What's the point of this blog? It's so random! Well: that's the whole point. Why waste your energy thinking of things to talk about, when we've put together the most creative list you'll find anywhere. Just refer back to this page the next time you are in danger of having a boring conversation. We've got you covered.

Striking up interesting conversations is a really important part of building closer friendships. But it can be really hard to find the right things to talk about, especially if you don’t know much about them yet.

Having a big repertoire of random questions to start conversations is crucial, and you’ve come to the right place for the best list of random questions.

Question Generator

If you are struggling to come up with good questions to serve as conversation starters, we have this convenient question generator that can instantly generate a question for you to use! Now you will never worry about running out of good questions to 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

Questions to Make Conversation

And now...for the most random questions ever!

1. If You Had Three Wishes, What Would You Wish For?

2. What Would You Rather Throw Away: Love Or Money?

3. What’s The Most Beautiful Place You’ve Ever Seen?

4. What Was Your Fondest Memory Of High School?

5. What’s Your Favorite TV Show?

6. What’s The Strangest Thing In Your Refrigerator?

7. Would You Rather Hear The Music Of Johann Sebastian Bach Played By A Barbershop Quartet, Or A Heavy Metal Band?

8. Have You Ever Been To A Five Star Resort?

9. What Was Your Favorite Toy Growing Up?

10. What’s The Funniest Way You’ve Ever Broken The Law?

11. What’s Your Favorite Sports Team?

12. What Talent Would You Want To Possess If You Could?

13. If You Could Trade Lives With Someone, Who Would It Be?

14. If You Could Erase One Event From History, Which One Would You Erase?

15. What Was Your Favorite Toy As A Child?

16. Who Do You Most Like To Poke Fun At?

17. If You Were Suddenly Transported To Another Planet, How Would You Assess The Situation?

18. When Do You Feel The Most In Control?

19. Would You Rather Have 10 Hobbies Or One Passion?

20. What’s Your Favorite Movie?

21. If You Could Interview A Famous Person, Who Would You Choose?

22. If Your Food Is Bad At A Restaurant, Would You Say Something?

23. If You Could Only Use One Word The Rest Of Your Life, What Word Would You Choose?

24. What Are Your Dreams And Ambitions?

25. You’ve Been Given An Elephant. You Can’t Get Rid Of It. What Would You Do With It?

26. What’s The Funniest Thing You’ve Seen On The News?

27. If You Had The World’s Attention For 30 Seconds, What Would You Say?

28. If You Could Be Best Friends With A Celebrity, Who Would It Be?

29. If You Were To Play A Song You Love Right Now, What Would It Be?

30. Would You Rather Look Like A Potato, Or Feel Like A Potato?

31. What Would You Do With 10 Million Dollars?

32. How Can You Tell If Someone Has A Sense Of Humor?

33. If You Were To Name Your Own Song, What Would You Name It?

34. If You Were In A Room Filled With You And Your Doppelganger And 2 Million Dollars, What Would You Do?

35. What Is In Your Fridge Right Now?

36. What Have You Learned About Life From Kids?

37. How Would You Want To Be Remembered?

38. What Do You Hope Your Deceased Relative Would Say About You If They Saw You Now?

39. If You Could Change Your Name, What Would You Change It To?

40. What’s The Strangest Thing That You’ve Ever Fallen In Love With?

Funny Random Questions to Ask

1. If You Could Have Any Super Power, Which One Would You Choose?

2. If You Were Invited To Attend Hogwarts, Which Hogwarts House Would You Choose?

3. What Were The Highlights Of Your Childhood?

4. Have You Ever Kept A Secret For More Than A Decade?

5. What’s The Most Important Thing You’ve Learned From A Celebrity?

6. Do You Care About Reviews?

7. What Would Be The Perfect Crime?

8. What’s The Stupidest Thing You’ve Ever Done?

9. Spontaneity Or Stability?

10. What’s The Funniest Movie You’ve Ever Seen?

Interesting Questions to Ask

1 . What’s your worst habit?

2 . Do they like to take a stand or just let things go?

3 . What’s your favourite song?

4 . How do you think the world would be if bananas were illegal?

5 . Would you rather be able to control time, or be able to know what other people are thinking?

6 . Is it difficult to do what you do? (for a living, hobby etc.)

7 . Who is your favourite celebrity?

8 . If you found $2,000 on the ground, what would you do with it?

9 . What’s your favourite pizza topping?

10 . What would you do if you could possess the abilities of your pet?

Random Questions to Ask Your Friends

1 . What is your favourite team game to play?

2 . Anything interesting you’ve watched lately?

3 . What is the one recent trend you can’t stand?

4 . Is there anything that annoys you about travelling?

5 . What is your favourite drink?

6 . What is one song you can’t help but sing along to?

7 . What is your current pet peeve?

8 . Who was the first YouTuber you discovered?

9 . Do you remember when you first logged onto the internet, and if so, what was the first website you visited?

10 . If you decided to run for President, what would your campaign slogan be?

Random Questions to Ask your Colleagues

1 . What did you do over the weekend?

2 . What do you do for fun?

3 . What was the last movie you watched?

4 . Where did you last travel to?

5 . When did you last take a flight?

6 . Where is your favorite place to get a drink?

7 . What is your favorite place to vacation?

8 . Where did you attend university?

9 . Have you lived in more than one country?

10 . What is your morning routine?

FAQ: Random Questions

1 . Are there any questions I shouldn’t ask?

A: Generally speaking, there isn’t anything that you cannot ask or a question you should avoid. As the saying goes: there is no such thing as a stupid question. However, if you feel a question you have in mind might be too sensitive or potentially asking for personal information, consider the context of who will be answering said question before bringing it up.

In addition, whoever is answering has the option to pass on the question or respond with “I’d rather not say”.

2 . Is asking random questions a good icebreaker?

A: Yes! In fact, aside from asking random questions directly, another great idea for an icebreaker is asking hypothetical ‘Would You Rather' questions. It is a great way to generate conversation within your group and get people thinking. Furthermore,  'Would You Rather' is one of many games available on Brightful.

If you are looking for more icebreaker ideas other than question-guided ones, check out our list of icebreaker games.

3 . Would I need to give serious answers to questions? Could I make up an answer?

A: Unless it's a hypothetical question or a question that is aimed at producing funny, outlandish, or creative responses, you should ideally keep your answers as realistic as possible.

4 . What if I can’t think of anything good as an answer?

A: Just like there is no such thing as a bad question, there is no such thing as a bad answer. Even if it's brief or not the first thing you can think of, any answer is fine!

If you really are stumped and cannot think of anything, you can ask to pass on the question or ask for the group to come back to you when you have thought of something to serve as your answer.

5 .  If I were to ask questions as an icebreaker, how long should I run it for?

A: You ideally should have a minimum of two questions prepared to serve as your icebreaker before you move forward with your agenda: you don’t want it to be too short but at the same time, not make the questions the focal point of your meeting.

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Final Thoughts

We are social creatures by nature and we want to feel connected to people. Asking questions is a great way to break the ice among everyone. Anything makes for a good conversation starter, so there are infinite possibilities of what you can ask anyone in your group to get everyone to open up and out of their personal bubbles.

You’d be surprised at what you might learn about some people! We hope you find our questions useful to start conversations!