83 Hypothetical Questions – Fun, but nearly 2021

sparrow jack
sparrow jack March 20, 2021
Updated 2021/04/26 at 9:53 AM

Here are the 11 best hypothetical questions:


1. You’re Walking In A Forest And You Found A Black Suitcase. Inside It, Holds 1 Million Dollar And A Piece Of Paper Stained In Blood With A Single Word “Don’t”. Would You Take The Suitcase Home Or Leave It?

It’s the start of a great story, if people make the right hypothetical choices.

2. You Are At War. Deciphering An Intercepted Code, You Learn Two Things About Your Enemy. A Single Spot In Their Defense Will Be At Its Weakest In Ten Days, And They Will Attack On Of Your Cities In Five Days. What Do You Do With This Information? What Is The Most Efficient Course Of Action?

Is victory or defending others the most important thing in life and war?

3. If You Could Really Sell Your Soul To The Devil, What Would You Sell It For?

The oldest bargain on offer, but what would actually make it worth it?

83 Hypothetical Questions – Fun, but nearly 2021

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4. You Find A Book And Begin To Read Only To Discover That It Is Your Life. You Get To The Point That You Are At Now, Do You Turn The Page Knowing That You Will Not Be Able To Change The Events To Come?

Would knowing the future be exciting or spoil the adventure?

5. If You Were Really A Robot, Would You Want To Know?

A deep question about how we define ourselves.

6. If You Got To Choose Between Fifty Years Of Being Incredibly Happy Or To Live Forever And Be Unhappy What Would You Choose?

What price would you pay to be immortal?

7. If You Could Learn Any One Skill In The World Without Trying (Like Matrix Learning Style), Which Would You Pick?

Find out what skills people really wish they had.

8. You Are Offered A Pill That Makes You 25% More Intelligent But Permanently Removes Your Hair Including Eyebrows. Do You Take It?

A fun way to examine the worth of beauty vs. intelligence.

9. If Jurassic Park Were Real, Would You Visit It?

An incredible vacation, although that park does have questionable security.

10. If A Zombie Plague Were To Start Right Now, Where Would You Hold Up?

Who doesn’t enjoy a good hypothetical zombie apocalypse?

11. If You Could Change One Thing About How The Human Body Has Evolved, What Would It Be?

Give everyone jetpacks on their feet, obviously.

11 Hypothetical Conversation Starters Questions

Getting beyond introductions is perhaps the hardest part of a conversation.

To life hack those problems, just use some of these hypothetical conversation starters to introduce interesting and amusing topics everyone will want to talk about.

Here are the 11 powerful hypothetical conversation starters questions:

12. If You Were A Superhero, Which Of Your Friends Would You Pick As Your Sidekick? And What Would Your Respective Powers Be?

A question about friendship and cool powers. Sure to get people talking.

13. What Historic Figure Would Make The Worst Ghost To Be Haunted By?

Who would be the most annoying or terrifying ghost from all history? A lot of options.

14. If You Could Ask Your Future Self From The Year 2050 One Question, What Would It Be?

Find out what people really want to know about the future.

15. Would You Accept A $30k/Week Job Offer Where You Get Paid To Sit In A Pitch Black Room And Do Nothing For 8 Hours A Day?

How much is that money worth to you?

16. If You Could Only Listen To One Band For The Rest Of Your Life, What One Would You Pick?

This isn’t just a favorite band, it’s one that would keep you from going crazy after so much repeated listening.

17. Would You Rather Travel For The Rest Of Your Life (Only Staying In One Place For Like 3 Months), Or Never Leave Your Home State Again?

This tells a lot about how a person approaches life.

18. If You Could Breed A Hybrid Animal Of Any Two Species, What Two Would You Choose?

The options are endlessly amusing: from the dog-whale to the pig-fish.

19. What Amount Of Money Per Month Would It Take For You To Give Up Your Mobile Phone Forever?

A dollar sign that says more about phone obsession than the cash in hand.

20. Would You Rather Be A Deep Sea Diver Or Astronaut?

Decide the best hidden world to explore.

21. Would You Prefer To Live In The Sahara Or In Antarctica?

Which extreme is worse?

