Hard Would You Rather - Main in postHard would you rather questions are great to have on hand because:

When you’re looking for a few good questions to ask in a conversation, there’s nothing better than the fail-safe “would you rather.” Would you rather questions are so great because they make the people you’re talking to make a choice.

Most questions have a built in escape option that allows someone to avoid hard decisions, that’s not the case with a “would you rather.”

Here you’re given a hypothetical and you have to pick option one or option two. No way out. Which leads to far more interesting conversations.

The trick, though, is getting a “would you rather” that is hard enough to make your conversation partners think. You don’t want a question that lets them off too easy, otherwise, it won’t lead to much conversation.

So, to enrich your next conversation, use these hard would you rather questions to get some great answers.

79 Extremely Hard Would You Rather Questions that Are Impossible to Answer

I recommend reading through all of these would you rather questions to find your absolute favorites… but if you’re looking for something specific, you can click the links below to jump to that section:

Contents

16 Best Hard Would You Rather Questions

The beauty of these hard would you rather questions is their simplicity.

Because if your question just gets you a “yes” or “no” answer, you’re not likely to discover much about your conversation partner.

But if you use a really great would you rather question, you’ll end up with a long response that tells you not just an interesting answer… but something interesting about the person.

Here are 16 of the best hard would you rather questions:

1. Would you rather be able to detect any lie you hear or get away with any lie you tell?

You’re asking if when pushed they’re more interested in the truth or getting away with lies.

Hard, Would You Rather - Would you rather be able to detect any lie you hear or get away with any lie you tell

2. Would you rather get with your boss to get promoted or give up the promotion?

Discover something about their ethics: what would they do to end up on top?

3. Would you rather be a hopeless romantic or hopeful unromantic?

Does your conversation partner feel it’s better to feel love or be loved?

4. Would you rather have too many friends or too few?

You can find out if deep down they are truly social or more introverted.

5. Would you rather have no taste buds or be color blind?

We all experience the world differently. Is there more joy to be found in tasting great food or in seeing all the colors of a sunset?

6. Would you rather never hear music again or lose the ability to read?

Another question that makes people decide the way they most love to interact with and enjoy the world.

Hard, Would You Rather - Would you rather never hear music again or lose the ability to read (1)

7. Would you rather find true love or be rich?

Money and love are perhaps the two biggest priorities in life. Find out which is more important to them.

8. Would you rather be the richest person in the world or the smartest?

Another tough one with money at the center. Money or intelligence, what would make life more enjoyable?

9. Would you rather have a high profile job with no family for life or an average job with a family to live by?

People make this choice every day in how they pursue their goals. Bring that choice out into the open.

10. Would you rather create history or delete it?

A question that tells you if someone is optimistic (wants to create more) or pessimistic (wants to destroy more) about life.

11. Would you rather create a great piece of art and not get credit or get credit for a piece of art you didn’t create?

This can lead to a great conversation about whether it’s better to be creative or successful at all costs.

Hard, Would You Rather - Would you rather create a great piece of art and not get credit or get credit for a piece of art you didnt create

12. Would you rather age from the neck up or the neck down only?

A bit silly, but you’ll learn if the person is vain or more interested in what their body can do for them.

13. Would you rather leave your unemployed son homeless or pay for his drug habits and illegal activities?

This question has far-reaching implications for our society.

14. Would you rather see the world but live in poverty or stay in one place and live rich?

You’re really asking whether this person define themselves by experiences or comforts.

15. Would you rather become famous or powerful?

A question for our age: is there more to be gained by being known or by having secret power?

16. Would you rather become a creative person or a technical person?

Find out if they wish they could be artistic or scientific.

Hard, Would You Rather - Would you rather become a creative person or a technical person

18 Hard, Incredibly Funny Would You Rather Questions

While many of the above questions are great in their own right, sometimes you want to make your would you rather questions funny.

Nothing gets people into a good conversation better than the chance of a good laugh. Having funny questions to ask takes care of that for you. Using one of the questions below ensures you’ll get them smiling and laughing, and giving you great “would you rather” answers.

Here are 18 hard, but incredibly funny would you rather questions:

17. Would you rather get a paper cut between your fingers every time you touch paper or bite your tongue every time you eat something?

Two of the most uncomfortable but frequent mishaps that everyone hates, but make people choose anyway.

