48 Questions to Help Make an Awkward Conversation Easier

42. What would I not believe about you?

43. If you were a chair, who would you want to sit on?

44. Would you rather be able to play all musical instruments or speak all languages ​​fluently?

45. Would you rather be buried or cremated?

46. ​​​​What do you believe that most people don't believe?

47. If you could choose a day to relive over and over again, what day would it be and why?

48. If you could ask one question and get a completely honest answer, what would you ask?

49. How dare you?

50. If you were a kitchen appliance, what would it be and why?

51. Would you rather lose an arm or a leg?

52. If you were given a million dollars today, how would you spend it?

53. What places do you visit, but don’t want anyone to know about it?

54. Who is number one on your hit list?

55. Do you sleep with your eyes open or closed?

56. If someone were to film your life up to this point, what would be on the soundtrack?

57. If you could play a song every time you walked into a room, what would it be?

58. Let's say the Genie gave you three wishes, what would you wish for (no infinite wishes or anything like that)?

59. What method of execution do you consider the most interesting in history?

60. Have you already pooped today?

61. If you had the opportunity to travel in time, where would you go, to the past or the future?

62. If you could shoot something out of your belly button (like a superhero), what would it be and why?

63. If you had to eat a crayon from a box, what color would it be?

64. What would you tell your 10-year-old self?

65. What's the biggest lie you've ever told?

66. If you were the opposite sex all day, what would you do?

67. When was the last time you took a shower?

68. If you could get away with it, how would you kill someone?

69. Cats or dogs? I mean, if there was a need for food, who would you eat?

70. What's the strangest question you've asked someone to get to know them better?

71. What is the strangest or most inexplicable thing that has ever happened to you?

72. What song should be played at your funeral?

73. If you had a choice, what animal would you be and why?

74. What crime do you think you would be arrested for?

75. If you had to stand in the middle of a human centipede, who would be in front and behind you?

76. If you were a convertible, would you need car or life insurance?

77. What breakfast cereal has impacted your life the most?

78. Would you rather eat poop-flavored ice cream or poop-flavored ice cream?

79. If you could have any mythical creature as a pet, what would it be?

80. If you had the ability to read my thoughts, provided I could read yours too, would you want that?

81. Where did you hide the body?

82. Where do you want to be in an hour?

83. How would your worst enemy describe you in one word?

84. If we were playing hide and seek now, where would you hide?

85. What vegetable would you choose to fight with a 10 year old?

86. Would you rather fight 1 cow-sized duck or 50 duck-sized cows?

87. What would make you valuable in a “doomsday” scenario?

88. What do you think about the human species? I need an outsider's opinion.

89. Do you want to build a snowman?

90. Would you rather have a dog or be a dog?

91. What are you proud of, but never had a chance to talk about?

92. Who do you want to be as your famous deathmatch opponent?

93. Where would you go in the event of a zombie apocalypse?

94. Do you think it's normal for couples to fart in front of each other?

95. What's the strangest thing you do in everyday life?

96. Have you ever touched human remains?

97. What question do you want to answer, but no one asks?

98. If you were invisible for ten minutes starting right now, what would you do?

99. You're not going to kill me, are you?

100. What are your cool pajamas?

110. If you could build anything you wanted, what would it be?

111. Would you eat a person if you really had to?

112. If you could live forever, what would you do?

113. What is your favorite color on a scale of one to ten?

114. If a strip of spaghetti accidentally came out of your nose, would you sniff it or pull it out with your fingers?

115. What is the most weight you have gained in your life?

116. Do you squeeze a tube of toothpaste from the top or bottom?

117. Milk before cereal or cereal before milk?

118. What did your parents or friends tell you about me?

119. What gives you the right?

120. Can I see your browser history?


1. If you didn’t work here, what would you most likely be doing now? 2. How did you become ... (job title)? 3. What surprised you most about this job? 4. What is the most ridiculous task your boss has ever given you? 5. What would be more preferable for you: working four days a week for 10 hours or five days for 8? 6. If you had guaranteed success in any position, what would you prefer to do? 7. What was your first job? Did you like her? 8. What is the most valuable piece of professional development advice you have ever received? Which one was the worst?