22. If You Were To Lose All Five Of Your Senses, How Would You Know If You Were Truly Alive?

A really deep thinker that leads to some very existential questions.

11 Hypothetical Questions To Ask A Girl

Use hypothetical questions to ask a girl something she hasn’t been asked a million times. These questions will help her to really open up and tell you about herself.

Here are the 11 powerful hypothetical questions to ask a girl:

23. If You Had To Give Up Television Or The Internet, Which Would You Choose?

Find out where she goes for most of her screen time.

24. If You Were The President Of The United States, What Would You Do On Your First Day?

A great way to find out about her feelings about society and what needs to change.

25. If You Owned A Bar, What Would It Look Like?

Give her a chance to design her ideal watering hole.

26. If The Job “President Of Earth” Actually Existed, Who Would You Want To Be Doing It?

Is she power mad or timid at heart?

27. If You Were Going To A Famous Historical Figure Dress Up Party, Who Would You Go As?

A great way to find out who and what she admires.

28. Would You Rather Live For Another 60 Years But Not Be Able To Leave Your House Ever Again, Or Live For 10 More Years And Be Free To Go Where You Wanted?

Is life about the time or the quality of the experience?

29. If You Had To Describe Your Life In 20 Words Or Less, What Would You Say?

Get her to summarize her whole life for you in a couple sentences.

30. If You Could Relive The Last Year, Would You Change Any Decisions You Made? If You Would, Which Ones?

This opens a whole conversation on regrets and missed chances.

31. If You Could Have Complete Knowledge Of Any 5 Things, What Would You Want To Know?

What is she really curious about?

32. If You Were Invisible For 12 Hours, What Would You Do?

A fun question that lets her imagine all the hijinks she could get into.

33. If You Ran Google, What Would You Do Differently?

Save the world or make even more money: get her priorities.

11 Hypothetical Questions To Ask Friends

Having some hypothetical questions to ask friends makes sure you never run out of fun things to talk about. Use some of the questions below.

Here are the 11 awesome hypothetical questions to ask friends:

34. In The Event Of A Zombie Apocalypse, What Would Your Hand Weapon Of Choice Be?

Always go for the chainsaw.

35. If You Could Organize A Car Race For You And Your Friends Where You All Drive The Same Car, What Car Would You Pick?

Just imagining the car race makes the question worth asking.

36. Which Ninja Turtle Is The Best? And Which Would Beat All The Others In A Fight?

Perhaps the toughest question on this list.

37. If When You Die, You Are Given The Choice Between Finding Out What Is Next Or Staying On Earth As A Ghost To Wander The Planet Alone For Eternity, Which Would You Choose?

This makes people question how brave they are when facing the unknown.

38. Imagine You Are On Top Of A 40 Storey Building, There Is A Giant Inflatable Landing Pad At Street Level, Its Big Enough That You Have A 95% Chance Of Surviving The Jump. Would You Jump Off To Save A Friends Life?

A lot of pressure on this one with other friends sitting around.

39. If, For Some Reason, Computers Had Never Been Invented, Do You Think The World Would Be A Better Place? Explain Your Answer 🙂

Deep and sure to lead to a long, interesting debate.

40. If You Could Buy Any Existing .Com Domain, Which Would It Be?

Mantelligence.com. Obviously.

41. You’re Fighting A War, You Can Pick Between Having A Tyrannosaurus Rex Or A Tank On Your Side, Which Do You Choose?

Fight the hypothetical battle out between the two for extra fun.

42. How Do You Think Your Life Would Change If You Didn’t Need To Sleep? What Would You Do With The Extra Time?

A deeper question that lets everyone examine how they use the time they have.

43. Would You Rather Know All Of The Languages In The World, Or Know How To Play All Of The Instruments?

Communication or music: what’s more important?

44. If You Had To Get $10,000 By Tomorrow And No Bank Would Give You A Loan, What Would You Do?

This can lead to the best bank heist ideas at the table.

12 Interesting Hypothetical Questions

Hypothetical questions are, at heart, all supposed to be interesting questions. Use these to add a little more quality to your next conversation.

