100+ tricky questions to ask a pen pal

Relationships between a guy and a girl are often complex and ambiguous. To get to know a guy better, his character and personality traits, you need to communicate with him correctly and ask him well-written questions. What questions to ask a guy to understand how he treats a girl, what he thinks about and how he lives? You should not be afraid of diversity: the richer and more extensive the questions, the richer the communication will be.

  1. What is something interesting to ask him?
  2. How to come up with funny questions for a guy?
  3. Questions with a spark: vulgar and intimate
  4. What to ask about love and relationships?
  5. Trick questions or how to make him nervous?

You need to be careful with questions. When asking them, a girl should take into account the following important factors: the stage of the relationship at which the young people are, the guy’s character traits, the current situation, the purpose of communication, etc. A well-written question will not only find the perfect key to any guy’s heart, but will also make communication brighter, more colorful, and add spice to it.

What is something interesting to ask him?

  1. What movie made a lasting impression on you?
  2. If you could star in a film, what genre of film would you star in?
  3. Who is your favourite actor?
  4. Can you sing songs?
  5. Do you eat in the shower?
  6. What do you do when you have free time?
  7. Have you ever been interested in extreme sports?
  8. What birthday gift do you dream of?
  9. Do you like giving gifts?
  10. What was the most original gift you were given and who was it from?
  11. Do you like visiting theaters?
  12. How do you feel about ballet?
  13. Who are you according to your zodiac sign?
  14. Do you believe that every person in this world has half a soul?
  15. Do you believe in magic?
  16. How do you feel about signs?
  17. If you suddenly had the opportunity to get into a time machine and take an unforgettable journey, where would you go first?
  18. What would you change about your past?
  19. Describe yourself to me, what will you be like in 20 years?
  20. If you caught a goldfish, what wish would you ask it to grant?
  21. What were you like as a child: a quiet, calm boy or a little robber?
  22. Tell me about your happiest childhood memory?
  23. Have you ever gone camping?
  24. What did you want to become as a child?
  25. Have you ever written poetry?
  26. Do you love traveling?
  27. Which countries have you visited and which ones would you like to visit?
  28. What cuisine do you prefer?
  29. How do you feel about exotic cuisine?
  30. Could you eat live insects for a very large reward?
  31. What is your greatest fear?
  32. Do you often visit discos?
  33. Do you believe in fortune telling?
  34. Did you have any interesting nicknames at home, at school, or in kindergarten as a child?
  35. How do you feel about the circus?
  36. Have you ever been to a children's camp?
  37. Do you have friends with whom you have known since early childhood?
  38. What should a true, good friend be like?
  39. Who knows you best in the world?
  40. Do you think it’s possible to lie “for the greater good”?
  41. Do you love the sea?
  42. How do you relax?
  43. Are you keen on reading?
  44. How do you feel about TV?
  45. What is your ideal day off?
  46. You're a night owl or an early bird?
  47. What's your family like?
  48. Do you have any pets?
  49. Who do you love more: cats or dogs?
  50. What are the names of your pets?

Don't worry about what interesting questions you can ask guys? They can relate to a wide variety of areas of a person’s life, the main thing is that they evoke a desire to respond and maintain a conversation. Interesting questions to a guy, asked in the right situation, will tell you about him much better than his best friend or your mutual acquaintance.

PLANS - Identify common desires

A couple is a living, developing organism in which partners try to combine personal self-realization and happiness together. Plans are an integral part of a couple’s life; they express its vital strength, as well as the degree of involvement of each person in their common life. One of the difficulties is combining general plans and personal ones. Reflect on this as you answer the questions:

40. Do you have at least one joint plan (vacation, leisure, work, family)? If not, why not? 41. Is this plan repeated regularly, is it like a habit? If so, do you enjoy it? 42. Do you find your partner invested enough in the future of the relationship? What about you? 43. Does only one person always propose important plans in the family? If yes, is it right for you? 44. Does your partner usually take your suggestions regarding joint plans well? 45. Does your partner support your personal plans?

