300 Uncomfortable Questions For Your Friends And Partner

Sometimes, to get to know your friends and partner better, you have to break the ice and ask some uncomfortable questions. Do you dare to make the conversation interesting?

You cannot deny that you would like to know everything about your friends and partner. After all, they are the people with whom you usually share time, moments and intimate things that you would not reveal to anyone else. Of course, to get to a good level of trust, sometimes you need to ask some uncomfortable questions. You dare?

In those moments in which conversations do not flow spontaneously, nothing better than breaking the ice and starting to investigate topics that are usually taboo or that are avoided for one reason or another. This allows you to learn more about the personality of the other and, by the way, it can become a good exercise in self-knowledge.

Awkward questions to gain confidence or to play

The idea of ​​asking uncomfortable questions is not to meddle in the life of the other, far from it. Its objective is that you can create an environment of trust , with the people with whom you usually share.

There are awkward questions of all sorts, as we’ll see later, to ask your friends (or have them ask you). In meetings, these questions can be used to play games of the truth or dare type and other similar ones.

You can even take the opportunity to answer them and get to know yourself better . Of course, we have the right not to answer some. Here we have a few for you. Begin!

Askward and interesting questions

1. Do you have a fear that you haven’t told anyone about?

Most people avoid exposing their fears so as not to appear vulnerable. However, gaining confidence, perhaps they can speak it naturally. Of course, try to be respectful when listening and only give your opinion if you have something good to contribute.

2. What has been your most embarrassing experience?

Inquiring about embarrassing experiences can cause discomfort in the first instance. However, as it is talked about, it will surely become a fun anecdote or one to reflect on.

3. What qualities do you think you have?

Talking about one can be quite complex. Sometimes there is a clear answer, but other times doubt appears. But, as the philosophers say, knowledge begins there, by knowing oneself .

4. What are your worst flaws?

There is no denying it; flaws are unpleasant and can cause discomfort in others. For this reason, it is not easy to talk about it and, in fact, many of us find self-acceptance difficult.

5. Do you consider yourself a happy person?

You can perceive that your friends or your partner are happy just because you see them smiling most of the time or because they have positive attitudes. However, sometimes this can be an appearance. Dare to listen to his answer and be careful with your opinion.

6. If you could erase any negative experience from your life, what would it be?

It is normal to go through negative experiences; this is part of life. Still, almost everyone has that moment that they wish they could erase and never remember again. Reasons? There’s a lot. Try to speak openly to find out.

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

Among the things that many tend to keep quiet about is what they would change if they had the chance. Even, it may not be one, but several things. The difficult thing is to admit it openly, since there is this tendency to “pretend that everything is fine”.

8. Have you ever been cruel to someone?

To act in a good way or not depends on the situation. Even if the person has hundreds of qualities that stand out, surely at some point they were cruel to someone. For example, with an ex-partner, a rival, or even someone close.

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

Throughout life, there are moments in which actions are taken that do not always match the personality or that are out of the ordinary. This can be remembered with shame or as an amusing anecdote.

10. Have you ever stolen anything?

The answers to this question can be quite funny, depending on the context behind the theft. Still, it can put the person in an awkward position.

11. What disgusts you the most?

Although it may seem hard to believe, many people experience disgust for things that may be common to you. You will be surprised by the answers!

12. When was the last time you were rude and why?

There are experiences that take a person to the limit of patience. Right there appears that rude personality that does not measure his comments. Sometimes it is justified, but other times not so much.

13. Do you have any security problem?

If something is difficult to answer, it is this question. Talking about insecurities is not easy, since it shows that vulnerable side that is often difficult to manage. It can be speaking in public, seeking approval from others, showing a talent for not considering it so good… there are many questions about it.

14. What part of your physical appearance do you not like?

Linked to the previous question, this question reveals an insecurity that everyone generally has. Body weight, acne, height… there are many answers. In the same way, possibly there are also reasons that explain it.

15. What has been your biggest failure?

Talking about triumphs is easy and causes well-being. The opposite occurs with failures. It is uncomfortable and can bring up some insecurities. It is important to speak carefully.

16. What is the biggest lie you have ever told?

There is no denying it; all people tell lies. Some are pious and others are not so much. What has been the worst? Why did you say it? Surely nothing will happen for the fact of remembering it.

17. What has been the time you have made a fool of yourself the most?

Many things can lead a person to make a fool of himself. Whether on purpose or not, surely there is a long story behind it.

18. What things do you think others admire you for?

Time to put modesty aside! Here it is not worth an “I do not know” for an answer. Surely that person is clear about those things that make him stand out from everyone.

19. What’s the worst thing you’ve done while drunk?

Going for drinks one night is normal. However, most of the time this entails doing crazy things that would not be done while sober, even incurring in risky situations due to excessive alcohol consumption.

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

There are many ways to break the law, even if it is not something serious. Looking at your mobile while driving, running a red light, etc.

21. What attitudes offend you from others, but you don’t say it?

For not having a moment of confrontation, or for fear of not being accepted, there are those who put up with attitudes from others that do not go with their way of being or thinking.

22. Have you ever betrayed someone?

There are various causes of infidelity , according to studies on the subject. Immaturity, circumstances, desire and others. Still, accepting it becomes quite uncomfortable.

