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If you’re looking for a fun way to get to know someone on a different level, playing ”Would You Rather” is your best bet.

Deep questions have a way of bringing out someone’s true desires. It has players thinking hard about their answers.

So if you want to understand the person you’re playing with, asking some deep questions during your Would You Rather game would add some fun!

How to play Would You Rather

If it’s the first time you (or your friends) are playing Would You Rather, here’s a simple rundown!

Step 1: Gather all players. The essence of this game is to communicate with one another. For as long as you guys can hear/see each other, the game will work fine!

Be it in person, or through video call!

Step 2: Decide on how the turns will go around. This is just so that we won’t miss anyone out. It also helps avoid the stress of having to think of questions on the spot.

Most people just have the turns go clockwise, but it’s really up to you. You could start from the oldest, or maybe even “who is the highest when you add all the digits of your phone number!”

Go creative!

Step 3: Have fun. Of course, this step is to ensure that people really engage and participate in the games. You’ll never know what kind of secrets you can unveil from playing Would You Rather

200+ Dirty Would You Rather Questions (18+)
Suggested read: 200+ Dirty Would You Rather Questions (18+)

25 of the Deepest Would You Rather Questions

We hope you guys really take some time to answer these questions! The following questions are definitely only for deep thinkers. Try them out and dive into a deep conversation with a person of your choice!

1. Would You Rather live forever or die in an instant?

Living forever can get lonely, but dying suddenly can also leave you with lots of unresolved feelings.

2. Would You Rather love or be loved?

There is a difference between the two, so would you rather be on the receiving end?

3. Would You Rather choose family or money?

Family and Money have always been two things that are hard to choose from.

👉 Suggested read: 100 Fun Would You Rather Questions for Teens

4. Would You Rather only re-live your childhood as an adult for a week or live as a child for the rest of your life?

Maybe getting only a taste of childhood again would be sufficient, but also, would you want to return to reality?

5. Would You Rather be humble or be successful?

Both traits are something that everyone wants to have. Which would you rather choose?

6. Would You Rather be lonely with people or be alone in general?

It’s hard to be surrounded by people but still feel lonely. It’s probably that feeling that you can reach out, but for some reason, you can’t.

So maybe just being alone in general is good too.

7. Would You Rather trade in your best friend or your pet?

They’re both best friends! How do you even choose between the two?

🤓 Suggested read: Top 100 Fun Would You Rather Questions

8. Would You Rather sacrifice a loved one or yourself for a stranger?

This question isn’t as easy as you would think. It can also tell you a lot about the person you’re playing with.

9. Would You Rather lose all the money you worked for or lose everyone in your life?

What’s the use of having all that money if you can’t share it with someone, am I right?

10. Would You Rather relive the greatest day in your life or get a glimpse of your biggest achievement in life?

It can be hard to live your life knowing your most significant achievement. Sometimes it can drive you to make decisions that you feel would lead to that, but you can also mess everything up in the process.

11. Would You Rather be religious or spiritual?

Being religious and spiritual are two different things. There are lots of people who can be spiritual without being religious. Try to analyze everything. See if it changes your decision!

Suggested read: Would you rather - Question List

12. Would You Rather get a tattoo or a piercing?

Doing something permanent to your body is always a big decision. Who’d want to live with a lousy tattoo forever, right?

13. Would You Rather lose a long-time pet or a pet that you just got?

Speaking from experience, losing either is just as painful.

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

We all know that sometimes a little white lie is necessary for life. So which would you rather “get in trouble” for?

15. Would You Rather work hard to live or just be a workaholic?

Being a workaholic is nice because you’ll always have that drive to work, but sometimes workaholics miss out on many things.

16. Would You Rather be an open book, or have people talk about you behind your back?

Sometimes it’s better to have everything come from you than to have the wrong information circling around.

🤓 Suggested read: Good Would you rather Questions List

17. Would You Rather get lost in space or down in the sea?

This brings out a lot of fears in some people. Getting lost in itself is already scary!

18. Would You Rather know about what other people think of you or have them tell it to you straight to your face?

Sometimes, just knowing about these things hurts less than hearing it for yourself.

19. Would You Rather eat only one meal for the rest of your life or eat only bland food forever?

Even if it’s your favorite food, we’re absolutely sure that you’d get sick of it. But then again, where’s the fun in eating bland food?

20. Would You Rather be good at something embarrassing or not be good at anything at all?

Either option would have you end up in some sort of embarrassment, have fun with the discussion on this!

21. Would You Rather know if God is real or discover the cure to cancer?

Ah, probably the biggest question in anyone’s life. Which would you rather know?

🤓 Suggested read: Fun Would You Rather Questions for Teens

22. Would You Rather be book smart or street smart?

Being book smart sometimes isn’t enough to get you through life. Street smart is also necessary!

23. Would You Rather contribute to today’s society or travel back in time and contribute to something then?

It’s hard to figure out how to contribute to today’s society. Unlike contributing to something in the past, you’d already know how to improve something!

24. Would You Rather always be placed in uncomfortable situations or face your biggest fear?

Just thinking about this makes my head hurt. Who would want to be placed in any kind of discomfort!

25. Would You Rather be single forever or live in an unhappy marriage?

Some people find it challenging to live alone, but would you really sacrifice yourself and suffer in silence?

Play Would You Rather Online

I’m too tired to think! Do you have simpler suggestions? Yes! If you feel like you’ve had enough of racking through your brain with these deep questions, we have other themes for Would You Rather!

Head on over to this link, and you’ll find over 500+ questions that are funny, for teens, for kids, and even the drinking version of Would You Rather!

The possibilities for Would You Rather are endless. Would you like to play the game online? Try out our free Would You Rather app:

Play Would You Rather online

✍️  September 17, 2021

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