Weird and Hard Would You Rather Questions for Teens

I was looking around for some would you rather questions for teens because it’s a fun game to play with friends, or even just to think about on your own.

What I found were a bunch of huge lists with like, 100 would you rather questions, but the vast majority of these questions were just dumb or boring. Beyond that, these other lists didn’t include any context or rules or explanations, which is kind of silly because a big part of playing Would you Rather is knowing what the specific rules or confines are.

Anyways, I hope you find these would you rather questions hard and interesting, and where you can see some benefits and disadvantages to both of the options. If there’s an easy answer, that’s okay for would you rather questions for students in a classroom, but I wanted to find some that were a little more fun than that.

Would You Rather for Teens…

Would You Rather for Teens
Playing Would you Rather for teens is a great way to connect with somebody and get to know them better.

Would you rather know when your life ends, or how it ends?

Rules: You will be magically imbued with one of these two pieces of knowledge. If you choose to know how your life ends, you won’t literally see a visual representation of it (because you would be able to tell roughly how old you look, so don’t try to use that loophole!)

On that same note, if you choose to know how it ends, you will just magically have this one single piece of knowledge, you won’t be able to determine when this happens, just how.

Thoughts about this would you rather question…

Knowing WHEN your life ends…

  • You could learn that you live well until your 80s, and this knowledge could lead to you spending your whole life feeling like you’re never in a hurry for anything, leading to you missing opportunities that someone might take if they were expecting greater uncertainty.
  • But that can work both ways, too, and you could end up having a ton of fun and taking risks, knowing that you’re going to make it to your later years.

Knowing HOW your life ends…

  • You could drive yourself mad, constantly trying to connect the dots in your life to find out how you arrive in the certain situation or predicament that leads to your final moments.
  • You and your friends can debate whether or not taking steps to avoid the scenario that ends you is something that you’re able to do in this hypothetical situation or not. It makes a huge difference in which choice you make, right?

Would you rather turn in your friend for a crime, or serve the punishment yourself?

Rules: Your friend is the only person who will know that it was actually them who committed the crime. They can’t overrule your decision by confessing, you have to serve the full punishment.

In this scenario, you get to choose what the specific crime and punishment are. You can choose the crime, and the consequence. For example, the crime could be stealing a chocolate bar and the punishment is having to sit in the back room with a mall cop for 45 minutes until your parents pick you up. Or, for higher stakes, the consequences of stealing the candy could be 5 years in prison.

Alternatively, you could pick a more heinous crime for this thought experiment. Part of what makes this question interesting is the fact that you choose the crime and punishment. You could choose a very harsh crime with a very minor punishment, or a very minor crime with a harsh punishment, since part of the punishment is having everyone think you did that crime, but not knowing that it was your friend who did it.

For the purpose of this, let’s assume its your best or one of your very closest friends.

Thoughts about this would you rather question…

Turning your friend in…

  • You won’t have to suffer the consequences of your friends actions, but you will have to turn them in.
  • As an alternative, you could assume that you committed the crime and you can either serve your time or have a friend serve it for you by turning them in.

Serving the punishment

  • Your friend is protected from consequences of their action, but you are responsible for it.
  • Everyone will think that you committed this particular crime, but nobody would know your friend actually did it.

Would you rather walk in on your parents, or have them walk in on you?

Rules: You can decide what this questions means by “walk in on”, whether it means holding hands, or making out, or whatever. Would you rather walk in on your parents (or one of your parents) doing something, or have them walk in on you doing something?

In this scenario, assume that all parties are aware this happened. For example, you aren’t just walking into their room and instantly turning around (to go throw up in the toilet) without them noticing. Your parents are aware that you walked in on them, and the same goes for the other option.

Thoughts about this would you rather question for teens…

Walk in on them…

  • You already know that your parents are into one another, presumably, but it’s still pretty weird and cringey to think about it, and seeing it would be that much worse.
  • Whether or not they ever bring this up again just depends on your parents and whether they like to embarrass you and to make things awkward for their own amusement or not.

