Asking questions breaks the ice and helps us find out more about others. However, not just any question elicits the desired response. This article provides thought-provoking questions designed to get one’s attention, requiring both the asker and answerer to think about their attitudes and opinions. We have both funny and serious questions, for both guys and gals. Whatever direction you wish the conversation to take, we have a question to help you get there.

Funny Thought Provoking Questions

A good sense of humor is an admired personality trait. Exhibit yours or find out if a friend or colleague has one by asking one or more of the following questions. Some are subtle, and some will make the person to whom you are addressing the question laugh out loud. Have fun!

  • Have you ever smiled at a stranger and then wished you hadn’t? Why or why not?
  • If you could eat as much of one food as you wanted without ever getting full or fat, which food would you choose?
  • If you could shop for free at any store, which store would you choose and why?
  • If you were one of the seven dwarfs, which one would you be?
  • If your pet could talk, what would it say to you?
  • What action or activity makes everyone doing it look stupid?
  • What comedy or drama movie would you make into a musical and what would be the name?
  • What is something popular now, but everyone will look back at five years from now and think it is stupid and embarrassing?
  • If you could make any small animal as large as a cow, which animal would you choose and why?
  • If you could make one thing illegal, what would it be?
  • There are people who believe the world is really flat. How would you convince them it isn’t?
  • What is the most embarrassing clothing item you have ever worn?
  • What is the silliest thing you have ever done?
  • What is the weirdest thing you have ever seen someone do?
  • What rumor or conspiracy theory would you start and how would you start it?
  • What superhero would improve the world most if he/she existed?
  • Who is the funniest person you know and why do you consider them the funniest?
  • Do you go online when feeling bad to diagnose your disease?
  • Do you speed when no one is watching?
  • Have you ever intentionally broken the law? When, where, and how?
  • If you could be an animal, which animal would you be and why?
  • If you could have a personal chef or a live-in maid, which would you choose and why?
  • What fictional character would you like to become real and why?
  • Are there any unwritten rules where you work? If so, what are they?
  • Do you prefer salty or sweet treats and snacks?
  • If you went to a store, what three items could you buy that would make the cashier uncomfortable?
  • If you were given $500 to spend on anything you wanted, what would you buy?
  • What is something you recently realized that you can’t believe you didn’t realize earlier?
  • What would be the worst name you might give a son? A daughter?
  • What would your family and friends think you had done if you were arrested?
  • Which would you rather be in, an insane asylum or prison? Why?
  • Would you describe yourself as a good loser when playing cards and board games?

Deep Thought Provoking Questions

Deep Thought Provoking Questions

These interesting, thought-provoking questions work well when you really wish to get to know someone. Try one or more with friends or family, in dorm rooms, classrooms, and at dinners when you want to start a stimulating conversation. You will find that many of them begin a long, interesting conversation. Choose wisely; you may discover more than you desire.

  • If you had enough money that you never needed to work again, what would you do with your time?
  • If you had to lose a body part, which one would you choose and why?
  • If you were given only one week to live, how would you spend it?
  • Who should be responsible for taking care of the elderly? The family, the government, or should the elderly take care of themselves?
  • Have you passed up any chances that you now regret? What were they?
  • How would you describe yourself in ten words or less?
  • If they made a movie of your life, what would the title be? Would it be drama, comedy, or musical?
  • If you could start your life over and change one thing, what would you change?
  • If you were told you would live forever, what would you change about your life?
  • What are you most afraid of?
  • What do you believe is keeping you from complete happiness?
  • What do you consider your greatest strength? Your greatest weakness?
  • What do you think is your greatest achievement in your life so far?
  • What do you think people will say at your funeral about you and your life?
  • What is one way two countries considering war could settle their differences without violence?
  • If you could be granted one wish of any kind, what would you wish for?
  • If you had no physical, financial, or other obstacles, what skill would you like to have?
  • What did you think you would be when you were a child?
  • What have you tried lately that is new and exciting?
  • What makes you happiest and when you think about it you cannot help but smile?
  • What one thing did you do in the last twenty-four hours to make someone’s life better or more enjoyable?
  • What was the greatest adventure in your life so far?
  • When you are old and look back on your life, what do you think will matter most to you?
  • Where in the world would you most like to live and why haven’t you moved there?
  • Who had the greatest impact on your life? What was it?
  • Whose life do you believe you have had the greatest impact on? What was it?
  • Would you lie to your friend or spouse for a large sum of money? How much?
  • Would you rather drive a luxury vehicle or a more practical one? Why?

