Hard would you rather questions are great to have on hand to have a great time with your friends. If you're looking for good questions to ask in a conversation, you're in the right place.

Would you rather questions are fun, and I've got a lot of those for you, but here, we'll take it up a notch and go for the hard to answer but more interesting questions.

Let's start enriching your next conversation.

41+ Deep & Hard Would You Rather Questions [2023]


15 Best Hard Would You Rather Questions For Worthwhile Conversation

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

Because if your inquiry just gets you a "yes" or "no" answer, you're not likely to discover much about your conversation partner.

But if you use a great would you rather question, you'll end up with a lengthy response that tells you not just an exciting answer... but something interesting about the person. You might even get a glimpse of their entire life. In short, tough questions like these are meant to make the conversation interesting, not dull.

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. This topic makes an interesting debate.

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

Another one that makes people decide the way they most love to interact with and enjoy the world. When faced with a challenging situation like this, which would you rather lose to enjoy the other?

3. 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. It's a tough question, but some people already have a set answer.

4. Would you rather have real political power but be relatively poor or be ridiculously rich and have no political power?

Do they view political power and wealth as separate entities when really the two can be wielded as one? You'll perceive any limitations they have around how they view wealth's potential.

5. Would you rather have the power to gently nudge anyone’s decisions or have complete puppet master control of five people?

The latter sounds like a much more insecure person would leap on that chance at power play. Big red flag.

6. Would you rather live in a utopia as a normal person or in a dystopia but you are the supreme ruler?

You'll presence the quality of their hunger for authority or lack thereof.

7. Would you rather snitch on your best friend for a crime they committed or go to jail for the crime they committed?

How loyal are their friendships, and how afraid are they of jail?

8. Would you rather lose the ability to read or lose the ability to speak?

You'll understand whether the person values their input or their output abilities more right now. The juiciness of this inquiry is why they chose what they chose.

9. 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? Being the smartest person can open up opportunities for you, but being the richest, you can open opportunities for others.

10. Would you rather have a high-profile job with no family for life or an average career 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. Discuss more your dream job with this one.

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11. Would you rather create history or delete it?

This one tells you if someone is optimistic (wants to create more) or pessimistic (wants to destroy more) about life.

12. Would you rather have a criminal justice system that actually works and is fair or an administrative branch that is free of corruption?

You might find out where they perceive systemic issues are most to blame.

13. Would you rather be born again in a totally different life or born again with all the knowledge you have now?

You'll find out how satisfied they are with their current state of incarnation.

14. Would you rather create a great piece of art and not get credit or get credit for a work of art you didn't create?

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

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

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

7 Tough WYR Questions But Are Incredibly Funny To Ask

While many of the above questions are excellent 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 like you're the funniest person ever and giving you great "would you rather" answers.

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

These are two of the most uncomfortable but frequent mishaps that everyone hates. But make people choose anyway. This situation makes you think it would be hard to enjoy your favorite food. But it's uncomfortable to have such pain on your finger, too.

17. 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. These kinds of things don't leave some people's mind that fast.

18. 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. Coming up with ideas can make for a fun game.

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

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

20. 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?

An excellent question for when you're at the bar. It gives you a chance to look around at your options and decide which is less gross. When you think about it, though, some drinks or food are hard to eat half-finished, just like ice cream.

21. 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 a businessman or a teacher... Maybe it's not as bad as wearing wet socks your whole life.

22. 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. Let's hope either one doesn't give you bad breath.

6 Clean Quiz Questions Perfect For Would You Rather Game

Would you rather questions often get a lot of their humor from being raunchy. You can see some of the questions above have a slight 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 challenging conversations that stay clean.

23. 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 would be worse to deal with.

24. 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. It's a good question if you're looking to get more insights into your friend's beliefs.

25. 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 doesn't want anyone seeing their stuff. This one might seem like one of those silly questions, but it's not! But can you imagine your celebrity crush cleaning your house?

26. 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.

27. 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. I mean, if you think about it, an unflattering selfie counts as a dumb face, right?

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

Do we need more people or shelter more to survive? Maybe it would be nice not to have a noisy neighbor for a year.

7 Thought-Provoking Would You Rather Questions To Get To Know Her Better

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.

29. 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 beautiful, especially if it can only be one or the other.

30. Would you rather spend $10000 on shoes or clothes?

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

31. 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.

32. 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.

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

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

34. 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.

35. 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.

 6 Would You Rather Inquiries To Spice Your Relationship

Every couple has a moment, 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.

36. 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.

37. 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.

38. 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. Let's hope you share the same answer.

39. 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.

40. 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.

41. 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.

Downloadable and Printable List of Hard Would You Rather Questions

Here is a downloadable and printable jpg/pdf list of hard would you rather questions (right-click the image and select Save Image As...):

Frequently Asked Questions

With all those tricky questions, we're sure you have questions of your own. We're here to answer them for you.

Can you ask would you rather questions to someone you have just met?

Maybe they're not ideal for date night, but depending on the question, you can ask it. If you're unsure, it's best to go for questions that are more on the funny side.

How do you ask a would you rather question to older people?

Find out what kind of topic they'd like to talk about first. Explain to them how would you rather questions work and then work from there. 

How do you react to questions that will make you give an awkward answer?

Try to limit the awkward silence. Picture yourself as a kid. Kids can make awkward moments funny, so try your best to turn it around that way.

Do couples need these types of questions to make them know each other better?

Of course. Asking your partner any question that would turn into a deeper conversation is even better than receiving a love letter because you get to see deeper into their heart. Sometimes discussions about sour milk, toilet paper, or pinky toes make your connection deeper and stronger.

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 many 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. Like 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 the 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 exciting answers. No matter who you're talking to, there won't be any need to worry about getting a decent response. 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."