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Would You Rather

  • 30 questions
  • 3 days free
  • No account needed
  • iPhone

A game with no right answers, which is exactly why it works. Every question offers two options, both of them awkward in some way, and you have to pick one. The interesting part isn’t the choice — it’s the next sentence: "why that one?"

Here are 30 dilemmas in three blocks. The first is light and gets things moving. The second is about relationships, and it starts showing how a person actually ranks what matters. The third is six uncomfortable ones, worth reaching for only once the first two have gone well.

The format survives any size of room: two people get a conversation, five get an argument, ten get a reason to finally hear from whoever has been quiet all evening.

The rules

Someone reads a dilemma and everyone names their option. Abstaining isn’t allowed — that’s the one hard rule. "Neither" kills a dilemma instantly, because the whole point is making a choice where both sides cost something.

Once everyone has answered, the real part starts: each person says why. This is usually where it turns out that two people picked the same option for opposite reasons, which is more interesting than the choice itself.

  • You must choose; "neither" doesn’t count.
  • Everyone names their option first, then explains.
  • Don’t clarify the terms — the ambiguity is deliberate.
  • No talking anyone out of their answer.
  • You can skip a dilemma entirely, but you can’t invent a third option.

Playing as a couple

For two people this is the easiest way to learn how your partner makes decisions. Answer at the same time, on a count of three, rather than in turn: hearing the other answer first quietly drags your own along with it.

The second block was written for couples. Those dilemmas aren’t about a hypothetical future but about what someone is willing to give up right now, and the answers usually outlast the game itself.

  • Answer simultaneously, not in turn.
  • Always ask why — without it the game is empty.
  • Don’t argue with your partner’s choice: you asked about them, not for the correct answer.

Playing in a group

A vote works best: everyone reveals their choice at once, then each camp briefly defends it. Two minutes per dilemma and the evening runs itself.

For a larger group, split the room: one option to the right, the other to the left. People physically see who they agree with, and the argument starts on its own without anyone hosting it.

  • Three players and up; ten is still comfortable.
  • Two minutes per dilemma, then move on.
  • Better not to open the third block in a large group.

When a dilemma turns into a fight

The third block slides into a real argument easily, and that isn’t a flaw in the game — it’s its nature: questions about closeness and trust sound the same whether they’re a game or not. That is why there are six of them and not twenty.

If your partner’s answer stings, the worst move is to prove the other option was correct. The best one is to ask what sits behind the choice. A hypothetical is almost always about something real, and the fight starts when it gets answered as an accusation.

  • A dilemma is neither a promise nor a confession.
  • If a topic lands hard, stop the game and talk about it directly.
  • Don’t bring someone’s answer back the next day as an argument.

Light dilemmas

Twelve to open with. Nobody is risking anything here.

  1. Never listen to music again or never watch a film again?

  2. Speak every language or play every instrument?

  3. Always wake at five in the morning or always go to bed at three?

  4. An extra day each week or an extra hour every day?

  5. Live by the sea with no friends or in a city with everyone you love?

  6. Always know when you’re being lied to, or be able to forget what you want to forget?

  7. Never be cold again or never be too hot again?

  8. One trip into the past or one into the future?

  9. Lose every photo you have or every conversation you’ve had?

  10. Give up internet search or give up maps?

  11. Eat your favourite meal every day for life or never eat it again?

  12. Perfect memory or perfect intuition?

About relationships

Twelve dilemmas that show how someone actually ranks what matters.

  1. A partner who always tells the truth, or one who spares your feelings?

  2. Learn about all of your partner’s mistakes at once, or never learn about them?

  3. A year apart, or a year without a single minute alone?

  4. A partner who forgets dates, or one who forgets conversations?

  5. Every evening together, or every weekend as two with no phones?

  6. Be understood without words, or always be heard out to the end?

  7. Fight often and make up fast, or barely fight and go quiet for days?

  8. Know in advance how long your relationship will last, or know nothing?

  9. A partner who is friends with your friends, or one with a separate circle?

  10. Five vivid years together or forty calm ones?

  11. Relive your first date or the best day you’ve had together?

  12. Forgive cheating and stay, or leave and always wonder?

Uncomfortable

Six for late in the evening. Don’t open with these.

  1. Read all of your partner’s messages, or let them read all of yours?

  2. Find out what your friends really think of you, or what your family does?

  3. Know your partner’s every thought for a day, or be transparent to them for a day?

  4. Say the thing you’ve been holding back, or hear the thing being held back from you?

  5. Lose physical closeness or emotional closeness?

  6. Know the date this relationship ends, or the date you die?

When the list runs out

In the app the topics don’t end after one evening: thousands of questions, sorted by mood and depth.

Get DeepJoin

Common questions

How many people do you need?

Two and up. With two it’s a conversation about how your partner decides things; with three to ten it’s an argument in which you finally hear from whoever has been quiet all evening.

Can you answer "neither"?

No, and it’s the one hard rule. A dilemma works because both sides cost something; the moment a third way out exists, the question stops revealing anything.

What if your partner’s answer stings?

Ask what sits behind the choice instead of proving the other option was right. A hypothetical is almost always about something real, and the fight starts when it gets answered as an accusation.

Is it good for a first date?

The first block is, and that’s what it was written for. The second already asks about priorities inside a relationship, which is early for a first date. The third isn’t for first dates at all.

How long does it take?

A couple gets through all 30 dilemmas in about forty minutes; a group moves faster, since it’s two minutes and a vote each. You don’t have to finish.

How is it different from Truth or Dare?

You don’t have to tell anyone anything about yourself. You pick between two hypotheticals and the confession arrives as a side effect — which is why dilemmas are easier to start with people you barely know than a direct question about the past.

Do we need the app?

No, all 30 dilemmas are on this page. DeepJoin comes after: when the format worked and the list ran out, the app has thousands of prompts sorted by mood and depth.

When the list runs out

Free for 3 days on the weekly plan. No account needed to start.