23. Who do you miss from your past?

Perhaps, for many, it does not fit into the concept of uncomfortable questions. Even so, it is still a sensitive subject that arouses curiosity. Bringing that person back to the present can be accompanied by feelings of nostalgia, joy, and many other mixed emotions.

24. What do you think of feminism?

Feminism is now one of the most contentious issues in society. For many it is not something to discuss, but a conviction. Meanwhile, others are more flexible to define it, debate it and present their opinion on it. You can have an interesting conversation if you know how to intervene respectfully.

25. What’s the weirdest thing you usually do when you’re alone?

Those moments of solitude are quite intimate for everyone. In general, they tend to take advantage to do things that would not be done in front of others. Many will say that dancing, others that writing, or perhaps investigating the social networks of their ex-partners… there are many answers.

26. In what area do you consider yourself lacking skills?

Each person stands out for having skills in various subjects. Still, there are areas where there is no talent at all. It may be that he never learned to dance, that he has trouble solving math problems, or that he couldn’t learn to drive.

27. According to you, what do you need to experience?

Getting to know another country, bungee jumping,  parachuting… there are many experiences that many want to experience at some point in their lives. Digging into these topics can help you discover what those close to you are passionate about.

28. When was the last time you felt envy and why?

As much as you try to avoid, envy is part of the feelings of all people. It is normal to experience it, but sometimes it is difficult to accept it.

29. How do you see yourself in 10 years?

Projection into the future can be difficult for some. There are those who prefer to live in the present and wait for everything to flow. In any case, seeing yourself in 10 or 15 years is an exercise that can help you take relevant steps.

30. Do you like your job?

There is no denying that, of all the questions, this is one of the most uncomfortable. The workplace plays an important role in everyone’s physical and mental well-being. Therefore, recognizing that this does not cause happiness is frustrating for many.

31. Do you have any kind of debt to settle (personal, emotional, financial)?

Nobody wants to talk about their debts; that’s clear. Whether personal, emotional or economic, it is a subject that is not entirely pleasant. But now that you have gained confidence, do you dare to investigate?

32. Do you consider yourself a spiritual person?

Spirituality can have many definitions, depending on the convictions of the person. Many, in fact, prefer to reserve it as something intimate. Perhaps you need to know more about this facet from your family, friends or partner. Try to treat the subject with respect.

33. Do you consider yourself a free person or is there something that limits or conditions you?

There are those who repress what they want to be or what they like because they are conditioned by their family, society, the media or their own social circle. If you ask that person if he really feels free, you will surely have a good debate.

34. Would you welcome an emigrant or refugee from another country into your home?

There are many possible answers and arguments to this question. In any case, although it may be uncomfortable, it is good to reflect on these current issues.

35. Do you believe in revenge?

While some people completely disapprove of revenge, others strongly believe in “an eye for an eye.” What side are you on?

36. If your life were a book, what title would it have?

The name that the person tells you can summarize their personality or part of their experiences. Perhaps you take it as if it were a comedy, or you prefer the tragic.

37. What is beyond death according to you?

Beyond being one of the uncomfortable questions, this topic is an opportunity to debate various points of view. It is evident that everyone has their own beliefs about what happens after death.

38. How would you like your funeral to be?

Anything related to death may not be so nice to talk about. Still, being confident, why not find out what that person wants their funeral to be like. The rituals could be interesting, depending on your beliefs.

39. Do you think we are alone in the universe?

A question that we not only ask ourselves when we look at the stars at night, but that many philosophers or thinkers, even scientists, have also asked. What do you think? Will we be alone or from some corner of the galaxy an alien civilization watches us ?

awkward and funny questions

40. Do you think that others think you are boring?

We often think that we are very smart and interesting. But what if we’re not? What if others consider us boring but don’t tell us? Have you ever wondered?

41. What is your weirdest hobby?

When it comes to others, we tend to judge their strange behavior more harshly. However, we always know that we have strange habits, although we do not recognize it . Which are yours?

42. What is your favorite tune to sing in the shower?

In the shower, we sing because we are happy or because we like to bathe, or because we are alone and we believe that no one is listening to us . What is the song that you remember the most at that moment? Do you have a favorite to sing?

43. A bad movie that you like?

There are movies that everyone criticizes, that those who know the subject say are rubbish. However, maybe you saw it and thought it was good. Tell us, what was it and why did you like it?

44. What is the strangest thing you have searched on Google?

Sometimes a strange idea crosses our minds . For example, you read that during the Black Death people drank cat urine. Then, you write in the search engine: what does cat urine taste like? Have you done something like that?

45. What do you think about when you are in the bathroom?

The bathroom can also be a place to meditate or philosophize , while we do our needs. And you, apart from looking at the tiles, what do you think about when you’re there?

46. ​​Do you sleep with your mouth open?

Everyone has their way of sleeping. Some do it with their mouths open, and even drool on the pillow. Are you one of those people? Or are you rather one of those who snore loudly? Tell us.

47. If you were in fight club, who would you get into a fight with?

Do you have a pending account with someone from the past and you would like to settle it like in the old days of the West, not with shots but with fists; Or you would just like to hit each other for fun. Who would you choose? Someone famous? Any relative or friend?

