500+ This or That Questions: The Ultimate List for Every Occasion

You know the feeling — someone asks “coffee or tea?” and suddenly you’re in a ten-minute debate about oat milk, pour-overs, and whether chai counts. That’s the magic of this or that questions. Two options, one choice, and a conversation that goes places you never expected.

This or That is the simplest conversation game there is. No complicated rules, no scoring, no setup. Just pick one and explain yourself. It works on road trips, first dates, family dinners, team meetings — anywhere you want to learn something real about the people around you.

This guide has 500+ this or that pairs organized by theme, plus game variations that keep things fresh whether you’re playing with two people or twenty.

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How to Play This or That

Basic Rules

1. One person reads a pair — two options separated by “or”
2. Everyone picks one — no “both” or “neither” allowed
3. Share your reasoning — the “why” is where the fun lives
4. Take turns reading so everyone gets to pick the questions

Game Variations

• Speed Round: Set a 3-second timer. No overthinking allowed. First instinct only. Go around the circle rapid-fire and watch people surprise themselves.
• Explain Your Answer: After everyone picks, the person with the most unusual choice has to defend their answer for 30 seconds. Great for groups that love a friendly debate.
• Debate Mode: Split into two teams based on their answers. Each side gets one minute to argue why their choice is superior. The room votes on the most convincing argument.
• Story Mode: After picking, share a memory or experience related to your choice. “Beach” might lead to a story about a childhood vacation that shaped who you are.
• Hot Take Round: Everyone writes their answer on paper before revealing at the same time. See where the group splits and where you’re all aligned.

Pro tip: The best this or that questions don’t have a “right” answer. If everyone picks the same thing, the question is too easy. You want a roughly even split — that’s where the interesting conversations happen.

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Food & Drink

These are the questions that start arguments at dinner tables. Everyone has opinions about food, and those opinions run deep.

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Travel & Adventure

Where someone wants to go — and how they want to get there — tells you a lot about who they are.

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Lifestyle & Daily Life

The small, everyday choices that shape how someone moves through the world. These questions feel light but often reveal the most.

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Entertainment & Pop Culture

These pairs spark passionate defenses and friendly arguments. Prepare for some strong opinions.

For more games that spark great conversation, check out Would You Rather or try Connection Cards’ Play preset for action-oriented prompts.

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Relationships & Social

These questions get at how someone connects with others — their love language, their friendship style, their boundaries. Handle with care and curiosity.

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Deep & Philosophical

When the room gets quieter and the conversation gets more real. These pairs go beyond preferences into values, identity, and what matters most. Save these for when the group is warmed up — or for late-night conversations with someone you trust.

For prompts that go even deeper, try Connection Cards’ Deepen preset — it’s designed for conversations that build real vulnerability and trust.

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Spicy This or That (18+)

These are for date nights, couples’ game nights, or friends who know each other well enough to go there. Keep the energy playful.

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Workplace & Professional

Perfect for team meetings, icebreakers at offsites, or that awkward silence before the Zoom call starts. These are all safe for work but interesting enough to actually learn something about your colleagues.

For more workplace conversation starters, check out our icebreaker questions for groups — they’re designed to warm up any room.

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Family-Friendly

Clean, fun, and interesting enough that adults enjoy them too. Great for road trips, dinner tables, and family game nights.

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Technology & Modern Life

Where you fall on these says a lot about how you navigate the digital world — and whether you’re fighting the algorithm or leaning into it.

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Seasons, Nature & Outdoors

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Rapid-Fire Pairs

For speed rounds. No thinking, no debating — just go.

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Tips for the Best This or That Game

Matching Questions to the Moment

• Just met: Stick to food, travel, and entertainment. Low stakes, high fun.
• Getting closer: Move into lifestyle, communication style, and values.
• Close friends or partners: Go for the deep and philosophical pairs.
• Work settings: The workplace section is designed to be safe but still interesting.
• Kids or mixed ages: The family-friendly section keeps it clean while still being genuinely fun for adults.

How to Keep the Energy Up

1. Alternate between light and deep — don’t stack five philosophical questions in a row
2. Let the conversation breathe — if a pair sparks something good, follow it before moving on
3. Use follow-up questions — “Wait, why?” is the most powerful phrase in this game
4. Change the format — switch between speed rounds and explain-your-answer rounds to keep the pacing interesting

Why This or That Works

You’re not asking anyone to bare their soul. You’re asking them to pick between coffee and tea. But in that small choice — and especially in the explanation that follows — people reveal themselves. Their priorities, their humor, their quirks. That’s connection happening without any pressure.

It works with strangers at a dinner party and it works with a partner you’ve known for decades. The questions are just a doorway.

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Related Articles

• 500+ Would You Rather Questions for Every Situation
• 400+ Never Have I Ever Questions for Every Occasion
• 150+ Icebreaker Questions for Adults
• 21 Questions Game: Complete Guide
• 150+ Conversation Starters for Any Situation

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Frequently Asked Questions

What is the This or That game?

This or That is a simple conversation game where someone presents two options and everyone picks one. There’s no scoring or winning — the fun is in the choices people make and the discussions that follow. It’s a lighter alternative to Would You Rather that moves faster and works well for all ages.

How many questions do you need for a This or That game?

For a casual round, 15-20 pairs is plenty. For a longer game night or road trip, 50+ keeps things going without repeating. This list of 500+ gives you enough material for dozens of sessions across every setting you can think of.

What’s the difference between This or That and Would You Rather?

They’re closely related. Would You Rather typically presents two hypothetical scenarios — often exaggerated or extreme. This or That tends to be simpler and more grounded: real preferences between real things. This or That moves faster and works better for speed rounds, while Would You Rather sparks longer debates.

Can you play This or That at work?

Absolutely. The workplace section of this list is designed for team meetings, offsites, and virtual icebreakers. Questions like “Email or Slack?” and “Work from home or work from office?” are safe for professional settings while still being engaging enough to learn something about your coworkers. Check out our icebreaker questions for groups for more work-friendly conversation starters.

How do you make This or That more interesting?

Try the variations: speed rounds with a timer, debate mode where teams argue for their choice, or story mode where you share a memory connected to your answer. The game gets more interesting the more you encourage people to explain their reasoning rather than just picking quickly and moving on.