Pookeez

50 Questions to Ask on a First Date (That Aren’t Awkward)

By the Pookeez team · · 7 min read

Worried about awkward silences? The right questions turn a first date from an interview into a real conversation. Here are 50 first date questions, from easy icebreakers to deeper ones, plus tips on how to use them without sounding like you’re reading from a list.

How to ask good first date questions

  • Follow up. The best question is often “wait, tell me more about that”. Listen to the answer instead of planning your next question.
  • Share too. Answer your own questions. A date should feel like a back-and-forth, not a quiz.
  • Read the room. Start light and only go deeper if the conversation is flowing.
  • Skip the heavy stuff. Exes, salary and marriage timelines can wait for later dates.

Easy icebreaker questions

  1. How’s your week been, honestly?
  2. What did you get up to last weekend?
  3. What’s your go-to order here?
  4. Filter coffee or chai, and how strong are your feelings about it?
  5. What’s the best thing you’ve eaten recently?
  6. How long have you lived in the city? What do you love about it?
  7. What’s one thing you’d recommend to someone new in town?
  8. What’s your favourite way to spend a Sunday?
  9. Are you a morning person or a night owl?
  10. What are you binge-watching right now?

Fun questions

  1. What’s your karaoke song?
  2. What’s the most spontaneous thing you’ve ever done?
  3. If you could live in any city for a year, where would it be?
  4. What’s a skill you’d love to learn?
  5. What’s your most unpopular opinion?
  6. Which fictional character are you most like?
  7. What’s the best concert or gig you’ve been to?
  8. Mountains or beaches?
  9. What’s your comfort movie?
  10. If you had a free day with no responsibilities, what would you do?

Getting-to-know-you questions

  1. What do you do, and do you enjoy it?
  2. What did you want to be when you were a kid?
  3. What are you excited about right now?
  4. What’s something you’re proud of?
  5. How would your best friend describe you?
  6. What’s your favourite thing about your hometown?
  7. Are you close to your family?
  8. What’s a hobby you could talk about for hours?
  9. What’s the best trip you’ve ever taken?
  10. What’s on your bucket list?

Deeper questions (if it’s flowing)

  1. What’s something most people don’t know about you?
  2. What’s the best advice you’ve ever been given?
  3. What does a perfect day look like for you?
  4. What’s something you’ve changed your mind about?
  5. Who has had the biggest influence on you?
  6. What makes you feel most like yourself?
  7. What are you working on in your life right now?
  8. What’s a small thing that always makes you happy?
  9. What’s your love language?
  10. What are your green flags in a partner?

Playful “would you rather” questions

  1. Would you rather have a weekend in Goa or a weekend in the hills?
  2. Would you rather cook dinner or plan the date?
  3. Would you rather be able to speak every language or play every instrument?
  4. Would you rather give up biryani or dosa forever?
  5. Would you rather have a dog or a cat?
  6. Would you rather travel back in time or into the future?
  7. Would you rather go to a concert or a comedy show?
  8. Would you rather sit in Bengaluru traffic or Mumbai rain?
  9. Would you rather never use social media again or never watch another movie?
  10. Would you rather do this again?

Questions to avoid on a first date

  • How much do you earn?
  • Why did your last relationship end?
  • When do you want to get married?
  • What’s your caste or religion? (If it matters to you, there are better ways and times to find out.)
  • Anything about their body or weight.

Before the date

Need somewhere to go? Try our first date ideas in Bangalore. And remember the basics: meet somewhere public, tell a friend your plans, and get there and back on your own.

On Pookeez, profiles include icebreakers, relationship goals, green flags and icks, so you’ll already have plenty to talk about before you meet.

First date question FAQs

What should you talk about on a first date?

Stick to light, open topics like hobbies, travel, food, work you enjoy and what you’re excited about. Follow up on their answers and share your own.

How many questions should you ask on a first date?

There’s no number. Ask a question, listen, follow up and share your own answer. If it feels like an interview, slow down.

What topics should you avoid on a first date?

Avoid salary, exes, marriage timelines and comments on appearance. Save serious topics for when you know each other better.

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