Romantic questions5

  • Which love story that actually happened do you think is the best?
  • What do you think the best romantic trip looks like?

  • What nickname would you affectionately call me?
  • What do you think the perfect romantic gift should look like?
  • What was it about me that first attracted you?
  • What did you think of me when you saw me for the first time?
  • Do you prefer a good hug or a good kiss?
  • What does your ideal date look like?
  • What makes you happiest in a relationship?
  • Name your favorite romantic song.
  • Would you like a big, luxurious wedding or a small and modest one?
  • How did you feel when we first kissed?
  • What is your idea of ​​a perfect honeymoon?
  • Tell me what you find attractive? Just let it be something you haven’t told anyone about yet.
  • Which kisses do you like more: passionate or tender?
  • Guess what I like most about you.
  • How do you prefer a guy to show his feelings?
  • Do you like hearing how beautiful you are?
  • In a relationship, do you value conversations or sex more?
  • What was the most romantic date you were taken on?


9. Are you reading any interesting book now? I would like some recommendations. What about the show? 10. Are there any apps on your phone that you can't live without? 11. If you could only watch one genre of cinema for the rest of your life, what would you choose? What about musical preferences? 12. Which book did you hate that everyone admired? And vice versa? 13. Do you have any podcast recommendations? 14. Which movie have you watched recently that made you cry? How about laughing out loud? 15. Who would you like to be your partner on the reality show Amazing Race? In our realities, you can ask a similar question about programs like “Fort Boyard” or “The Last Hero”. 16. Who is your Instagram favorite? And vice versa? Oh, you don't have Instagram? Why?


Intimacy is formed when people have a genuine interest in each other. At the same time, accepting your partner for who he is. This is a state that is often called “souls touching.”

Agree, it is much more comfortable to be in the company of a person when you can be sincere with him than to communicate with someone, “putting on” a mask and playing the expected role. Is not it?

Psychologist Arthur Aron once asked this question, what exactly helps to form intimacy. Therefore, in 1997, I decided to undertake an experiment, which is known in the world as “36 questions”.

Its essence was that complete strangers had to ask each other a list of questions provided by Arthur.

Students took part, and the couples consisted not only of representatives of the opposite sex. There were significantly fewer men, so some of the girls talked to each other.

The questions were divided into three parts, 12 in each. Time was limited, only 45 minutes for the entire study cycle.

As a result, it turned out that most of the couples participating in the experiment soon started families.

The girls, deprived of a partner of the opposite sex, remained on friendly terms.

This way they not only got to know each other better, but also shared information that sometimes even close relatives are not aware of. For one simple reason – they weren’t interested.


17. If you were told that you could only eat one food for the rest of your life, what would it be? 18. What is the strangest dish you have ever tried in your life? 19. What is your comfort food? 20. Is there any food that you will never eat? 21. Advise what can be easily and without problems taken to work/school as lunch, but it should not be sandwiches. 22. Where can you eat inexpensively here? 23. Do your family have any culinary secrets or traditional recipes? 24. What is your favorite restaurant/cafe that is not very well known to a wide circle of people?

A few words to think about:

When you use these questions to get to know a guy, you are trying to establish a connection with him.

Conversations are not meant to impress people. Instead, they create a bridge where the two of you can meet halfway and move beyond formal communication.

Remember that the deeper the connection, the stronger your relationship with that person.

Now it's time to ask yourself how well you really know the person and evaluate your relationship with them. We hope you enjoyed these questions to get to know a guy better.


25. Is there a “heavenly” place to relax somewhere nearby? 26. If you could fly anywhere absolutely free, where would you go? 27. What's the coolest road trip you've ever taken? 28. What trip did you take during your last vacation? What were you doing there? What do you remember? 29. What type of holiday do you prefer - active or relaxing somewhere on a cozy beach? 30. What next trip have you already planned? 31. If you were able to take time off, or had the opportunity to work remotely, where would you go and what would you do? 32. What is your favorite thing to do on the weekend?

