205 awkward questions (for your friends or your partner)
We all like to ask questions and learn more about other people. Surely you are curious to find out certain things from some acquaintances, but when they ask you those questions, out of shame, you prefer to keep the answers to yourself.
These uncomfortable questions can be embarrassing for different reasons: considering it a taboo subject, regretting it, wanting to pretend that everything is going great ...
- Related article: "56 questions to get to know someone better"
A list of awkward questions
Then you can find a list of awkward questions which may make you prefer to avoid the answer.
1. What's the most embarrassing thing your parents have caught you doing?
Our parents have seen us being born and growing up, however, there are certain situations that we prefer not to share with them. It is possible that at some point in our lives, we have been caught doing things that we would not want them to see.
2. Have you ever been mean or mean to someone?
Be good or bad often depends on the situation. When they put us on the ropes we can lose our roles, as well as in times of need. We can also be cruel to someone for the pain they have made us feel, for example,
an ex partner. It is impossible to be good to everyone and in all situations.3. Do you have any fear that you have not told anyone?
Some individuals may feel anxious about certain situations. And many of these people have not accepted it, so they do not talk about it completely naturally. In these cases, this question can be embarrassing.
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, rejections often have a strong negative impact. Nobody likes to feel rejected, much less talk about it.
5. What is the most bizarre thing you have done alone?
When we are alone, we do not have to show ourselves how people want us to show ourselves, we do not have to give any image. It is possible that in those moments one relaxes and even carries out certain ideas that you have in mind and that others will not share.
6. Is there a secret you haven't told your parents?
If in the first question we talked about how uncomfortable it can be if our parents catch us in an embarrassing situation. That is why sometimes we keep secrets from them, things that we would not tell them.
7. What's the biggest lie you've ever told and you haven't been caught?
It is impossible that someone has never told a lie, because lying is totally human. However, there are different types of lies and some of them hide something really embarrassing.
- Related article: "Can you spot a liar? The 8 types of lies"
8. Do you consider yourself a happy person?
In the face of others we all tend to put aside that everything is always going well for us, that we are strong and that we can bear whatever they throw at us. Now, it is impossible to be happy all the time.
9. What do you like the most about yourself?
When answering these questions, you can appear a bit cocky, depending on the qualities you highlight. However, it is always better to have high self-esteem and self-confidence.
10. What do you like least about yourself?
If in the previous question it is possible to be conceited, in this question the opposite happens. Depending on the answer, it may seem that someone does not value themselves enough.
11. If you could erase a negative experience from your life, what would it be?
We have all been through some negative experience in our life. Ideally, accept it and move on, however, there are individuals who are still unable to speak openly about these experiences.
12. What's the craziest thing you've done for love?
Love is a truly magical experience, which can change our perception of the world and our behavior. We may have done things out of love that we find embarrassing over time.
13. What is the last lie you ever told?
It has already been said that we have all lied at some time in our life, but talking about the most recent lie can be quite uncomfortable.
14. What is your limit in intimate relationships?
Not everyone has the same beliefs about sex. While there are very conservative individuals, others, on the other hand, are very liberal. It is not always easy to talk about these issues.
15. What would you change about your life if you could?
There may be something in our life that we would like to change. But admitting it openly can be tricky, because we like to pretend we're okay with ourselves.
16. If you could make a wish right now, what would it be?
This question can make you reflect on what you would change in your life and, as said in the previous question, it is not always easy to expose your own weaknesses.
17. Would you like to have an intimate experience with someone of the same sex?
In the case of boys, perhaps not so much, but there are many women who would like to experiment with the same sex. Recent research claims that all women are bisexual.
- You can learn 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, since they think that sex is a taboo subject.
19. Have you given your arm to twist?
Many times, when it comes to interpersonal relationships, we don't play hard. It seems that giving in in certain areas (and even forgiving) is a sign of weakness. Nothing could be further from the truth, then forgiveness honors you and giving your arm to twist when necessary is a symptom of maturity and emotional intelligence.
20. Have you used any object for sexual purposes despite not being your objective?
In moments of intimacy, and in which one decides to pleasure himself, he may have used objects to stimulate himself. Especially women.
21. Do you have any sexual fantasy?
We all have sexual fantasies, but not everyone talks openly about them. Fantasies are unconventional, and often have the appeal that they are prohibitive.
22. Have you ever broken someone's heart?
It is not pleasant to say goodbye to someone who would give his life for you, but, sometimes, one stops feeling for his partner and has to mark distance.
