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120 this-or-that questions worth actually asking

This-or-that questions for friends, couples, teams and group chats — sorted by situation, with notes on which ones start the best arguments.

A good this-or-that question is not the hardest one. It is the one where the room splits. If everyone answers the same way in a second and a half, you have found a fact, not a question. The list below is grouped by the situation you are in, because the question that works in a group chat dies in a team meeting.

Food and drink

The most reliable category, because everyone has a position and nobody is embarrassed by it.

  • Pizza or sushi?
  • Coffee or tea?
  • Sweet breakfast or savoury breakfast?
  • Pineapple on pizza: yes or no?
  • Cook at home or order in?
  • Ketchup in the fridge or in the cupboard?
  • Thin crust or deep dish?
  • Chocolate or vanilla?
  • Sparkling or still?
  • Brunch or dinner?
  • Ice cream or cake?
  • Burgers or tacos?
  • Spicy or mild?
  • Breakfast for dinner: yes or no?
  • Cereal before milk or milk before cereal?

The last three start the most arguments, in ascending order.

For couples

These work because the answer is usually known and the ranking is not.

  • Night in or night out?
  • Beach holiday or city break?
  • Plan the whole trip or wing it?
  • Split the bill or take turns?
  • Big wedding or small wedding?
  • Cat person or dog person?
  • Early bird or night owl?
  • Cinema or streaming at home?
  • Cook together or order together?
  • Surprise party or absolutely not?
  • Text or call?
  • Save it or spend it?
  • Mountains or ocean?
  • Same taste in music or separate playlists?
  • Talk it out tonight or sleep on it?

For friends and group chats

  • Where are we eating?
  • Bar or someone's flat?
  • Leave at ten or stay out?
  • Board games or a film?
  • Group holiday or separate trips?
  • Book the table or just show up?
  • Brunch or hangover recovery?
  • Karaoke: yes or never?
  • Camping or hotel?
  • Split evenly or pay for what you had?
  • Loud bar or quiet pub?
  • Plan a month ahead or decide on the day?

Any question that ends an actual group-chat stalemate is worth more than a clever one. "Where are we eating" has settled more evenings than any icebreaker.

For teams at work

Keep these concrete. Abstract preference questions produce agreeable, useless answers.

  • Ship Friday or ship Monday?
  • Fix the bug or finish the feature?
  • Meeting or written update?
  • Option A or option B for the homepage?
  • Onboarding first or search first?
  • Hire now or wait a quarter?
  • Refactor it or live with it?
  • Demo internally or go straight to customers?
  • Cut the scope or move the date?
  • Async standup or fifteen minutes live?

"Cut the scope or move the date" is the single most useful question on this page. It is the trade-off most teams avoid naming out loud, and a poll makes it impossible to keep avoiding.

Would-you-rather

For when the goal is entertainment rather than a decision.

  • Fly or be invisible?
  • Always ten minutes early or twenty minutes late?
  • Never use headphones again or never use a keyboard again?
  • Read minds or see one week ahead?
  • Live without music or without films?
  • Unlimited time or unlimited money?
  • Always too hot or always too cold?
  • Know how you die or when you die?
  • Restart your career or restart your education?
  • Never scroll again or never stream again?

Icebreakers for a new group

Low stakes, no wrong answers, everyone can go first.

  • Window seat or aisle?
  • Print book or e-reader?
  • Morning shower or evening shower?
  • Sneakers or boots?
  • Playlist or podcast?
  • Text back instantly or three days later?
  • Tidy desk or productive chaos?
  • Big city or small town?
  • Handwritten notes or typed?
  • Dark mode or light mode?

Making them work

Three things separate a question that gets answers from a list nobody reads.

Pick the split, not the winner. If you can guess the result, do not ask it. Aim for the ones where you genuinely do not know.

Give it a deadline. A question that closes tonight gets answered tonight. One that stays open forever gets answered by four people.

Show the result. The reason people vote is to find out whether they were in the majority. Withhold that and they stop voting.

Pick the one you cannot call and put it to a vote.

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