18. Would you rather have legs as long as your fingers or have fingers as long as your legs?

This question directly leads to the equally funny conversation about what exactly you’d do with those long fingers and super short legs.

19. Would you rather wake up in the morning looking like a giraffe or a kangaroo?

The mental image alone will get a few chuckles, then think of the consequences.

20. Would you rather walk in on your parents making out or have them walk in on you making love?

You’ll get a lot of laughing “ewws” for this one, and the grossed out debate will be fun.

Hard, Would You Rather - Would you rather walk in on your parents making out or have them walk in on you making love

21. Would you rather have a foot long nose or a foot long tongue?

The best part of this is the discussion of just what you could do with those foot-long organs.

22. Would you rather eat a small can of dog food or six overripe bananas?

This is another good chance to get some laughs from the eww factor; unless your friends enjoy a good can of dog food.

23. Would you rather drink all the half-finished drinks in the bar or eat all the half-finished food at the end of the night?

A great question for when you’re at the bar. It gives you a chance to look at around at your options and decide which is less gross.

24. Would you rather bleach your hair neon green for the rest of your life or only have one eyebrow?

An easy question for a punk, but for a businessman or a teacher…

25. Would you rather brush your teeth with hot sauce or with ranch dressing?

Someone is bound to think ranch dressing isn’t that bad an idea.

Hard, Would You Rather - Would you rather brush your teeth with hot sauce or with ranch dressing

26. Would you rather be able to speak whale or read babies’ minds?

A nonsense question that may just lead to some interesting answers.

27. Would you rather have a head too big for your body or a high pitched baby voice?

Just wait until everyone gives their best baby voice impressions.

28. Would you rather have two permanent lazy eyes or always get nose bleeds at extremely embarrassing moments?

Working through the practical problems of either is almost as fun as the answer.

29. Would you rather accidentally “like” a two-year-old photo of your significant other’s ex whom you were in the middle of Facebook stalking, or accidentally send a sext to your mom?

You’re sure to get a nervous laugh here, since everyone’s been afraid of at least one of these.

30. Would you rather sound like Jar-Jar Binks for the rest of your life or Siri?

Give everyone a chance to practice their voice impressions after they make their choice.

31. Would you rather take a look at your Mom or your Dad’s internet history?

A good chance to find out which parent is more of a prude, and who people want to impress more.

Hard, Would You Rather - Would you rather take a look at your Mom or your Dads internet history

32. Would you rather give your wedding vows using only Family Guy quotes or using sign language you made up?

Ask this to couples who may be getting ready to tie the knot.

33. Would you rather your name be Little Caesar or Papa John?

You may just end up giving someone a new nickname after this one.

34. Would you rather see a happy picture of every animal you ate when it was still alive or go without meat for the rest of your life?

An easy question for vegetarians, hunters, and butchers, but for everyone else…

15 Hard but Clean Would You Rather Questions

Hard, Would You Rather - 15 Hard but Clean Would You Rather Questions

“Would you rather” questions often get a lot of their humor from being raunchy. You can see some of the questions above have a little edge that can turn talk to the more indiscreet.

But not every conversation needs to be raunchy, and sometimes you just need some clean would you rather questions to help enjoy the tamer side of life.

Use a few of the questions below for fun and hard conversations that stay clean.

Here are 15 hard, but clean would you rather questions:

35. Would you rather eat pizza every day or never be able to eat pizza again?

Perhaps the greatest food ever invented, but could you eat it every day?

36. Would you rather always get stuck in traffic or always have a really slow internet connection?

It’s tough to choose which of the two greatest annoyances of modern life it would be worse to deal with.

37. Would you rather have to hunt for everything you eat or eat only McDonald’s for every meal?

An easy one for hunters and fast food lovers, but everyone else will have to weigh this one carefully.

38. Would you rather have a higher IQ or a photographic memory?

This is a great way to find out just how people interpret the idea of being smart or a genius.

39. If you came into some money, would you rather invest or spend it all?

Use this one to open a conversation on whether we should live for the moment or plan for the future.

Hard, Would You Rather - If you came into some money, would you rather invest or spend it all

40. Would you rather spend all day cleaning someone’s house, or let your crush clean yours?

Find out who is a neat freak and who really doesn’t want anyone seeing their stuff.

41. Would you rather become a millionaire by winning the lottery or for some work you did?

Is the money worth it if you didn’t earn it? There’s a great discussion to be had there.

