156 uncomfortable questions (for your friends or your partner)
We all like to ask questions and learn more about other people. You may be curious to find out certain things about some people you know, but when they ask you those questions, out of embarrassment, you prefer to keep the answers to yourself .
These uncomfortable questions can be embarrassing for different reasons: because you consider it a taboo subject, because you regret having done it, because you want to pretend that everything is going great…
A list of uncomfortable questions
Below you can find a list of uncomfortable questions that may make you prefer to avoid answering them.
1. What is the most embarrassing thing your parents have caught you doing?
Our parents have seen us born and raised, 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 cruel or mean to anyone?
Whether it’s good or bad often depends on the situation. When we are put on the ropes we can lose our temper, as well as in times of need. We can also be cruel to someone because of the pain they have made us feel, for example, a former partner. It is impossible to be good to everyone in every situation.
3. Do you have any fears that you haven’t told anyone?
Some individuals may feel anxiety in certain situations . And many of these people have not accepted it, so they do not talk about it 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, rejection often has a strong negative impact. No one likes to feel rejected, let alone talk about it.
5. What is the most bizarre thing you’ve ever done on your own?
When we are alone, we don’t have to show ourselves as people want us to show ourselves, we don’t have to give any image. Maybe in those moments one will relax and even carry out certain ideas that one has in mind and that others will not share.
6. Are there any secrets 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 some embarrassing situation. That’s why sometimes we keep secrets from them, things we wouldn’t 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.
8. Do you consider yourself a happy person?
In the face of others, we all tend to think that everything is always going well for us, that we are strong and that we can bear what they throw at us. Now, it is impossible to be happy all the time.
9. What do you like most about yourself?
In answering these questions you may seem a little conceited, 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 sin of conceit, in this question the opposite occurs. Depending on the answer, it may seem that someone does not value himself enough.
11. If you could erase one negative experience from your life, what would it be?
We’ve all had some negative experience in our lives. The ideal is to accept it and move on, however, there are individuals who still cannot talk openly about these experiences.
12. What’s the craziest thing you’ve ever 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, over time, we find embarrassing .
13. What’s the last lie you told?
It has already been said that we have all lied at some time in our lives, 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 some individuals are very conservative, others are very liberal. It’s not always easy to talk about these issues.
15. What would you change about your life if you could?
It’s possible that there’s something in our lives that we’d like to change. But openly acknowledging it can be difficult, because we like to pretend that we are okay with ourselves.
16. If you could make one wish right now, what would it be?
This question can make you reflect on what you would change about your life and, as stated in the previous question, it is not always easy to expose one’s weaknesses.
17. Would you like to have an intimate experience with someone of your own 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 states 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 turns you on the most?
Not everyone talks freely about what excites them most, because they think 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 to get. It seems that giving in on certain aspects (and even forgiving) is a symptom of weakness. Nothing could be further from the truth, since forgiveness honours you and giving your arm to twist when necessary is a symptom of maturity and emotional intelligence .
20. Have you ever used an object for sexual purposes even though that was not its purpose?
In moments of intimacy, and when you decide to give yourself pleasure, you may have used objects to stimulate yourself. Especially 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 incentive to be prohibitive.
22. Have you ever broken someone’s heart?
It’s not nice to say goodbye to someone who would give his or her life for you, but sometimes you stop feeling for your partner and you have to put some distance between you and them.
23. Will you call me tomorrow?
And of course, in situations like the above, it is not easy to say things to the face, as the other person may feel offended. You will always say yes, even if you know it’s not true.
24. Have you ever 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 mall). This does not mean that they talk about it openly.
25. Have you ever been unfaithful?
Infidelity is something that many people have gone through , either as a victim or as a person who has carried out the infidelity. This is a subject that is best kept secret.
26. What do you find most satisfying?
A question about the more 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 capable of admitting that they are lying.
28. Have you ever been with someone to get over someone else?
The love of others can be used unconsciously to make up for shortcomings.
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, conflicts can sometimes arise.
31. Have you ever played with someone’s feelings?
Sometimes manipulation can occur spontaneously, almost automatically.
32. Are you lonely?
These kinds of confidences are often painful.
33. What’s the most extravagant thing you’ve ever done?
There are times when what says most about oneself are those actions that one considers unrepresentative of how one really is.
34. Do you often approach people you like, or can shyness get in the way?
This awkward question refers to the seduction techniques used by someone (or the absence of them).
35. How long was the shortest love relationship you’ve ever had?
Sometimes, remembering short relationships can make us wonder if we made mistakes we didn’t fall into.
36. Have you ever thought about having a thing with a friend’s mother?
Sometimes this question is a taboo that very few will be able to confess. Because, let’s admit it, there are some very attractive mothers (and very attractive fathers).
37. Would you have an affair with one of your cousins?
Another taboo but very common: having a relationship with someone with whom you share many genes.