Once you've explored your feelings, communication, intimacy, sex life, and plans, ask yourself additional questions:

46. ​​Did you begin this study of a couple's life willingly, with a desire to better understand your couple and contribute to their happiness? 47. Were you surprised by any positive aspect of your relationship that you weren't aware of? 48. Were you surprised by any negative aspect? 49. Did your partner also answer all these questions? If not, why not? 50. What do you feel at this stage - enthusiasm or anxiety? What are they related to?

How to come up with funny questions for a guy

To defuse the situation and fill communication with bright colors, you need to, without fear, ask the guy funny, amusing questions. They will help to identify whether he has a sense of humor and what it can be like in different situations? Competently asked funny questions with humor provide a unique opportunity to see a real guy. They can be complex or, on the contrary, simple, not requiring much thought.

  1. Can any animal love a skunk?
  2. How to behave if you accidentally fart in a public place?
  3. Do you have a beautiful hairstyle in the morning immediately after waking up?
  4. What is your relationship with your alarm clock?
  5. How could you be a flower?
  6. Would you agree to kiss a frog who will turn into a beautiful person?
  7. Do you talk to your car?
  8. Which letter of the alphabet are you partial to?
  9. If you were locked in a hypermarket for the night, what would you do there all night?
  10. What will be your reaction if suddenly people on the street start taking off their clothes?
  11. If you could commit a crime for which you would not be punished, what would you do?
  12. If you had to inhabit the body of an animal, which animal would you prefer?
  13. Are you talking to yourself?
  14. Do you pick your nose?
  15. What moment in life are you ashamed to remember?
  16. If you could switch bodies with anyone, who would you switch with?
  17. Have you ever wanted to be in a woman's body?
  18. When you were a child, did your mother buy or sew festive costumes for you at matinees? What animal or character costumes have you dressed up as?
  19. Do you talk to animals like you talk to people?
  20. Can you croak like a frog or bark like a dog?
  21. Are you able to change a child's dirty diaper?
  22. Have you ever left the house wearing slippers?
  23. What were you afraid of as a child?
  24. What words did you pronounce incorrectly as a child? Can you repeat it for me?
  25. What clothes do you sleep in?
  26. Do you compliment yourself in front of the mirror?
  27. If you could talk to any fruit in its fruit language, which fruit would you choose to talk to?
  28. Why is the fifth point the softest and most attractive?
  29. How would you behave if you suddenly found yourself among real Indians?
  30. How much noodles can the ears of a gullible and naive person withstand?
  31. What joke did you laugh at the most?
  32. Have you given your teachers nicknames?
  33. What should you do if you are itching very badly in one place on the minibus?
  34. Do you bite your nails? What might they taste like?
  35. Why is the donkey so stubborn?
  36. Which nation can you call the most fun?
  37. Can there be order in a woman's handbag?
  38. Where would you rather be: in a girl's shower or in the shower with a girl?
  39. How do you feel about family panties?
  40. Are kangaroos happy in their mother's pouch?
  41. If you were the weather, what would the weather be like in our city?
  42. What tree do you look like?
  43. Where can I find your socks?
  44. Can you be harmful?
  45. What kind of vegetable are you?
  46. What kind of aliens do you imagine?
  47. Is it possible to get a job as an engineer in a company if you know by heart all the episodes of the cartoon about fixies?
  48. If they made a series about your life, what would it be called?

SEX LIFE - Check how satisfied you are

When it comes to sex life, each couple writes their own score and moves at their own pace. The frequency or duration of intimate meetings is not important - only the satisfaction of each and the ability of the partners to talk about changes that one of them may desire. Sylvain Mimoun brings you these questions:

31. Is the frequency of intimate contacts right for you? 32. During sex, do you feel that you are not only desired, but also respected? 33. Do you sometimes (sometimes/often/all the time/never) feel bored? 34. Do you (sometimes/often/always/never) agree to sex just to please someone else? 35. Do you (often/sometimes/always/never) agree to certain practices just to please your partner or to give in to his pressure? 36. Would you like to make changes in a couple's sex life? If yes, which ones? 37. Do you feel closeness and understanding with your partner when you talk about your sex life? 38. What would you say about your sex life - is it generally satisfactory or does it have problems? 39. If everything continued as it is now, would you say: “everything is going well” or “something is missing”?

