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Weird Questions to Ask a Guy

Looking for weird questions to ask a guy? Sometimes, a little odd or unique question can get an interesting conversation started between you and that special someone. Maybe it’s a guy friend that you want to get the attention of. Or your boyfriend. See if these weird questions get interesting answer!

Weird questions to ask a guy
Weird questions to ask a guy

Best Q’s to ask a guy

  1. Which two items won’t you ever spend cash on?
  2. What or who do you always have time for?
  3. How many smartphones have you lost or broken?
  4. What skill do you possess that is the most useless?
  5. Who or what do you consider to be your nemesis?
  6. Which game are you the best at when you play it?
  7. What is your biggest apprehension?
  8. Which childhood landmark was demolished, and what was erected in its place?
  9. What kind of double standard is absurd and must be stopped?
  10. What do you presume to be well-versed in but probably aren’t?
  11. In the middle of the night, you suddenly awaken. What noise would be the most terrifying when you first wake up?
  12. What high-level position do you believe you could falsify your qualifications for and get hired for without anyone noticing?
  13. When did the proverb “appearance can be deceiving” start to sink in?
  14. How frequently does your mind switch to automatic mode?
  15. The longest you’ve ever stayed awake was how long?
  16. How will dating evolve in the future?
  17. Which is your favorite file on your computer/laptop?
  18. What calculated risk of yours has actually paid off?
  19. What movie moment left you permanently scarred?
  20. What is your worst fast food experience?
  21. Which task could possibly be the most boring?
  22. What topics do you find boring to hear?
  23. What caused you a lot of stress that ended up not being a huge deal?
  24. What was the most stressful circumstance you have ever faced, and how did you overcome it?
  25. Who in history wasn’t as extraordinary as most people believe?
  26. What did you enjoy doing the most when you were younger but now find it silly?
  27. Which famous person would make the worst president or prime minister?
  28. What three things had the greatest influence on the person you are today?
  29. What is the most intriguing fact you are aware of?
  30. What is the “go-to” dish you are most proud of cooking?
  31. What is the worst possible phobia one might have?
  32. What would be inside and how would it look if you planned and built a treehouse?
  33. What film can you watch over and over again without getting bored of it?
  34. What would happen if humans could live 500 years longer thanks to scientific advancements?
  35. What is the most effective trick you can pull?
  36. How do you define friendship?
  37. Which video game would you prefer to be more like in real life?
Weird questions to ask a guy
Weird questions to ask a guy

Funny wones to use on a guy

  1. What will be the funniest funeral of your life?
  2. What would you choose to be in your next life—a Lion or a woman?
  3. What was the blandest meal you have ever had?
  4. What was the craziest thing you’ve ever done?
  5. Do blind people have dreams where they see?
  6. Can you finish a whole pizza in ten minutes?
  7. Which would you choose: 10 wives or 10 kids?
  8. Ever unintentionally caught yourself naked?
  9. What is one thing you are truly horrible at but are afraid to admit?
  10. If you met the head of state by chance, what would you say to them?
  11. Which movie, in your opinion, deserves a sequel?
  12. Which incident from your childhood did you find the funniest?
  13. Which well-known movie or television catchphrase do you frequently use?
  14. Where would you put a camera if you could put it anywhere in the world?
  15. What particular badge would you wear if you or your family were to do so?
  16. When you witness two individuals getting into a fight or when you are getting into a fight yourself, what song pops into your head?
  17. How loudly do you sing in the restroom, on a scale of 1 to 10?
  18. What was the worst icebreaker you ever used?
  19. Have you ever had any amusing nicknames?
  20. How do you act when you’re drunk?
  21. Which of your past actions was the stupidest?
  22. Which body part is the most delicate?
  23. Do you use dating apps? Which ones?
  24. What would make you laugh the most? Name the top three.
  25. What strange smell attracts you?
  26. Which comedy film is your favorite?
  27. What would you do if you could spend the day as a ghost or an invisible person?
  28. Do you prefer women with makeup or without it?
  29. If you were a waiter, would you spit on a customer’s meal if they were being irritating?
  30. What kind of cult would you start, if any?
  31. What offense would you accuse me of if you saw me in handcuffs?
  32. Which kitchen incident has been the worst for you?
  33. What would you do first if there were just the two of us left on earth?
  34. What was the stupidest thing you’ve ever done to damage yourself?
  35. Which non-living thing would you most like to see disappear?
  36. What place in the universe would you visit if you could stay there for a day?
  37. Which outfit has ever caused you the most embarrassment?
  38. Which would you choose: the capacity to teleport or fly?
  39. What did you have last on your mind?
  40. What name would you use if you were a rapper?

