Fun and Flirty “Would You Rather” Questions for Your Boyfriend

Who hasn’t played the classic game of “Would You Rather?” It’s perfect for killing time in the car, spicing up a party, or even getting to know your boyfriend better on a date. Did you know that this game actually originated in the 60s during sociological experiments? But it didn’t stay locked away in the study lab – it’s now a fun way to learn more about your significant other.

Today, we’re here to provide you with 56 flirty “Would You Rather” questions that are perfect for any date, whether it’s your first or fiftieth. These questions range from lighthearted to deep and will add a touch of excitement to your conversations. So without further ado, let the games begin!

First Date “Would You Rather” Questions

  1. Would you rather plan a holiday a month in advance or book a last-minute flight?
  2. Would you rather star in a romantic comedy or a bone-chilling horror movie?
  3. Would you rather date someone who’s head over heels for you or someone you’re head over heels for?
  4. Would you rather pay for a meal or have someone treat you to a delicious dinner?
  5. Would you rather be with a partner who shares your interests or someone completely different?
  6. Would you rather live in the bustling city or the serene countryside?
  7. Would you rather make a reservation or explore a restaurant spontaneously based on your mood?
  8. Would you rather spend the whole day at home or venture out all day?
  9. Would you rather take your time dating or jump into a relationship as soon as possible?
  10. Would you rather go to a trendy bar or enjoy a romantic dinner at a cozy restaurant?
  11. Would you rather indulge in a decadent dessert, a mouthwatering main course, or a delectable starter?
  12. Would you rather share a meal with your partner or savor separate dishes?
  13. Would you rather have a wild night of drinking or stay sober?
  14. Would you rather give up alcohol forever or bid farewell to smoking?
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Romantic “Would You Rather” Questions

  1. Would you rather sleep under a blanket of stars or have a luxurious stay in a hotel?
  2. Would you rather spend a day at the beach or experience the thrill of bungee jumping?
  3. Would you rather receive a bouquet of flowers or be the one sending them?
  4. Would you rather share a warm hug or hold hands with your partner?
  5. Would you rather be told the destination of a date or be taken on a surprise adventure?
  6. Would you rather receive material gifts or create unforgettable experiences on your birthday?
  7. Would you rather indulge in a chocolate fondue or savor juicy strawberries with cream?

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Silly “Would You Rather” Questions

  1. Would you rather get matching tattoos or piercings with your partner?
  2. Would you rather hit the dance floor or belt out your favorite tunes at a karaoke bar?
  3. Would you rather read minds or change people’s minds?
  4. Would you rather let me shave off your hair or your eyebrows?
  5. Would you rather stay up all night texting or have a long phone conversation?
  6. Would you rather be with someone who’s hilarious or drop-dead attractive?
  7. Would you rather sleep with your dad’s best friend or your arch-nemesis?
  8. Would you rather go a year without television or a year without music?
  9. Would you rather remember all your dreams or never recall them at all?
  10. Would you rather go on a date with a fictional TV character or a character from a book?

Deep “Would You Rather” Questions

  1. Would you rather know how long your relationship will last or live in uncertainty?
  2. Would you rather have your dream job or your dream partner?
  3. Would you rather live forever without a partner or have a shorter life with the love of your life?
  4. Would you rather have amazing friends or the perfect partner?
  5. Would you rather be with an outgoing partner or someone who’s shy?
  6. Would you rather have your parents’ approval or your friends’ approval of your partner?
  7. Would you rather have many children or a house filled with pets?
  8. Would you rather always hear the truth or be lied to occasionally?
  9. Would you rather be in a committed relationship or explore multiple partnerships?
  10. Would you rather date someone who has dated both men and women or only men/women?
  11. Would you rather cut ties with your ex or remain friends with them?
  12. Would you rather never get married or tie the knot?
  13. Would you rather be with someone who has had many partners or no partners before you?
  14. Would you rather be with someone you can’t trust or someone you trust but don’t love?
  15. Would you rather never experience love or never have children?
  16. Would you rather have a passionate love without commitment or a committed relationship without passion?
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Sexy “Would You Rather” Questions

  1. Would you rather spend an entire day or night together with your partner?
  2. Would you rather give up food forever or give up sex?
  3. Would you rather go swimming in the sea or enjoy sunbathing?
  4. Would you rather have breakfast in bed or a delicious midnight snack?
  5. Would you rather have passionate sex indoors or explore your desires in the great outdoors?
  6. Would you rather be with a passionate lover or someone who’s reserved?
  7. Would you rather have a steamy shower or a tantalizing bath together?
  8. Would you rather share a long, passionate kiss or a quick, playful peck?
  9. Would you rather engage in a playful pillow fight or indulge in a steamy role-play session?

So, are you ready to embark on an exciting journey of “Would You Rather” questions with your boyfriend? Be prepared to laugh, get to know each other better, and spice up your conversations. Let the fun begin!

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