20 Excellent Conversation Questions Everyone Loves

Once you have experimented asking questions for a while, you will realize just how great questions are for starting conversations, helping them flow and for getting to know someone better. Now it is time to have some fun with it!

What makes an excellent conversation question?

  1. It is easy to answer
  2. It does not cause offence
  3. It includes everyone
  4. People will not be judged on their responses!

This last point is particularly important, as people will be reluctant to talk if they feel they will be judged. So you can see a good conversation question is also about tone and circumstances.

Below is a list of excellent conversation questions to delve deeper into the personalities of people you feel comfortable with and find out a few more things about them. These are great for social gatherings and parties or anywhere where you want to have fun and get to know someone in the process.

It is a great spin on the old party game “Twenty Questions” but see where each question leads you when you get the answers. Do not turn your questioning into an interrogation and listen to the answers you get.

Pick up on these answers and as subsidiary questions, add your own answers: ask whatever seems appropriate and whatever the other person seems to want you to do. Just go with the flow and enjoy it!

  1. If you were God for a day, what would you do?
  2. If you could be the parent of one famous person, who would you want it to be and why?
  3. What was the last thing you regret buying?
  4. If you had a chance to bring one person back from the dead, who would it be and why?
  5. What three things you regret not learning to do?
  6. If you had a crystal ball that could tell you the truth about any one thing you wished to know about yourself, life, the future, or anything else, what would you want to know?
  7. What’s worse… having expectations that are too high, or having no expectations at all?
  8. How do you know when you’re in love?
  9. What is the most important invention or innovation that has happened during your life-time?
  10. How would you spend your ideal day?
  11. What, if anything, is too serious to be joked about?
  12. What three adjectives might other people use to describe your personality?
  13. Who would you choose to be shipwrecked on a desert island with?
  14. What is your idea of a perfect romantic evening?
  15. If you were to be remembered for one thing, what would you like it to be?
  16. If you were guaranteed honest responses to any three questions, whom would you question, and what would you ask them?
  17. If you saw someone shoplifting, what would you do?
  18. Is there anything you would willingly give your life for?
  19. If you could re-live a day of your life again, which would it be and why?
  20. If you could be invisible for a day, what would you do?

These are all light-hearted questions that should cause no-one offence, but they also touch on philosophical issues and allow you to really get to know a person – if they are honest with their answers. You make it a lot more likely that they will tell the truth if you set the scene and provide a relaxed atmosphere and if you are prepared to chip in with your own answers.

Under those circumstances, these provide excellent conversation questions to enable you to know more about your friends than you might ever have found out in any other way.