My experience asking relationship-building questions in relationships…

Okay, okay… So I’ve had a few relationships myself. And here’s what I learned… if I had asked a few tailored questions in the beginning, I might have saved myself from getting into a poor relationship. That’s what brought me to relationship questions. They help you save yourself from future misery. Or help you find future happiness.

Here are my BEST tips based on my own experiences…

  • Remember a few that you like – Keep a couple of your favorite questions in mind. Try to remember a few for when the moment strikes you.
  • Don’t forget these as a tool – Whenever there’s a dull moment, whether you’re with a spouse or family… pull out a few of these questions.
  • Don’t take it too seriously – Especially when it comes to spouses or those you might be romantically interested in. This isn’t a time to start digging! Have fun, make it silly, and don’t take it all too seriously.

Flirty and weird ones to use on him

  1. What would you do with a girl if you could take her anywhere in the world?
  2. What would you say if I told you that I find you to be adorable?
  3. Do you think that love at first sight or soul mates exists?
  4. What do you wear to bed at night, then?
  5. Which of your past dates was the worst?
  6. Do you like more relaxed or adventurous dates?
  7. Do you have any fantasies that you haven’t yet shared with me?
  8. Would you make any changes if we could redo our honeymoon?
  9. What might you say or do to lure me?
  10. After a long day at work, what do you like to do to unwind?
  11. What sort of exercises do you like to do?
  12. What food would you choose if you had to eat only one thing for the rest of your life?
  13. Would you like to get painted?
  14. Do you have a favorite food for which you would sacrifice a relationship?
  15. What qualities most appeal to you in a possible partner?
  16. Who was your first crush?
  17. Which aspect of me is your favorite?
  18. Do you work out?
  19. How about going skinny dipping together?
  20. What quality about you would surprise me?
  21. Do you think fate or destiny exists?
  22. Do you enjoy neck kisses?
  23. Do you enjoy flirting with women?
  24. Do you like softer, sweeter women or those who are more confident?
  25. What action of yours has ever been the most careless?
  26. How about a pleasant surprise?
  27. What characteristics do you value most in a girlfriend?
  28. Do you prefer gentle or in-depth massages?
  29. Do you prefer committed relationships? What aspects do you prefer?
  30. What gives you the best sexy vibe?
  31. What would you like to hear me say in our private space?
  32. Would you like me to make you feel amazing for the whole day?
  33. What in the bedroom do you believe you excel at?
  34. Which NSFW SMS have you ever sent or received was the dirtiest?
  35. Which of my flaws do you like to exploit the most?
  36. When do you feel the most drawn to me?
  37. What do you suppose my darkest fantasies are? Would you like to contribute to making it happen?
  38. What is your favorite memory of us together?
  39. What would you say about us if you could only use emojis?
  40. What kiss would you rank as your favorite if we had to order them?
Weird questions to ask a guy
Weird questions to ask a guy

Fun weird questions to ask a guy

  1. What was the funniest pickup line you’ve ever heard of or been the target of?
  2. You’re a dream guy in every way; how are you even single?
  3. Which couple would you pick if we could be a couple on television?
  4. Which organ would you replace with a better mechanical version if you could?
  5. What meme most accurately sums up your life?
  6. What are some things that, despite not having seen or read about them, you are completely familiar with?
  7. What would be written on your forehead, if you had a sign?
  8. What traditional practice is superior to the way it is currently practiced?
  9. What scares you the most?
  10. What has ever been the most enjoyable thing you’ve done with friends?
  11. Which superpower would you most like to have?
  12. Which movie do you consider to be the worst ever?
  13. Which place would you choose for a vacation—the beach or a hip city?
  14. On a first date, which question do you always pose to women?
  15. Which personality type best describes you—introvert or extrovert?
  16. What would you choose as your present if you could?
  17. Which Starbucks drink do you usually order?
  18. What is something that always gets under your skin?
  19. What is the biggest turnoff for you when dating?
  20. Which do you prefer: camping or nightclubs?
  21. Which of your past vacations was the most exciting?
  22. Would you like to share something that you’ve never told anyone before?
  23. Which would you prefer to have as a lifelong pet: cats or dogs?
  24. Even on your worst days, what brings a smile to your face?
  25. What aspects of social media would you change?
  26. Which aspect of dating aggravates you the most?
  27. Which Instagram user do you prefer to follow?
  28. What could go wrong on a first date that would be the worst possible outcome for you?
  29. Which show would you be able to continue watching multiple times?
  30. What in your resume do you simply make up?
  31. Which item on your bucket list do you believe you will never actually accomplish?
  32. Why are you best friends with your friend?
  33. Which famous person would you choose to marry if you could?
  34. What sport, if any, would you choose to pursue professionally?
  35. What accomplishments do you really regret?
  36. Which of your talents is the most absurd?
  37. If you were to win the lottery, what would you do?
  38. Which destination would you choose if you could travel anywhere in the world without worrying about money?
  39. When you were a child, what did you want to be when you grew up?
  40. Which film is your all-time favorite and have you seen it a million times?

