Would You Rather

The rules

There is only one that matters

You have to pick. No “both”, no “neither”, no clever third option. Everything else about this game is optional; that one rule is the game. The moment somebody is allowed to opt out, you are having a conversation instead, and conversations do not make anybody defend an indefensible preference for duck-sized horses.

The rest is scaffolding, and you can take whichever pieces are useful:

• Answer together, on three. Otherwise the first person to speak sets the answer for everyone after them.
• The minority explains. Fifteen seconds, no more. This is where the entertainment actually is.
• Skip anything that dies. A question that draws a shrug is a bad question, not a bad room.
• Anybody may swap a question without saying why. Costs nothing, removes almost every reason to refuse to play.

Three variants worth knowing. Prediction: before answering, everyone writes down what they think the majority will say — a point per correct guess, and it turns the game into one about reading the room rather than about yourself. Escalation: whoever wins a round reads the next and may add one condition — “same question, but you are eighty”. Two truths: answer for yourself, then answer as the person on your left; the table votes on which was which.

Where it came from

The game nobody owns, and the trademark two companies went to court over

Forced-choice dilemmas are not really datable. They are how ethics seminars open, how children argue in the back of cars, and how the trolley problem got famous. What can be dated precisely is the moment the phrase stopped being a thing people said and became a thing people sold.

Justin Heimberg and David Gomberg filed a trademark application on 31 July 1997. That October they published Would You Rather…? Over 200 Absolutely Absurd Dilemmas to Ponder through their company, Falls Media. The registration itself did not come through until 19 July 2005 — eight years after the filing.

During that gap, a California company called Zobmondo Entertainment released a board game under the same three words. Zobmondo had filed its own application and been refused, because Heimberg and Gomberg had got there first. Both companies were now selling books and games of humorous forced choices under an identical name.

The argument that followed is more interesting than a trademark fight has any right to be. Zobmondo’s position was that “Would You Rather…?” is merely descriptive — it simply describes what the product is, the way “Cold Beer” describes cold beer, and descriptive phrases get very thin protection because no one should be able to fence off ordinary English. Falls Media argued the mark was suggestive, which requires a small leap of imagination and is protectable.

A district court granted summary judgment for Zobmondo. On 26 April 2010 the Ninth Circuit reversed it, holding that a reasonable jury could land on either side and that the question was not one a judge could settle on the papers. The case went back for trial.¹

The part worth keeping: what was fought over was the label. The questions have never belonged to anyone, which is why every list on the internet is different and why every one of the hundred on this page was written for it.

Writing your own

What separates a question that works from one that dies

Most published lists are padded, and the padding is always the same mistake: one option is obviously correct. “Would you rather be rich or poor” is not a question, it is a statement with a question mark.

Four things a working question has.

Both options have a real defender. The test is whether you can imagine an intelligent person picking either one and having a reason. If you cannot, you have written a poll, not a dilemma.

The trade-off runs along a different axis than the surface. “A twenty-minute commute you hate or an hour-long one you enjoy” looks like it is about travel. It is about whether you value time or experience, and that is why it produces an argument.

It is short enough to hold in your head. If the reader has to re-read it, the room has already moved on. Both options should fit in one breath.

It is specific. “Lose your keys or lose your wallet” beats “lose something important or lose something valuable” every time. Concrete nouns make people picture it; abstractions make them shrug.

And one thing to avoid: questions where the honest answer would embarrass someone in the room. The game runs on people saying the unpopular thing cheerfully. Anything that makes the true answer costly turns it into an interrogation, and the table goes quiet in a way that is hard to recover from.

Keep going

More from this side of the house

Cut for a particular room: 200 questions for teens, sorted from harmless to genuinely hard, 200 for work, built for the first two minutes of a meeting, and 200 for Halloween, from harmless warm-ups to the properly grim ones.

Not a list of questions but a list of games: fifteen Halloween party games, each with the rules, the number of players and how long it runs, and 200 charades ideas sorted from one-gesture warm-ups to abstractions, and twenty Christmas party games, nine of which need nothing at all.

If one game is not enough for the evening, Party Battle Book has 117 rounds across seven kinds — charades, bluffs, debates, letter storms, rapid-fire challenges — one page per round, nothing to set up and no phones involved.

Everything on the party and games shelf