60 First Date Questions That Won’t Bore Them (Or You) To Tears

When you go out with someone for the first time, there are certain questions you’re likely to ask to help you decide whether you have solid chemistry and if your date would make a good partner. However, once you get the preliminary screening out of the way, you want to keep the conversation going. The problem is that the more general and stereotypical your queries, the more likely your date is to get bored. To keep them (and yourself!) engaged while still illuminating different parts of their personality, here are some more unconventional first date questions to ask the next time you’re out with someone new.

Why asking questions is so important for a successful first date

Obviously, the whole purpose of going on a date with someone is to feel them (and your connection) out. Do you gel well or is it a total disaster? That requires not just paying attention to body language and the general vibe, but also asking some probing questions. By finding out who they are, what they like and dislike, and what they’re looking for, you can decide whether or not a second date is on the cards.

Asking questions on a first date is also a vital way to show interest. There’s nothing worse than going out with someone who only talks about themself. Doing so will make you seem self-centered, disengaged, and kinda obnoxious. By inquiring about their life and interests, you prove that you’re there to forge a connection. That’s important!

First date questions that will keep the conversation flowing

Coming up with interesting first date conversation starters can be tough, but these questions will give you plenty to talk about. Just be prepared to answer them yourself!

  1. If you could choose anyone in the whole world to have dinner with, who would you choose? Why?
  2. Would you ever want to be famous? In what way?
  3. Before making a phone call, do you rehearse (or have you ever rehearsed) what you are going to say?
  4. What does your perfect day look like?
  5. If you live until you’re 90 and could retain either the mind or body of a 30-year-old, which one would you choose? Why?
  6. Do you have a secret hunch on how you’ll die?
  7. In your opinion, name three things that you think (or know) that we have in common.
  8. What are you most grateful for?
  9. If you could change anything about the way you were raised, what would it be? Why?
  10. If you could wake up tomorrow having gained one quality or ability, what would it be? Why?
  11. If a crystal ball could tell you the truth about yourself, your life, or the future, what would you want to know? Why do you want to know this?
  12. Is there something you’ve dreamed of doing for a long time? What’s holding you back?
  13. What’s your biggest regret?
  14. What’s the greatest accomplishment of your life so far?
  15. What do you value most in a friendship?
  16. What’s your most treasured memory?
  17. What’s your most terrible memory?
  18. If you found out that in one year you would suddenly die, would you change anything about the way you’re living now? If yes, what would it be?
  19. What does friendship mean to you?
  20. What roles do love and affection currently play in your life?

Fun and creative first date questions

  1. How close and warm was your family growing up? Do you feel your childhood was happier than others?
  2. What is your relationship like with your mother? Your father? Your siblings?
  3. Finish this sentence, “I wish I had someone with whom I could share ….”
  4. What is your most embarrassing moment?
  5. When was the last time you cried in front of another person? By yourself?
  6. What do you like (or treasure) about me that surprised you?
  7. What, if anything, is too serious to be joked about?
  8. If you die this evening without the opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?
  9. Your house containing everything you own catches fire. After saving your loved ones and pets, you have time to make one final dash to save one last item. What would it be? Why that item?
  10. Of all the people in your family, whose death would you find it most difficult to get over? Why?
  11. What’s something you’ve always wanted to try but haven’t? What’s holding you back?
  12. If you were on death row and had to pick your final meal, what would you choose?
  13. If a zombie apocalypse happened, would you fight them or run and hide?
  14. Are you an early bird or a night owl?
  15. Who were your heroes as a kid and why?
  16. If you could be an animal for one day, which would you be? What’s the worst thing about dating for you?
  17. Did you have a pet as a kid? What was it/what was its name?
  18. If you won the lottery tomorrow, what’s the first thing you would do? Who’s the first person you’d tell?
  19. Who’s your best friend and how did you meet?
  20. What’s your favorite comfort food?

Casual first date questions to keep the conversation light and easy

  1. What were your favorite shows to watch as a kid?
  2. What’s your favorite alcoholic drink? Favorite non-alcoholic drink?
  3. Do you prefer crunchy or smooth peanut butter?
  4. What’s the corniest joke you know that makes you laugh?
  5. What’s the best city you’ve ever traveled to?
  6. If I looked in your Google search history, what’s the most embarrassing thing I’d find?
  7. Do you believe in astrology? What’s your sign and do you think it suits you?
  8. If traveling back in time was possible, which era would you go to?
  9. What snacks do you like to buy when you go to the movies?
  10. If they were making a movie of your life, what actor would you choose to play you?
  11. What’s the best concert you’ve ever been to and why?
  12. If you could have any job in the world, what would it be?
  13. What’s the best you’ve ever received? What’s the best one you’ve ever given?
  14. What’s the biggest luxury purchase you’ve ever made for yourself?
  15. What’s your ideal way to spend a day off work?
  16. What’s the best piece of advice you’ve ever received that you find it difficult to follow?
  17. If you were going to write your autobiography, what would it be called?
  18. What do you think the world will be like in 20 years? 50?
  19. If you found $500 on the sidewalk, would you turn it in or keep it?
  20. What’s a unique experience you’ve had that most other people haven’t?
Jennifer Still is a writer and editor with more than 10 years of experience. The managing editor of Bolde, she has bylines in Vanity Fair, Business Insider, The New York Times, Glamour, Bon Appetit, and many more. You can follow her on Twitter @jenniferlstill