Weird questions to ask a guy
Weird questions to ask a guy

Interesting weird questions to ask a guy

  1. Are you more of a cat or dog person?
  2. What do you enjoy doing that no one else appears to?
  3. Which subject won’t let you stop talking?
  4. What is the best way to flirt?
  5. Do you find it unappealing if the girl you’re seeing changes her appearance dramatically, such as her hairstyle or color?
  6. Would you do it if you could earn money from your hobby? Would you continue doing it as a hobby instead?
  7. Which situation with your parents caused you the most trouble?
  8. Do you follow any family customs?
  9. Would you hold off on seeing the upcoming episode of the TV series we watched together until I did?
  10. What kind of a student were you in high school?
  11. What is one offense you have committed, whether it be silly or serious?
  12. Which book is your favorite?
  13. What one goal do you have before you pass away?
  14. Who has influenced you or helped you become the person you are today?
  15. What stupid memento from your childhood do you still have stashed away in your room?
  16. What disturbs your sleep?
  17. Which word best describes you?
  18. What title would you give your life if you were to write a book about it?
  19. Who is your favorite musician?
  20. What will your life look like in five years?
  21. Who in your immediate or extended family do you most resemble?
  22. What was the scariest incident you ever experienced as a child?
  23. What do you typically consume, eat, or do when you’re ill and confined to bed?
  24. What has been your most outrageous act of kindness toward a woman?
  25. Have you ever experienced heartbreak?
  26. What definition would you provide for “love”?
  27. What one factor influences your decision whether or not to trust someone?
  28. Which family memory is your favorite?
  29. What is your favorite phrase, verse, or sentence?
  30. Who is someone you simply cannot live without?
  31. What kind of family do you envision having in the future?
  32. What is a strange activity that you have always wanted to do but haven’t?
  33. Would you choose to press the reset button to start your life over if you had the option?
  34. Which one aspect of yourself would you like to change?
  35. What can lift your spirits no matter what?
  36. What sign do you belong to? And do you feel that it applies to you?
  37. Has your life ever been completely altered by a choice you made? And if so, what was it?
  38. Which college memory is your favorite?
  39. What would you do if you had a complete day off from all jobs and obligations?
  40. Which three wishes, if any, would you make?

Weird questions to ask a guy
Weird questions to ask a guy

Deep weird questions to ask a guy

  1. What was your childhood secret?
  2. If you had $5 million, what wouldn’t you do?
  3. What is a common error that people make?
  4. In your younger years, what did you want to be?
  5. What are the advantages and disadvantages of being a man?
  6. Have you ever bullied someone or been the victim of bullying yourself?
  7. Whom have you totally lost respect for?
  8. Which childhood activity do you still find appealing?
  9. What do you feel most grateful for?
  10. What would you consider a relationship-ending behavior?
  11. If you learned you had been adopted, what would you do?
  12. Do you value looks or brains more?
  13. What is your all-time favorite book or movie, and why did it have such a profound impact on you?
  14. What was the biggest challenge you overcame?
  15. Would you ever forgive someone who betrayed you?
  16. What one aspect of the modern world most irritates you?
  17. When did you have the biggest burst of adrenaline?
  18. What recent change has been the most exciting?
  19. Which would you choose if you were in a bad mood: being left alone or having someone cheer you up?
  20. Do you recall ever losing a loved one?
  21. To whom do you go when you want to talk about anything?
  22. Are you a proponent of second chances?
  23. What stage of your life was the best?
  24. What do you think about tinder or online dating in general?
  25. What have you learned from your past relationships?
  26. Does what you’re doing now match your childhood aspirations?
  27. Have you kept a journal before?
  28. What do you consider to be the appropriate age for marriage?
  29. What guiding principles do you live by?
  30. When was the last time you hurt someone else’s feelings?
  31. What would you change about yourself if you could?
  32. Do you ever judge a book by its cover?
  33. When you’re alone, what do you prefer?
  34. What professions exist as a result of human selfishness?
  35. Do you think it’s okay to tell your partner your password?
  36. What would prevent you from accepting immortality if it were offered to you with one condition?
  37. Which genre, rap or country, would you prefer to listen to?
  38. What song would you want to be playing loudly on the radio if you were engaged in a race?
  39. If money was no object, what brilliant idea would you like to try?
  40. What would an amusement park that was created with your happiness in mind look like?