42. Would you rather be caught doing bathroom singing or making extremely dumb faces?

We’ve all got embarrassing stories about being caught being silly when we think we’re alone.

43. Would you rather spend a year all alone or without a home?

Do we need people or shelter more to survive?

44. Would you rather have a missing finger or two extra fingers?

The question itself is enough to get a laugh, and the answers will be amusing and still clean.

Hard, Would You Rather - Would you rather have a missing finger or two extra fingers

45. Would you rather talk like Yoda or breathe like Darth Vader?

Here’s an amusing chance to practice your Yoda voice and Darth Vader breathing while laughing about the consequences of always talking like that.

46. Would you rather be forced to wear wet socks for the rest of your life or only be allowed to wash your hair once a year?

It’s a tough call on which would be more uncomfortable, and which would make you less popular.

47. Would you rather stay forever at your current age or be 10 years younger?

This is a roundabout way of discussing what you think the best age to be is.

48. Would you rather have $1,000,000 now or $5,000 a week for the rest of your life?

To splurge or to spend smartly: that is the question.

49. Would you rather have your dream job or one that pays four times as much?

This one gives people the chance to talk about whether money or job fulfillment is more important to them.

Hard, Would You Rather - Would you rather have your dream job or one that pays four times as much

17 Hard Would You Rather Questions for Girls

Perhaps the questions we worry about the most are those we ask girls. After all, when we talk to friends or colleagues, even casual strangers, a question going wrong is easily laughed off.

But when it’s a question with a girl you’re interested in, you may only get one shot. So make sure you have great questions to ask a girl on hand. Keep a few of these ready for the next time you want a good “would you rather” question to intrigue the girl you’re talking to.

Here are 17 of the best hard would you rather questions for girls:

50. Would you rather be married to someone extremely attractive or be someone who is extremely attractive?

It’s a tough choice between being attractive and getting to be with someone attractive, especially if it can only be one or the other.

51. Would you rather spend $10000 in shoes or clothes?

Just let them imagine what they could buy with all that money.

52. Would you rather have great friends or a great boyfriend?

No matter her answer, get her to explain why and what she loves about either.

53. Would you rather give up Instagram or eat the same meal for the rest of your life?

Is she addicted to Instagram? You’ll know the answer if she struggles with this one.

Hard, Would You Rather - Would you rather give up Instagram or eat the same meal for the rest of your life

54. Would you rather have a good looking, rich and dumb boyfriend or an average, poor and caring boyfriend?

Money, looks, or emotional connection: what is she looking for in a partner?

55. Would you rather have the power to make anyone fall in love with you or be able to read minds?

Both are invasive, but one shows a need for love and the other a snoopy kind of curiosity.

56. Would you rather share a toothbrush with a random stranger or kiss a random stranger on the mouth?

A good way to judge if she’s a germaphobe. And also how open she is to kissing someone new.

57. Would you rather have your parents go through your text messages or your employer?

This is a good introduction to find out just what she likes to text about that she doesn’t want some people to know.

58. Would you rather eat at McDonald’s with a great guy or at a five-star restaurant with a jerk?

You’ll find out if she’s looking for the right guy or just the right perks.

Hard, Would You Rather - Would you rather eat at McDonalds with a great guy or at a five-star restaurant with a jerk

59. Would you rather look young and feel like an old person or look old and feel like a young person?

A little philosophical just under the surface: how do we define youth? And what is the best part about it?

60. Would you rather be allergic to chocolate or allergic to smartphones?

These may well be her two favorite things in the world. You’re making it hard for her with this one.

61. Would you rather have five ex spouses or never get married?

Is she desperate for a partner or independent enough to face life alone if she doesn’t meet Mr. Right?

62. Would you rather marry your soulmate who annoys you or settle for someone who is perfectly fine and makes you feel content but always know your soulmate is out there?

Again, a bit of a thinker underneath: what’s the purpose of love? And what makes a good relationship?

63. Would you rather date a guy who gets along with your family or gets along with your friends?

Finding out whose opinion matters more to her is a great way to know who to impress later.

Hard, Would You Rather - Would you rather date a guy who gets along with your family or gets along with your friends

64. Would you rather wear comfortable clothes or make a fashion statement?

This question leaves the door wide open for compliments about how she dresses. A sure winner.

