200 tricky questions (for your friends or your partner)

We all love to ask questions and learn more about others. You are probably curious to find out some things from certain acquaintances, however when these questions are put to you, out of shame, you prefer to silence the answers.

These delicate questions can be compromised for different reasons: to consider it a taboo subject, to regret having done it, to want to show that all is well for you …

    Table of Contents

    A list of tricky questions

    Then you can find a list of tricky questions which may make you prefer to avoid the answer.

    1. What’s the most engaged thing your parents caught you doing?

    Our parents saw us being born and growing up, but there are some situations that we prefer not to share with them. It’s possible that at some point in our lives we were caught doing things we wouldn’t want them to see.

    2. Have you ever been cruel or bad to someone?

    Whether that’s good or bad often depends on the situation. When they put us against the ropes, we can lose roles as well as when needed. We can also be cruel to someone because of the pain they caused us, such as an ex-partner. It is impossible to be good to everyone and in all situations.

    3. Are you afraid you haven’t told anyone?

    Some people may feel anxious about certain situations. And a lot of these people haven’t accepted it, so they don’t talk about it with absolute naturalness. In such cases, this question can be boring.

    4. What is the biggest rejection you have had in love?

    Love can bring out the good and the bad in us. For our self-esteem, refusals often have a strong negative impact. No one likes to feel rejected, let alone talking about it.

    5. What is the strangest thing that you have done on your own?

    When we’re alone, we don’t have to show ourselves how people want us to be, we don’t have to give a photo. It may be that right now we are relaxing and even carrying out some ideas that we have in mind that others may not share.

    6. Are there any secrets that you did not tell your parents?

    So in the first question we talked about the embarrassment it can be if our parents surprise us in a compromised situation. That’s why we sometimes keep them a secret, things we couldn’t tell them.

    7. What is the biggest lie that you told that you haven’t been caught?

    It is impossible that someone has never told a lie, because the lie is totally human. However, there are different types of lies and some of them hide something that is really compromised.

      8. Do you consider yourself a happy person?

      In the face of others, we all tend to shy away from the fact that everything is always good for us, that we are strong, and that we can resist what they do to us. Now it is impossible to be happy all the time.

      9. What do you like the most about yourself?

      Answering these questions can make you look a little incredible, depending on the qualities you put forward. However, it is always better to have high self-esteem and high self-confidence.

      10. What do you like least about yourself?

      If in the previous question it is possible to sin in vain, in this question the opposite occurs. Depending on what is answered, it may seem that someone is not valued enough.

      11. If you could erase negative experiences from your life, what would it be?

      We have all had a negative experience in our lives. The ideal is to accept it and move on, however, there are some individuals who still cannot speak openly about these experiences.

      12. What is the craziest thing you have ever done for love?

      Love is a truly magical experience, which can change our perception of the world and our behavior. Maybe we’ve done things for love that over time get boring to us.

      13. What was the last lie you told?

      It’s been said that we’ve all lied at some point in our lives, but talking about the most recent lie can be quite embarrassing.

      14. What is your limit in intimate relationships?

      Not everyone has the same beliefs about sex. While some people are very conservative, others, on the other hand, are very liberal. It is not always easy to talk about these issues.

      15. What would you change in your life if you could?

      There might be something in our lives that we would like to change. But recognizing it openly can be tricky, as we like to show that we are okay with ourselves.

      16. If you could ask for one wish right away, what would it be?

      This question can get you thinking about what you would change in your life, and as the previous question stated, it is not always easy to expose your weaknesses.

      17. How would you like to have an intimate experience with a person of the same sex?

      In the case of boys, maybe not so much, but there are a lot of women who would like to experiment with the same sex. Recent research indicates that all women are bisexual.

      • You can find out more about this in our article: “Research: 3 out of 4 women are lesbian or bisexual”

      18. What excites you the most?

      Not everyone talks freely about what turns them on the most because they think sex is a taboo subject.