Here are the 12 best interesting hypothetical questions:

45. If A Person Could Go To The Center Of The Earth, What Would Be His Weight ?

A question for the physicist at the table.

46. Does The Fact That We Don’t Know Of Anyone From The Future Time Traveling Back To Our Time (Or Our Past), Prove That Time Travel Will Never Be Possible?

This can lead to all sorts of explanations why we don’t see time travelers everywhere.

47. If Animals Had Evolved At The Same Rate Of Humans (In Terms Of Intelligence), What Do You Think Would Be The Dominant Species On Earth Today?

The emperor penguin: it’s more than just a name.

48. How Would The World Be Different If Humans Commonly Ranged Anywhere From 4 Foot To 12 Foot Tall?

Other than different sized doorways, what else would happen?

49. What Do You Think Would Happen If It Was Somehow Proved There Was No God And Every Religion Is Pointless?

A tough question full of huge consequences.

50. What Do You Think Would Happen To The World If Somehow One Religion Was Proved Beyond A Doubt To Be Correct And All The Others (Including Atheism) Were Useless?

A twin to the question above. It’s sure to lead to lively debate.

51. How Would You Change Your Life Today If The Average Life Expectancy Was 400 Years?

A deep question about how our assumptions about time affect us.

52. Two Kingdoms Are Poised To Erupt Into War, The Course Of Which Will Kill Many Of The Populations On Both Sides. War Can Be Avoided Through Marriage Of A Princess From One Kingdom To The Prince Of The Other. The Marriage Will Be Loveless. Should The Marriage Be Forced?

Is the good of many outweighed the misery of a few, or not?

53. If The Government Gave You The Responsibility Of Coming Up With A Plan To Combat Online Piracy, What Would You Do?

Put yourself in the public policy chair and solve one of the world’s biggest problems.

54. If You Were A Scientist, You Rather Discover Something Huge, But Die Before Tell Before Telling Someone, Or Discover Nothing At All?

Is the point of discovery the knowledge or the fame you get from it?

55. Do You Think The World Would Be A Better, Worse Or Just Different Place If All Land Was Connected (Like It Was Millions Of Years Ago)?

Would we get along better or far, far worse?

56. How Long Do You Think You Would Survive If Food Stopped Being Shipped And You Had To Grow It / Forage It Yourself?

Find out who you know is a real survivor.

11 Random Hypothetical Questions

Sometimes, the best answers to hypothetical questions come from random questions. Throw a few curve balls using these questions.

Here are the 11 awesome random hypothetical questions to ask:

57. How Would You Change How You Live Your Life If Life Was Like A Video Game Where You Respawn Back At Home After Dying?

A great way to imagine the crazy adventures re-spawning would allow you.

58. If You Had To Describe Each Of Your Friends With You Right Now Only Through Hand Signals (Like Sign Language), How Would You Do It?

A lot of fun to be had from translating those hand signals.

59. If You Had To Be Renamed After One Of The Planets In The Solar System, Which Would You Pick?

Uranus is obviously right out.

60. Do You Think The World Would Be A Better Place If Someone Like Iron Man Really Existed?

Dream up a world of superheroes and imagine the real consequences.

61. Imagine You Lapsed And Cheated On Your Partner – You Felt Horrible And Knew You’d Never Do It Again, Would You Confess?

One of the all-time tough hypotheticals.

62. If You Were The Captain Of A Pirate Ship, What Would You Name Your Ship? And What Would Your Title Be?

A great game to play over a few rums.

63. If You Were To Have Either A Teleporter Or A Time Travel Machine, Which One Would You Want?

Would it be better to go anywhere or anytime?

64. What Would Win A Fight Between A Rhinoceros And Hippopotamus?

Work the battle out yourselves.

65. You Can Make One Change To Any Winter Olympic Sport To Make It More Exciting, What Would It Be?

Ice hockey with a beach ball or bobsled without the sled?

66. If All Swear Words Became Socially Acceptable, What Existing Word Would You Use To Replace Them?

Try it in practice for extra fun. Oh, cottage cheese!

67. If You Could Send Yourself From 10 Years Ago A Message No Longer Than 20 Seconds, What Would You Say?

Invest in Bitcoin? Or would it be more personal?