48. What is the strangest place you have had to use as a bathroom?

When the need arises, there is no choice but to obey the call of nature . Sometimes it’s behind a tree, in an abandoned house, any place hidden from view can work. Which has been yours?

49. How long have you gone without bathing?

This topic is currently being discussed: bathing every day with soap and water is not only unnecessary, but it can affect the skin, causing greater dryness in people with xerosis. There are cultures in which, due to some tradition, they must go up to 15 days without bathing. What has been your maximum?

50. Did you get head lice when you were at school?

Head lice can become an epidemic at school , with an incidence of more than 25%, according to studies . Have you ever had lice? Or do you still have them?

51. Have you worn underwear that has holes?

Either because you did not have a cleaner one, because you did not realize it at the moment, or it is your favorite garment, have you ever had to wear panties with holes . Has it happened to you?

52. What is the strangest thing you have ever eaten?

Out of curiosity or by chance, everyone has tried foods that are truly unpleasant. Although the story can even end in anecdotes of food poisoning or vomiting.

53. Something that smells bad but still pleases you?

There are bad odors and bad smells. Some we dislike but others attract us, despite how disgusting , and we bring our nose closer to perceive them. Has it happened to you?

Awkward questions about love and relationship

54. Have you fallen in love with several people at the same time?

There are those who think that it is not possible to fall in love with several people at the same time ; but others think otherwise. What do you say? what is your experience with that?

55. Do you find someone of the same sex attractive?

Regardless of our orientation, we may find a person of the same sex attractive or pretty . An athlete, an actor, actress or singer, or maybe someone you know or are closer to. Tell us.

56. Something that would never fail to seduce you?

We all have our weak point, something like the Achilles heel, before which we lower our guard. If they tell us, we would definitely be at the other person’s feet. What is that phrase or action for you?

57. Is there something you would say no to the love of your life, even if he asked you on his knees?

And so, too, there is something that we would not do for the world , not even for money, not even if the person we adore the most in this life asked us to. What is that point of honor for you, before which you would not give in?

58. If polygamy were allowed, who would be your second partner?

Polygamy is allowed in some countries and cultures, for example among Muslims. Although not in Western civilization, where it is penalized. Now, if that were the case and they allowed it, and you already had a partner, who would you choose for a second marriage?

59. If you went to a dating site, who would you allow your partner to be with?

Some people have fantasies of seeing their partner with another person. And there are even spaces where you can have this type of experience. If you had to do a swap, who would you want your partner to be with?

60. What is the couple that has made you cry the most?

At least once or twice in life, maybe more, we are going to meet someone who makes us cry . Because he doesn’t love us, because he doesn’t treat us well, because he leaves us and goes off with someone else. Tell us, who made you cry?

61. And who did you make cry?

But, we will also have to be on the other side ; and willingly or unintentionally, we will make someone who falls in love suffer and who will cry silently or openly for us.

62. Have you ever hung out with someone for convenience?

Circumstances can provoke behaviors that are not entirely admirable. Therefore, it can be difficult to give an answer to this question. Still, most people have. For example, faking a friendship for academic benefit or being in a romantic relationship for financial gain.

63. What is the worst thing you have done for love?

Undoubtedly, questions related to the sentimental field are somewhat uncomfortable. Despite this, it makes the conversation more interesting. How about you start with this question?

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

Love experiences are not always as desired. Almost everyone has experienced some form of rejection at some point in their lives.

65. Would you have an open relationship?

If you want to dare a little more, this will be an awkward question, but an interesting one. Open relationships or polyamory are becoming more normal in society.

66. Have you ever broken someone’s heart?

Perhaps your friends or your partner once broke the heart of someone who gave everything for them. It is normal. After all, love is not always reciprocated.

67. Have you ever said “I love you” without really meaning it?

You have to be honest. The truth is that most people have said “I love you” or “I love you” without it being true. Revealing this can be difficult, as it is hard to accept the fact that you have faked feelings.

68. Have you ever been stood up?

Nothing sadder than waiting for an appointment with a special person and that it does not arrive. Talking about it may not be so comfortable, but surely you agree with one of these anecdotes.

69. Have you ever been unfaithful?

Infidelity is difficult to accept, especially in the midst of a new romantic relationship. Still, it’s worth digging a little deeper into what this experience was like and whether it had any repercussions.

70. Have you ever been with someone to forget another person?

That “one nail drives another nail” is not always true. You will realize that many have made the mistake of getting involved with someone just to fill the gaps left by another person.

71. Do you have a suitor right now?

Often, people prefer to keep their suitors’ information private. Do you dare to ask this uncomfortable question? Perhaps in the middle of the trivia game your friend will reveal the information to you.

72. Do you usually approach the people you like, or are you overcome by shyness?

There are almost always two types of people. The one who manages to approach who she likes through seduction techniques and the one who prefers to keep quiet and wait to see if it happens.

73. How long was the shortest love relationship you’ve ever had?

You don’t have to lie. Almost everyone at some point has had a love relationship of just a few days. Well, remembering this can become a moment to reflect on the mistakes made.

