Hmmm...

144 "This Or That" Questions That Really Make You Think

Would you rather have teeth for hair or hair for teeth?

by Mackenzie Sylvester
Updated: 
Originally Published: 
Two friends playing the This or That questions game on the couch to get to know each other better
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Sometimes, the conversationalist in you takes a sabbatical — usually at the most inopportune times. Maybe your snappy quips are having a short-circuit moment or you're dealing with a bout of social anxiety as you’re getting to know someone new. It’s moments like these when some simple, tried and true “this or that” questions come in handy.

The game is pretty straightforward: Present your counterpart with two options and they must choose one over the other. No skipping, no choosing both. One answer must come out on top. The “this or that” questions game is not only a quick go-to for lulls in conversation, but you’d be surprised just how deeply these little prompts can allow you to get to know a person. There’s always more to learn about someone, even your besties or significant other. You never know which question may launch them into a full-fledged storytime. It’s also a surefire way to suss out which friendships or dates have the most in common with you and also makes a highly entertaining party game — cocktails optional.

Icebreakers don’t have to be boring or cliche. The best “this or that” questions will make you think, laugh, debate, and get to know your friends, coworkers, or significant other on a whole new level. Whether you’re just playing for giggles over drinks or looking to spark a deep discussion, these are the conversation starters you’ll want in your chit-chat arsenal to bring you closer to the people around you.

Best “This Or That” Questions

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  1. Peanut butter: crunchy or smooth?
  2. Movies or TV shows?
  3. Iced or hot?

“This Or That” Questions About Weather & Seasons

  1. Winter or summer?
  2. Rain or snow?
  3. Warm and cloudy or cool and sunny?
  4. Build snowmen or sandcastles?
  5. Grow flowers or carve pumpkins?

“This Or That” Questions About Social Media

  1. TikTok or IG Reels?
  2. Memes or GIFs?
  3. Send TikToks or receive?
  4. Pinterest or Etsy?

Deep “This Or That” Questions

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  1. Sunrise or sunset?
  2. Live one immortal life or reincarnate every 10 years?
  3. Ultra-talented but nobody knows or everyone thinks you can do something you can’t?

“This Or That” Questions About Work

  1. Have Mondays off or Fridays off?
  2. Sleep in and work late or get up early and get off early?

“This Or That” Questions About Superpowers

  1. Visit the past or the future?
  2. Breathe underwater or fly?
  3. Photographic memory or time travel?
  4. Pause time or rewind?

“This Or That” Questions About Style

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  1. Cottagecore or coastal grandma?
  2. Crocs or sandals?
  3. Trend follower or trendsetter?
  4. Makeup or skincare?
  5. Hair or outfit?
  6. T-shirts or sweaters?
  7. Jeans or leggings?

“This Or That” Questions About Lifestyle

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  1. Early bird or night owl?
  2. Camping or glamping?
  3. Sleep or eat?
  4. Friday night or Sunday morning?
  5. Have a pet or have a plant?
  6. Sleep with sounds or silence?
  7. Sleep with a night light or complete darkness?

“This Or That” Questions About Personal Aesthetics

  1. Tattoos or piercings?
  2. Silver or gold?
  3. Rings or necklaces?
  4. Bold lip or bold eye?

Funny “This Or That” Questions

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  1. Have teeth for hair or hair for teeth?
  2. Vampires or werewolves?
  3. Silent but deadly or loud and odorless?

“This Or That” Questions About Shopping

  1. Shop online or in person?
  2. Cash or card?
  3. Clothes shopping or products?
  4. Reciept emailed or printed?

“This Or That” Questions About Entertainment

  1. Audiobook or hardcovers?
  2. Board games or video games?
  3. Comedy or drama?
  4. Music or podcasts?
  5. Live action or animation?

“This Or That” Questions About Food

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  1. Hamburgers or hot dogs?
  2. Bagels or donuts?
  3. Guacamole or salsa?
  4. Soup or salad?
  5. Salty or sweet?