Questions with a spark: vulgar and intimate

It has been noticed that men love not only lovemaking itself, but also everything that directly or indirectly leads to it. If you add a little “pepper” to your communication and come up with the most vulgar questions for a guy, you can count on the development of relationships, on the fact that he will become more courageous, relaxed and show his interesting sides when communicating with a girl. What questions should guys ask to take them to the next level or just make the conversation more spicy, playful, and memorable? Below are some dirty questions, a list for guys who can be relaxed and confident in any situation.

  1. Which phrase from those listed below will you choose and why: make love, have sex?
  2. How often do you watch films for grown men? Which films in this genre turn you on the most?
  3. Have girls ever sent you intimate photos of themselves on the Internet?
  4. Are you proud of your sexual organ? Is it big?
  5. Have you ever self-satisfied your physical needs?
  6. Which girls turn you on the most?
  7. Who can be hot in bed: blonde, brunette or redhead?
  8. Have you ever had sex with a virgin?
  9. What word would you use to describe your orgasm?
  10. In what places have you made love?
  11. Have you ever had group sex?
  12. Do girls touching each other turn you on?
  13. Are you shaving “there”?
  14. What would you say is your most extreme sexual experience?
  15. Where is the best place to make love?
  16. Have you ever seen a girl satisfy herself?
  17. Have you ever approached girls of easy virtue?
  18. Are you a good lover?
  19. What type of sex would you most like to try?
  20. Do you caress girls between their legs?
  21. Do you like blowjob?
  22. What are your erotic fantasies?
  23. How do you feel about making love in public places?
  24. What pose do you idolize?
  25. Do older women turn you on?

You should not raise vulgar, provocative questions about sex when communication with a guy is just beginning. Such conversations will give a guy the wrong idea about a girl. A list of vulgar questions for a guy can only be prepared when there is trust, love and mutual respect between the young people. In this case, they will bring new, unknown sensations into the relationship, which are sometimes often lacking.

Checking IQ: smart questions for a girl without a hint of tediousness

How can you understand that a new acquaintance is not only beautiful, but also at least not stupid? You shouldn't take an IQ test before asking your friend out on a date! It is enough to ask a girl interesting questions from the proposed list - and you will immediately understand how educated she is.

  • What was the last book you read? Share your impressions.
  • What would you like to learn, but haven’t found the time yet?
  • What do you prefer - cartoon, film or TV?
  • Make a list of three famous people you would like to invite to dinner.
  • How many clubs did you attend as a child? Which ones were the most useful?
  • What do you do best?
  • Comment: classic, the question will help you understand your talents and hobbies.

  • Were you a diligent student or a hooligan girl?
  • Which historical era do you find most attractive to live in? Why?
  • What does your dream career look like? What efforts are you making to implement it?
  • Make a list of five cities and countries that you dream of visiting. Why?
  • How do you spend your free time - with a book, a tablet or people?
  • What is the most important thing in communicating with colleagues?
  • What hobbies take up most of your time?
  • Comment: a trivial question, but overall a good one.

  • Are there any hobbies in your life that have remained since childhood?
  • How often do you watch news sites? Which sections do you pay the most attention to?
  • If you were offered to compete for the Nobel Prize, which field would you prefer?
  • Give an example of an inspiring quote from a successful person you admire.
  • What literary genre do you like best?
  • Name your favorite writer and his works.
  • What TV series did you watch last?
  • What mark would you like to leave behind?
  • Name at least 5 reasons that make you go to work/school every morning.
  • What would you not do even for a very large salary?
  • Do you think you chose the right profession? Are you ready to devote the rest of your career to her?
  • Comment: a typical question for a girl after 18-20 years old worries almost everyone.

