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63 First-Date Questions Worth Asking

Great dates aren't about impressing each other. They're about real conversation. Here are 63 questions, sorted by category, that get past the small talk and help you actually get to know someone.

How to use this

  1. Memorize five favorites. Skim the list and pick the five you'd genuinely love to ask. Commit them to memory so the conversation flows naturally, no phone required.
  2. Save all 63 to your phone. Tap Download / Save as PDF below and keep it in your files. A quick glance in the car beforehand and you'll never run out of things to talk about.
  3. Let it breathe. Ask, then really listen. The best follow-up question is usually just "why?"
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On the print dialog, choose “Save as PDF” as the destination. On a phone, tap Share → Print → pinch to save.

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Wild card: just for fun

Bonus round. No rules, no deep meaning; just pull one out when the mood is light and see where it goes.

  1. Most annoying commercial from childhood?
  2. If we went back into oldtimey days, what would your profession be? (Alchemist, cartographer, etc.)
  3. If you were on Real Housewives of [your city], what would your opening tag line be?
  4. Longest time you've been awake consecutively?
  5. Aliens land and will only negotiate with whoever wins one game. What game are you picking?
  6. What would your pet's profession be if they were human?
  7. If we adopted a puppy together, what kind, what name, and what would we tell people is its backstory?
01

Icebreakers & easy laughs

  1. What's a hill you'll happily die on that absolutely does not matter?
  2. What's something you're weirdly, unreasonably competitive about?
  3. Have you ever been mistaken for someone else?
  4. Favorite restaurant in the city?
  5. What's the strangest thing you've googled this month?
  6. Your best purchase ever that's under $1k?
  7. What's the app on your phone you'd be a little embarrassed to show me?
  8. What's a slang word or expression you never understood?
02

Growing up

  1. Most embarrassing college (or high school) moment?
  2. Favorite childhood toy, and why?
  3. What's something from the '90s you wish they'd bring back?
  4. What did ten-year-old you want to be, and what would they think of you now?
  5. What's a ridiculous belief you had as a kid?
  6. Oddest family member, and why?
  7. If you were to relate your family to a TV sitcom, which sitcom?
  8. Who shaped the person you turned into more than anyone?
03

Getting to know the real you

  1. What's something people are always surprised to learn about you?
  2. How do you actually recharge when you're running on empty?
  3. How would you be cast in a reality show?
  4. Have you ever saved a life, or had your life saved?
  5. Have you ever been kicked out of a building?
  6. What's one thing that everyone else can do but you haven't yet mastered?
04

Passions & what lights you up

  1. What's something you dislike that the rest of the world likes?
  2. If CNN called you on as an expert correspondent, what topic would they be requesting your expertise in?
  3. Most meaningful contribution you've given to the world?
  4. What's the one book, show, or song you make everyone you love try?
  5. What's something you taught yourself just because you wanted to?
  6. What's a tiny, unremarkable thing that often makes your day better?
  7. What have you made or built that you're quietly proud of?
05

Values, faith & what matters

  1. If you could have the best thing happen to you tonight, what would that be?
  2. What role does faith or spirituality play in your life?
  3. What's a value you were raised with that you still carry?
  4. What's a compliment you've never been able to forget?
  5. What's something in your home that you'll never get rid of?
  6. What's your proudest moment?
  7. What's something happening in the world you can't stay quiet about?
06

Love, dating & relationships

  1. What makes you feel truly appreciated by someone?
  2. What's the kindest thing anyone has ever done for you?
  3. What's the best lesson an old relationship left you with?
  4. How do you show someone you love them when words aren't enough?
  5. What's your one true non-negotiable in a relationship?
  6. What does a great partnership look like on an ordinary Tuesday?
  7. What are you really hoping to find in the right person?
07

Dreams, travel & the future

  1. What's been your most random night out?
  2. What's your favorite secret spot in the city?
  3. If you could live anywhere for a year, no strings, where?
  4. Most awkward airplane story?
  5. Paint me your ideal life five years from now.
  6. What's the trip that changed you, and why?
  7. What's a dream you've quietly carried since you were young?
08

Would you rather

  1. Would you rather clone one giant version of you or 100 tiny versions of you?
  2. If we swapped professions, who do you think would do a better job?
  3. Would you rather your laugh sound fake or your serious voice sound sarcastic?
  4. Would you rather always wave back even if they weren't waving at you, or never wave back at all?
  5. Would you rather replace every handshake with a high five, or every hug with a fist bump?
  6. Would you rather have to repeat everything you said, or dance while you walked, for the rest of your life?
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