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We know, we know. Playing Would You Rather is somewhat tedious because it’s just so hard to think of questions!

But what would you say if we told you that we’d help you in that area?

How to Play Would You Rather

Before we go on any further, just if you’re playing with someone new, here’s a simplified version of the rules.

Step 1: Gather all players. The primary purpose of this game is to get the players to interact with one another.

So be it having everyone in the same room, in a call, whatever it is– for as long as everyone gets to talk to each other.

Step 2: Talk about how the turns will go. This is to make it easier for

25 Hard Would You Rather - Questions You Can Go With

If the rounds are going too fast, maybe we’d suggest introducing harder questions. Questions that will really get players to think.

Here are some Would You Rather questions that are really hard to answer. We (secretly) hope everyone struggles! 😈

1. Would You Rather be with someone you love or with someone who loves you?

Sometimes being in love with someone who doesn’t love you back causes more pain than it should. Then again, to be loved by someone who you don’t love can also be problematic. Which life would you rather have?

2. Would You Rather be the first to die or the last?

The underlying question here is: Would you rather die feeling lonely or feel like you weren’t done living?

3. Would You Rather be a child and never grow up or instantly be an adult and never age?

Children always say that they “can’t wait to grow up,” but little do they know that all adults want is to be a kid again. There are pros and cons to both choices. Discuss!

4. Would You Rather lose all the money that you worked for or lose all your memories?

What’s the point in having all the money in the world if you can’t remember the things you love, right? Ah, the debate to choose love and money. Always a hard decision.

5. Would You Rather know the date of when you’ll die or the cause of it?

If you know the cause of your death, you might end up living out of fear, whereas if you know the date, you might get that YOLO mindset and end up being careless. Either way, there are pros and cons to everything.

6. Would You Rather work in your dream job but be paid only minimum wage or at a job you hate but pays well?

Happiness or Wealth? One of life’s most challenging questions.

7. Would You Rather have a one-night stand then accidentally get pregnant or hear the words “I have STD” the morning after?

Both options are something no one wants to hear– ever. But if you had to, which would you rather experience?

8. Would You Rather always bite your tongue whenever you eat something or always stub your toe on corners?

So much pain in one sentence 😫 We can’t even choose ourselves!

9. Would You Rather find your one true love or win the lottery?

Would it be worth it to have all that money if you can’t share it with someone? Hmm? 🤔

10. Would You Rather always tell the truth or to always tell a lie?

We all know that telling a lie is sometimes necessary. But at the same time, telling the truth is always better.

11. Would You Rather watch only badly produced movies for the rest of your life or not watch anything at all?

Both options can make your life slightly more boring. Pick your poison!

12. Would You Rather use hot sauce for eye drops or sandpaper for toilet paper?

It’s hard to even think about choosing from either one of the options.

13. Would You Rather always be overdressed or underdressed?

There can be some instances where either option can be embarrassing. This will be a fun conversation to have!

14. Would You Rather find out if God is real or have the cure to cancer?

One of life’s most challenging questions that everyone wishes they can address.

15. Would You Rather be cheated on by your husband/wife or stay in a marriage that’s already dead?

Both options will require so much effort and sacrifice. You might be surprised by which option one chooses!

16. Would You Rather know about your future or go back in time to change something in the past?

Many people have a “live in the moment” mindset, which makes this question hard. They probably want to avoid getting anxious about the future.

17. Would You Rather always fight with family or never really have true friends?

Either way, you should always have good people by your side, no matter what!

18. Would You Rather be the lenient parent with a child who’s hard to control or the scary parent with a child who’s terrified of you?

As a parent, there’s nothing you want more than to keep your child safe. So which way would you rather choose to bring them up?

19. Would You Rather lose all of your teeth or all your hair?

Losing either would suck for anyone!

20. Would You Rather apologize for something you didn’t do or be looked down on for not confessing?

You might be surprised by which option people choose. It can say a lot about their personalities!

21. Would You Rather have a happy family but living in poverty or live in comfort but with a broken family?

Family and money have always been hard to choose from.

22. Would You Rather be able to change only one thing in your life or have a do-over?

You could have that opportunity to change one major thing that happened to you or simply just do everything all over again and hopefully lead a different life.

23. Would You Rather make the same mistakes over and over again or to never be given a 2nd chance at anything?

It’s hard never to be able to learn from your mistakes – or to improve yourself.

But at least, even if you’re never given that second chance, you get to move forward with your life.

24. Would You Rather have a prolonged and painful death or a quick and sudden one?

Most people fear leaving the world suddenly. Not being able to say resolve anything.

But everyone should also be scared of suffering a painful death. This could be an interesting discussion!

25. Would You Rather lose your sense of taste or sense of smell?

Imagine never being able to genuinely enjoy food. That sucks!

Final Reminders

Don’t forget that these questions have players really think about their answers. It should still be fun, nonetheless!

If you find these Would You Rather questions too hard to answer, you can head over to this link for other themed Would You Rather questions!

From questions for couples, funny questions, and even the drinking version of Would You Rather! You’d find it all there.

Have fun!

✍️  October 28, 2020

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