      19. Did you give your arm a twist?

      Often times, when it comes to interpersonal relationships, we don’t make it the hardest part. It seems that giving in to certain aspects (and even forgiving) is a symptom of weakness. Nothing could be further from the truth, because forgiveness honors you and giving your arm a twist when needed is a symptom of maturity and emotional intelligence.

      20. Did you use an object for sexual purposes even if that was not your purpose?

      In moments of intimacy, and in which we decide to give ourselves pleasure, there may have been objects used to stimulate ourselves. Especially the women.

      21. Do you have any sexual fantasies?

      We all have sexual fantasies, but not everyone talks about them openly. Fantasies are unconventional and often have the attraction of being prohibitive.

      22. Have you ever broken someone’s heart?

      It’s not nice to say goodbye to someone who would give their life for you, but sometimes you stop feeling for your partner and it’s time to take a step back.

      23. Will you call me tomorrow?

      And of course, in situations like the one above, it’s not easy to face it because the other person may feel offended. He will always tell you yes, even if you know it’s not true.

      24. Did you have sex in a forbidden place?

      There are people who like to have sex in different unconventional places (for example, in a forest or in a shopping mall). This does not mean that they talk about it openly.

      25. Have you ever been unfaithful?

      Infidelity is something that a lot of people have experienced, Either as a victim or as a person who has committed an infidelity. It is a subject that is best kept secret.

      26. What are you most satisfied with?

      A question about more personal preferences.

      27. When was the last time you lied?

      Lying is a socially frowned upon, but incredibly widespread thing. This question seeks to see to what extent someone is able to admit that he is lying.

      28. Have you ever been with someone to forget someone else?

      Love for others can be used subconsciously to make up for shortcomings.

      29. Do you have any suitors at the moment?

      A question as direct as it is delicate.

      30. Have you ever had a fight with the partner of a friend?

      When friends start dating someone, sometimes conflicts can arise.

      31. Have you ever played with someone’s feelings?

      There are times when manipulation can arise spontaneously, almost automatically.

      32. Do you feel lonely?

      Such confidences are often painful.

      33. What is the most extravagant thing you have done?

      There are times when what he says the most about himself is those actions that he sees as unrepresentative of who he really is.

      34. Do you usually approach people you love or can you be shy?

      This delicate question concerns the techniques of seduction used by someone (Or their absence).

      35. How long was the shortest love affair you ever had?

      Sometimes remembering short relationships can make us wonder if we’ve made any mistakes we haven’t made.

      36. Have you ever considered having something with a friend’s mother?

      Sometimes this question is a taboo that very few people will be able to admit. Because, let’s face it, there are the most attractive mothers (and the most attractive fathers).

      37. Are you having an affair with one of your cousins?

      Another taboo but very common: having a relationship with someone with whom you share many genes.

      38. Did you have an intimate encounter with someone you met on the same day?

      In the Tinder Age, it’s hard for someone to deny that this has happened to them at least once.

      39. Would you leave it to your current partner if you earned a million dollars in return?

      The old dilemma between love and money.

      40. Have you ever met someone who you will forgive all your faults?

      The typical case of unconditional love.

      41. How much money do you earn?

      An opportunity to ask questions about this person’s salary.

      42. How much money did you save in the bank?

      To find out about your friend’s legacy. In some cases, you might be surprised if one of them received a large inheritance or has a high income that you did not know.

      43. Do you think you can time travel?

      One of those scientific questions which can generate fascinating debates.

      44. Have you ever been arrested or imprisoned?

      More people than you might think have had some sort of legal problem.

      45. Did you sleep with a stuffed animal when you were little?

      A tender moment to remember childhood (and not so small) and the animals that accompanied us at night.

      46. ​​Which political party do you vote for?

      When it comes to politics, you can open Pandora’s Box, so be careful.

      47. Are you a feminist?

      In line with the above: to know your friend’s ideas and scale of values.

      48. Have you ever had a car accident?

      Who more who less has had accidents at the wheel.

      49. Have you ever dressed in your partner’s clothes?

      Chances are we’ve all done it on some occasion, even though it’s like makeshift pajamas.