74. Have you ever thought about having something with a friend’s mother?

These very personal questions are quite uncomfortable. In fact, it is difficult for someone to confess. Still, it must be admitted that there are quite attractive mothers or fathers.

75. What do you not tolerate in a relationship?

This question can lead to an interesting debate. Some will say that lies, others that rude behavior or, perhaps, betrayal. There are many possible answers and a long conversation around this.

76. Would you have a relationship with someone of the same sex?

This topic is taboo for almost everyone. Therefore, it is one of the most uncomfortable questions you can ask. Even so, it may surprise you that many already speak openly about the subject and are not afraid when it comes to giving their answer.

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

Answering this question is not easy at all. Loyalty to friends is generally considered to be above all else. Even so, there are many cases in which this situation occurs.

78. With which actor or actress would you like to spend a night?

It is impossible to deny it. There is always an actor, actress, singer, athlete or famous person who is part of everyone’s fantasies. What’s yours? Or are there several?

79. Would you tattoo your partner’s name?

This action has become something normal among many couples. Still, it’s clear that it’s not always the best decision. Therefore, you will like to hear your friend’s answer.

80. What is the first thing you notice when you have a date with someone?

Whether it is a physical, psychological or emotional characteristic, there is always something that is attractive during the first date.

81. What line would you never cross to conquer someone?

There are many seduction techniques to conquer a person. There are those who affirm that they would do “even the impossible”. However, many do have a limit.

82. Do you give importance to the money of your potential partners?

Many will say that money is not important when there is love. Others may answer that it is very necessary. Either way, it is a topic that can be controversial.

83. What is the most uncomfortable gift an ex-partner has given you?

There are many anecdotes to tell about gifts from ex-partners. Stuffed animals, flowers, clothing, underwear… the answers are varied, as are the reasons why they are considered uncomfortable.

84. What were you ashamed of your ex and never told him?

I’m sure you’ll have fun with the answers! In sentimental relationships there are always things that are hidden so as not to make the other feel bad, or for fear of their reaction.

85. Have you ever used drugs just to try to flirt with someone?

Wanting to make a good impression on another can lead to behaviors that are not always part of the personality, such as drug use.

86. Would you trade your partner for a million euros?

If the couple in question is present at this interrogation, this will be one of the most uncomfortable questions. In the event that the person does not have a partner, the protagonist of the question can be changed with a friend or with the parents, for example.

87. What has been your worst date?

Dating isn’t always perfect. In fact, sometimes they turn out worse than expected. Inappropriate conduct, an accident with food or clothing, outings in which the guest ends up paying the bills… in short, varied experiences that are remembered with grace.

88. If you suddenly impregnated someone and you don’t consider yourself ready to be a father, what would you do?

Here you can discuss one of the most controversial issues today: abortion. Is it within the possibilities? Listen and discuss the answer.

89. Do you usually flirt even if you have a partner?

Nowadays, social networks facilitate communication and flirting. There are even those who flirt with others in person. Does your friend or relative do it even if they have a partner?

90. Who is the person you most regret having kissed?

For many reasons, one can regret a kiss. The person was a bad kisser, it was in an inappropriate circumstance, it involved hurting someone… find out what happened after that repentance.

91. What would you do if you caught your partner being unfaithful?

Imagining this situation can cause many conflicting emotions. In this sense, there are various possible reactions to infidelity . Some will say they would react violently, while others may plan revenge or take it easy.

92. Do you observe yourself?

Do you like to look at yourself naked in front of the mirror and observe your private parts? Have you taken photos like this and then look at them?

93. Have you ever gotten married or thought about getting married in a crazy moment?

Getting married implies a great commitment to the couple. Even so, in moments of madness, there are those who make the decision and simply do it without thinking about all that it implies.

94. What is the most embarrassing thing you have done in front of someone you like?

Sometimes, for show or by accident, embarrassing situations occur in front of the person you are flirting with. How was this experience? Don’t miss a single detail!

95. If your date was a disaster, how would you get away from it?

Expectations with a person can end during a date. Do not stop asking how that person would act if she wants to escape so as not to continue with that uncomfortable experience.

96. Have you declared to someone who did not reciprocate?

Many tend to repress that bitter moment when someone has broken their hearts or illusions. Even this topic can be somewhat sensitive.

97. Have you ever been attracted to someone much older than you?

There is no defined age to be attracted to another person. However, some will feel uncomfortable or modest when accepting that they like someone who is even twice their age.

98. Have you ever fallen in love with a person and later regretted it?

Sometimes, with the desire to have a relationship, a real conquest is made. But after a few days, regret comes for not being what you really wanted.

99. What physical characteristic would make you not date a person?

There is no denying that physical appearance has a lot to do with wanting to date someone. Although for many it is something superficial, it depends on personal preferences.

100. Has it crossed your mind to get back together with your ex?

Perhaps they will answer you with a resounding “no”, since there are relationships with quite toxic stories. Even so, there will be those who do consider it as a possibility.

101. Do you think relationships should be nice and romantic or intense and passionate?

Everyone has their preferences: romance, sweetness, passion, wild sex. Many will say that a little is better of all.

102. Have you kissed someone with bad breath?

An experience that is never forgotten is that unpleasant moment when you shared a kiss with a person who had bad breath. It will surely please you.

