Having a daring role in front of another person can allow us to get closer and generate some kind of effect (in many cases of interpersonal attraction or admiration), as well as facilitating support to achieve our objectives. Likewise, it allows us to assess the attitudes and thoughts of the person asked, according to the way in which he or she manages stress or nerves.

This article focuses on trying to reflect various compromising questions that we can or may be asked in different settings.

A short collection of compromising questions to ask

There are topics of conversation that we cannot or at least do not usually touch on with everyone. Beliefs, dilemmas, taboos such as sex and compromising situations in general can generate some discomfort among the interlocutors. But on the contrary, they allow us to leave the comfort zone and make stimuli and information appear that otherwise would not be expressed.

Below are 27 engaging questions that can help us break through the comfort zone and explore other facets of the people we are talking to. However, we must take into account that some people may not consider them appropriate and may not answer them, and may even get angry or react negatively. Whether it is appropriate to do them or not will depend on the type of person we are talking to, the type of relationship we have , the relational climate and even the situation in which they are carried out.

1. What makes you feel alive?

It may not be the most committed question we can ask, but depending on the type of person we are interacting with we may find it difficult to express our deepest motivations , the things that make us vibrate the most.

2. What is your greatest fear?

What generates the greatest fear is usually something that tends to be hidden, since can be experienced as something intimate that others might judge . Likewise, if it is answered it allows us to know the other person and the things he or she values much better.

3. What would you change about yourself?

Most people have some aspect of themselves they’d like to improve. Confessing it means exposing the aspects of oneself that do not fit with one’s ideal self.

4. What is your biggest dream?

Our greatest desire, what we would like to achieve, is also something that is not usually told in regular conversations .

5. Have you ever been cruel or used someone?

Many people have at times used someone, or been cruel to someone who did not deserve it, sometimes even unwillingly. This generates in the long run (in most cases) feelings of guilt and denial . One of the most direct compromising questions.

6. Do you have any unmentionable vices?

Tastes and habits that have been socially and historically sanctioned and considered as vices are often hidden.

7. When did you last lie about something important?

Although it is not unusual, lying has a negative connotation that makes us often uncomfortable indicating how and when we have done it .

8. What is the most embarrassing thing anyone has ever caught you doing?

We may find our own behavior embarrassing in some situation or context, such as in front of our parents, friends or partner. Dancing naked or being discovered in relationships are examples of this.

9. What do you think of yourself as a person?

Defining oneself is not as easy as it seems, and most people do not usually reflect on what they think and what they would criticize about their way of being and doing .

11. Do you have a complex? Which one?

Our complexes, fears and doubts are subjects that most people do not usually share, especially if it is something we consider embarrassing.

12. Which of the other candidates would you not take and why?

This question is generally limited to the business area, although it can be modified to insert it in other areas. In the labour field, it is, in fact, a relatively common question that seeks to observe both the respondent’s reaction and his/her answer or lack thereof.

13. What is the part of your body that you like best?

Although this question is very similar to one of the previous ones, in this case we limit the answer to the physical aspect, which can be much more uncomfortable or disturbing. It also allows us to see what aspects of yourself you value most on a physical level.

14. What about mine?

Much bolder than the previous one, especially if there is an attraction to the subject being asked. It allows us to see in which aspects the other person is fixed, besides being able to suppose by the reaction if we provoke something to this person .

15. What do you regret most?

To answer this question is to acknowledge that we have done something wrong or have not done something we feel we should have done.

16. How far would you go to fulfill a whim?

We live in an individualistic and competitive society. Asking whether we would set a limit on what we can do to reach our most basic goals can be compromising.

17. What’s the craziest thing you’ve ever done for love?

When we fall in love, we can do crazy things. Some of them can be ridiculous, bizarre or exaggerated if seen from the outside or objectively, even though they may be worthwhile.

18. Do you prefer to be the author of an injustice or its victim?

Basically, we’re asking if you’d rather be a victim or an executioner. Although the type of injustice can be qualified, helps us to see how the other person reflects on and justifies his or her choice (neither of which is usually well valued), as well as his or her moral position in life.

19. Have you ever given up on anything in your life?

Answering this question can be hard if the answer is positive, since it means acknowledging the existence of a defeat.

20. Have you ever been unfaithful?

Infidelity is something socially frowned upon and tends to be hidden by those who practice it. If it has been, this question may be compromising .

21. What is it that you have never dared to ask me?

If the relationship with the questioner is good, it is possible that he could not or wanted to ask us any question that he never dared to ask. If this is the case, this question can be quite compromising, but it can help clear up doubts and strengthen the relationship .

22. What would you do if a stranger kissed you in the street?

This is an unusual and surprising situation, and considering it can be uncomfortable.

23. What’s the worst mistake you’ve ever made?

Mistakes are often seen as embarrassing or as failures, even though they may be seen as opportunities. Confessing them can be difficult for some people.

24. Would you be happy to see someone you hate having a hard time?

If someone has hurt us to the point of hate, the idea of seeing them suffer can give us some perverse satisfaction.

25. Have you ever taken revenge on anyone?

Wanting revenge when someone hurts us is common. But there is a stretch from saying to doing.

26. If all the people in your life were in one house, it would catch fire and you could only save one person, who would you save?

A difficult question to answer.

27. What would I have to do to seduce you?

The idea that the person we are talking to is trying to seduce us can be shocking and disturbing, as well as answering what would be necessary for a mutual attraction to exist.