      50. What’s the most ridiculous costume you’ve ever worn?

      Moment of laughter guaranteed.

      51. Have you ever considered getting a tattoo?

      Surely we have all thought about it before. It’s time to wonder what design would be chosen.

      52. Would you like to tattoo your partner’s name?

      It’s probably the worst decision in the world, but there are people for everything.

      53. When have you experienced the most physical pain in your life?

      Falls, stupid blows, fractures … surely many anecdotes appear in the conversation.

      54. Which artist would you like to spend a crazy evening with?

      With this tricky question, we can assess the taste of the person in front of us.

      55. If you had to choose, who would you save from a fire: a man or a family of dogs?

      A question that serves to reflect on the moral preferences of each.

      56. What was it that frustrated you that you couldn’t tell the last person that I disappointed you?

      Bringing up this topic of conversation can be awkward for those who haven’t yet come through the end of an emotional or friendship relationship.

      57. If you had to hide one of the parts of your body that you normally show publicly, what would it be?

      This question is used to express insecurities.

      58. Have you ever discriminated against someone?

      Prejudices and stereotypes they are able to make us treat others differently simply because of their superficial aspects.

      59. What physical characteristic would require you not to have a date with a person?

      Another of the questions related to personal preferences. Of course, a lot of people could answer that none.

      60. Have you ever repressed the urge to steal something?

      Behavior against private property can lead to embarrassing impulses to recognize.

      61. How many consecutive days did you approach a different person each day?

      A question that many will not want to answer.

      62. Would you do a striptease?

      On the ability to expose yourself to others.

      63. Will you allow me to see my smartphone’s browser history?

      Giving in to a privacy issue like this isn’t easy.

      64. Would you like to try sadomasochism?

      An opportunity to discuss topics that arouse curiosity in the sexual field.

      65. Have you ever fallen in love with a friend’s partner?

      These events can lead to conflict situations, for example that many prefer to hide.

      66 … and a parent?

      A variation of the previous question, which can be even more annoying.

      67. Do you think I’m in good shape?

      Answering this question can generate sexual tension.

      68. Have you ever regretted having slept with someone?

      The snatches of the night can lead to repentance.

      69. In what way do you think you are better than others?

      Some people find it difficult to recognize their strengths.

      70. What situations make you want to behave badly?

      Another tricky question to tackle moral limits.

      71. What was the first thing you thought about seeing?

      About the sensations that appear on first eye contact.

      72. What was the first thing you thought of when you met me?

      A version of the previous question, based more on personality.

      73. Have you ever been with a partner much taller or much shorter than you?

      Curiosities that can be aesthetically pleasing.

      74. What do you think of the Islamic veil?

      A controversial topic that can lead to long conversations.

      75. Are you satisfied with your sex life?

      The answer to this can be very revealing.

      76. Are you in debt with anyone?

      They can be economic or symbolic debts.

      77. What was the last thing you searched for on Google?

      This research can be a bit boring.

      78. Who is your favorite YouTuber?

      Sometimes the YouTube channel in question may not have a good reputation.

      79. Why do you think there is poverty?

      These complicated questions give rise to many kicks in the legs.

      80. Have you had jobs that you love deeply?

      Parts of our CV that we would rather forget …

      81. Which singer makes you ashamed to admit you love him?

      Indescribable tastes.

      82. Are there any secret words that you only use with your friends?

      Sometimes slang used with friends and private humor they can be a little ridiculous.

      83. What was your worst sexual experience?

      Events that are remembered with shame or humor.

      84. Have you ever hung onto some really bad TV shows?

      Another of the delicate questions which refer to cultural tastes.

      85. What do you think your IQ is regardless of what the tests say?

      Intelligence is often a controversial issue.

      86. Have you ever seen adult family movies in another room?

      Stocks considered risky in most households.

      87. What do you think of capitalism?

      Another question you can highlight controversial opinions.

      88. How many years of uninterrupted work do you think it would take you to get rich?

      If this was our top priority … how long would it take to get there?

      89. Who would you dare to discuss politics with?

      A delicate question which leads to recognize its own ignorance.

