156 Hardest Questions to Answer for Friends and Yourself

We all like to think of ourselves as problem solvers and enjoy testing our wits with challenging questions. Sometimes, finding an answer can be even harder than asking a question.

If you’re looking for a way to challenge yourself and your friends, here’s a list of the 150+ hardest questions to answer for friends and yourself!

Each question encourages an open dialogue that will challenge both parties to dig deeply into the depths of their thoughts and feelings.

Whether it’s about relationships, life choices, or random trivia – these questions will definitely test your knowledge and push you out of your comfort zone.

So, let’s dive into the list of hardest questions to answer.

Hardest Questions to Answer for Yourself

Asking yourself challenging questions can help you better understand yourself and your beliefs. Here are some hard questions to ask yourself:

1. Who had the biggest influence on me as a child?

2. What do I need to change about myself?

3. Are am living the life of my dreams?

4. What dreams have I given up on?

5. What do I want to be remembered for at the end of my life?

6. What would I do if fear was not a factor and I could not fail?

7. What worries me the most about my future?

8. Am I in control of my life?

9. What were am doing when I felt most passionate and alive?

10. Am I too hard on myself or not hard enough?

11. What makes me happy?

12. What I am most grateful for?

13. Are there any toxic relationships in my life that need to be dealt with?

14. Am I a good friend?

15. Am I truly proud of the person that I am?

16. Who would I trust with my life?

17. What causes me stress in my life?

18. What am I most afraid of?

19. What gives me a deep and profound sense of joy?

20. Do I understand what universal elements are needed for a happy life?

21. Am I contributing to the world?

22. What do I lose track of time doing?

23. When do I confuse my own happiness with the happiness of others?

24. Am I a good communicator?

25. What do I feel most proud of?

26. Can I identify what limiting beliefs get in the way of my happiness?

27. Who am I most jealous of and why?

28. If I could map out a perfect day, what would it consist of?

29. How do I define happiness? Do I understand what’s needed for happiness?

30. When do I prioritize what makes me happy? When do I neglect it? Why?

31. How did my upbringing shape my view of what I wanted for a healthy family? A relationship?

32. What helps me recharge my energy levels?

33. What is something that happened in my childhood that still bothers me?

34. What did I feel most ashamed of as a child? How might this shame still be affecting me now?

35. What hopes and dreams did I have as a child that I have given up on?

36. What did I not like about my childhood that I want to change for my adult life?

37. What lesson from childhood has stuck with me the most?

38. What primary coping strategy did I develop as a child that I still use today?

39. What communication patterns did I develop as a child? Are they effective or ineffective?

40. What messages did I receive about what I needed to do to receive love?

Hardest Questions to Answer about Life

Life is full of complex questions that can be difficult to answer. Here is a list of a few deep questions that will make you think about life, challenge your beliefs, and encourage you to reflect on what truly matters.

1. When have you failed in life?

2. Can you live a materialistic life and still feel fulfilled?

3. How did you handle each failure in your life? What was your reaction to failing?

4. What is the meaning of life?

5. What determines a successful life?

6. What do you value more in life, experiences or possessions?

7. Are you envious of other people’s lives?

8. Do you believe your life is predetermined?

9. If your life was to end today, would you be happy with what you’ve achieved?

10. Are we making our lives harder or easier?

11. How do you feel about where you are in life?

12. Do you believe in having regrets in life?

13. What advice would you give your younger self?

14. Where do thoughts come from?

15. What is your greatest failure in life?

16. How do the worst moments in our lives make us who we are?

17. What is your greatest success in life?

18. Why do some people succeed and others don’t?

19. How do you know you are not wasting your life?

20. Do we really see reality as it is?

21. Are you a body with a mind or a mind with a body?

22. How was failure treated in your upbringing?

23. Does the past really exist?

24. How do you explain consciousness?

25. When in your life have you repeated the same mistakes over and over again?

26. What is your most harmful pattern when faced with stress?

27. What challenges in your life defined you the most?

28. What do you feel most shameful about in your life?

29. How comfortable are you asking for help when you’re faced with a challenge?

30. What is one of your biggest regrets? What did you learn from it?

31. What is your attitude when facing a challenge?

Hardest Questions to Answer | Philosophical

Philosophical questions delve into the nature of existence, reality, and knowledge. They challenge our beliefs and push us to think critically about the world around us. Here are some of the most intriguing philosophical questions.

