Are you an introvert and don't know how to start deep conversation? Then this article is perfect for you.


16 Deep Questions To Ask If You Really Want To Know Someone

  1. 1. What is your favorite family vacation?

  2. My favorite family vacation was a trip to the mountains. We spent our days hiking, enjoying the scenic views, and evenings around the campfire. It was a perfect blend of adventure and relaxation.


  4. 2. What is your biggest complaint about your job?

  5. My biggest complaint about my job is the occasional lack of work-life balance. There are times when the demands can be overwhelming, impacting personal time.


  7. 3. Which would you rather do: wash dishes, mow the lawn, clean the bathroom, or vacuum the house?

  8. I would rather clean the bathroom. It might not be the most enjoyable task, but the satisfaction of having a clean and fresh space makes it worthwhile.


  10. 4. What is your proudest accomplishment?

  11. My proudest accomplishment is completing a challenging project that required dedication, creativity, and perseverance. The sense of achievement and recognition for my efforts was truly rewarding.


  13. 5. Would you rather win the lottery or work at the perfect job? And why?

  14. I would choose to work at the perfect job. While winning the lottery provides financial freedom, the fulfillment and purpose derived from a meaningful career are priceless.


  16. 6. What's your favorite zoo animal, and why?

  17. My favorite zoo animal is the majestic giraffe. Their grace and unique appearance have always fascinated me, making them a joy to observe.


  19. 7. What makes you laugh the most?

  20. I find that witty and clever humor makes me laugh the most. Whether it's in a stand-up comedy show or a well-written sitcom, clever wordplay and observational humor resonate with me.


  22. 8. Who would you want to be stranded with on a deserted island?

  23. I would want to be stranded with someone resourceful and optimistic, like a survival expert or an engineer. Teamwork and problem-solving would be crucial for our survival.


  25. 9. If you could go back in time to change one thing, what would it be?

  26. If I could go back in time, I would choose to spend more time with loved ones and cherish moments that passed too quickly.


  28. 10. If you could share a meal with any four individuals, living or dead, who would they be?

  29. I would love to share a meal with Albert Einstein, Maya Angelou, Steve Jobs, and Michelle Obama. Each person brings a unique perspective and has made significant contributions to the world.


  31. 11. How many pillows and blankets do you have to sleep with?

  32. I prefer two pillows for optimal comfort, and I usually use a warm blanket, especially during colder nights.


  34. 12. What's the longest you've gone without sleep (and why)?

  35. The longest I've gone without sleep is around 24 hours during a particularly demanding work project. It was challenging, and I learned the importance of prioritizing rest.


  37. 13. What's the tallest building you've been to the top in, and how did it make you feel?

  38. I visited the top of a skyscraper with breathtaking views of the city. It felt exhilarating to be so high above, and the panoramic scenery was awe-inspiring.


  40. 14. What was the last movie you went to? What did you think?

  41. The last movie I watched was a thought-provoking drama. I found it engaging and appreciated the storytelling and performances.


  43. 15. What did you want to be when you were small?

  44. When I was small, I wanted to be an astronaut. The idea of exploring space and visiting other planets fascinated me.


  46. 16. Where do you see yourself in five years?

  47. In five years, I envision myself in a position of greater responsibility and leadership, contributing to meaningful projects and personal growth. I hope to have achieved a good balance between professional success and personal well-being.