  • Do you have a humanitarian or technical mind? Which school subjects were easier for you?
  • Who do you think is the smartest person you know?
  • How many books have you read in the last year?
  • Imagine that you have to give a half-hour report without preparation. Which topic/field will you choose?
  • If you became the president of the country, what decree would you sign first?
  • What piece of art evokes mixed emotions in you?
  • Do you like speaking in front of an audience?
  • What competition was the most important for you in your life? Were you successful?
  • What new skill have you learned in the last year?
  • What part of the country's cultural heritage are you proud of?
  • What achievement was the most significant for you, even if others did not appreciate it?
  • What decade's fashion would you like to bring back?
  • What do you think is the main drawback of the current education system?
  • What missed opportunities do you regret now?
  • Comment: with such a question, it is important not to slip into a whining vest; you need the right context.

  • If you could spread only one idea around the world, what would it be?
  • Which non-standard monument seems most positive to you?
  • What do you think, which things from modern use will become antiques after a few centuries, and which ones will turn into dust?
  • What is the main difference between generations for you?
  • What job do you think will not be replaced by artificial intelligence for at least the next 50 years?
  • What outdated traditions do you still follow, even though they seem pointless to others?
  • What's the most meaningful lesson you've learned from a work of literature?
  • What is more important to you – education, career or emotional balance?
  • What startup might interest you?
  • Comment: if a girl is interested in business and entrepreneurship, then why not? Not a bad question.

  • How many hours a day do you spend on work/study?
  • What profession do you think might appear in the near future that no one knows about yet?
  • What modern trend would you like to continue for the coming decades?
  • What to ask about love and relationships

    Girls often ask themselves what questions can they ask a guy to find out his intentions, how he relates to the innermost feelings that arise between young people? Questions to a guy about love and relationships will help a girl make a final decision, make up her mind and find a way out of a difficult situation. The main thing is to be able to listen to the answers and be insightful.

    1. Tell me, what should an ideal woman be like?
    2. Have you fallen in love at first sight?
    3. Can a guy and a girl be friends?
    4. At what age did you first kiss a girl?
    5. Can a man and a woman have a big age difference?
    6. What do you value most in a relationship?
    7. Has a girl ever confessed her love to you first?
    8. How do you feel about cheating? Is it possible to forgive a loved one who has cheated?
    9. What does a girl need to do to attract your attention and impress you?
    10. Are you a loving person?
    11. How do you usually prove your feelings and intentions?
    12. Do you arrange romantic dates?
    13. Can you describe me with 3 adjectives?
    14. What do you associate with the word “love”?
    15. Have you ever experienced unrequited feelings in your life?
    16. Have you ever cheated?
    17. How do you perceive same-sex love?
    18. How do you feel about open relationships?
    19. What kind of wedding do you dream about?
    20. What will you never forgive the woman you love?
    21. How much are you willing to do for the one you love?
    22. Is it possible to be a happy couple when there is no material well-being?
    23. Could you marry a girl with three children?
    24. Do you know how to surrender to feelings?
    25. Who should be the head of the family: a man or a woman?
    26. Should each spouse have personal space after the wedding?
    27. Do loved ones need a break from each other?
    28. Is it acceptable to maintain friendly relations with ex-partners?
    29. How do you feel about artificial beauty: applied hair, eyelash extensions, silicone lips, etc.
    30. Would you call yourself a jealous person?
    31. Do you want to have children?
    32. Have you brought breakfast to your girlfriend in bed?
    33. Is it possible to hate the person you love or love the person you hate?
    34. What makes a relationship strong and lasting?
    35. How do you feel about civil marriage?
    36. Should a woman work or should she be a housewife?
    37. Who controls the family budget in the house?
    38. Does love kill everyday life?
    39. Could you be in a relationship with a girl knowing that you would never be intimate with her?
    40. What should you give a woman on March 8?
    41. Do you often compliment girls?
    42. Your friends must like your girlfriend?
    43. Who should be the first to ask for forgiveness and why?
    44. How to avoid conflicts in relationships?
    45. What is your priority: wealth, career or family, love?
    46. Why do many representatives of the stronger sex feel afraid of serious relationships?
    47. How should you deal with your partner's shortcomings?
    48. What age is best to get married?
    49. Could you live with a woman who earns more than you?
    50. Should the parents of a man and a woman interfere in their personal relationships and family affairs?
    51. How do you feel about a prenuptial agreement?