Vulgar and intimate

If you don’t know how to ask a pen pal about sex or erotic experiments, use ready-made message templates. With these phrases you will not embarrass yourself and your interlocutor.

  1. If you were giving me a massage, where would you start and end with it?
  2. If a girl is very tired, how can you help her relieve tension?
  3. Do you sleep in shorts or naked?
  4. Do you like it when a girl makes the first move?
  5. What kind of lingerie turns you on?
  6. Imagine that we went to a party together and drank well. What will we do next? And where?
  7. Do you often think “about this?”
  8. Do you have sexual fantasies?
  9. Have you seen the movie “50 Shades of Grey”? How do you like it?
  10. What part of your body is the most sensitive?


33. Where did you live before? How is that city different from your current place of residence? 34. As a child, what did you want to be when you grew up? 35. Do you have any hidden talents or unexpected hobbies? 36. What did you like to do in elementary school (outside the school curriculum)? 37. What accessory or item was your “must-have” in childhood/teenage, i.e., growing up? 38. What was the most incredible thing that has ever happened to you? 39. Who was the most significant person, mentor, role model for you? 40. What was the most valuable piece of advice you've ever been given?

Ways to know your interlocutor

During a conversation, especially with a new person, some people become confused, not knowing what to talk about. This is a natural reaction, because it’s difficult to say right away what topics are interesting to your interlocutor and what he is not ready to share.

To better understand the information needs of a new acquaintance, it is worth observing him in the first few minutes. You need to try to determine the type of temperament, if possible: choleric, melancholic, phlegmatic or sanguine. You will also need to evaluate features of appearance, appearance, voice, and note details of behavior such as gestures. If this is, for example, a new colleague, then it’s worth seeing how he feels in an unusual environment. If this is a girl on a first date, you need to analyze how often she adjusts her hair and clothes, and whether she is shy. All this will help build an interesting and meaningful conversation in the future.

Simple questions allow you to establish contact: “How are you?”, “How are you feeling?”, “Are you okay?” They relax the interlocutor and set them up for conversation. Such designs have long ceased to be questions. Rarely does anyone answer them seriously and honestly.

Then you can ask mirror questions: “Yesterday I tried mango for the first time. Have you tried it? This way, the conversation will not completely shift to the speaker, but will also throw hooks of interest to the interlocutor. Such formulations relieve stiffness and enable memory and analysis. But you shouldn’t dwell on them for a long time, because you might think that the instigator of the conversation loves to talk about himself too much. Any person will be willing to make contact if his figure is the center of the conversation. This key opens the door to the third group.

Next are full switch questions that change the topic. There is already room for creativity here. These structures help build an interesting dialogue and will not let you get bored. They can develop into a discussion, a friendly argument, or a collective discussion. In any case, the goal will be achieved, and a dry, uninformative conversation will develop into an exciting conversation.

You can achieve greater favor with your interlocutor if you ask clarifying questions during his answers. This is an indicator of respect and interest, a kind of hidden sign of attention.


41. If you were entrusted with choosing eight objects that would receive the status of “8 Wonders of the World,” what would you add to this list?
42. What would you put in a time capsule 15 years ago? 43. Which of all the compliments you have received was the strangest? 44. Have you ever thought about “cool” inventions or starting companies that, as it turns out, have already been made or founded? 45. If you could teach any course in college, what subject would you choose? 46. ​​What is something completely out of character for you that you have ever done? 47. What superpower would you like to have? 48. If you could have absolutely any pet, which one would you choose? PS We recommend another useful article on the topic of working on yourself - 30 websites that will make you much more educated

The author of the translation is Vyacheslav Davidenko, founder of TESTutor

Beautiful questions to ask a girl about relationships

What question can you ask a friend to hint about your feelings? How to delicately move from the friend zone to the next level? Just find out from her how she feels about you and whether she is ready for a relationship, and the rest is a matter of technique! Just don’t do it too intrusively - just one wrong question to a girl can ruin everything! Use our cheat sheet - it will tell you how to direct the conversation in the right direction.