9 Funny Hypothetical Questions To Ask

If hypothetical questions are good for anything, it’s a good laugh. Use these hypothetical funny questions to ask something sure to add a little comedy to your conversation.

Here are 9 funny hypothetical questions to ask:

68. Why Do We Drive On Parkways And Park On Driveways?

A question for the ages.

69. Why Is It That If Someone Tells You That There Are 1 Billion Stars In The Universe You Will Believe Them But If They Tell You A Wall Has Wet Paint You Will Have To Touch It To Be Sure?

This may require philosophical, and potentially messy, answer.

70. Would A Fly Without Wings Be Called A Walk?

Sure to get a groan and a laugh, but what would it be called?

71. Why Are There No ‘B’ Batteries?

Sure to elicit an online search for these mythical object.

72. When Does It Stop Being Partly Cloudy And Start Being Partly Sunny?

A real test in defining terms.

73. If A Kid Refuses To Sleep During Nap Time, Are They Guilty Of Resisting A Rest?

A question sure to get an exhausted laugh from every parent.

74. If God Sneezes, What Should You Say?

You bless you?

75. If A Bunch Of Cats Jump On Top Of Each Other, Is It Still Called A Dog Pile?

Or is it a cat dog pile?

8 Deep Hypothetical Questions To Ask

Add some depth to your conversation with hypothetical deep questions to ask. Use these hypothetical questions to lead your conversation in far more thoughtful directions.

Here are 8 deep hypothetical questions to ask:

76. You Lost Your Fortune, Everyone Turns On You. You Manage To Get $1000, What Will You Do With It To Work On Creating Wealth Again?

A unique way of examining the best ways to get rich.

77. Would You Rather One Of Your Dreams Came True, Or Two Of Your Best Friends’ Dreams?

Selfishness or altruism, what matters more?

78. If Time Can Be Divided Into Infinitely Decreasing Segments, Does That Mean We Live Infinitely Long In Just One Second?

A great way to examine the nature of time.

79. If The Whole World Was Going To Die Out, Would You Sacrifice Your Self To Save It Or Let Yourself Live And Everything Else Die?

Is your world defined by you or by everything around you?

80. If The World Was “Reset” To The Same State It Was 5,000 Years Ago, Do You Think By The Time The Alternate World Got To Our Timepoint, Would It Look Much The Same? Or Would It Be Quite Different?

You’re asking if things must happen as they have or if it was all chance.

81. Would You Live Your Life Differently If Nobody Would Ever Judge You For Anything You Did?

Do you behave as we do because of our morals or because others watch and judge us?

82. How Do You Think The World Would Be Different If Advertising Didn’t Exist? Do You Think We’d All Be Better People, “Wanting” Less? Or Is It Human Nature To “Want More”?

A question straight to the heart of what it means to be human.

83. If Animals Could Talk, Or At Least Communicate In A Basic, Intelligent Manner, How Do You Think The World Would Change? Would You Still Eat Meat?

A vegetarian vs. meat-eater question for the ages.

Downloadable And Printable List Of Hypothetical Questions

Here is a downloadable and printable list of hypothetical questions (right click the image and select Save Image As…):

More Great Questions To Ask

If you’re looking for more great questions that go a little beyond the hypothetical, Mantelligence has even more on offer. Try some of these:

  1. Looking to get a little strange? Try these weird questions to ask.
  2. Go a little deeper in the speculative with these what if questions.
  3. Keep digging deeper with some philosophical questions for your next gathering.

How To Ask Hypothetical Questions

Asking hypothetical questions are as easy as they are fun. Just follow these 3 tips to introduce them into any conversation.

Here’s how to ask hypothetical questions:

1. Know Your Audience

Make sure your audience will be game for a few questions. Find people with fun, creative minds that like to be a little intellectually playful.

2. Know Your Questions

Choose questions that fit the mood of the people and the place you’re asking. Don’t ask a risqué question at a business meeting, and don’t go too bland when hanging out with friends at a bar.

3. Know Your Moment

Some questions are great to start a conversation, some to add something midway through. Pick the right moment for your question, then ask away.

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