1. Why is there something rather than nothing?

2. Is love different from sexual desire? Passion? How?

3. Is our universe real?

4. Do people really have free will?

5. How much freedom should people be allowed to have?

6. Do we have free will?

7. Is there a cause for every event?

8. Should governments have penalties for those who live unhealthy lifestyles?

9. Does God exist?

10. Do wars ever solve the problems of countries and governments?

11. Should the government make organ donation compulsory?

12. Is there life after death?

13. Do computers have the ability to be creative?

14. Should people be allowed to sell their organs and should organ donors be financially compensated?

15. Can you really experience anything objectively?

16. What rights, if any, do animals have?

17. Should people have the right to live and travel anywhere they wish with no state or country boundaries?

18. Does democracy work for every country?

19. When you are driving and see one shoe on the side of the road, what do you think happened to the other shoe?

20. What is the best moral system?

21. Are there universal human rights? What are they?

22. Since the birthrate is down in the U.S., should people be required to have at least one child?

23. Are emotions rational or irrational?

24. If someone is killing themselves and you simply watch and refuse to interfere, are you responsible for that death?

25. What are numbers?

26. Should we limit the amount of money people can earn and save to avoid an unequal distribution of wealth?

27. Is torture ever justified?

Hardest Questions to Answer | Unanswerable

Some questions are so complex that they may never be fully answered. These unanswerable questions can spark deep discussions and encourage us to think beyond what we know. Here are some of the hardest questions to answer.

1. Can love really last a lifetime?

2. Can spenders and savers stay married?

3. Why do married folks begin to look like one another?

4. Can a man and a woman ever just be friends?

5. Do siblings who fight really end up liking each other?

6. Can a marriage survive betrayal?

7. Do you have to love your job?

8. How do you know when to end a friendship?

9. Why does summer zoom by and winter drag on forever?

10. When is your future behind you?

11. Why do we turn into our parents when we swore we wouldn’t?

12. Do animals really have a sixth sense?

13. Where do traffic jams come from?

14. Can a half-empty person become a half-full person?

15. By what age should you know what you want to do with your life?

16. When do kids become adults?

17. Why does the line you’re in always move the slowest?

18. Can a mother be friends with her teenage daughter?

19. What do you do if you see a parent berating a child?

20. Does money really buy happiness?

21. Why is it so hard to say you’re wrong?

22. Is money the root of all evil?

23. When should you reveal a secret you said you wouldn’t?

24. Does the toast really always fall buttered-side down?

Hardest Questions to Answer for Interview

Job interviews can be nerve-wracking, and some interview questions can be difficult to answer. These challenging interview questions test your abilities, creativity, and problem-solving skills. Here are some of the hardest interview questions:

1. What is your greatest weakness?

2. Describe a time when you have failed?

3. Why should we hire you?

4. What are your strengths?

5. Why should we choose you for this role?

6. What’s something that you didn’t like about your last job?

7. What has been your greatest achievement?

8. Why did you apply for this job?

9. Why do you want this job?

10. If you were a flavour of ice cream, what would you be and why?

11. How will you contribute to the team?

12. How do you deal with conflict with a co-worker?

13. If you were a fruit or vegetable what would you be and why?

14. Describe a situation where you have gone above and beyond?

15. Describe yourself in three words?

16. Describe a project you have handled?

17. What are your weaknesses?

18. What do you think the chief executive thinks of the company?

19. What are you hoping to get out of life?

20. What did you like or dislike about your previous job?

21. What attracted you to this company?

22. Are you a competitive person?

23. Who was your best supervisor and who was the worst?

24. Why are you leaving your current position?

25. How would your friends describe you?

26. What attributes do you have that will support you in this role?

27. What was the most and least rewarding about your last position?

28. Name a time where you have worked under pressure?

29. Tell me about a time you overcame an obstacle

30. Describe a situation where you have had others follow your lead?

31. What have been your most positive and negative management experiences?

32. How many pennies if stacked on top of each other would equal the height of the Empire State building?

How to Use These Hard Questions

Asking hard questions can be intimidating, but it is a valuable tool for learning and growth. When used appropriately, these questions can lead to deep conversations and a greater understanding of the person being asked.

Here are some tips on how to use hard questions effectively:

Set the tone: Let the person know that you are interested in their thoughts and experiences and want to have an open and honest conversation.

Timing is key: Choose a time when both parties are relaxed and have enough time to discuss the topic.

Start with easier questions: Gradually build up to the harder questions, starting with easier ones to establish trust and comfort.

Avoid judgment: Be non-judgmental and listen to their response with an open mind.

Examples of hard questions that are difficult to answer include: “What is the meaning of life?” or “What is the most difficult thing you’ve ever had to face?”

These types of questions can spark meaningful conversations and help to reveal deeper insights into a person’s thoughts and beliefs.

Remember, the purpose of asking hard questions is not to get the “right” answer but to start a conversation and gain a deeper understanding of the person you are talking to.

Final Thoughts

The toughest questions to answer can provide a valuable opportunity for self-reflection and growth.

Whether you’re answering questions about yourself or your friends, or even during a job interview, these complex inquiries can challenge your beliefs and push you to think critically.

While some questions may never be fully answered, they can still spark meaningful conversations and encourage us to question what we know.

So embrace the challenge, and don’t be afraid to ask and answer some of the toughest questions that life has to offer.

Anyway, don’t forget to write about your experience while asking or answering these most challenging questions.