23. Are you going to call me tomorrow?
And of course, in situations like the previous one, it is not easy to say things to your face, because the other person may feel offended. He will always say yes, even if you know that it is not true.
24. Have you made love in a forbidden place?
There are people who enjoy practicing sexual activities in different unconventional places (for example, in a forest or in a shopping center). That does not mean that they speak openly about it.
25. Have you ever been unfaithful?
Infidelity is something that many people have been through, either as a person who is a victim or a person who has carried out the infidelity. This is a topic best kept secret.
26. What satisfies you the most?
A question about the most personal preferences.
27. When was the last time you lied?
Lying is socially frowned upon, but incredibly widespread. This question seeks to see to what extent someone is able to admit that they are lying.
28. Have you ever been with someone to forget someone else?
The love of others can be used unconsciously to supply deficiencies.
29. Do you have any suitors right now?
A question as direct as it is uncomfortable.
30. Have you ever argued with a friend's partner?
When friends start dating someone, conflicts can sometimes arise.
31. Have you ever played with someone's feelings?
There are times when manipulation can appear spontaneously, almost automatically.
32. You feel lonely?
These types of confidences are often painful.
33. What's the most extravagant thing you've ever done?
There are times that what says the most about oneself are those actions that oneself consider not very representative of what one is really like.
34. Do you usually approach people you like, or can you shy away from it?
This awkward question is about the seduction techniques used by someone (or the absence of them).
35. How long was the shortest love affair you've ever had?
Sometimes reminiscing about short relationships can make us wonder if we made mistakes that we had not made.
36. Have you ever thought about having something with the mother of a friend?
Sometimes this question is a taboo that very few will be able to confess. Because, let's face it, there are the most attractive mothers (and the most attractive fathers).
37. Would you have an affinity with one of your cousins?
Another taboo but one that is very common: having a relationship with someone with whom you share many genes.
38. Have you had an intimate encounter with someone you met earlier that day?
In the days of Tinder, it is difficult for anyone to deny that this has happened to them on at least one occasion.
39. Would you leave your current partner if you won a million dollars in return?
The old dilemma between love and money.
40. Have you ever met someone to whom you would forgive all the failures?
The typical case of unconditional love.
41. How much money do you earn?
An opportunity to inquire about that person's salary.
42. How much money do you have saved in the bank?
To know the heritage of your friend. In some cases, you may be surprised if any of them have received a significant inheritance or have high incomes that you did not know about.
43. Do you think you can travel in time?
One of those scientific questions that can spark exciting debates.
44. Have you ever been detained or in the dungeon?
More people than you think have had some kind of legal problem.
45. Did you sleep with a stuffed animal when you were little?
A tender moment to remember childhood (and not so childhood) and the animals that accompanied us at night.
46. What 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 the line of the previous one: to know the ideas and the scale of values of your friend.
48. Have you ever had a car accident?
Who else who less has had a mishap at the wheel.
49. Have you ever dressed in your partner's clothes?
We have all probably done it at some point, not even like makeshift pajamas.
50. What's the most ridiculous costume you've ever worn?
Laughter moment guaranteed.
51. Have you ever thought about getting a tattoo?
Surely we have all thought about it at some time. Time to ask what design would be chosen.
52. Would you tattoo your partner's name?
It is surely the worst decision in the world, but there are people for everything.
53. What is the time when you have felt the most physical pain in your life?
Falls, dumb bumps, fractures... sure many anecdotes appear in the conversation.
54. With which artist would you want to spend a crazy night?
With this uncomfortable question we can evaluate 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 one.
56. What frustrated you not being able to tell the last person that I let you down?
Raising this topic of conversation can be uncomfortable for those who have not yet overcome the end of a relationship or friendship.
57. If you had to hide one of the parts of your body that you normally show publicly, what would it be?
This question serves to express insecurities.
58. Have you ever discriminated against someone?
Prejudices and stereotypes they are capable of making us treat others differently only because of their superficial aspects.
59. What physical characteristic would make you not date a person?
Another question related to personal preferences. Of course, many people could answer no.
60. Have you ever suppressed the urge to steal something?
Conduct against private property can lead to impulses that are ashamed to recognize.
61. How many days in a row have you gotten to be sleeping with someone different every day?
A question that many will not want to answer.
62. Would you do a striptease?
About the ability to expose yourself to others.
63. Can you let me see the history of your smartphone browser?
Giving in on a privacy issue like this isn't easy.
64. Would you like to try BDSM?
An opportunity to talk about topics that produce curiosity in the sexual sphere.
