have a very close friend or you have many friends?
8) What do you do in your spare time?
9) Where can I catch you if you’re not in the house?
10) What do you like to push through without stopping?
11) What can make you cry?
12) What matters most to you in a relationship?
13) Do you think the world can heal eventually?
14) Do you think we can succeed in preserving our planet or we will eventually destroy it?
15) Do you believe man will conquer Mars someday?
16) Which time of the day are you most active?
17) Would you consider yourself a politician or an economist? Why?
18) Do you often see the world as a sociologist or as a psychologist?
19) Can your friends rely on you to fight them?
20) Have you ever volunteered in a charity before?
21) Would you rather work more or use the power of leverage?
51 Interesting Questions to Ask a Guy During Question Games
1) Do you love your voice on tape?
2) Have you ever tried recording yourself singing? Why or why not?
3) Do you consider yourself photogenic?
4) What is the weirdest dream you’ve ever dreamt of?
5) Did you have a childhood crush?
6) What was special about the first girl you loved?
7) What one word would you used to describe the character Moana in the animation film?
8) Which superhero is your favorite?
9) Would you go back in time or dive into an unknown future if you had a time machine?
10) Do you want to be rich and famous or you want to be just rich and not famous?
11) Do you like celebrity status or you want a quiet life?
12) A fruit wine to chill in the night or a little alcohol?
13) Who is your best artist?
14) Would you tell a white lie to save your friends?
15) What would you consider your strength?
16) What is your worst weakness?
17) What makes you stay awake at night?
18) Where would you like to see yourself in the next 5 years?
19) Do you have a written to-do list for every day or you have your plans in your head?
20) Who do you prefer to be with now your mum or dad?
21) What would you change about yourself?
22) Who was your most valuable person in the last year?
23) Who will make your most valuable person of the year?
24) If you lost everything you have how would you start over?
25) If you must lose one of your senses, which would you lose?
26) What makes you happy the most?
27) What do you love most about your family?
28) If your family were to have a flag, what design would it be?
29) What is your biggest fear about your career?
30) Why did you choose the career path you’re on now?
31) Who influenced the choice of your career the most?
32) Are you often strict or lenient?
33) Do you enjoy solving puzzles?
34) Are you up for a math game or never?
35) Are you often the lucky one amongst all?
36) Do you think horoscopes affect human behaviors?
37) Do you think you might have lost a gift from childhood?
38) Who was your childhood idol?
39) Which brand would you sell? “Just Do It” or “Good for You”?
40) Which conspiracy theory is most striking to you?
41) What is the toughest situation you’ve ever faced?
42) Would you want to do most direct a movie or play a character at the moment?
43) What fairy tale did you almost believe?
44) Which of the important world problems would you solve if you had the power to solve it?
45) You can have only one superpower. Which would you have?
46) Which wild animal would you talk to if given the choice and why?
47) Would you forgive your girlfriend if you found out she cheated when you’re away for only two weeks?
48) Can you bear having a fruit fast for a whole week?
49) Who is your mentor?
50) Do you consider yourself a starter or a finisher?
51) Are you a team player or a born leader?
31 Important Questions to ask a Boy You’re Dating
1) Are you ready to take up a new challenge soon?
2) What exactly are you looking for?
3) Would you still date another person or we should meet again?
4) What factor do you think will make you succeed as you intend?
5) Do you spend time waiting for the best or the available becomes desirable quickly?
6) What other things matter to you as much as happiness?
7) What do you find positive within you?
8) What simple thing is important to you in your relationship?
9) What is special about your friends?
10) Do you have any unique skills that you don’t look the path?
11) What is your spec for someone you can go out with any day?
12) What target do you find the most interesting to follow?
13) What is the most important thing you want now?
14) When last a woman?
15) Why did you choose to invite me on a date with you?
16) Have you been into a relationship before? You should ask this if he’s young.
17) What was the story of your last relationship?