      90. Do you think you should be able to vote on anything?

      It is difficult to know what is the correct answer to this question.

      91. How many people in the world do you think hate you?

      About old conflicts and enmities.

      92. Does anyone think you are very unintelligent?

      One way to learn about the unfavorable image that was given in front of other people.

      93. Which line would you cross to win someone over?

      At the limits of seduction.

      94. Have you ever woken up late at night to play a video game?

      Moments of play so catchy that they deprive us of well-being.

      95. Have you ever traveled to another province just for sex?

      Some might find it too boring just for this reward.

      96. And in another country?

      Variation of the above, even more extreme.

      97. How do you think others admire you?

      An opportunity to put modesty aside.

      98. Have you ever regretted not having insulted someone?

      Another tricky question on old repentances.

      99. Do you value the money of your potential partners?

      On the shallower side of each.

      How long would you be without getting out of bed if they paid you a dollar for every minute?

      A curious mental experience.

      101. Is there an athlete you would give your all to get through a night?

      The world of sport has a particular attraction …

      102. Have you done anything illegal so far this year?

      Even if we only look at the phone when we are driving, it is likely that we have broken some law or another.

      103. Have you ever had a drink on the floor in a restaurant or nightclub?

      This bad trance is quite common.

      104. What is the skill that you would like to have with all your might but have never been able to develop?

      Play an instrument, learn a particular language …

      105. If you were a dinosaur, what would you like to be?

      The important thing is to know the reasons why you prefer to be an individual.

      106. Have you ever felt lonely despite having people around you?

      A very common feeling. Even in the most populous cities, we can feel abandoned.

      107. Have you ever written a poem to someone you love?

      With this tricky question, you can rate the romance of your friends or partner.

      108. Have you ever damaged the public road?

      Whether on purpose or not, we may have caused havoc.

      109. Are you one of those people who can only go to the bathroom at home?

      There are a lot of people who literally cannot get a lot of water in a public toilet.

      110. What would you do to protect yourself from a zombie invasion?

      There are many films and series that help us imagine what strategies we would adopt to sustain life.

      111. Do you consider your pet to be “one more in the family”?

      Some animals have an almost human status.

      112. Do you like pineapple pizza?

      With lovers and detractors alike, this is one of the pizzas that arouses the most controversy for such an extreme mixture of flavors.

      113. Have you ever tried screws?

      Quite popular lunch in Catalonia, not everyone dares to throw a little snail in their mouth.

      114. What would you do if the lottery hit you tomorrow?

      We can find out: what would be the first purchase, what would be the most expensive, etc.

      115. When you are sad, do you put on sad music?

      It sounds counterproductive, but it helps some people get through tough times.

      116. Have you dreamed of spending a crazy night with someone over 50?

      A fantasy that few people admit to having had.

      117. Do you have prejudices about the inhabitants of a region of your country?

      Almost everyone, whether we like to admit it or not, throw away clichés.

      118. What is the ugliest gift they’ve given you?

      It’s quite common to have to look good at a frightfully ugly or unnecessary gift.

      119. Have you ever worked at university, lost everything and had to start from scratch?

      A disaster that has happened to almost everyone.

      120. What is the hour that you made the most ridiculous?

      The perception of ridicule is very subjective, and there are people who don’t even know what it is.

      121. What quality do you value most?

      It’s time to turn up the heat and move on to a more intimate or romantic atmosphere.

      122. What is the part of your body that you like the least?

      This way, you will be able to assess whether the person in front of you is feeling complicated by a physical trait.

      123. If you were the head of a multinational, would you be a strict and demanding boss or rather relaxed and friendly?

      We can all put ourselves in the shoes of a great manager and assess which leadership style best matches our personality.

      124. Among your group of friends, who is the most (or the most) irresponsible?

      To remove dirty rags.

      125. Who do you need the most in your life right now?

      Give way to a more sentimental conversation.

      126. Do you consider yourself to have sexist attitudes?

      Almost everyone, at one time or another, can have a discriminatory attitude.