65. Have you ever fallen in love with a friend's partner?
These events can generate conflict situations, for what many prefer to hide.
66... And of a relative?
A variation on the previous question, which can be even more uncomfortable.
67. Do you think I'm in good shape?
Answering this question can create sexual tension.
68. Have you ever regretted sleeping with someone?
One-night stands can lead to regret.
69. In what ways do you think you are better than others?
Some people have a hard time recognizing their strengths.
70. What situations make you want to misbehave?
Another awkward question they talk about the moral limits.
71. What is the first thing you thought when you saw me?
About the sensations that appeared with the first eye contact.
72. What is the first thing you thought when you met me?
A version of the previous question, based more on personality.
73. Have you ever been with a partner who was much taller or much shorter than you?
Curiosities that can turn out to be aesthetically funny.
74. What do you think about the Islamic veil?
A controversial topic that can lead to long conversations.
75. Are you happy with your sex life?
The answer to this can be very revealing.
76. Do you have any debt to someone?
It can be financial or symbolic debts.
77. What is the last thing you googled?
These searches can be somewhat embarrassing.
78. What is your favorite youtuber?
Sometimes it can happen that the YouTube channel in question does not have a good reputation.
79. Why do you think there is poverty?
These complicated questions lead to many gaffes.
80. Have you had a job that you deeply hated?
Parts of our CV that we would rather forget ...
81. Which singer are you ashamed to admit that you like?
About unspeakable tastes.
82. Is there a secret word that you only use with your friends?
Sometimes jargon used with friends and private humor they can be a bit ridiculous.
83. How was your worst sexual experience?
Events that can be remembered with shame or humor.
84. Have you ever been hooked on some really bad TV series?
Another of the uncomfortable questions that refer to cultural tastes.
85. What do you think your IQ is regardless of what the tests say?
Intelligence is often a controversial topic.
86. Have you ever watched adult content movies with your family in another room?
Actions considered risky in most homes.
87. What do you think of capitalism?
Another question that can bring up controversial opinions.
88. How many years of nonstop work do you think it would take to get rich?
If that was our absolute priority... How long would it take to get it?
89. With what person would you not dare to debate politics?
An uncomfortable question that leads to admitting one's 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.
91. How many people do you think hate you in the world?
About old conflicts and enmities.
92. Is there anyone who thinks you are very unintelligent?
One way to inquire about the unfavorable image that has been given to other people.
93. What line would you ever cross to conquer someone?
About the limits of seduction.
94. Have you ever been up very late at night playing a video game?
Gaming moments that engage so much that they rob us of well-being.
95. Have you ever traveled to another province just to have sex?
Some might consider it too much hassle just for that reward alone.
96. And to another country?
Variation of the previous one, even more extreme.
97. In what things do you think others admire you?
An occasion to put modesty aside.
98. Have you ever regretted not insulting someone?
Another awkward question about old regrets.
99. Do you give importance to the money of your potential partners?
About the shallowest side of each one.
100. How long would you be without getting out of bed if they paid you a dollar for every minute?
A curious thought experiment.
101. Is there an athlete you would give your all to get through one night?
The world of sport has a special appeal ...
102. Have you done anything illegal so far this year?
Even if it is just looking at the phone when we are driving, it is likely that some law or another we have broken.
103. Have you ever dropped a drink on the floor in a restaurant or nightclub?
That bad drink is quite common.
104. What is the skill that you would like to possess with all your might but that you could never 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 one in particular.
106. Have you ever felt lonely despite having people around?
A very common feeling. Even in the most populated cities we can feel abandoned.
107. Have you ever written a poem to someone you loved?
With this uncomfortable question you can evaluate the romanticism of your friends or your partner.
108. Have you ever caused any damage to the public highway?
Willingly or not, we may have caused some damage.
109. Are you one of those people who can only go to the bathroom at home?
There are many people who literally cannot make larger waters in public baths.
110. What would you do to protect yourself from a zombie invasion?
Many movies and series help us to imagine what strategies we would follow to maintain life.
111. Do you consider that your pet is "one of the family"?
Some animals have an almost human status.
112. Do you like pizza with pineapple?
With equal parts lovers and detractors, it is one of the pizzas that generates the most controversy due to the extreme mixture of flavors.
113. Have you ever tried snails?
Quite popular food in Catalonia, not everyone dares to put a small snail in their mouths.
114. What would you do if you won the lottery tomorrow?
We can inquire: what would be the first purchase, what would be the most expensive, etc.