18) What was the most annoying girl problem you’ve had to deal with?
19) How old are you? This may be simple but you make some judgments about his experience and maturity.
20) Do you have any allergies? This can come deep into your conversation about what you like. And asking this should give him the clue that you are imagining a certain future where you care about things he doesn’t like.
21) Do you smoke?
22) Have you smoked before? How about socially?
23) Do you drink? Do you drink socially?
24) What project are you working on?
25) You look nice! Does work seem to be good for you? Even if he’s self-employed he’ll talk about
what he does for a living.
26) I hope you’re not a cheater?
27) If you don’t mind me asking, how are you coping with the current situation?
28) I hope I’m not taking it too personally but what is your survival strategy in a hostile environment?
29) What is your motto in life?
30) How do you think we will end? To what end, is a good question for when you want to know what he already thinks about having a relationship with you at the moment. It’s not the easiest question to ask.
31) What is the one thing you’re so happy to talk about?
21 Serious Relationship Questions to Ask Your Guy
1) Am I the only girl on your mind?
2) Am I the most beautiful girl you’ve ever met?
3) Are you sure you’re not carried away by just my outward appearance?
4) Do I only make you smile or I give you peace?
5) Do you think I’m ready to be your wife? It’s crazy how people can live together but they don’t have the same vision. It’s a surprise that ladies reject proposals and some men run away when the
topic of marriage is brought up.
6) Am I the only girl you feel very free to express your feelings with? You can ask him this question just to figure out why he’s interested in you. Also, you’ll get to know if he’s a player or he’s serious.
7) Why have you decided to choose me over other girls?
8) Why do you think that I can do better than some of the ladies you’ve met?
9) Why are you so confident that I’m a nice person?
10) Why are you so interested in getting into a relationship with me?
11) Why do you think I’m the right one to be your woman?
These questions may sound serious but if he’s really into you he’ll get to give a truthful answer for them.
Then continue with questions that focus more on him, like…
12) What if the love you have for me now fades?
13) What if I get to find out this is how you approach lots of ladies as well?
14) What if you get to figure out that some qualities you think I have are not there?
15) What if we keep arguing over silly issues?
16) What if you find out that I’m not good in bed?
You want to know a little about his lifestyle and it will result in questions like below…
17) Do you believe in working hard?
18) Do you think you’re ready to start a family with me if I fall pregnant?
19) Do you think we can be great at parenting?
20) Are you constantly reviewing your set goals for yourself?
21) Do you think your family is going to accept me with open arms?
30 Funny Questions to Ask a Guy
1) Compared to soccer, when is one’s girlfriend offside?
2) As in sports, what is ‘a goal’ in your relationship?
3) What is the most exciting memory you have?
4) What entertaining TV show would you like to be on?
5) What would you do if you won the lottery?
6) What would stage name be if you’re an artist?
7) What is the funniest sitcom you’ve seen?
8) Something must kill a man but what is it?
9) Would you be an ostrich or a dragon?
10) Do you remember the funniest scene from Harry Potter?
11) What do you think about the scene in Maleficent where the evil princess is turned into a goat?
12) What food that when you eat it makes you fart a lot?
13) Have you ever come across that one person that seems to fart at will?
14) When are you going to be as rich as Jeff Bezos with your current income rate? Beware not to
make this sound insulting!
15) Who is the funniest person you want to be like when you grow up?
16) Which clown would you like to be like in your next life?
17) How many times do you stand in a day?
18) Could you ever be funnier than about Mr. Bean?
19) How do you handle people that you don’t like?
20) What conspiracy theory makes you laugh the most?
21) Where would you want to be in the next day?
22) What game makes you laugh the most?
23) Did you know that someone could orgasm from wounds?
24) What would you do if your partner cannot stop laughing while making love with you?
25) Who told Jonah how many days he was in the fish’s belly?
26) Can you help your wife to carry her pregnancy?