      127. What is the last book that you read?

      Many of your friends won’t even remember it …

      128. How many hours per day do you spend surfing the Internet?

      Unfortunately, many people spend long hours just browsing Facebook and Instagram.

      129. What is the most embarrassing gift an ex-boyfriend has given you?

      Sometimes the gifts are ridiculous and unnecessary.

      130. What is the worst concert you have attended?

      There’s always a show where everything fails or the band was really horrible.

      131. What is the worst sport for you?

      Almost all of them have a sport that we are really denied.

      132. Have you ever run out of gas? How did you resolve the situation?

      Many drivers have had this bad experience on certain occasions.

      133. Do you want more from your father or your mother?

      The classic tricky question. Some people have a clear preference, while others prefer not to get wet.

      134. Are you ashamed of the musical tastes you had when you were a teenager?

      High School Musical, Justin Bieber … that kind of music we’d rather forget.

      135. Have you ever met a celebrity? What happened?

      We all probably have a little anecdote when we first met a celebrity.

      136. Over the years, have you changed your ideology?

      You probably don’t think the same at 15 as you do at 30 years.

      137. What is the worst cave you have visited?

      There are absolutely loud nightclubs and pubs.

      138. Have you ever seen a deceased person?

      It’s not very common, but a lot of people have had it.

      139. If you could choose, where would you go to live?

      You have the choice between cities and countries.

      140. What is the worst subject given to you in school?

      Mathematics, language … which one have you always suspended?

      141. Have you ever been in the street?

      If there were people watching, the situation was certainly very uncomfortable.

      142. What’s the trickiest question you hate to be asked?

      The “troublesome meta-question”.

      143. Have you ever recycled a gift they gave you to give to someone else?

      A classic among the rancid.

      144. Do you prefer half a million euros to spend in 1 day or 300,000 € to spend for a month?

      Maybe thinking better about how to invest money makes us go for the second option.

      145. If the lottery hit you, would you tell your friends?

      It is not at all prudent to speak in this circumstance.

      146. Does anyone in your family have a mental disorder?

      More or less serious, almost all of us have a family member in difficulty.

      147. Have you ever broken furniture to get drunk?

      Losing your balance and falling on a table is a fairly common thing.

      148. What was your favorite comic book when you were a child?

      Mortadelo, Asterix, TBO, Rompetechos, Tintin, 13 Rue de l’Percebe … which was your favorite?

      149. If you could choose one quality among these three, which one would you keep? Be tall, beautiful, or be successful.

      Argumentation can be a lot of fun.

      150. Have you ever eaten something that made you vomit (or almost)?

      Surely we have all tried foods which, due to their bad condition or bad smell, have produced arches in us.

      151. Have you ever slept with someone for a reason it wasn’t love or attraction?

      Maybe it could be out of heartache, money, boredom …

      152. Which public figure do you consider to be an erotic myth?

      There is always a presenter who we find extremely attractive.

      153. What is most important in your life: your personal life or your professional career?

      Even though we want to control both aspects of life, there is always one side that weighs a little more and for which we sacrifice part of the other.

      154. Can you imitate the voice of a celebrity?

      Who more who less took his first steps in the world of imitation.

      155. The sentence ends: “I couldn’t live in a house that didn’t have …”

      Perhaps the answers will be in relation to the specific characteristics of the house (being bright, central, spacious …) or in relation to who should live there.

      156. Which of your group of friends do you consider to be the least reliable?

      There is always someone in the gang who is best not to deal or do business with.

      157. How old would you like to live?

      Address a taboo subject.

      158. Do you believe in the right to bear arms?

      A controversial political issue in some countries.

      159. What kind of people do you think you can seduce?

      Many times it is difficult to recognize these limitations.

      160. What talent frustrates you the most that you don’t have?

      A very personal question to find out more about this person.

      161. What is the most disgusting thing that has happened to you?

      This question will probably give way to quick and concise descriptions so as not to give details.

      162. How many of your friends would you hand over to the police if you knew they had committed crimes?

      A delicate question on the limits of friendship.