103. Who is the platonic love that you are most embarrassed to admit?

Platonic loves can be famous people or close friends. But some are embarrassed to admit, since others do not like them, they are involved in controversies or their physical appearance is not so socially accepted.

104. What do you do if you find out you don’t have the money to pay on a date?

This situation would be very embarrassing. How would your friends act? What possibilities do you consider to get out well? You will certainly have fun with the answers.

105. Have you ever sneaked out of school to see your boyfriend or girlfriend?

The follies of adolescence are impossible to forget. One of them is having run away from school to have a date or to spend time with the couple of that time.

106. Would you beg someone for love?

Emotional dependence can lead to these types of situations. Do you agree? Is it worth begging another for love? This can become one of the most uncomfortable questions, depending on the sentimental situation that the other is going through.

107. Have you ever fallen in love with a teacher?

The platonic love of many was their teacher or teacher, from high school or university. There are even those who went a step further and managed to have some kind of bond.

108. Do you still have contact with your first love?

In general, almost everyone loses a bond with the first person they fell in love with. However, some retain a friendly relationship.

109. When do you think a person is ready for marriage?

The questions associated with marriage and life as a couple are very uncomfortable for many. Sometimes this is not even in your plans. On the contrary, there are those who believe that it should be at an early age. Opinions will always be divided.

110. Have you faked being sick to avoid dating someone?

We know that calling off a date with someone is not always easy. Surely if you ask your relatives, more than one has invented being sick so as not to meet others.

111. How to ruin a date with three words?

The answer varies according to the expectations of the person. What words do you choose?

112. What has been your worst jealous attack?

Questions about jealousy episodes are pretty awkward. And it is that most people have experienced moments of jealousy that completely change the way they are. In fact, remembering it may be cause for embarrassment.

Awkward questions about sex

113. What is the part of the body that you look at the most in a person?

Whether we are with or without clothes, there is a part of the body of people that tends to attract more attention . The breasts, the butt. Although it does not have to be a part related to sex, it can also be the hair. What attracts you?

114. Have you had fantasies with animated characters?

There are cartoons that have very good proportions. How to forget He-man, some Evangelion characters, or Jill, the protagonist of Resident Evil . Have you ever been drawn to a comic book character to the point of fantasizing?

115. What do you like to be told when you make love?

There are words that can help to ignite more passion. Some can be compliments related to our ability, cute and sweet things, declarations of love, or even swear words.

116. Do you scream, moan, whisper or do it in silence?

It may be difficult to remain silent at such times, especially when we climax. But, not all of us produce the same sounds during sex . Some scream, others moan. To which group do you belong?

117. For a threesome, would you choose someone of the same sex or the opposite sex?

An uncomfortable question and often difficult to answer. Do you prefer someone of the same sex? Who would you choose? Have you ever asked your partner, to see what he thinks?

118. Do you like foreplay or do you prefer to get straight to the point?

Although it is said that previous games and caresses stimulate, and can make women lubricate better or have a better quality of erection, not everyone is so enthusiastic about this idea and they prefer to do it and that’s it . What do you prefer?

119. Have you had strange thoughts while making love?

With the phrase strange thoughts we refer to ideas that have nothing to do with the subject or that are irrelevant . For example, suddenly remembering that we have to change the oil in the car’s engine.

120. How important is intimacy in a romantic relationship to you?

Being intimate is relevant in all relationships. Even so, for many the importance is exaggerated or, on the contrary, it is in the background.

121. Have you been able to satisfy your most bizarre sexual fantasy? Which was?

Sexual fantasies are quite diverse and interesting. Even for many they are taboo. Therefore, they should not be missing from your game of uncomfortable questions.

122. Do you have sexual fetishes?

There are different types of sexual fetishes , they can be objects or parts of the body : lingerie, leather boots, shoes, feet… And you, do you have any in particular?

123. How many people have you slept with?

These intimate questions are always uncomfortable. Still, they lead to topics that often turn into entertaining conversations.

124. What is your limit in intimate relationships?

Just as there are limits to romantic relationships, there are also limits when it comes to having sex. Not everyone has the same preferences. So while some enjoy being very liberal, others prefer to be traditional. It is not always comfortable to talk about it.

125. What turns you on the most?

Anything associated with sex is still taboo for many. This being the case, it will not always be easy to talk about what turns you on the most in bed.

126. Have you used any object as a sex toy?

In the moments in which one decides to give pleasure, the imagination flies. For this reason, many everyday objects end up becoming sex toys.

127. Have you made love in a forbidden place?

Sex in forbidden places causes adrenaline. For many it is one of the most pleasant experiences. Even so, there are those who prefer to silence them out of modesty.

128. Have you had an intimate encounter with someone you met that same day?

Having sex on the first date is for many something controversial. Despite this, with applications like Tinder it is becoming more common. You’ve done it? What did they answer you?

129. Would you do a striptease ?

In private there are many ways to get out of the routine; one of them is the striptease. Not everyone is willing to do it.

130. Would you like to try BDSM?

In case you didn’t know, BDSM stands for “Bondage, Discipline, Dominance and Submission, and Sadism and Masochism.” It is a sexual practice desired by many and controversial for others. What do your friends or your partner think?