115. When you are sad, do you play sad music?
It seems counterproductive, but for some people it helps them get through bad times.
116. Have you fantasized about having a crazy night with someone over 50?
A fantasy that few people admit to having had.
117. Do you have any prejudice about the people of any region of your country?
Almost all of us, whether we want to admit it or not, pull on clichés.
118. What's the ugliest gift you've ever received?
It is quite common to have to put a good face on a hideously ugly or useless gift.
119. Have you ever been doing a college job and lost everything and had to start from scratch?
A catastrophe that has happened to almost all of us.
120. What is the time that you have made a fool of yourself the most?
The perception of ridicule is very subjective, and there are people who do not even know what that is.
121. What quality of mine do you value the most?
Time to raise the tension and move to a more intimate or romantic atmosphere.
122. What is the part of your body that you like the least?
This way you can assess whether the person in front of you feels self-conscious about some physical feature.
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 suits our personality.
124. Of your group of friends, who is the most (or the most) irresponsible?
To take out the dirty laundry.
125. Who is the person you need the most in your life right now?
To make way for a more sentimental conversation.
126. Do you think you have macho attitudes?
Almost everyone, at one time or another, can have a discriminatory attitude.
127. What was the last book you read?
Many of your friends won't even remember ...
128. How many hours a day do you spend browsing the internet?
Unfortunately, many people spend long hours just scrolling on Facebook and Instagram.
129. What is the most uncomfortable gift that an old boyfriend / girlfriend has given you?
Gifts are sometimes ridiculous and useless.
130. What's the worst concert you've ever been to?
There is always a show where everything fails or where the group was really horrible.
131. What is the sport that you are worst at?
Most of us have a sport for which we are genuinely denied.
132. Have you ever run out of gas? How did you resolve the situation?
Most of the drivers have had this bad experience on occasion.
133. Do you love your father or mother more?
The classic awkward question. There are people who are clear about their preference, while others prefer not to get wet.
134. Are you ashamed of any musical taste you had as a teenager?
High School Musical, Justin Bieber... that kind of music that we prefer to forget.
135. Have you ever met a famous person? What happened?
Surely we all have a little anecdote when we have met a celebrity.
136. Over the years, have you changed your ideology?
Surely you do not think the same when you are 15 years old than when you are around 30.
137. What is the worst club you've ever been to?
There are absolutely filthy discos and pubs.
138. Have you ever seen a dead person?
It is not very common, but it has happened to quite a few people.
139. If you could choose, where would you go to live?
There are cities and countries to choose from.
140. What is your worst subject in school?
Mathematics, language... Which was the one you always failed?
141. Have you ever fallen down the street?
If there were people watching, the situation was sure to be very uncomfortable.
142. What's the most uncomfortable question you hate being asked?
The "uncomfortable meta-question".
143. Have you ever recycled a gift that was made to you to give it to someone else?
A classic among the stale.
144. Would you rather have half a million euros to spend in 1 day or € 300,000 to spend for a month?
Perhaps being able to think better how to invest the money will make us opt for the second option.
145. If you won the lottery, would you inform your friends?
It is not wise to give voices in that circumstance.
146. Does anyone in your family have a mental disorder?
More serious or less, almost all of us have a family member with difficulties.
147. Have you ever broken a piece of furniture because you were drunk?
Losing your balance and falling onto a table is quite common.
148. What was your favorite comic when you were a child?
Mortadelo, Asterix, TBO, Roofbreaker, Tintin, 13 Rue del Barnacle... What was your favorite?
149. If you could choose one quality among these three, which one would you choose? Be tall, be handsome, or be successful.
Arguing can be a lot of fun.
150. Have you ever eaten something that made you vomit (or almost)?
Surely we have all tried some food that, due to its bad condition or its smell, has caused us to retch.
151. Have you ever slept with someone for a reason other than love or attraction?
Maybe it could be out of grief, money, boredom ...
152. What public figure do you consider an erotic myth?
There is always a presenter that we find extremely attractive.
153. What is more important in your life: your personal life or your professional career?
Although we want to have both aspects of life under control, 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 famous person?
Who else who least has made their first steps in the world of imitation.
155. Finish the sentence: "I couldn't live in a house that didn't have ..."
Perhaps the answers will be in relation to specific characteristics of the house (being bright, central, spacious ...) or in relation to who will inhabit it.
156. Who in your group of friends do you consider to be the least trustworthy?
There is always someone in the gang who is better off having no dealings or business with.
157. How old would you like to live?
Addressing 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 could ever seduce?