Weird questions to ask a guy
Weird questions to ask a guy

Personal weird questions to ask a guy

  1. How many women have you had affairs with?
  2. What is it that you would like to know but are afraid to ask me?
  3. How recently did you cry, and why?
  4. What was the most embarrassing situation you ever faced?
  5. What gives you the most uncomfortable feelings?
  6. How experienced are you?
  7. How healthy do you think masturbation is?
  8. Have you ever felt a draw to another man?
  9. Whom do you like least among your friends?
  10. What was the first time you had sex? How was it?
  11. Which of your memories of us is the sexiest?
  12. What was the sexiest act you ever committed in bed?
  13. What is something new about you that I don’t know?
  14. What was the most difficult choice you ever had to make?
  15. What was the biggest gamble you ever made?
  16. What unfavorable behavior would you prefer to change?
  17. Do you still keep in touch with your ex-partner?
  18. Ever had to call it quits with a friend?
  19. Have you ever visited a therapist?
  20. Which person are you envious of?
  21. Which love song is your favorite?
  22. Which of your past sacrifices for a relationship was the biggest?
  23. What Halloween costume for a pair has always piqued your interest?
  24. Whose relationship do you most admire among your friends and family?
  25. Which movie scene makes you cry the most?
  26. What about your family now seems strange that seemed normal when you were a child?
  27. Do you prefer to spend the day in a museum of art, history, or science?
  28. When you were a child, which holidays did your family really make a big deal out of?
  29. Which interaction with someone was the most uncomfortable for you?
  30. What area of your life is currently doing exceptionally well, and which area could need some assistance?
  31. Do you give money to a homeless person if you see them begging?
  32. What brings tears to your eyes when you consider it?
  33. How frequently have you felt overburdened?
  34. How well do you get along with your parents?
  35. Which porn star is your favorite?
  36. What is a fact about you that nobody is aware of?
  37. Do you have a history of using drugs? Do you know anyone else who uses it?
  38. What country would you pick if you could immigrate anywhere? Why?
  39. Which fictional character most closely resembles you?
  40. How did you experience reaching adulthood?
Weird questions to ask a guy
Weird questions to ask a guy

Uncomfortable weird questions to ask a guy

  1. Did you ever had sex while having thoughts of someone other than your partner?
  2. When did you first experience a wet dream?
  3. Will you kiss another man if I give you $100,000?
  4. How often do you wash your boxers each week?
  5. Ever had feelings for a friend’s girlfriend?
  6. Have you ever witnessed a couple having sex in public?
  7. Has someone ever caught you masturbating?
  8. What number of guys have I kissed?
  9. How often do you think about having sex?
  10. Which organ would you replace with a better computerized replica if you could?
  11. What was the SMS you ever received that was the most embarrassing?
  12. How many sets of undies do you have?
  13. What do you frequently think about while using the restroom?
  14. Which color underwear do you currently have on?
  15. What was your most embarrassing moment?
  16. Your current bank balance is how much?
  17. Have you ever attempted to urinate while seated?
  18. Who would be the most unsuitable choice if you were to go on a date with one of our pals tomorrow?
  19. How often have you neglected to brush your teeth?
  20. Have you ever been discovered eyeing up a woman?
  21. Which of our friends would make the best kisser, in your opinion?
  22. Which of your drunken actions was the worst?
  23. What was the strangest food you ever loved to eat as a kid?
  24. How many girls’ phone numbers do you have?
  25. What was the strangest habit you ever developed as a kid?
  26. Has your clothing ever failed you in front of others? Which was it?
  27. Which animal most closely resembles your eating habits?
  28. Do you think you and your duplicate would get along?
  29. Have you ever made up a medical condition to avoid getting caught?
  30. How recently have you let out a scream?
  31. What was the awkwardest outfit you have ever worn?
  32. What is your oddest guilty pleasure?
  33. Which of your lies to your parents was the worst?
  34. What was the most embarrassing act you ever committed while dating someone else?
  35. What enters your mind when you wake up most frequently?
  36. Do you think any of my pals are physically appealing?
  37. What does it take to make you feel like having sex?
  38. Do you feel at ease using labels in relationships?
  39. If you discovered that I was cheating on you, what would you do?
  40. Ever got into trouble because of a naughty text?
  41. If I told you I was pregnant, what would you say?
  42. What would you do if another girl made advances toward you while I was present?
  43. What would you pick if you had to choose between kissing a guy in this room and spending an hour in public wearing nothing but your underwear?
  44. Would it be okay if I asked you to get a blood test before we got further involved?
  45. Ever look back on a relationship or an affair with regret?
  46. Has there ever been a time when you betrayed one of your ex-girlfriends?
  47. I want to make you feel wanted. What can I do?
  48. Do you feel there is anything missing from our physical connection?
  49. Do you feel comfortable discussing sex with me?
  50. Are you a virgin?

