76 First-Date Questions to Really Get to Know Someone

When in doubt, pull out a would-you-rather first-date question. You will 1000 percent learn something interesting about your date this way, at the very least.

  • Would you rather go to a nice restaurant or get takeout for an anniversary dinner?
  • Would you rather know your partner’s complete dating history or be in the dark?
  • Would you rather get a good-morning or a goodnight text?
  • Would you rather only text or talk on the phone?
  • Would you rather go on three mini staycations or a week-long destination vacation?
  • Would you rather meet your favorite actor or artist?
  • Would you rather go on a date with your most recent ex or the person you lost your virginity to?
  • Would your rather date a relative’s ex or a friend’s ex?
  • Would you rather give up sex or your favorite food?
  • Would you rather be handcuffed or blindfolded?
  • Would you rather have sex in a car or an airplane?
  • Would you rather accidentally send a nude photo to your parent or post it to your Instagram Story?

Emily Weaver is an entertainment and lifestyle contributor for POPSUGAR. Her writing focuses on celebrity relationships, movie and book news, and product shopping guides. Her bylines include PEOPLE, Real Simple, Better Homes & Gardens, HelloGiggles, Scary Mommy, and more.

Taylor Andrews is a Balance editor at POPSUGAR who specializes in topics relating to sex, relationships, dating, sexual health, mental health, and more. In her six years working in editorial, she’s written about how semen is digested, why sex aftercare is the move, and how the overturn of Roe killed situationships.

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