Ice Breakers

50 uncomfortable questions to ask friends and couples


When we are in a conversation and want to know more about our interlocutor, we try to be educated and think about the right questions that do not bother the other person.

However, there are a number of questions that can be uncomfortable for different reasons, either because their answers are embarrassing, because they are too intimate questions or because they deal with topics that no one wants to talk about.

Today we bring you a list of uncomfortable questions to ask your friends, your partner or whoever you want to have a hard time. Or to be aware of what types of questions you should avoid if you do not want to bother the other person.

List of 50 uncomfortable and indiscreet questions

The questions that we propose below can help you to annoy your interlocutor or to leave him upset with questions that do not leave anyone indifferent.

1. What is your most embarrassing experience?

And what better than to start with the most embarrassing anecdote of his life. One of the classic uncomfortable questions to ask your friends and tell their most embarrassing experiences.

2. What opinion do you have of me?

Nothing bothers more than having to be honest with the person in front of us and having to confess what we think of her.

3. Would you want to have dash with me?

A question of the most uncomfortable and that puts in a commitment to the interpolate person.

4. Why are you still single?

This other indiscreet question can reveal much of the other person’s intimacies. Will she be honest when answering?

5. Who is the worse for you in this room and why?

This question is ideal to do in a group, especially if you are playing with friends the real game or challenge.

6. How many people have you slept with?

Either because they have been too few or too many, this question can be very uncomfortable for many people to answer.

7. Have you ever had an addiction?

To the drugs, to the game, to the internet … Will the other person dare to confess a problem of this type?

If you’ve ever gotten drunk, chances are you have some shameful story that you’re sure it bothers you to tell.

9. What is the worst crime you have committed?

Step on a forbidden lawn, steal in a store … Where is the ethical and moral threshold of the other person?

10. Would you exchange your partner for a million euros?

This question is especially uncomfortable if the couple in question is ahead. If the other person does not have a partner, it can always be changed by a friend or relative.

11. Who did you tell the last lie?

Admitting that you have lied can already be sufficiently indecorous. Will he also be able to admit who and why?

12. Have you ever lied to me?

One of the most uncomfortable questions you can ask your friends or your partner. Will your answer be another lie?

13. What do you like most about yourself?

It is not easy for everyone to draw their most egocentric side. Having to explain what we like most about ourselves can be uncomfortable.

14. What is the worst about you?

And in the same way that confessing what we like can give us a second thought, having to think about what you like the least is not an exception.

15. What score would you give from 1 to 10?

As in the previous questions, having to do an exercise of self-assessment and expressing it in public can draw colors from more than one.

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

We have all been able to commit madness for love, some unspeakable or too shameful to share.

17. What is the last thing you searched on Google?

Our internet search engine knows all our deepest desires and secrets, and bringing them to light can be most uncomfortable.

18. How often do you shake your little brother?

Another very intimate question to make your friends uncomfortable. Talking about s3x is always intimidating.

19. What is the dirtiest thought you have ever had?

Impure thoughts, inconceivable fantasies … What is the most daring thing that the other has thought about?

20. What is the most extravagant thing you have done in bed?

The weirdest or the most daring. Having to explain the strangest anecdote lived in one of your nights of passion certainly is uncomfortable.

21. Do you regret having slept with someone?

There can always be that person with whom we feel embarrassed when we remember that we share a bed or with whom we should not have had anything.

22. What is the greatest madness you have done?

If you’re not ashamed of the craziest thing you’ve ever done, there’s no problem. Now, some people may have stories that they are reluctant to tell.

A question to know if they have lived the uncomfortable situation of being caught in bed with someone by surprise.

24. Have you ever fantasized about someone of your same s3x?

Intrusive question for heterosexual people, but can be adapted to the preferences of each one.

25. Have you fantasized about someone in this room? With whom?

Another of the uncomfortable questions ideal to do in a group with your friends. Or is it more uncomfortable if you perform it with only one person? You will see.

26. How much is the longest time you have been without showering?

Personal hygiene is an intimate topic, especially if we talk about the lack of it, so this can be a rather indiscreet question.

27. Does size matter?

Another question related to s3x that may be uncomfortable for our interlocutor. Do you dare to ask him about his size if he is a man?

28. How was your worst date?

Having to remember a failed or disastrous appointment is not always pleasant, so having to explain it can be quite annoying.

29. Have you ever been unfaithful?

One of the most committed questions we can ask someone, especially if your partner is in the same room.

30. What three adjectives describe you best in bed?

And when we talk about the bed, we refer to your best description during your most intimate relationships.

31. Have you ever used a daily object as a dash toy?

Few people would dare to answer this question so indiscreet with honesty and without blushing.

32. What is your worst secret?

To ask about the most unspeakable secret of someone is at least uncomfortable. Perhaps it is even more uncomfortable to know the answer.

33. Have you ever had dash in the workplace?

Another question that may be embarrassing. It will be especially committed if your interlocutors are co-workers and respond affirmatively.

34. Have you had an STD?

Venereal or dash transmitted diseases are an unpleasant affair, and asking about them is putting the person in a compromise.

35. What has been your greatest achievement in bed?

And it is not worth answering that sleep more than 12 hours. We refer to the greatest s3xual milestone of your life. For some it will be an honor to explain it; for others an uncomfortable question more.

36. If you could change something from the past, what would it be?

We all have moments from the past that embarrass us and that we wish we could eliminate from our history. What episode would you erase?

37. When was the last time you were rejected?

We have all experienced rejection at some point in our lives, and it is not particularly comfortable to talk about it openly.

38. What is the worst you have said to someone?

At some point in your life, you will have released some barbarity to someone you regret (or not). What is the most you have said to offend someone?

39. What did you think the first time you saw me?

First impressions are important, but over time the image we had of someone can change. This question is perfect to make your friends uncomfortable.

40. What is the weirdest thing you have done alone?

In our moments of solitude, we are free to do what we please without the fear of being judged. Now it’s time to talk about the strangest thing you’ve done without anyone seeing you.

41. What is the most embarrassing nickname you have been given?

It may be a nickname that you would have put the schoolmates or the most ridiculous nickname for which you may have called your partners. Which is the most embarrassing?

42. What is your biggest fear?

All people have some fear, but many may be uncomfortable talking about their worst fears.

A very committed question that will give the person questioned to think about.

44. Describe what your ideal person would be physically like.

Having to talk openly about what attracts us physically from someone has a certain shameful point. Having to describe it can be quite uncomfortable.

45. How much do you earn?

It seems that speaking openly about each one’s earnings is still a taboo subject for many, who are leery of commenting on this part of their lives.

46. What is your most unpleasant anecdote?

That time you felt bad Indian food, once you vomited what you should not … Make the other person uncomfortable explaining the most disgusting moment he has ever lived.

47. What is the worst thing you have done to someone?

Admitting to behaving badly with someone is very complicated, but it is more difficult to confess to others about it.

Who has not suffered from love? Opening up to others to explain the traumatic experiences of love is not so easy.

49. When was the last time you cried?

The same happens with our most vulnerable moments. Not everyone is comfortable talking about the times they have had a bad time and they have cried.

50. How far do you go?

Do you miss this question? To us too. Ask someone without waiting for him to surprise him and create an uncomfortable situation.

Andy Johnson

Degree in Psychology from the University of Buenos Aires. Master in Human Resources and expert in business communication and coaching. Postgraduate in Nutrition and Sanitary and Social Feeding by the UOC. Especially interested in wellness and sports.

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