    Results: useful tips and general conclusions

    Question is the key to knowledge. By asking questions (to a guy, to ourselves, or to the world), we will inevitably get an answer. And that’s why, before you ask, think: are you ready to hear the answer? The answer, and this happens all the time, you may not like it very much. But here, choose for yourself - the bitter truth or the sweet ignorance.

    • Don't be afraid to miss something. If there are cornerstone issues - for example, a guy prefers a raw food diet or is an adherent of some sect - this will quickly come up. Everything else can be figured out slowly.
    • When asking, know when to stop. At the fiftieth question, the guy will definitely have a strong feeling that he is being tested. This feeling should not arise.
    • Don't influence his answer. Don't interrupt, offer answers, or share your personal experience on the matter before he speaks. Let him speak out independently.
    • When asking questions, remember the answers. If you're bad at remembering, write it down. So that there is no awkward situation when you offer to go on a picnic and fry pork kebab to a vegan.
    • Accompany your questions with an introductory speech. That is, put them into context. For example, “Oh, the neighbors are fighting again. She constantly nags him for drinking. Well, this is how a person relaxes. I was working and tired. By the way, how do you relax?”

    And if you have no one to ask questions but yourself, register on a dating site. Read our review and choose what suits you. Choose guys according to the same principle - the one who fits. And don't settle for less. Good luck!

    Trick questions or how to make him nervous

    Guys are not like girls in that they are secretive creatures who do not like to show feelings and open the way to their inner world. Everything that happens in their soul remains there and does not leave the cherished boundaries, so it’s worth coming up with questions for the guy to get to know him better. These questions should be tricky, tricky, smart and interesting. The guy will have to think carefully before giving his answer. Trick questions for a guy, like a mirror, will show the truth and tell you everything about your beloved young man that interests a girl.

    1. If you don't like something about a person, are you ready to tell him about it directly?
    2. Have you ever stolen?
    3. Should a husband receive a full account of his actions from his wife?
    4. Would you be able to lend money to someone you don't know well?
    5. Have you made love with your ex-partners?
    6. What would you say if a beautiful stranger asked you for intimacy on the street?
    7. What incident or moment in life would you like to completely forget?
    8. How often do you lie?
    9. If you became invisible for a whole day, how would you spend that day?
    10. If there was a fire in your house, what item would you be sure to save?
    11. If you could send one person to a mental hospital, who would you send there?
    12. How do you behave when a person smells bad and is wearing dirty clothes?
    13. Should each spouse manage their salary separately or should husband and wife have joint money?
    14. Is it necessary for a wife to always report to her husband how she spent her money?
    15. Can you be friends with a gay person?
    16. What lengths are you willing to go to in order to get the beauty you have noticed for a long time into bed?
    17. How many girls did you have before me?
    18. Are you satisfied with your manhood and its size?
    19. What things about girls can make you angry?
    20. Who would you like to erase from your memory and why?
    21. Which body part would you say is the sexiest?
    22. Would you be able to take a person’s life if you knew that you would not be punished for it, but would be given a lot of money?
    23. Would you go to the wedding of an ex-girlfriend you loved deeply in the past?
    24. Are there any dishes from which it is impossible to eat anything? What kind of dishes is this?
    25. If you became a woman for 1 day, what would you like to do for that day?
    26. Do you think the size of the penis is important for girls?
    27. Is it possible to achieve success with women by only being rich?
    28. Have you ever had a holiday romance?
    29. What fruit do you associate the word “delight” with?
    30. Should guys shave their groin, armpits or chest?
    31. Is it bad to be henpecked?
    32. Do you believe that there can be heaven in a hut?
    33. Would you like to be on a nudist beach?
    34. Whose thoughts would you like to know?
    35. Is there anything you can't eat during breakfast?

    Communication - identify misunderstandings

    This is a reality that everyone can observe: the way communication actually occurs between two people unmistakably indicates the degree of intimacy in their couple. However, “the life of a couple can be paved with misunderstandings, difficulties and misunderstandings,” reminds Robert Neuburger.