Often times, it is difficult to recognize these limitations.
160. What is the talent that frustrates you the most not having?
A very personal question to learn more about that person.
161. What's the grossest thing that ever happened to you?
This question will likely give way to hasty descriptions and summary so as not to give details.
162. How many of your friends would you turn over to the police if you knew they had been committing crimes?
An awkward question about the limits of friendship.
163. Have you ever used drugs just to try to pick someone up?
A question about the irrationality of the consumption of certain substances.
164. Have you ever tried to get better grades by cheating?
Once again, bringing up the subject of breaking the rules, in this case to progress academically.
165. Do you think there are areas of knowledge that you would never be able to learn?
Asking about the limits of the mind.
166. Have you ever been refused 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 flirt?
Lying to try to flirt with someone is foul play, we must be honest with the person we like.
168. What is your definition of "love"?
Love is the great subject that everyone thinks they know a lot about, but when it comes down to it, it's hard to define precisely.
169. Have you found someone having sex?
A very intimate question that can reveal funny anecdotes.
170. Believe in God?
One of the most recurrent questions in the history of humanity, which today continues to inspire conflict.
171. Have you had a partner much older or younger than you?
Asking about people's tastes is usually a topic that can make some people uncomfortable.
172. What is your opinion on euthanasia?
A debate that is also very recurrent in the political landscape of today.
173. Would you like to be a millionaire?
This question may seem simple but has a number of implications to take into account.
174. What opinion do you have about the government?
Questions about politics are usually always the most uncomfortable in a meeting.
175. What do you think about communism?
Political and ideological issues often arouse the low passions of the 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 hang out.
178. What's the worst thing you've ever done to sleep with someone?
Some people use the grossest tricks to get them to sleep with someone.
179. What's the worst insult you've ever given 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, especially in those countries that continue to have a monarchy at the head of state.
182. Up to what age did you wet the bed?
Some children continue to wet the bed until quite late in life.
183. What is your opinion of the police?
A tricky subject, without a doubt, depending on who we ask that question.
184. What do you think of the Jews?
Jews have historically been a persecuted people, and today there is still prejudice against them throughout the world.
185. What do you think of Asians?
A question that can also generate controversy in some situations.
186. If you were to be born again, would you repeat your life in the same way?
Sometimes it is convenient to reconsider what has happened, look back and take stock.
187. If you could choose, in which country would you like to be born?
Depending on what decision we make, hypothetically we would find ourselves in one situation or another.
188. Do you think the poor don't try hard enough?
A controversial approach, which will undoubtedly reflect what kind of person he is, who responds.
189. What do you think of infidelity?
A complicated and subjective subject. Depending on the person, we can have an opinion one way or another.
190. What do you think of marriage?
Such an important institution in our society, such as marriage, must be carefully considered and valued.
191. What do you think of the Church?
Today we can be critical of any nineteenth-century institution, including the Church.
192. What do you think of abortion?
Controversial topic. Recurring debate on civil rights.
193. Do you think all races are equally intelligent?
Racism is something that should not be tolerated in public discussion.
194. What do you think about prostitution?
Another question that opens a controversial debate; that of the abolition or legalization of prostitution.
195. What do you think about life imprisonment?
Some countries have more restrictive criminal laws and others less, the same is also true for some people.
196. What do you think about immigration?
The immigration debate is the order of the day today.
197. Do you think everyone should be able to vote?
A debate that some people have is whether voting should be a privilege for a few or a right for all, as at present.
198. What is your opinion of homosexuals?
Social debate on the rights and freedoms of people who are attracted to the same sex.
199. What do you think of Jeff Bezos?
The opinion we have about the richest people on the planet will also say a lot about us and our way of seeing the world.
200. What is your opinion of identity policies?
A very hot topic today is that of identity politics and its influence on the dominant agenda in Western society.
201. What is the food that you can't even smell?
We all have some gastronomic mania.
202. Would you live isolated in a cabin for 1 month in exchange for € 15,000?
Here we can get to know if he is a person who can survive on his own or if he has a great desire for money.
203. If you could only eat one food for the rest of your life, what would it be?
Although it is a popular food, surely we would end up getting tired quickly.
204. What is the urban legend that you have longest believed to be true?
More than one of us have wanted to deceive ourselves for a long time, until we realized that there was no evidence to support the story in question.
205. What do you think of the new law in Spain that makes it possible for a person to change her sex without having to undergo medical or psychological tests?
A controversial issue that has legal and social implications.
