55 Great Questions to Ask on a First Date

September 21, 2023

First dates can be equal parts exciting and nerve-wracking. While it's normal to have some jitters, solid preparation can help take the edge off. One key way to get ready for a successful first date is coming armed with great questions to ask.

Having a list of thoughtful, open-ended questions can keep conversation flowing naturally. The right questions help you get to know your date on a deeper level while avoiding awkward silences.

To help make your next first date a little smoother, here are 55 great questions to ask:

Fun Icebreaker Questions

  1. What's your favorite way to spend a Saturday?
  2. If you could live anywhere in the world, where would you choose?
  3. What's one small thing that brightens your day without fail?
  4. Who's your favorite fictional character and why?
  5. If you could only eat one food for the rest of your life, what would you pick?

Life and Career Questions

  1. What do you do for work? Do you enjoy it?
  2. What did you want to be when you grew up?
  3. What are your future career or life goals?
  4. What accomplishment are you most proud of?
  5. What motivates you most in life?

Family and Friends Questions

  1. Where did you grow up? What was your family like?
  2. Do you have any siblings? Are you close with them?
  3. What were you like as a kid? Any funny stories?
  4. Who's impacted you most in your life so far?
  5. Who do you admire most and why?

Personality Questions

  1. How would your friends describe you in three words?
  2. What are some of your best personality traits?
  3. What are your passions and interests outside of work?
  4. What are your top pet peeves or annoyances?
  5. What qualities do you value most in your friends?

Lifestyle and Routine Questions

  1. What does a typical day look like for you?
  2. Where do you see yourself living long term?
  3. What do you enjoy doing in your free time?
  4. How do you like to spend your weekends?
  5. What are your favorite local spots or hangouts?

Travel and Adventure Questions

  1. What's one place you'd love to visit? Why there?
  2. Where's the most amazing trip or vacation you've taken?
  3. Do you prefer traveling alone or with others?
  4. Are you an adventurous traveler or more a planner?
  5. What's on your travel bucket list?

Entertainment and Pop Culture Questions

  1. What's your favorite movie genre? Favorite specific movie?
  2. What TV shows are you into right now?
  3. Who's your favorite music artist or band?
  4. What's the best concert you've ever been to?
  5. Do you have a favorite book? Author? Genre?

Relationship and Date Questions

  1. What do you look for most in a partner?
  2. What positive qualities could you bring to a relationship?
  3. What's your idea of a perfect date?
  4. How do you envision your future family life?
  5. What lessons have past relationships taught you?

Deep Dive Questions

  1. What are you most grateful for in life?
  2. What are your biggest fears or anxieties?
  3. What's one thing on your bucket list?
  4. What keeps you up at night?
  5. What personal weaknesses are you working on?

Fun Hypothetical Questions

  1. If you won the lottery, what would you do first?
  2. If you could have any supernatural ability, what would you choose?
  3. Would you rather be twice as smart or twice as happy? Why?
  4. Would you rather always be 10 minutes late or 30 minutes early?
  5. Would you rather give up your phone or TV?

Wrapping Up Questions

  1. How do you think this date went?
  2. Would you be open to another date together?
  3. Is there anything else you'd like me to know about you?
  4. What question would you like to ask me next?
  5. Are you free next Friday?

With this wide-ranging list of 55 questions, you'll be ready for an engaging first date full of meaningful conversation. Show your attentiveness by following up on their responses to learn even more. Most importantly, don't be afraid to open up and be your genuine self. Good luck!

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