27) When you spell BOOK, do you put the first O before the next or the other way round?
28) Did you want to grow beards early or it came on time?
29) How did you feel trying to fight your deep voice at puberty?
30) Would you ever be man enough in the eyes of your father?
21 Flirty Questions to Ask a Guy
1) Can you describe how you felt butterflies?
2) What do I get as a reward if you make me come?
3) I’ve always fallen in love with your name [Harry]. Be honest which female name attracts you the most?
4) How much does your sexy look cost?
5) Did you ask God to make this dentition of yours?
6) Do you like taking photographs of yourself because you’re the finest photogenic person on earth?
7) I like your eyes. Did you edit it with Photoshop?
8) Why does thinking about you make me feel?
9) What do you hate about your parent?
10) What type of girls are you most attracted to?
11) What is the weirdest place you’ve had sex?
12) What do you think makes you sexiest?
13) What is your idea of the perfect date?
14) How are you this cute and still single?
15) What pill did you take to make you so handsome?
16) Do I turn you on?
17) What turns you on?
18) How would you describe me in three words?
19) Do you have a secret crush?
20) Where would you like to kiss me?
21) What sexy scene from a movie would you like to recreate with me?
25 Conversation Starters to Ask a Guy over Text
1) What do you think girls would first like about you?
2) Where did you grow up?
3) What is your best memory from your hometown?
4) Are you fascinated by futuristic technologies?
5) What do you expect from a new friendship?
6) What will make a more good conversation with you?
7) What is unique about your best friend for life?
8) What other courses would you have studied?
9) What did you want to become when you were 6?
10) Are you still going to be who you thought you were early on?
11) What is the biggest lie you’ve been told?
12) Can you remember the most brutally honest moment in your life?
13) Which name is so unique to you?
14) Do you think it will be nice to chat with you already?
15) Hey, what are you doing online all by yourself?
16) I want to gist. Are you going to let me wait?
17) What would you like to talk about with someone?
18) Could you drop your phone and talk to me?
19) Why do we love to chat online instead of connecting?
20) If you could be more open and not worry about being judged what would you tell me now?
21) Which type of films make you have a lot to say in reviews?
22) How do you deal with boredom?
23) Do you think talking about it would help? When he’s not happy about something.
24) What can make you happier than anyone else?
25) How else would you describe man if not biologically?
26) What maxim did your head of school always say? Mine was, “life is a choice. One day you’ll reach a crossroad where you have to decide should I stay back and have my pet cat or should I go abroad and miss her for so long?”
21 Weird Questions to Ask a Guy
1) How would you feel if people are scared of you for no reason?
2) What do you think I might be thinking right now?
3) Would you show me the hidden files on your computer? You may know something about his
personality based on how he responds to this.
4) Why do people care only when we seem to care?
5) Would you dance with my mum if she asks you to?
6) If I cheat on you what would you do?
7) What is the dark side of you?
8) Do you believe in magic?
9) What mystical questions did you have as a child?
10) Do you still have mystical doubts about reality?
11) Would you join a cult if you’re told you’d be very wealthy after joining?
12) What in this life can you give up for financial freedom?
13) Have you thought of how old you want to live before you die?
14) What adage did either your parents always tell you when you were growing up?
15) What household chore do you detest the most?
16) Do you miss being a child?
17) Do you remember the most extraordinary person from the past in your life?
18) What do you sometimes remember that was weird and it makes you laugh at yourself?
19) Have you ever asked yourself if you’re going insane and it makes you laugh?
20) What is the one thing you hate yourself for?
21) Would you be a great influencer while impersonating funny people?
120 Would You Rather Questions to Ask a Guy
1) Would you rather try foreign food or a foreign dress?
2) Would you rather invest in a block and brick business or invest in the money market?
3) Would you rather receive money or gifts on your birthday?
4) Would you rather give up brushing your hair or brushing your teeth?