38. Have you ever had an intimate encounter with someone you met that day?
In Tinder’s time, it is hard for anyone to deny that this has happened to him at least once.
39. Would you leave your current partner if you earned a million dollars in return?
The old dilemma between love and money.
40. Have you ever known someone who would forgive every failure?
Typical case of unconditional love.
41. How much money do you make?
A chance to ask about that person’s salary.
42. How much money do you have saved in the bank?
To know your friend’s heritage. In some cases, you may be surprised if one of them has received a large inheritance or has a high income that you did not know about.
43. Do you think you can travel in time?
One of those scientific questions that can trigger exciting debates.
44. Have you ever been in detention or 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 little animals that accompanied us at night.
46. Which political party do you vote for?
When you talk about politics, you can open a pandora’s box, so watch out.
47. Are you a feminist?
Along the lines of the previous one: to know your friend’s ideas and scale of values.
48. Have you ever been in a car accident?
Who else has had some mishaps behind the wheel.
49. Have you ever dressed in your partner’s clothes?
We’ve probably all done it at one time or another, not even as impromptu pajamas.
50. What’s the most ridiculous costume you’ve ever worn?
Moment of laughter assured.
51. Have you ever thought about getting a tattoo?
I’m sure we’ve all thought about it at some point. Time to ask which design would be the one.
52. Would you tattoo your partner’s name?
It’s probably the worst decision in the world, but there are people for everything.
53. What is the moment when you have felt the most physical pain in your life?
Falls, dumb hits, fractures… I’m sure many anecdotes come up in conversation.
54. Which artist would you like to spend a crazy night with?
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 one’s moral preferences.
56. What frustrated you that you couldn’t tell the last person that you were disappointed?
Raising this topic of conversation can be uncomfortable for those who have not yet overcome the end of an affective or friendly 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 serves to express insecurities.
58. Have you ever discriminated against anyone?
Prejudices and stereotypes are capable of making us treat others differently just because of their superficial aspects.
59. What physical characteristic would make you not have a date with a person?
Another question related to personal preferences. Of course, many people could answer that none.
60. Have you ever repressed the urge to steal anything?
Conduct against private property can lead to impulses that are embarrassing to recognize .
61. How many days in a row have you been 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 I see your smartphone browser history?
Giving in on a privacy issue like this is not easy.
64. Would you like to try BDSM?
A chance to talk about topics that make you curious about sex.
65. Have you ever fallen in love with a friend’s partner?
These events can generate conflicting situations, because what many prefer to hide .
66… and a relative?
A variation of the previous question, which may be even more uncomfortable.
67. Do I look like 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 uncomfortable question that talks about moral boundaries .
71. What was the first thing you thought when you saw me?
About the sensations that appeared with the first eye contact.
72. What was 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 couple that was much taller or much shorter than you?
Curiosities that can be aesthetically pleasing.
74. What do you think about the Islamic veil?
A controversial subject that can give for long conversations.
75. Are you happy with your sex life?
The answer to this can be very revealing.
76. Do you have any debts to anyone?
These may be financial or symbolic debts.
77. What’s the last thing you googled?
These searches can be somewhat embarrassing.
78. What 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 a lot of blunders.
80. Have you ever had a job that you deeply hated?
Parts of our CV that we’d rather forget…
81. What singer are you ashamed to admit that you like?
About unutterable tastes.
82. Is there a secret word that you only use with your friends?
Sometimes, the jargon used with friends and private humor 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 a really bad TV series?
Another uncomfortable question that refers 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 watched adult movies with your family in another room?
Actions considered risky in most households
87. What do you think of capitalism?
Another question that may bring up controversial opinions .
88. How many years of non-stop work do you think it would take to get rich?
If that were our top priority… how long would it take to get there?
89. With which person would you not dare to discuss politics?
An uncomfortable question that leads to the recognition of one’s own ignorance.
90. Do you think you should be able to vote on anything?
It’s hard to know what the right answer to this is.
91. How many people do you think hate you in the world?
About old conflicts and enmities.
92. Is there anyone who thinks you’re too unintelligent?
A way to find out about the unfavourable 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 stayed up late at night playing a video game?
Playing moments that are so engaging that they rob us of our well-being.
95. Have you ever traveled to another province just to have sex?
Some might consider it too much trouble just for that reward.
96. What about another country?
Variation of the previous one, even more extreme.
97. In what ways do you think others admire you?
An occasion to put aside modesty.
98. Have you ever regretted not insulting someone?
Another of the uncomfortable questions about old regrets .
99. Do you give importance to the money of your potential partners?
About the shallower side of each.
100. How long would you stay in bed if you were paid a dollar a minute?
A curious thought experiment.
101. Is there a sportsman or woman for whom you would give everything to spend a night?
The world of sport has a special appeal…
102. Have you done anything illegal in the last year?
Even if we only look at the phone when we are driving, it is likely that we have broken some law or other.
