30 Examples of Awkward Questions

Uncomfortable questions

The uncomfortable questions are those questions that can generate embarrassment or shame when answering. For instance: Did you cheat on any exams?

Uncomfortable questions can be inappropriate depending on the context, that is, depending on who the sender is, who the receiver is, and the relationship between the two. For example, if a person has just met another and the latter asks how much he earns from her work, the question may be misplaced and therefore an uncomfortable question.

But if a colleague asks that person the same question, it would not be an inappropriate question, because have another type of relationship and, therefore, can talk about what is charged for doing a certain job.

In any case, uncomfortable questions are not always inappropriate, because the recipient may agree to answer them. In this case, these questions can be useful to get to know other people better.

Examples of awkward questions

1. What's the most embarrassing thing you've ever done in your life?
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2. Who is the person you like the worst?
3. What is the last lie you told?
4. Do you believe in love at first sight?
5. What are you afraid of?
6. Would you change any aspect of your life?
7. Do you usually save or waste money?
8. Who have you voted for?
9. What's the worst job you've ever had?
10. Have you written love letters or poems?
11. Have you ever made a fool of yourself?
12. Have you ever not liked something that you have been given as a gift?
13. What sport are you not good at?
14. Have you fought with a friend?
15. Do you believe in any urban legend?
16. Is there a movie or series that you like but say you don't like out of shame?
17. When was the last time you cried?
18. Would you rather be a millionaire or find your better half?
19. Do you consider yourself a mature person?
20. Could you live without the Internet and without electronic devices?
21. What do you think of revenge?
22. What things put you in a bad mood?
23. Have you laughed at a time when it was not appropriate to do so?
24. If for one day you could be someone else, who would you be?
25. Do you consider yourself a happy person?
26. What do you think are your worst flaws?
27. What attitudes of people do you usually dislike?
28. How do you think you will be in ten years?
29. Is there something that makes you feel insecure or vulnerable?
30. Do you believe in ghosts or aliens?

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