5) Would you rather die before your wife or after your wife when you’re old?
6) Would you rather watch your funeral or be able to take revenge on your killer?
7) Would you rather always say everything on your mind or never be able to speak again?
8) Would you rather impregnate me before we get married or have more than the desired number of kids with another woman?
9) Would you rather be shorter and richer or be taller?
10) Would you rather be a character in an action film or a romantic comedy?
11) Would you rather be a kid your whole life or an adult your whole life?
12) Would you rather marry a little late or too early?
13) Would you rather have an arranged marriage that will last or end up being married three times?
14) Would you rather be able to breathe underwater or be able to fly?
15) Would you rather be able to playback anything you ever saw or be able to have books saved in your head?
16) Would you rather be able to talk with all animals or speak twenty foreign languages?
17) Would you rather be an Olympic gold medalist or a Nobel Peace Prize winner?
18) Would you rather be the richest person to ever play a sport or the most valuable sportsperson?
19) Would you rather be an unpopular basketball player or a famous badminton star?
20) Would you rather be Batman or Spiderman?
21) Would you rather be filthy rich in the BCs or be poor and live longer in the present day and age?
22) Would you rather be fluent in all languages or be a master of every musical instrument?
23) Would you rather be given a lifetime supply of delicious food or all flight tickets for all your trips
for life?
24) Would you rather be gossiped about or never talked about at all?
25) Would you rather be in your pajamas or a suit all day?
26) Would you rather be known for creating the best-animated film for kids or for writing the best song ever?
27) Would you rather earn from your intelligence or your good looks?
28) Would you rather be locked in an amusement park or a library?
29) Would you rather be on a survival reality show or dating game show?
30) Would you rather be poor and work at a job you love, or rich and work at a job you hate?
31) Would you rather propose to the girl you love in private or in front of family and friends?
32) Would you rather have your girlfriend propose to you when you’re or you have to do it now?
33) Would you rather be stuck on a broken ski lift or in a broken elevator?
34) Would you rather be stuck on a train or a bus?
35) Would you rather be stuck on an island alone or with someone you love dearly?
36) Would you rather be the most valuable person at work or the smartest student?
37) Would you rather be the star player on a losing basketball team or be a bench player on a winning team?
38) Would you rather be the youngest or the oldest sibling?
39) Would you rather marry a girl who is the youngest or the oldest sibling in their family?
40) Would you rather be too busy or be too bothered by friends?
41) Would you rather be too sad or be too bored once in a while?
42) Would you rather live in temperate regions or tropical climates all around the year?
43) Would you rather be without the internet for a week, or without your phone?
44) Would you rather be your boss or work for someone else?
45) Would you rather be your boss after 5 years of graduating without a job or work for someone else
for the rest of your life?
46) Would you rather achieve all your dreams now while being someone else or just stay you and succeed much later?
47) Would you rather change your eye color or your hair color?
48) Would you rather date someone you met online or go on a blind date?
49) Would you rather eat a meal of cow tongue or turtle?
50) Would you rather eat pizza or ice cream as the only food for eternity?
51) Would you rather end hunger or war in the world?
52) Would you rather be an astronaut or a sea diver?
53) Would you rather get rich through hard work later or win the lottery now?
54) Would you rather get rich as a B as a C student?
55) Would you rather go deep-sea diving or bungee jumping?
56) Would you rather go to the past and change a dismal history or be able to go into the future and
watch over your great-great-grandchildren?
57) Would you rather go on a cruise with friends or with your spouse?
58) Would you rather go to the movies or dinner alone?
59) Would you rather go without TV or junk food for the rest of your life?
60) Would you rather have a scandal that will end your political career or become a religious leader?
61) Would you rather have a cook or a maid?
62) Would you rather have an affair with a mistress who is poorly educated but sexy or a rich but not
sexy girl?
63) Would you rather give a handjob to save your life or have a sword fight to the death?