103. Have you ever dropped a drink on the floor of a restaurant or nightclub?
That bad drink is pretty common.
104. What is the ability that you would like to possess with all your strength but could never develop?
Playing an instrument, learning a particular language…
If you were a dinosaur, which one 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 you?
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 partner.
108. Have you ever caused any damage to the public highway?
Whether 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 can’t make major water in a public toilet.
110. What would you do to protect yourself from a zombie invasion?
Many films and series help us imagine what strategies we would follow to sustain life.
111. Do you consider your pet to be “one of the family”?
Some animals have a quasi-human status.
112. Do you like pineapple pizza?
With lovers and detractors in equal parts, it is one of the most controversial pizzas due to the extreme mix of flavours.
113. Have you ever tried snails?
Food that is quite popular in Catalonia, not everyone dares to put a small snail in their mouth.
114. What would you do if you won the lottery tomorrow?
We can ask: what would be the first purchase, what would be the most expensive, etc.
115. When you’re sad, do you put on sad music?
It seems counterproductive, but for some people it helps them get through the bad times.
116. Have you ever fantasized about having a crazy night with someone over 50?
A fantasy few people admit to having.
117. Do you have any prejudices about people in any region of your country?
Most of us, whether we want to admit it or not, pull out all the stops.
118. What is the ugliest gift you have ever been given?
It is quite common to have to put a good face on a frighteningly ugly or useless gift.
119. Have you ever been doing a college job and lost everything and had to start all over again?
A catastrophe that has happened to almost all of us.
120. What’s the one time you’ve made a bigger fool of yourself?
The perception of ridicule is very subjective, and there are people who don’t even know what that is.
121. What quality of mine do you value most?
Time to raise the tension 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 can assess whether the person in front of you is feeling self-conscious about any physical trait.
123. If you were the head of a multinational company, would you be a strict and demanding boss or more relaxed and friendly?
We can all put ourselves in the shoes of a great manager and assess which leadership style best fits our personality.
124. Of your group of friends, who is the most (or the most) irresponsible?
To get the dirt out.
125. Who is the person you need most in your life right now?
To make way for a more sentimental conversation.
126. Do you think you have sexist attitudes?
Almost everyone, at one time or another, may have some 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 surfing the Internet?
Unfortunately, many people spend long hours simply scrolling on Facebook and Instagram.
129. What is the most uncomfortable gift an old boyfriend/girlfriend has given you?
Sometimes gifts are ridiculous and useless.
130. What’s the worst concert you’ve ever been to?
There’s always a show where everything fails or the group was really horrible.
131. What is the sport that you are worst at?
Almost everyone has a sport for which they are genuinely denied.
132. Have you ever run out of gas? How did you solve the situation?
Most drivers have had this bad experience at one time or another.
133. Do you love your father or mother more?
The classic awkward question. Some people have a clear preference, while others prefer not to get wet.
134. Are you ashamed of any musical tastes you had as a teenager?
High School Musical, Justin Bieber… that kind of music we’d rather forget.
135. Have you ever met a celebrity? What happened?
I’m sure we all have a little story when we’ve coincided with a celebrity.
136. Over the years, have you changed your ideology?
You probably don’t think the same when you’re 15 as when you’re in your 30s.
137. What’s the worst joint you’ve ever been to?
There are absolutely filthy clubs and pubs.
138. Have you ever seen a dead person?
It’s not very common, but it’s 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 was the worst subject you were taught in school?
Math, language… what 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 is the uncomfortable question that you most detest being asked?
The “awkward meta-question.”
143. Have you ever recycled a gift that was given to you to give to someone else?
A classic among the rancid.
144. Would you rather have half a million euros to spend in 1 day or 300,000 euros to spend for a month?
Perhaps being able to think better about 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 at all wise to give voice in that circumstance.
146. Does anyone in your family have a mental disorder?
More or less, almost all of us have a family member in difficulty.
147. Have you ever broken any furniture because you were drunk?
Losing your balance and falling on a table is quite common.
148. What was your favorite comic book as a child?
Mortadelo, Asterix, TBO, Roofbreaker, Tintin, 13 Rue del Percebe… which one was your favourite?
149. If you could choose one quality out of these three, which one would you take? To be tall, to be handsome or to 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 tasted some food that, because of its bad condition or its smell, has made us retch.
151. Have you ever slept with someone for a reason other than love or attraction?
Maybe it could have been pity, money, boredom…
152. Which public figure do you consider an erotic myth?
There is always some presenter that we consider extremely attractive.
153. Which is more important in your life: your personal life or your professional career?
Even if we want to have both aspects of life under control, there is always a 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 has done the least in the world of imitation.
155. Finish the sentence: “I could not live in a house that did not have…”
Perhaps the answers will be in relation to specific characteristics of the house (being bright, central, spacious…) or in relation to who will live in it.
156. Who in your group of friends do you consider to be less reliable?
There’s always someone in the gang it’s better not to have deals or business with.