Have you ever been in a social situation where it feels like you are having the same old conversations again and again? We can easily fall into the trap of asking canned questions and giving canned responses. It can begin to feel as if our conversations are just automated scripts, repeating themselves again and again.

We have created a list of Questions of the Day for you to try in your next conversation. Below are our top 75 thought-provoking and fun questions to ask at your next social gathering. You will be sure to have some fun and unexpected conversations!

If you are hosting your gatherings over video conferencing and are looking for more ways to break the ice and form deeper connections to fully engage with your team or friends, then be sure to try Brightful Meeting Games. You’ll find a whole selection of games, including Question of the Day, completely free and with no ads or downloads.

Fun Question Generator

If you find it difficult to come up with questions that make everyone think or are light-hearted, you can always refer to this handy question generator below that can instantly come up with a thought-provoking or fun question you can ask!

Brightful Games: Q of the Day

Trying to have more meaningful conversations? The best way to connect with your friends, family and colleagues is by inviting them to a game of Question of the Day on Brightful. The rules are simple - you are given a prompt and 30 seconds to answer. It's free to play, and there are thousands of conversation starter prompts.

  • No downloads needed
  • 14-day free trial
  • No credit card required

Brightful Games: Would You Rather

If you are still looking for an interesting team activity to play that is still based on asking questions, but one that demands a little more critical thinking, try out Would You Rather - also on Brightful. Everyone is shown two prompts or real-life scenarios, and you must pick which one you personally would rather be in. When everyone has made their choice, you are shown who voted for what, and your group then takes some time to discuss why you chose what you chose. There are thousands of prompts & scenarios available, so don't worry about running out of possible scenarios!

  • No downloads needed
  • 14-day free trial
  • No credit card required

75 Fun Questions to Ask

Questions About Life

1. What’s the best thing you've got going on in your life at the moment?

2. In the seconds before you die, you are allowed to know everyone who was secretly in love with you at some point. Do you want to know?

3. In 10 years' time, will you be proud of what you are doing now?

4. What does your inner voice tell you?

5. What do you need to stop doing to make space for bigger changes?

6. What have you done recently to overcome one of your fears?

7. What do you fear?

8. What’s the most courageous thing you have ever done?

9. What are your strongest beliefs?

10. What’s the dialogue you really need to have but haven't had so far?

We all have our vices. What's yours?

Personal Questions

  1. What do you need help with most often?
  2. What’s something that no one knows about you?
  3. What kind of challenges are you facing these days?
  4. What do you miss most about?
  5. When was the last time you were lost?
  6. What book had the most significant impact on you?
  7. What unethical experiment would have the biggest positive impact on society as a whole?
  8. When are you most creative?
  9. What thoughts come to mind when you are relaxed?
  10. What’s missing in your life?

Questions about Life Ambitions

  1. Is there anything you want to say to your loved ones but haven't said enough?

2. When are you most receptive to critical feedback?

3. What messages are you refusing to hear?

4. What could you do to make it easier to accept feedback?

5. How could you achieve more by doing just half as much?

6. If you can complete one important task this week, what would that be?

7. What is important but not urgent in your to-do list?

8. What’s the number one thing you want to achieve?

9. What’s something that you would really hate to lose?

10. Whom are you trying to avoid being like?

Questions about the Future

  1. What do you want to be known for?
  2. Do you think that children born today will have better or worse lives than their parents?
  3. What makes you feel most fulfilled?
  4. What goal do you think humanity is not focused enough on achieving?
  5. Who do you admire most in your life?
  6. If you could change two things about the world, what would you change?
  7. If you were offered the chance to feel happy all of the time, would you take it?
  8. What is the meaning of life?
  9. Do you think it is better or worse for people to know whether they have the genetic marker for a debilitating disease?
  10. How do you define friendship?
What does the future hold for our little ones?

Spiritual Questions

  1. What self-limiting beliefs do you have?
  2. What do you need to change to become the person you want?
  3. What habits do you have that you would like to replace?
  4. What problem are you running away from?
  5. How would you want your loved ones to remember you when you are gone?
  6. Do you think that humans will ever be able to live together in harmony?
  7. In the past people were buried with the items they would need in the afterlife, what would you want to be buried with you so you could use it in the afterlife?
  8. What was the biggest realization you had about yourself?
  9. What’s the most physically painful thing you've ever experienced?
  10. What were you completely certain of until you found out you were wrong?

Relationship/Friendship Questions

  1. Do you believe that love has to be mutual?
  2. If you were in charge of the universe, would you make an afterlife?
  3. When you disagree with someone, is it more important to ensure you both get the facts or do you both feel heard?
  4. What are you still learning about yourself?
  5. If you could ask God questions, what would you want to know?
  6. If the most challenging thing to ever happen to you happened again, would you handle it differently?
  7. What adjectives would you use to describe the human race?
  8. When you look at the world, what is most fascinating to you?
  9. When do you underestimate yourself?
  10. Is it best to judge people by their intentions or their actions?

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Final Thoughts

It can be a challenge to keep the conversation going or interesting. Even if you might have a lot to talk about, it can be difficult to think about what else is there to discuss or ask someone - provided it isn't too sensitive or controversial.

Thought-provoking questions or questions that make you really think to provide excellent means to stretch a conversation longer than a simple "Yes/No" question to ask someone, especially to serve as an icebreaker to kickstart a meeting in person or virtually. Keep our list of thought-provoking and fun questions in mind the next time you need to keep the conversation fun and interesting!