1. What makes you forget about everything in the world?

2. Are you ready to kiss the first person you meet? What about me?

3. Where would you like to go on a first date?

4. What is more important to you – the voice of reason or the heart?

5. How do you imagine your happy life in 5 years?

6. Do you believe in horoscopes and compatibility of zodiac signs?

7. How do you feel about cheating and its other side – jealousy? Do you think these concepts are interrelated?

8. What masculine quality can turn you off?

9. If you and I were locked on a desert island for one day, how would you prefer to spend this time?

10. What kind of relationships do you like - explosive or predictable?

11. How many children do you want to have?

12. What do you first pay attention to when meeting a guy?

13. Would you start a relationship if you knew in advance that a breakup was inevitable?

14. Do you prioritize “bad boys” or “nerds”?

15. What is the worst betrayal you have experienced in a relationship?

16. Do you have many friends? How many of them can be called close?

17. Do you believe in “different-sex” friendships?

18. What would you choose - a winning lottery ticket for a million dollars or the guy you like?

19. Name three essential traits in the man of your dreams.

20. What do you mean when you talk about love?

21. What accident changed your life forever?

22. What qualities do you value in friends?

23. Could you date two guys at the same time if you were sure that they wouldn’t find out about each other?

24. What is your idea of ​​the most romantic marriage proposal?

25. Do you dream of a lavish wedding with hundreds of guests? Or do you prefer modest gatherings in a small circle?

26. Could you fall in love at first sight?

27. How long was your longest relationship?

28. Who do you think cheats and lies more often – guys or girls?

29. Which compliment stuck with you the most?

30. Which movie character would you be willing to go on a date with?

31. Can you be called amorous? How many guys have you had feelings for?

32. If you could paint a picture, write a song or a book, who would you like to dedicate it to?

33. Is there at least one person around you whom you trust 100%?

34. Can you imagine that you will spend the rest of your life with a single man “both in sorrow and in joy”?

35. What is more important to you – emotions or obligations?

36. What place does family occupy in your life?

37. Do you love children?

38. Have you ever had a crush that you had to hide?

39. Have you ever regretted missed acquaintances or forced separations?

40. Imagine that you need to write the most dramatic, romantic or shocking SMS to a guy. What will it contain?

41. If you had just one question, what would you ask your future husband?

42. Without what is it impossible to build a harmonious relationship between a guy and a girl?

43. Have you ever been able to communicate with your lover all night long without noticing how time flies?

44. What is the most romantic thing anyone has ever done for you?

45. Do you like to demonstrate close relationships (hug, kiss, etc.) in public?

46. ​​What is the stupidest reason for breaking up that you can name from your own experience?

47. Do you adhere to gender stereotypes about a woman as a keeper of the hearth and a man as a breadwinner?

48. Do you think relationships change after marriage?

49. Is family life more than love? What is it impossible to build a family without?

50. What do you think about civil marriage?

Where to start communication?

Our mood for communication may not always coincide with the guy’s mood - perhaps he is busy with serious matters at that moment. Therefore, in order to “test the waters” it is worth starting with questions of a general nature.

For example:

  1. Hello! How are you?
  2. It's so cold here. What about you?
  3. How did you get home from work yesterday?
  4. Did you go for a run this morning?
  5. I would like to please you so much. How can i do this?
  6. The mood is somewhat sad. Can you recommend a good movie?
  7. What interesting happened to you today?
  8. Have you already had lunch today? What was delicious?
  9. Did you hear what happened to...?

The main thing here is not to panic if a person does not answer for a long time - no one has canceled his business. By sending a message, you hooked the guy - he will answer as soon as possible.

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