Date Night Fun: 50 “Would You Rather?" Questions for Couples

Whether you are just getting to know your partner, or have been together for years, you don’t know everything about them. Sometimes the best way to get to know someone is to ask questions, even if they are ridiculous questions. At your next date night, consider playing a round or two of “would you rather” to learn more about them. For those of you that don’t know, “would you rather” questions are questions that force you to pick the best (or in some cases, the least bad) option of two choices. The questions are all hypothetical and can get pretty ridiculous, but they are a fun and playful way to learn more about your partner. Because these questions are hypothetical, they might not naturally come up in conversation, so you will likely learn more about your partner than you initially expect to. Plus, answering these questions might reveal more than you think about their general philosophies and preferences. There is no need to ask all these questions at once (afterall, it isn’t 20 questions), but “would you rather” is a fun game to have in your back pocket for anytime conversation gets dull or you are feeling bored.

Here are a couple practical ‘would you rather’ questions to help you get to know a newer partner:

  1. Would you rather ask for help or figure it out on your own?
  2. Would you rather get up early or stay up late?
  3. Would you rather have a pet dog or a pet cat?
  4. Would you rather always be 10 minutes late or always be 20 minutes early?
  5. Would you rather be vegan or gluten-free?
  6. Would you rather talk on the phone or text?

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Here are a few questions that show a glimpse of your partner’s life philosophies:

  1. Would you rather lose all of the money you earned this year or lose all of the memories you made this year?
  2. Would you rather have more time or more money?
  3. Would you rather be rich or famous?
  4. Would you rather be able to fly or read minds?
  5. Would you rather travel back in time, or travel to the future?
  6. Would you rather explore the deep sea or outer space?
  7. Would you rather be an artist or an athlete?
  8. Would you rather be a good singer or a good dancer?
  9. Would you rather give up social media or be an influencer?
  10. Would you rather be bored or busy?
  11. Would you rather be feared or loved?
  12. Would you rather know how you die or when you die?
  13. Would you rather be able to see into the future or not?
  14. Would you rather be really funny or really smart?
  15. Would you rather die in 10 years with no regrets or live for 30 years with lots of regrets?
  16. Would you rather die before or after your partner?
  17. Would you rather be your own boss or work for someone else?
  18. Would you rather go to jail for a crime you didn’t commit, or get away with a crime but be paranoid about being caught for your entire life?

Here are a few questions that are critical to ensure you’re on the same page:

  1. Would you rather have 10 children or no children?
  2. Would you rather live in a big city or a small town?
  3. Would you rather have a public or private proposal?
  4. Would you rather have a huge wedding or just get a marriage license?

Here are a few silly questions that can give you insight into your partner:

  1. Would you rather eat only ice cream for the rest of your life, or never eat ice cream again?
  2. Would you rather have a personal chef or a chauffeur?
  3. Would you rather be too hot or too cold?
  4. Would you rather spend time at the beach or the ocean?
  5. Would you rather live without movies or live without music?
  6. Would you rather read a book or watch a movie?
  7. Would you rather be able to teleport or have a private plane?
  8. Would you rather look 10 years older from the neck up or down?
  9. Would you rather always be underdressed or always be overdressed?
  10. Would you rather be 45 minutes late or 45 minutes early to every event or engagement?
  11. Would you rather know every language, but never be able to travel to another country, or would you rather travel, but never be able to speak another language?
  12. Would you rather be remembered in history books for doing something terrible, or be completely forgotten after you die?
  13. Would you rather not brush your teeth for a week or not take a shower for two weeks?
  14. Would you rather be beautiful and dumb or smart and unattractive?
  15. Would you rather be able to speak any language or be able to speak to animals?
  16. Would you rather have your least favorite song played on a constant loop, or never listen to music ever again?
  17. Would you rather have a photographic memory or perfect pitch?
  18. Would you rather get stranded by yourself on a desert island, or stranded on a snow mountain?
  19. Would you rather be on a dating show (like The Bachelor or Love Island) or a survival show?
  20. Would you rather always have a runny rose or always have a cough?
  21. If you were an animal, would you rather be a horse or a dog?
  22. Would you rather be serenaded by Snoop Dog or Mariah Carey?

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