64) Would you rather have a desk job or an outdoor job?
65) Would you rather have a family of 10 children or never be able to have children till you’re very old?
66) Would you rather have a rewind button or a pause button on your life?
67) Would you rather have an unlimited gift certificate to a restaurant?
68) Would you rather have many good friends or only one best friend and many enemies?
69) Would you rather have more time or more money?
70) Would you rather have too caring neighbors or noisy neighbors?
71) Would you rather have neighbors whose cats come by to eat your food or neighbors whose dog comes to mate with yours?
72) Would you rather have Rambo or The Terminator on your side?
73) Would you rather have Christiano Ronaldo or Ronaldo Delima on your soccer team?
74) Would you rather have the best house in a bad neighborhood or the worst house in a good neighborhood?
75) Would you rather have Trump’s tax history or his shady deals made public?
76) Would you rather have to make a movie of your life or be able to replay all the dreams you’ve ever had your entire life?
77) Would you rather have to sew all your clothes or grow your food?
78) Would you rather have a telescopic vision or be able to hear secret conversations remotely?
79) Would you rather be financially free now or never have to worry about anything?
80) Would you rather have your first child when at 18 or when you’re 50?
81) Would you rather lose your luggage or have your flight delayed by 5 hours?
82) Would you rather hear the good news or the bad news first?
83) Would you rather break the good news or stop the bad news from happening?
84) Would you rather listen to music from the ’70s or music from today?
85) Would you rather invent a device that no one would know about till the next 30 years or create a
current innovative design?
86) Would you rather live at the top of a tall apartment building where everyone has to do control jumps down to save energy or you will use the stairs?
87) Would you rather live in Antarctica or the Sahara Dessert?
88) Would you rather live the rest of your life as a monk or followed continuously by paparazzi?
89) Would you rather live where it always rains or where it is always dry?
90) Would you rather lose your house key in the middle of the night and have to sleep in your car or your cell phone?
91) Would you rather lose your vision or your hearing?
92) Would you rather make a phone call or send a text to me now?
93) Would you rather meet Donald Trump or former US President Obama?
94) Would you rather meet the president of the United States or a movie star of your choice?
95) Would you rather mentally or physically never age?
96) Would you rather own a house or rent a residence?
97) Would you rather own your boat or your private jet?
98) Would you rather end inequality in the world or end wars?
99) Would you rather read a romance novel or watch a horror movie?
100) Would you rather sing a song in front of strangers or your closest friends?
101) Would you rather sing like an opera star or cook like a gourmet chef?
102) Would you rather suffer for a crime you’re innocent to save your friends or save your friends and put your friends at risk?
103) Would you rather spend a year as a cop in a crime-prone area or 6 months as a soldier?
104) Would you rather spend the day in a pub or a room with priests?
105) Would you rather spend the day with your favorite athlete or your favorite movie star?
106) Would you rather spend the next year exempt from all taxes or have an all-expense-paid vacation?
107) Would you rather spend the night in a luxury hotel room or have the best ecotourism ever?
108) Would you rather be mistakenly sent to a psychiatric hospital or mistakenly tried for a criminal offense?
109) Would you rather be an alien captured by humans or be captured by some aliens?
110) Would you rather travel from the UK to India in an auto home or by sea?
111) Would you rather watch your club’s big game at home or live at the stadium?
112) Would you rather have a free season ticket or return flight ticket to any destination of your choice?
113) Would you rather win the lottery or win a reality TV game show?
114) Would you rather work in a group where you’ll do most of the work or work alone from home?
115) Would you rather work more hours per day but fewer days or work fewer hours per day but more days?
116) Would you rather put your kids in school where they’ll wear a uniform to school or no uniforms?
117) Would you rather eat the rats or be a vegetarian for the rest of your life?
118) Would you rather lie to your mum or dad?
119) Assuming you lose all your current skills, would you rather be a gun maker or a farmer? Why?
120) Would yo