131. Have you regretted sleeping with someone?

The reasons for this regret can be many: a bad experience in bed, having agreed to meet because of a simple outburst or because of infidelity.

132. Have you found someone having sex?

A rather uncomfortable moment for anyone is discovering others in the middle of the sexual act. Whether it’s parents, friends or siblings, there are some pretty funny stories.

133. What are the three adjectives that best describe you in bed?

Answering this will be very easy. There are only 3 words that describe sexual performance.

134. Have you ever had sex in a workplace?

This can become one of the most awkward and embarrassing questions, especially if other co-workers are present.

135. Have you had any STD?

Talking about sexually transmitted diseases (STDs) is not easy. Still, it can be an opportunity to reflect on the importance of having safe sex.

136. Do you like to take or take the initiative in bed?

Some feel turned on when their partner takes the initiative in bed. Others, on the contrary, prefer to be that person who lights up the night.

137. When was the first time you felt aroused and how was it?

The first sexual experience is never forgotten. There are many possible triggers for that feeling of excitement. You will surely have fun hearing the answer.

138. Do you watch adult content regularly?

With the facilities that technology offers, many tend to watch adult content quite frequently. Also ask what types of videos or photos are their favorites.

139. Have you ever seen someone naked by accident?

Seeing someone naked by accident is a very embarrassing moment. How was she? What did the other person say? Ask everything about this anecdote.

140. What is for you the difference between having sex and making love?

You will be surprised to hear that many do not believe that there is a difference between these concepts. Others, on the other hand, will say that it is better to make love and will explain the importance of the sentimental bond.

141. What is the most uncomfortable place in which you have done it?

Continue with the uncomfortable questions and have a fun time listening to these experiences. Maybe it was on a bus, a public bathroom, a friend’s house, etc.

142. Have you ever faked an orgasm?

As sad as it sounds, almost everyone has faked an orgasm at least once. Reasons there are many. They weren’t having such a good time or the other person didn’t meet her expectations.

143. Do you have any compromising photos that you would rather remove from the face of the earth?

Photos can become a real problem if they get into the wrong hands. For this reason, there are those who wish they could eliminate them from all sides.

144. Have you thought about having a threesome?

Threesomes are among the most common sexual fantasies. Still, this is one of the uncomfortable questions that many prefer not to answer honestly.

145. What is the longest sexual relationship you have had?

Almost everyone has had a lasting and passionate sexual encounter. As was? Let your curiosity investigate even the smallest detail.

146. What is the most embarrassing thing that has happened to you while you were having sex?

Many things can happen in sex; among those, really embarrassing situations. Which do you remember?

147. Do you think about your ex when you are with your partner?

Of the questions asked so far, this is one of the most uncomfortable. It is very likely that they will not answer you honestly, since it is something that not everyone wants to accept.

148. In what three places would you love to have sex?

There are many ways to break the sexual routine and one of them is by doing it in different places. You will be surprised with the curious places that your friends will tell you.

149. What do you like more: to be dominated or to dominate?

During the sexual act there is almost always someone who assumes the role of dominant and the other dominated. What team are you from?

150. Do you have any wishes that might seem shameful?

In all people, the desire can vary considerably. Some are so strange that it is embarrassing to comment on them.

151. Have you slept with a person without even knowing their name?

On a night out, for a simple adventure, during a trip… many have had this experience and the story is most interesting.

152. Have you traveled to another city to have sex with someone?

In the days of Tinder and social networks, more than one has crossed borders just to have a sexual encounter with the person who turns them on through messages.

153. How often do you masturbate?

One of the most uncomfortable prying questions. Despite the fact that today masturbation is considered the most normal thing, many still feel ashamed when talking about it.

154. What is your favorite sexual position?

The taste for one sexual position or another can vary greatly according to preferences in bed. You will even realize that there are positions that you have not tried.

155. What has been the biggest compliment someone has said about your naked body?

The naked body usually causes a certain degree of insecurity. However, almost everyone has had that moment where they have felt more than praised.

156. Have you slept with more than one person on the same day?

Of course, this will be one of the most uncomfortable questions for both your friends and your partner or family. It is not easy to accept that different sexual encounters have been had in the same day. In this regard there is much taboo and divided opinions.

157. Do you like to set the scene with music while you are intimate?

How about expanding your playlist  to make love? Inquire about this topic and discover songs that will make your next meeting more interesting.

158. Who would you hate to see naked?

Just as there is a desire to see someone in particular naked, it is also clear who one would hate to see in this way. It may be a very unpleasant situation.

159. Are you a voyeur?

Voyeuristic people like to watch others while having sex. It is a most common paraphilia. Maybe you have someone voyeuristic closer than you think.

160. Is there a scene from a movie that turns you on?

There is no denying it; There are too hot movie scenes . Some even arouse sensations that end up igniting sexual desire.

161. What is your weirdest fetish?

Fetishes are quite curious because they differ so much between people. Some are too weird and may intrigue you.

162. What was the last erotic dream you had?

If there is something that is not usually forgotten, it is those erotic dreams. Inquire about how and with whom it was.