“This Or That” Questions About Bodies

  1. Have baby feet or baby hands?
  2. Have an extra arm or an extra leg?
  3. Toes for fingers or fingers for toes?

“This Or That” Questions About Animals

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  1. Cats or dogs?
  2. Speak to animals or speak all languages?
  3. Horses or ponies?
  4. Pets sleep in the bed or on the floor?
  5. Horseback riding or dog mushing?

“This Or That” Questions About Life

  1. Country or city?
  2. Minimalism or maximalism?
  3. Go out or stay in?
  4. TV in the bedroom or no devices before bed?

“This Or That” Questions About Money

  1. Fame or fortune?
  2. Growth or security?
  3. Poor and happy or rich and miserable?
  4. Save or spend?

“This Or That” Questions About Love

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  1. Love or happiness?
  2. Love and lose or never love at all?
  3. Know who you’ll fall in love with next or keep it a surprise?
  4. Win the lottery or find your soulmate?

“This Or That” Questions About Hygiene

  1. Smell like onions or garlic?
  2. Look like you haven’t showered or smell like you haven’t showered?
  3. Shaving cream for shampoo or conditioner for deodorant?

“This Or That” Questions About Hair

  1. Mullet or mutton chops?
  2. Bad haircut or bad dye job?
  3. No eyebrows or no eyelashes?
  4. Bangs or no bangs?
  5. Hairspray or au naturel?

“This Or That” Questions About Travel

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  1. Road trip or fly?
  2. Driver or passenger?
  3. Solo or group travel?
  4. Swimming pool or ocean?
  5. Spotaneous or planned?
  6. Hotel or Airbnb?
  7. Somewhere new or an old favorite?

“This Or That” Questions About Books

  1. Fiction or non-fiction?
  2. Books or movies?
  3. Reading or writing?
  4. Romance or fantasy?
  5. Paperback or hardcover?
  6. Audiobook or e-book?

“This Or That” Questions About Mind & Spirit

  1. False hope or unnecessary anxiety?
  2. Regret or doubt?
  3. Yoga or meditation?
  4. Journaling or affirmations?

“This Or That” Questions About Subscriptions

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  1. Netflix or Hulu?
  2. Apple or Spotify?
  3. Prime Video or Max?

“This Or That” Questions About Cheating

  1. Cheat or be cheated on?
  2. Lie or cheat?
  3. Catch your partner cheating or your parent cheating?

“This Or That” Questions That Make You Think

  1. Time or money?
  2. Logic or emotion?
  3. Quality or quantity?

“This Or That” Questions About Scenery

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  1. East Coast or West Coast?
  2. Ocean or mountains?
  3. Rivers or lakes?
  4. Cliffs or valleys?
  5. Beaches or pools?

“This Or That” Questions About Drinks

  1. Coffee or tea?
  2. Oat milk or almond milk?
  3. Beer or wine?
  4. Coke or Pepsi?
  5. Red wine or white wine?
  6. Water or seltzer?
  7. Gatorade or coconut water?

“This Or That” Questions About Phones

  1. Call or text?
  2. iOS or Android?
  3. No Wi-Fi or no service?
  4. Case or no case?
  5. Smart phone or flip phone?

“This Or That” Questions About Friends

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  1. Group hang or one-on-one?
  2. Introvert or extrovert?
  3. Large gathering or small and intimate?
  4. Guest or host?
  5. Paperless Post or Partiful?

Annoying “This Or That” Questions

  1. Listening to loud chewing or endless hiccups?
  2. Sprint or skip everywhere you go?
  3. Hold in a sneeze or a yawn for hours?
  4. Loud neighbors or nosy neighbors?
  5. Be too hot or too cold?
  6. Speeding ticket or parking ticket?

“This Or That” Questions About Learning

  1. Learn about ancient Egypt or ancient Rome?
  2. Learn what was in the Library of Alexandria or the truth about the Lost City of Atlantis
  3. Learn a new instrument or a new language?
  4. History museum or art gallery?
  5. Space or ocean exploration?

Philosophical “This Or That” Questions

  1. Always tell the truth or always hear the truth?
  2. Be the fastest person or the smartest person?
  3. Endless knowledge or endless imagination?
  4. Sacrifice the few for the good of the many or let ill fate befall everyone?
  5. Hear or see the supernatural?

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