Walk in on you…

  • Whether or not your parents make this awkward for the rest of eternity just depends on their personalities and your relationship with them. It’s based on your own life. With some parents, it would be a lot more awkward than others, since some parents would be cool about it but some would be really awkward, or tease you about it, etc.

Would you rather questions for teens: Have unlimited money for your lifetime, or live for 200 years?

Rules: You can’t pass on any of your fortune to future generations, and you can only spend the money on stuff that directly impacts you.

For example, you can’t use the unlimited money to solve world hunger or to pay off everyone’s student loan debts and mortgages, but you can use it to pay off your own student loan debt, to buy yourself whatever home you’d like, and so on.

Thoughts about this Would you Rather for teens…

Unlimited Money

  • You can do just about anything you want without there being very many obstacles to hold you back.
  • You will often have to wonder, when meeting people, if they actually like you or they’re just looking to get close to you for your money.
  • Even though your family can’t inherit it, you can still give people extravagant gifts or have them share experiences with you.

Live for 200 Years

  • You’ll get to see everyone you know until their very last day on earth, like getting to see your great, great grandchildren grow old.
  • You’ll have to experience the loss of everyone you’ve known or loved, generation after generation.
  • You’ll be able to earn a lot of money during this time, it won’t be unlimited but you can pass it down to your descendants, though.

More Would You Rather Questions for Teens…

Here’s a list of some other Would You Rather questions for teens that came up while I was looking around. These are the ones that I thought were the most interesting and have the most potential to lead to lively conversations and interesting debates.

would you rather questions
  • Would you rather never use any paper products again, or never use any plastic products again?
  • Would you rather never be able to shop in person again, or never be able to shop online again?
  • Would you rather get back together with your first ex, or your most recent ex?
  • Know what everybody thinks about you all the time, or not know what anybody thinks about you ever?
  • Look and feel 3 years younger for the rest of your life, or look and feel 3 years older?
  • Live right next door to your work, with your boss in the apartment right next to you – or live 50 minutes away from work?
  • Cook dinner every night and choose what’s for dinner, or have dinner cooked for you but never get to choose?
  • Have a very early curfew for teens, or have to stay out late every night?
  • Have a long distance relationship where you never fight and get along perfectly, or live with your partner but argue every week?
  • Would you rather marry someone who you find incredibly attractive but lose your own looks, or marry someone who you find less attractive, but look amazing yourself?
  • Would you rather be the smartest person at your school, or the most athletic?
  • Would you rather accidentally show up to school in your underwear one day (a very common nightmare that many people experience, often induced by stress), or have terrible breath and body odor for an entire semester?
  • Would you rather only be able to listen to your favorite 3 bands for the rest of your life, or be able to listen to everything except your favorite 3 bands for the rest of your life?
  • Would you rather break up with someone, or have them break up with you?
  • Would you rather lose your job, or lose your relationship?
  • Never have another sleepover to play sleepover games for teenagers, or never play sports again?
  • Would you rather strangers knew exactly how much money was in your bank account, or know exactly what you’ve eaten for the past week?
  • Would you rather have an incredible car (luxury, sports, Tesla, whatever you like) and a small house that’s not in great shape, or an ugly old car that barely runs, but a gorgeous big home?
  • Would you rather be locked inside of a warehouse overnight with your significant other, or locked inside an amusement park with a celebrity of your choice to hang out, go on rides, etc?
  • Would you rather be given $1,000,000 today, or start a business and earn $750,000 over the next 5 years?

That’s All The “Would You Rather” Questions for Teens for Now…

Can you think of any other fun questions for a game of Would You Rather for teens? Leave a comment and let us know because the more questions we have, the more fun everyone else can have talking about them! We’ll add the best suggested would you rather questions for teens to our list.

Sara Dylan

Author Information

Sara Dylan is passionate about researching and writing interesting articles to help people. Sara is a prolific writer at, and enjoys a nice cup of tea as much as the next person.