163. Have you sent nudes ?

Sexting and sending nudes to your partner or someone you are starting a relationship with has become a relatively common practice. You’ve done it?

Awkward questions about friends and family

164. Did you have an imaginary friend in your childhood? What was his name?

This is a fairly common game, although it is also said to be a lonely children’s pastime . Do you remember who was your imaginary friend in childhood?

165. What would be the last thing you would say to your best friend if you knew they were going to die?

If we knew that a person is going to die soon, and it is our friend, it could be the moment to tell him something that perhaps we always keep silent about . Maybe it’s time to apologize. What would you say?

166. Have you gotten upset with a friend to the point of never speaking to them again?

No matter how much we appreciate someone, sometimes pride takes over and we get so upset that we decide not to speak to that person again. Has it happened to you?

167. Have you fallen in love with a relative?

There are many cases in which falling in love occurs between close relatives. Although it is quite controversial, it happens with some frequency.

168. Who do you love more: your father or your mother?

This, perhaps, is one of the most uncomfortable questions, especially when both parents have been present. Even so, there is always that “favorite”.

169. Have you spoken ill of a close friend?

There are those who will want to omit this question from the list of uncomfortable questions, since the answer can say a lot. But hey, it’s better not to lie. Most people have made negative comments about their close friends with other people.

170. Have you ever argued with a friend’s partner?

Relationships tend to greatly change routines with friends. Therefore, sometimes conflicts appear.

171. Who is the person you need most in your life right now?

The answer will not always be the couple. It can be a friend, parents or a relative. With this question, you will give way to a sentimental conversation.

172. If you knew that your friend’s boyfriend was cheating on her, what would you do?

In these types of situations, some may not be afraid to tell the deceived person. Others, however, will prefer to keep quiet because they do not have enough evidence or end up as the “bad guys”.

173. Have you ever flirted with your best friend’s brothers?

If you ask your best friend this question, they may not want to answer you. In a way, accepting that it is uncomfortable.

174. What is the most embarrassing thing your parents have caught you doing?

With parents there must be a relationship of trust. That’s clear. Despite this, there are situations that nobody wants to share with them. For example, when you have intimate encounters with your partner or are watching an adult movie.

175. What would you be able to do for your family?

It is worth imagining difficult situations to determine what can be done for loved ones.

176. Is there something you can’t forgive your parents for?

Among the uncomfortable questions, this is a rather sensitive one, since it forces us to talk about problematic childhood issues . And it is that, often, parents make mistakes that can cause traumas or experiences that are not always overcome.

177. Have you checked your friends mobile phone without their permission?

Do not forget to include this question in the uncomfortable questions. Surely your friend will be in trouble and will not want to answer honestly. After all, entering the other’s mobile is violating part of his privacy.

178. Do you think that men and women can be friends (and only friends)?

You will be surprised by the number of people who believe that men and women cannot just be friends without a sexual or sentimental relationship involved.

Other awkward questions about you

179. From 1 to 10, how do you rate your physique, your personality and your intellect?

There are three important aspects that we must develop. However, not in all cases they are well balanced . What do you think you should improve?

180. When you talk to yourself, what do you talk about?

It is important to keep in touch with our thoughts. We can talk about different issues, try to reach agreements. But be careful if you do it out loud and they are watching you.

181. What should I say on your grave?

The epitaph can sum up a person’s life in one sentence. What do you think yours should be? Have you ever thought about it?

182. What was your most embarrassing experience in high school?

Remembering the embarrassing situations of youth will never be comfortable. Although some can be funny, others can evoke moments of insecurity, sadness and bullying .

183. What is the first thing you would do if you were invisible?

It is a fantasy that sometimes some of us have had. Being invisible and taking advantage of getting even or doing some mischief. What would yours be?

184. Do you think that all the wealth in the world should be shared equally?

This is a discussion that could take hours, about whether it is fair that we all have the same or that it should be distributed to each person according to their abilities. What do you think?

185. If all laws were abolished, what would be your first offense?

Laws and regulations are what often make us hold back, avoiding behaviors that could harm others. But if they were abolished, what would you do? Would you commit a crime?

186. To which place would you never return, not even for all the money in the world?

There are places we don’t want to go back to, because we didn’t have a good experience. Has it ever happened to you?

187. If you could make someone disappear, without leaving any trace, who would it be?

This would be like a crime but without weapons and without leaving evidence; With just the thought, we would make someone vanish. Would you do it?

188. If you reincarnated in a fictional character, which one would you like?

You can choose between characters from comics, movies or literature. Who would you like to be? Robin Hood? Peter Pan? Or would you prefer someone real, like Joan of Arc?

189. Have you ever been slapped?

Getting punched in the face is not pleasant at all. Undoubtedly, it is a situation whose cause is not always easy to reveal. Has it happened to you?

190. What would you take to a deserted island?

Many things can happen on a deserted island. Imagine this situation with your friends or partner and listen to what they would wear and why.

191. If you see a fight in the street, do you try to mediate or do you walk past it?

The answer is most likely “it depends”. Few will want to get involved in a problem with strangers. Still, if the cause warrants it, there may be someone brave.

192. Have you ever pretended to like a gift?

In the interest of not making the person giving the gift feel bad, some prefer to pretend that they loved it.

