In the mood for a deep and stimulating conversion with thought provoking questions? The following questions will get things started. My wife and I have used most of these over dinner and we enjoy the discussions that follow. 

Some of these questions err on the more serious end and others will make you laugh as you try to come up with an intelligible response. They are indeed some of the best questions to ask to get conversation rolling. 

Good luck and may your thought provoking conversations be stimulating and engaging!

Funny Thought Provoking Questions (1-30)

These questions will get your mind going and may even make you laugh just reading them. If you can read of all these questions without busting a gut I’ll buy you a coke.

  • What’s the weirdest food you’ve ever eaten?
  • What’s the most embarrassing thing you’ve ever said?
  • If you could only wear one type of shoe for the rest of your life, what would it be?
  • Which is the better eye, left or right?
  • You can only see the world in one color, what would that color be?
  • Your Dad just asked you to rob a sock store, what do you tell him?
  • You can fish-slap one person with no repercussions, who do you choose?
  • Give yourself a new nickname on the spot. What is it?
  • Name a time you were scared so bad you jumped out of your skin. 
  • What’s the most ridiculous song you’ve ever heard? (If you have google home, ask it to play the banana bread song, it will make your day)
  • What’s the ugliest piece of clothing you’ve ever worn?
  • Who is the weirdest person you’ve ever met? What did they do that made them so weird?
  • Who is your favorite cartoon villain?
  • Create a new word to describe the sound rain makes when it bounces off your face.
  • What’s the worst animal name you’ve ever heard?
  • Someone is walking by you on the street, do you high five them or smile the most awkward smile you’ve ever smiled?
  • As that person walks away what do you whisper to creep them out?
  • How do you feel about putting mayonnaise on french fries?
  • What was your favorite thing to do as a child that you would love to still be able to do as an adult?
  • What’s worst smell you have ever experienced?
  • What is your hidden talent you don’t want people to know about?
  • What’s the worst meal you’ve ever cooked?
  • Describe what your dessert island would look like? ??
  • Choose one, a pie to the face, ice cream in your shoe, chocolate sauce down the back of your neck.
  • What is your superhero identity, and why is it important than no one find out who you are?
  • Describe what it would be like to walk backwards instead of forwards for a full day.
  • You have the ability to exchange the words hello, goodbye, and thank you with any words you want. You’ll hear people speak these words for a full day. Choose these words carefully. What are they?
  • What was the craziest thing that happened to you in high school?
  • Describe a time you made a group of people laugh (even if it wasn’t on purpose).
  • What is the dumbest thing you’ve ever done?

Deep Thought Provoking Questions (31-82)

thought provoking questions

The following questions will get you thinking deeply about the meaning of life, your dreams, and your place in the world. These are great for the kind of soul stirring discussions that turn a normal Friday night into a lasting memory.

Here is that long list of thought provoking questions you’ve been waiting for:

  • If you could do ONE thing for the rest of your life what would it be?
  • You need to give three non family members $100,000 by tomorrow. Who gets the cash and why?
  • How did you meet your best friend?
  • What is something you’ve always wanted to try but have been too afraid to?
  • If you only had 1 week left on Earth, what would you do?
  • How do you want to be remembered by your family and friends at your funeral?
  • What are four concrete achievements you would like accomplish before you die?
  • If you could go back in time and tell your younger self one thing, what would it be?
  • What is your favorite thing about yourself?
  • What is your most improved skill or character trait since high school?
  • Do you like yourself? If yes, why, if not, why?
  • What are you doing with your life? (If this question stumps, see my post here on the subject.)
  • What three items would you take with you to a desert island?
  • Do people deserve second and third chances?
  • The internet shuts down and will never come back on, what do you?
  • Is it better to wake up early or stay up late?
  • Will we one day be completely replaced by machines?
  • Do aliens exist?
  • What is mankind’s greatest invention/contribution to the world?
  • Does your life have a purpose?
  • Are rules made to be broken?
  • Explain the time you felt most alive.
  • What is one action step you’ve been meaning to take towards your goals? (Hint: take that step!)
  • What song best explains the mood you are in right now?
  • What is the biggest problem with society today?
  • What are you doing about it?
  • What would you describe as the perfect life?
  • Who is your role model and why?
  • What is your lifelong dream?
  • Is recycling important?
  • What do we need to be doing better to save the planet?
  • What are three things that really grind your gears?
  • Two of those annoying things go away forever, the other one will occur every single day for the rest of your life. Which two go away and which one stays?
  • What is your definition of a truly evil act?
  • What is the nicest thing you have ever seen someone do?
  • What period in time would you prefer to live in?
  • Have you ever made someone cry? What did you do?
  • What movie or book influenced you the most?
  • Would you live on the Moon if given the chance?
  • If not the moon, what about Mars?
  • Would you rather invent a cure for cancer or a time machine?
  • Where is your happy place?
  • What is your greatest accomplishment?
  • Who is your hero and why?
  • How would you prefer to die?
  • What is one habit you should start?
  • What’s one habit you can break?
  • Is it possible for the world to be at peace?
  • Do you think we will ever again live with the dinosaurs?
  • What is your single biggest regret?
  • Why are you doing your current job?
  • What is the one question you might never get an answer to?

Thought Provoking Questions for Couples (83-102)

thought provoking questions for couples

This set of questions should spark deep conversation between the two of you. Use this as a night out away from the house with the TV off. Build your connection with a cheap date night and good discussion.

Caution! Make sure you are in a good place before asking some of these, no need to stir up arguments if you aren’t ready.

  • How do people fall in love?
  • What are three things you look for in a good partner?
  • What is your favorite room in the house?
  • What’s the longest you’ve ever gone without showering?
  • Have you ever been skinny dipping?
  • What’s your favorite thing about your partner?
  • What was your most memorable anniversary?
  • Who has the better memory?
  • How far would you go to protect the person you love the most?
  • What skill or talent do you most envy in the other person?
  • When do you feel the most connected to me?
  • Who is better at board games? Prove it!
  • What has been the biggest challenge in your life that you have had to overcome?
  • Do you feel as if I am there for you when you need me most?
  • What is something we could accomplish together?
  • Which couple do you look up to the most?
  • How would you describe our relationship in just one word?
  • How can I be a better partner for you?
  • Where do you want to retire?
  • What’s something we could cross off our bucket list this year?

Interview Questions for the Interviewee (103-107)

If you are looking to jazz up your upcoming interview look no further. These questions may not get you the job, but you will be remembered as a deep thinker and a thought provoking individual. Ask at your own peril, but do report back if they got you the job.

  • Why do you think I’m the best person for the job?
  • What are three things I could say to convince you I’m the person for the job?
  • On a scale of 1 to 10 how did I do today?
  • What’s the best interview you’ve ever lead? How did I compare?
  • I’m hungry, where does one find the best tacos around here?

Questions for Teens that Aren’t Yes or No (108-112)

If you have a teen in your family, work with one, or just want to interact better with the younger folk, give these questions a try.

  • Would you rather have $1 Million right now or free food everywhere you go for the rest of your life? (only you are allowed to eat the food)
  • You’ve been selected on a deep space mission, who would you pick to go with you, knowing that you will never see anyone else again?
  • What is one skill that you have that will prove useful for the rest of your life?
  • What is the hardest thing you’ve ever had to do?
  • What is your best argument for the world being flat? Sell it like you believe it!

I hope you enjoyed these thought provoking questions!

Do you have some of your own? Email me and I will add them to the post if I deem them worthy of admission.


PS: For more see this list of 213 Questions!