    Digital and analogue communication

    Human communication is inherently complex, the psychoanalyst notes. The fact is that we use two methods that complement each other, but do not coincide: “digital communication” (words subject to interpretation) and “analog communication” (intonation, gestures, postures). In couples who get along well, speech and facial expressions are easy to decipher. But in those couples who do not get along, misunderstandings, misunderstandings and misinterpretations arise all the time.

    Communication failures

    Added to these difficulties is what psychologists call “communication deadlock” (everyone wants to express their point of view, but at the same time feels that they are not understood or not being listened to), or communication falsifications (secrecy, “white lies” or simply lying , hypocrisy, misinformation). To understand how you communicate with each other, ask yourself the following questions:

    8. Are you satisfied with the way you communicate as a couple? 9. Do you have a feeling that you understand your partner, and does he understand you? 10. Do you think there are significant shadow areas in your communication—topics that are difficult or impossible to talk about? 11. Do you happen to intentionally hide certain actions and thoughts from your partner? 12. Has it ever happened that you deliberately lied to him? 13. Do you think your partner can hide something from you and even lie? 14. Has your couple already encountered the discovery of deliberate lies of one or another of the partners? 15. If yes, how did you deal with this situation?

    List of questions for a guy

    What questions should I ask a guy so that they are tricky, difficult, but at the same time do not humiliate him, but become a source of good mood and positivity? After all, each person has his own “weak points”, about which it is better to remain silent. To prevent the dialogue from ending in conflict, it is important to feel the guy’s emotional state and monitor him so as not to step on his “weak points.” After all, asking a guy about love, family, relationships, friends can cause mixed reactions.

    1. If you suddenly find yourself in a situation where one of your parents becomes seriously ill and has to be cared for around the clock, what will you do: use the services of a nurse, go to a nursing home, or take the situation into your own hands?
    2. If you don't have children of your own, are you ready to adopt strangers?
    3. What will you do if you find out that someone has raised their hand against your child?
    4. If your wife wants to change religion, how will you react to this?
    5. Are you ready to call your wife's parents mom and dad?
    6. If the bride wants to keep her last name after marriage, how will you react?
    7. What is better: to get a well-paid job, a good position through bed, or to be a faithful, honest, but unsecured man?
    8. If your child committed a crime, would you cover for it?
    9. How to please your parents?
    10. How will you introduce me to your friends?
    11. Do you still watch cartoons?
    12. Have you ever spied on your classmates in the locker room?
    13. Have you tried drugs?
    14. What do you consider the strangest thing about yourself?
    15. Have you ever been so angry with someone that you wanted to kill the offender?
    16. If you could have dinner with anyone on the planet, who would you have dinner with?
    17. Do you dream of becoming famous?
    18. Do you rehearse before calling a girl?
    19. If you were told that you could live to be 90 and still have either the body of a thirty-year-old man or the mind, which would you keep?
    20. Have you ever thought about how you will leave this life?
    21. What are you most grateful for?
    22. If you woke up tomorrow with a new personality quality, what would it be?
    23. What do you consider your greatest achievement?
    24. Do you often consult with your mother before making an important decision?
    25. Whose death affects you the most and why?

    What questions should you not ask?

    Don't ask the guy about himself. You should also avoid including strong, inappropriate compliments in your questions. Thus, instead of effectively developing a conversation with a guy, you will lower your importance in his eyes.

    Examples of such inappropriate questions:

    #1 Am I beautiful?

    #2 How does it feel to be the most attractive guy in town?

    #3 How would you rate my appearance from one to ten?

    Article on the topic: 100 questions for a guy

    Questions should be asked purposefully. For example, to get necessary and useful information from a guy. Or so that your communication turns to a burning topic.

    Adviсe

    From the examples given, select your own topics that interest you. Don't interrogate the guy. Ask any questions casually, during neutral conversations.

    When meeting a guy, if he doesn't show initiative in conversation, start talking first. Tell us a little about yourself, and then feel free to ask the guy.

    To hear reasoning answers, ask more additional, leading questions during the conversation. Learn to listen to your partner when he speaks and do not interrupt. Show your loved one that you really want to know more about him.

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