Expert advice: According to this study, laughter truly is a medicine! Playing a “would you rather” game might seem cheesy at first. Although a few laughs later and you may be improving your overall health.

Popular weird questions to ask a guy

  1. Do you have any funny stories that you can share with me?
  2. What do your guy friends think about you?
  3. What’s your favorite physical feature in a woman?
  4. What’s your favorite ice cream flavor?
  5. What does a healthy relationship look like to you?
  6. What was the most embarrassing thing to happen to you when you were at school?
  7. What interesting answers have you gotten to the question, “What’s up?”
  8. What’s your biggest guilty pleasure?
  9. What would your dream job be and why?
  10. Do you have anything on your sexual bucket list?
  11. What attracts you most about the opposite sex and why?
  12. What would you tell your younger self if you could go back in time?
  13. What did you think was perfectly fine in your last relationship but actually wasn’t?
  14. How do you know that you’re losing interest in a person?
  15. Would you be offended if I looked through your search history?
  16. Which personal questions do you absolutely hate answering?
  17. How do you know that there’s another cute guy in the room?
  18. Where’s the strangest place you’ve ever farted?
  19. What was your first kiss like?
  20. If you could eat one food for the rest of your life, what would it be?
  21. What was the grossest thing you’ve ever done?
  22. Where’s your favorite restaurant to eat at?
  23. Who is your current love interest?
  24. What do you think makes a solid foundation for a relationship to get built on?
  25. Are you a dog person or more of a cat person?
  26. What do you think makes you different from most guys?
  27. If you could have any superpower, what would it be and why?
  28. What’s the worst movie that you’ve ever seen?
  29. If you could have endless winter or permanent summer, which would you have?
  30. What interesting response have you gotten from teachers when you submitted your homework?
  31. Do you know of any funny questions to ask people?
  32. What one thing about a girl makes you really have a crush on them?
  33. What was the last song that you listened to, and why do you like it?
  34. What TV show could you watch over and over and never get tired of it?
  35. What’s your favorite food to eat during the weekends or on a cheat meal day?
  36. What reality show could you see me being on and why?
  37. Do you still talk to your ex-girlfriend? If so, what do you talk to her about?
  38. Do you think that kids today are learning everything they need to get them to a successful future?

Weird questions to ask a guy (images to share)

Weird questions to ask a guy
Weird questions to ask a guy
Weird questions to ask a guy
Weird questions to ask a guy
Weird questions to ask a guy
Weird questions to ask a guy
Weird questions to ask a guy
Weird questions to ask a guy
Weird questions to ask a guy
Weird questions to ask a guy
Weird questions to ask a guy
Weird questions to ask a guy
Weird questions to ask a guy
Weird questions to ask a guy

More questions for guys


Fact checked:
Board reviewed by Marianne Tomlinson, LCSW (Couples and Family Therapy). Content is rigorously reviewed by a team of qualified and experienced fact checkers. Learn more.

About the author

Ryan Sanderson (LCSW) Ryan is a game and relationship enthusiast who enjoys all things quizzes, games, fun, love, relationships, and family. He's a licensed social worker and helps families, couples, and children in need. He's spoken about love and relationships on Salon.com, Forbes, and Mirror, to name a few.

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