65. Would you rather be invisible at a party or be the life of the party?

Most of us fall somewhere in between, but here she has to come down on either the shy or sociable side.

66. Would you rather try something new or stick to what you know?

Find out if she’s adventurous, and in what areas she’s a little more conservative.

13 Hard Would You Rather Questions for Couples

Every couple has a moment, every now and again, when the question arises: what is there to talk about?

If you spend all your time together, you know each other’s schedules and most of each other’s daily events. What you need are some questions for couples that can keep things interesting.

Basically, you need a set of questions to ask a girlfriend or boyfriend that can not only get a decent conversation going but that can lead to some quality talk that allows you to learn a little more about each other. Use these would you rather questions for couples to smooth over the gaps in your couple conversations.

Here are 13 hard would you rather questions for couples:

67. Would you rather release your diary or a film of your most embarrassing moment?

Use this as an introduction to discuss a few secrets and embarrassing moments you haven’t shared before.

Hard, Would You Rather - Would you rather release your diary or a film of your most embarrassing moment (1)

68. Would you rather receive a gift made by hand or purchase it from a store?

This is an easy way to get better ideas for future gifts.

69. Would you rather go to an expensive restaurant with great food or a cheaper one with a relaxed atmosphere and okay food?

A pretty important thing to know for future dates and anniversaries.

70. Would you rather eat the food prepared by your mom or your partner?

Who’s the better cook, Mom or you? If she says Mom, get some recipes.

71. Would you rather have your first child when you are 18 years old or when you are 40 years old?

Family planning is a bit part of a serious relationship. Find out if she’d rather start one now or wait a while.

72. Would you rather have a bad partner and a great love life or a great partner and a mediocre love life?

Hopefully it isn’t a choice between the two in your relationship, but still, find out which she wants more.

Hard, Would You Rather - Would you rather have a bad partner and a great love life or a great partner and a mediocre love life (1)

73. Would you rather fly all over the world with your true love or be marooned on an island with your favorite celebrity?

The world and island bits are just extra fun. This question tells you how much you like being together.

74. Would you rather stay up all night helping an irritating family member with a problem or babysit a baby that will not stop crying?

How good is your partner at dealing with annoyances? And which ones really irk her?

75. Would you rather get everything you want materially or find your true love?

It’s a chance to discuss the things you both want, and hopefully, to both agree that what you have now is better than any object to be purchased.

76. Would you rather have everyone know the details of your finances or the details of our love life?

Another question that can lead to a few shared secrets (financial this time), and to giggle over the scandalous things you’ve done together.

77. Would you rather have every photo on your phone play as a slideshow for your family or let your grandmother read your text messages?

Laugh over what grandma would say if she read your messages to each other.

78. Would you rather live with your parents or live with mine for the rest of your life?

If your relationship is serious, you can have fun here and still find out which set of parents you both get along with better.

79. Would you rather have someone do everything for you or do it yourself?

This one leads to important questions about independence and what you expect from each other.

Hard, Would You Rather - Would you rather have someone do everything for you or do it yourself

Downloadable List of Hard Would You Rather Questions

Here is a downloadable list of hard would you rather questions (right click the image and select Save Image As…):List of Hard Would You Rather Questions

Looking for More Great Questions?

“Would you rather” questions are by no means the be all and end all of the question world. In any situation, you want to have a lot of different kinds of questions at hand to ensure some variety.

Not to worry, though. We’ve got all the questions you need right here:

  1. Similar to the “would you rather” questions, get people to make some interesting choices with our this or that questions.
  2. If you want to make sure to keep it light and enjoyable, use some of our fun questions to ask.
  3. On the other hand, if you’re looking for something a little more engaging, take a gander at our interesting questions to ask page for a few ideas.

In Conclusion

If you’re in a situation where you need some questions to ask, there aren’t many better ways to go than these hard would you rather questions.

Once you’ve mastered a few of these hard questions, you’ll be able to ensure interesting answers. There won’t be any need to worry about getting a decent response, no matter who you’re talking to. Getting your conversation partners to think even as they’re entertained is the key to becoming a real master of conversation.

And with a good combination of the above would you rather questions, you’ll have the perfect retinue for any situation: Whether you’re at a party, a business conference, or just hanging out at a bar, you’ll have all the questions you need… and it should all start with a “would you rather.”