193. Have you ever practiced kissing in a mirror?

This experience is certainly embarrassing and funny. However, more than one has done so.

194. What would you do if you were in the bathroom and there was no toilet paper left?

One of the most uncomfortable moments a person can experience is when they enter a bathroom and there is no toilet paper. In your case, what would you do?

195. What is the first thing you would do if you woke up as someone of the opposite sex?

Imagining this situation can be a lot of fun. Often, the conversation tends to go to the sexual or sentimental side. What did they answer you?

196. Do you feel lonely?

The feeling of loneliness usually occurs at many times in life, even when you have friends and family nearby. It is a subject that is interesting to investigate.

197. Have you ever been caught doing something you shouldn’t?

This situation has put more than one person in trouble. There are many possible answers and anecdotes.

198. Have you ever met someone who you would forgive all the mistakes?

It is true that many have limits in terms of their sentimental relationships. But there are those who have that “someone” who makes them unconditional, no matter what.

199. What would you be able to do to have your life financially resolved?

You will realize that some of your friends would be willing to take significant risks to solve their financial situation for life. What do you think of it?

Money is a taboo subject. Many do not want to admit that they would do anything to have more.

200. Would you like to operate on any part of your body?

Talking about cosmetic surgeries can be somewhat uncomfortable, since it implies bringing up the insecurities of the body.

201. What do you think of genital waxing?

In these times, opinions on genital hair removal are very divided. It is a matter of taste, but it can become a matter of debate.

202. Do you think that you have to be a good person above all things?

The philosophy that many of your friends have is to be good people at all times. But is it better that this is the case above all things? Maybe not quite. Do not stop giving your point of view.

203. Have you ever thought that you would like to kill someone?

Like other uncomfortable questions, this one is very difficult to answer. In moments of anger, perhaps it has crossed your mind, although the idea disappears when calm returns.

204. If you could only do one of the two, would you travel to the future or the past?

They may tell you that they prefer to go to the past to change something or see someone who is not there again. Still, many will be more curious to see what will happen in the future.

205. Have you ever been kicked out of a nightclub?

In disco environments many things can happen. For this reason, there are people who have been expelled at some point. Either way, it’s an embarrassing situation.

206. Do you think that people are envious of you?

Sometimes, there are those suspicions that there are others envying the life you have. Perhaps there is no evidence, but there are attitudes or comments that lead to deducing this.

207. Have you ever been arrested?

There are many ways to break the law. Some less serious than others, of course. Ask what this experience was like and what the person did to get away with it.

208. What is the most ridiculous punishment that you have had to do in a game?

Games with family or friends almost always have penalties. Many of these are so ridiculous, it’s embarrassing to remember them.

209. Do you fear old age?

About old age there are many ways of thinking. Some see it for what it is, a natural process; but others are afraid of the changes it brings.

210. What makes you feel vulnerable?

Speaking in public, telling sad childhood stories, recalling a romantic relationship… there are many possible triggers for that feeling of vulnerability.

211. Have you suffered any type of discrimination?

Due to body weight, race, social status… discrimination situations occur in many contexts.

212. What goals do you have in life that you haven’t been able to achieve yet?

It can be carrying out a project, taking a trip, getting married.

213. Have you had paranormal experiences?

What if you make the conversation more interesting with horror stories? Surely most of your relatives have had some experience of this type. Ask for all the details and tell yours too.

214. What childish thing do you think you keep doing?

Sleeping with a stuffed animal, sleeping in mom’s corner, eating certain sweets, watching cartoons… there are many things from childhood that can still be present.

215. Would you spy on someone if you had special powers?

Who and why? Many will say that to their partner, or perhaps to their friends to find out what they are like when they cannot be present.

216. What famous person do you pretend you don’t like, but really do?

That usually happens a lot with singers. Before the world it is said that there is no taste for their music, but at home, when no one else is watching, they hear their songs.

217. What is your weirdest bad habit?

In addition to daily habits, sometimes we have bad habits, which can harm us, but we don’t always tell others. Did they give you an answer? Would you reveal yours?

218. In a fire, would you save your life savings or your pet?

Awkward questions to put the other between a rock and a hard place. Many will say that obviously to your pet, because the money can be recovered. Still, you may be surprised by the answer.

219. Do you think you are an intelligent person?

Recognizing your own abilities is not easy. But you have to put modesty aside. In addition, it must be remembered that there are several types of intelligence.

220. What pleasure makes you feel guilty?

To answer this question, all kinds of pleasures are used: sleeping, eating, having sex, traveling, and so on.

221. What things do you want to achieve before you die?

It is inevitable not to think about death sometime. Therefore, almost everyone is clear about what those things they want to achieve before leaving this world.

222. Have your parents influenced the goals you have?

Parents influencing their own decisions can be embarrassing for many. Hence, this is one of those uncomfortable questions that not everyone answers honestly.

223. What is the craziest and most ambitious thing you want to achieve?

Life plans or projects can be for many something too crazy or impossible to achieve. Well, by now it is clear that success comes from there.

224. What do you hope to achieve in your professional life?

Professional challenges play an important role in everyone’s life project. There are those who are clear about where they want to go, while others feel frustrated for not knowing.