Thought Provoking Questions to Ask a Girl

Thought Provoking Questions to Ask a Girl

Although there are times for cute, probing questions, sometimes you wish to know more about a person than their favorite color and book. Our thought provoking questions to ask a girl are, as the name implies, designed to elicit some deep thoughts and uncover truths about someone’s life and beliefs. Whether you are using them on a date or to get to know a friend better, you will find many of these questions lead to long, interesting conversations. Make sure you pick the perfect questions for that special gal.

  • Do you really enjoy wearing make-up or do you do so because of peer pressure?
  • Who or what would you sacrifice your life for?
  • What would you choose to do to improve yourself?
  • Do you prefer wild clothes with pattern and color, or more conservative attire?
  • What single person in your life has most impacted who you have become?
  • Do you believe the future will be better or worse than the present? Why or why not?
  • Are some people’s lives worth more than others? Why or why not?
  • Do you believe war can be ever be ended completely or is it inevitable that wars will continue?
  • Are you ever lonely, even when in a crowd? Why or why not?
  • Is there anything that keeps you awake at night? What and why?
  • Would you take a vacation away from all technology? For how long?
  • What do you think is the nastiest tasting food?
  • What animal would you most like to have as a pet if you were guaranteed it would be tame and friendly?
  • What product would you stockpile if you found out it was not going to be sold anymore?
  • Would you rather wear a t-shirt and cut-off denim shorts, or a fancy outfit?
  • Have you ever seen or experienced extreme poverty? When and where?
  • What do you think is the biggest mistake parents make in raising children?
  • What was your most embarrassing moment?
  • What do you believe is standing in your way of achieving complete happiness?
  • If your entire life was a movie, who would play you?
  • If you showed someone a film of everything in your life, would they consider it a drama or a comedy?
  • If you could ask any person any question which they had to truthfully answer, who and what would you ask?
  • Are you happy with what you do and have in your life?
  • If you could start your life over, what would you do differently?
  • If you could travel to any place in the world, where would you go?
  • Do you have any bad habits you wish you could break? What are they?
  • Do you have any crazy or weird family members? Who are they and what are they like?

Thought Provoking Questions to Ask a Guy

Thought Provoking Questions to Ask a Guy

Many guys are naturally reticent when it comes to talking about themselves. This can make it difficult knowing those little details that help us understand someone and know more about them. When you want to know more about that special guy, use these thought provoking questions to discover what he is really like.

  • What hobbies or free-time activities do you enjoy the most?
  • What is the first thing you notice about a girl?
  • What is the craziest thing you have ever done?
  • Would you rather stay home for a good meal and a movie or go out?
  • At what age did you have your first crush? What happened?
  • What person, event, or idea has impacted your political beliefs the most?
  • What one thing could our government realistically do to improve our lives?
  • What is the worst movie you have ever seen? The best?
  • Which food do you most often crave?
  • Is lying ever the right thing to do? When?
  • If you opened a business, what would you sell and why?
  • What one appliance would you rather not live without?
  • Whose advice do you almost always listen to? Why?
  • What is your dream job and have you done anything towards getting it?
  • What are you most afraid of?
  • Do you think robots will ever take over the world? Why or why not?
  • If you could learn any new skill, what would you choose to learn?
  • What are three occupations you believe robots will replace first?
  • What do you believe is the most the most worthwhile goal an individual can dedicate their life to?
  • What has been the greatest adventure in your life so far?
  • What movie made you cry?
  • What period of history would you most like to live in? Why?
  • What would you consider to be a wasted life?
  • What’s your favorite sport to watch? To participate in?
  • Who is your biggest hero?
  • What do you believe is your greatest strength? Your greatest weakness?
  • What do you think makes you special?
  • What is integrity? Do people still have it? Why or why not?
  • If you had a friend who spoke to and treated you the same way you speak to and treat yourself, would you remain friends?
  • If you lost everything you own tomorrow, who would you run to in order to feel okay?
  • Is there a difference between living and existing? What is it?
  • Is there anything or anyone you passed on that you now regret?
  • Is there anything you are holding on to that you should let go? What? Why do you keep holding on?
  • Who do you consider the hero and the villain in your life?
  • Would you break the law to save someone you loved?

This article has provided some of the best deep and thought-provoking questions to ask someone with whom you wish to establish a deeper relationship. Some may prove challenging to answer. Answers are neither right or wrong, but designed to make both the asker and answerer think. Choose carefully and find the right question for your specific special person and occasion. Ask away!

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