      163. Have you ever used drugs to try and flirt with someone?

      A question on the irrationality of the consumption of certain substances.

      164. Have you ever tried to get better grades by cheating?

      Again, raising the issue of skipping the rules, in this case to progress academically.

      165. Do you think there are areas of knowledge that you could never learn?

      Question the limits of the mind.

      166. Have you ever been rejected for a kiss?

      The so-called “cobra” kiss is one of the worst things they can ever do to us.

      167. Have you ever lied to tie up?

      Lying to try to connect with someone is a dirty game, we have to be honest with the person we love.

      168. What is your definition of “love”?

      Love is the big topic that everyone thinks they know a lot about, but when it comes to the truth, it’s hard to pinpoint exactly.

      169. Did you find someone having sex?

      A question, certainly, very intimate which can reveal funny anecdotes.

      170. Do you believe in God?

      One of the most recurring questions in human history, which continues to inspire conflicts today.

      171. Have you had a couple that is much older or younger than yourself?

      Asking about people’s tastes is often a topic that can bother some people.

      172. What is your opinion on euthanasia?

      A very recurrent debate in the political landscape today.

      173. How would you like to be a millionaire?

      A question which may seem simple but which has a number of implications to consider.

      174. What is your opinion on government?

      Questions about politics are usually the trickiest in a meeting.

      175. What do you think of communism?

      Political and ideological issues often arouse the weak passions of people.

      176. would you date a porn actress?

      A curious approach that not everyone has questioned.

      177. At what age did you lose your virginity?

      The classic question of meeting friends to go out.

      178. What’s the worst thing you’ve done to sleep with someone?

      Some people use the crudest ploys to have sex with someone.

      179. What is the worst insult you have ever done to someone?

      A curious question. We all have stories to tell about past conflicts.

      180. Have you ever fought?

      Getting involved in a fight is not something to be proud of.

      181. What do you think of the king?

      A controversial issue, mainly in countries that still have a monarchy in the state prefecture.

      182. Until what age did you urinate in bed?

      Some children continue to urinate in bed until quite old age.

      183. What do you think of the police?

      A thorny question, no doubt, depending on who is asked this question.

      184. What do you think of the Jews?

      The Jews were a historically persecuted people, today there is still prejudice against them all over the world.

      185. What do you think of Asians?

      A question which can also generate controversy in certain situations.

      186. If you were born again, would you repeat your life in the same way?

      Sometimes it’s worth reflecting on what you’ve been through, looking back, and taking stock.

      187. If you could choose, in which country would you like to be born?

      Depending on the decision we make, we would hypothetically end up in one situation or another.

      188. Do you think that the poor do not try hard enough?

      A controversial approach, which will certainly reflect what kind of person he is, who responds.

      189. What do you think of infidelity?

      A complicated and subjective question. Depending on the person, we may have an opinion one way or another.

      190. What do you think of marriage?

      An institution too important in our society that marriage should be carefully considered and appreciated.

      191. What do you think of the Church?

      Today we can criticize any institution of the nineteenth century, including the Church.

      192. What do you think of abortion?

      Controversial subject. Recurrent debate on civil rights.

      193. Do you think all races are equally intelligent?

      Racism is something that should not be tolerated in public debate.

      194. What do you think of prostitution?

      Another question which opens a controversial debate; that of the abolition or legalization of prostitution.

      195. What do you think of life imprisonment?

      Some countries have more restrictive criminal laws and others less so for some people.

      196. What do you think of immigration?

      The immigration debate is on the agenda today.

      197. Do you think everyone should be able to vote?

      One debate some people have is whether voting should be a privilege for a few or a right for all, as it is today.

      198. What opinion do homosexuals deserve?

      Social debate on the rights and freedoms of people attracted to their same sex.

      199. What do you think of Jeff Bezos?

      How we think about the richest people on the planet will also say a lot about us and how we view the world.

      200. What opinion do identity policies deserve?

      A very hot topic today is that of identity politics and its influence on the dominant agenda of Western society.

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