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Dating Tips
February 10, 2024ā€¢10 min read

25+ Questions to Ask on a First Date (That Actually Work)

Skip the awkward small talk. These first date questions will help you connect, have fun, and see if there's a real spark.

#first date#dating#conversation starters#relationship advice

25+ Questions to Ask on a First Date (That Actually Work)


First dates can be nerve-wracking. You want to get to know the person, but you also want to keep things light and fun. The right questions can make all the difference between an awkward evening and a great connection. Here are 25+ questions that actually work on first dates.


Why Good Questions Matter on First Dates


First dates are about:

- Getting to know each other: Beyond the surface level

- Creating connection: Finding common ground

- Having fun: Making the experience enjoyable

- Assessing compatibility: Seeing if there's potential

- Building comfort: Making both people feel at ease


The Best First Date Questions


Light & Fun Questions (Start Here)


These questions are perfect for breaking the ice and keeping things light:


1. What's the best meal you've ever had?

  • - Why it works: Everyone loves food, creates positive memories, leads to stories
  • - Follow-up: "Where was it?" "Who were you with?"

    • 2. What's something you're really good at that people don't know about?

  • - Why it works: Reveals hidden talents, creates interest, shows personality
  • - Follow-up: "How did you learn?" "Can you show me sometime?"

    • 3. What's your go-to karaoke song?

  • - Why it works: Fun, reveals personality, creates laughs
  • - Follow-up: "Have you actually sung it?" "What's the story behind it?"

    • 4. What's the weirdest thing in your fridge right now?

  • - Why it works: Specific, relatable, funny, reveals habits
  • - Follow-up: "Why do you have that?" "When did you buy it?"

    • 5. If you could have any superpower, what would it be and why?

  • - Why it works: Creative, reveals values, easy to answer
  • - Follow-up: "What's the first thing you'd do with it?"

    • Getting to Know Them


    These questions help you understand who they are:


    6. What's something you're passionate about?

  • - Why it works: Reveals what drives them, creates meaningful conversation
  • - Follow-up: "How did you get into that?" "What do you love about it?"

    • 7. What's the best trip you've ever taken?

  • - Why it works: Positive memories, reveals interests, creates stories
  • - Follow-up: "What made it special?" "Where would you go next?"

    • 8. What's a goal you're working toward right now?

  • - Why it works: Current, aspirational, shows ambition
  • - Follow-up: "How's it going?" "What's your plan?"

    • 9. What's something you believed as a kid that you now know is wrong?

  • - Why it works: Funny, relatable, creates laughs, shows growth
  • - Follow-up: "When did you realize?" "What's the story?"

    • 10. What's the best piece of advice you've ever received?

  • - Why it works: Meaningful, reveals values, creates sharing
  • - Follow-up: "Who gave it to you?" "How has it helped?"

    • Deeper Questions (When Comfortable)


    These questions go a bit deeper, use them when you've built some rapport:


    11. What's a book, movie, or show that changed your perspective?

  • - Why it works: Meaningful, reveals values, creates recommendations
  • - Follow-up: "How did it change you?" "Would you recommend it?"

    • 12. If you could give your younger self one piece of advice, what would it be?

  • - Why it works: Reflective, meaningful, shows self-awareness
  • - Follow-up: "Why that advice?" "Do you follow it now?"

    • 13. What's something you're really proud of?

  • - Why it works: Positive, reveals achievements, creates connection
  • - Follow-up: "What made it special?" "How did you achieve it?"

    • 14. What's a challenge you've overcome?

  • - Why it works: Shows resilience, creates deeper connection
  • - Follow-up: "How did you handle it?" "What did you learn?"

    • 15. What makes you feel most alive?

  • - Why it works: Deep, reveals what energizes them
  • - Follow-up: "When was the last time you felt that?" "How often do you do it?"

    • Fun & Playful Questions


    Keep things fun and lighthearted:


    16. What's your most useless talent?

  • - Why it works: Funny, unique, creates laughs
  • - Follow-up: "Can you demonstrate?" "When did you discover it?"

    • 17. What's the worst fashion trend you've ever followed?

  • - Why it works: Self-deprecating humor, relatable
  • - Follow-up: "Do you have photos?" "What were you thinking?"

    • 18. What's a food you used to hate but now love?

  • - Why it works: Relatable, creates food discussions
  • - Follow-up: "What changed?" "When did you try it again?"

    • 19. What's the weirdest thing you've ever googled?

  • - Why it works: Funny, relatable, creates laughs
  • - Follow-up: "Did you find the answer?" "Why did you need to know?"

    • 20. If you could have dinner with anyone (living or dead), who would it be?

  • - Why it works: Reveals values, creates interesting discussions
  • - Follow-up: "What would you ask them?" "What would you eat?"

    • Questions About Them


    Learn about their life and experiences:


    21. What's something you do that drives your friends/family crazy?

  • - Why it works: Self-aware, funny, relatable
  • - Follow-up: "Do you do it on purpose?" "Have you tried to stop?"

    • 22. What's the best gift you've ever given someone?

  • - Why it works: Positive, reveals thoughtfulness
  • - Follow-up: "Who was it for?" "Why was it special?"

    • 23. What's the best compliment you've ever received?

  • - Why it works: Positive, meaningful, creates good feelings
  • - Follow-up: "Who said it?" "Why did it mean so much?"

    • 24. What's something you're looking forward to?

  • - Why it works: Positive, future-oriented, creates excitement
  • - Follow-up: "Tell me more about it" "When is it happening?"

    • 25. What's a skill you'd love to learn?

  • - Why it works: Aspirational, reveals interests
  • - Follow-up: "What's stopping you?" "How would you start?"

    • Questions to Play Together


    Truth or Drink


    Perfect for first dates! The AI asks bold questions. Each person must either tell the truth or take a sip/shot. Great for breaking the ice!


    Why it works on dates:

  • Interactive and fun
  • Reveals interesting facts
  • Creates conversation
  • Low pressure
  • Can be played anywhere

    • Want to try it with an AI twist? [Play Truth or Drink](/game) with our AI bartender for personalized questions that make first dates even more fun!


    Would You Rather


    Simple choices that reveal preferences:

  • "Would you rather travel the world or have a dream home?"
  • "Would you rather be able to fly or be invisible?"
  • "Would you rather have perfect memory or be able to forget anything?"

    • How to Use These Questions


    Timing is Everything


    Start light:

  • Begin with fun, easy questions
  • Build comfort before going deeper
  • Let the conversation flow naturally

    • Go deeper gradually:

  • As you build rapport, ask more meaningful questions
  • Pay attention to their comfort level
  • Don't push if they seem uncomfortable

    • End on a positive note:

  • Finish with fun or light questions
  • Leave them feeling good about the date
  • Create positive memories

    • Reading the Room


    Signs they're comfortable:

  • Asking you questions back
  • Sharing stories and details
  • Laughing and smiling
  • Leaning in and making eye contact

    • Signs they're uncomfortable:

  • Short answers
  • Changing the subject quickly
  • Looking away or closed body language
  • Not asking questions back

    • What to do:

  • If comfortable: Continue with deeper questions
  • If uncomfortable: Lighten up, go back to fun questions
  • Always respect boundaries

    • Making It a Conversation


    Don't just fire questions:

  • Share your own answers
  • Ask follow-up questions
  • Listen actively
  • Find connections

    • Create flow:

  • Let one question lead to another
  • Build on what they say
  • Don't stick to a script
  • Be present in the moment

    • Questions to Avoid on First Dates


    Too Personal Too Fast

  • Relationship history (unless they bring it up)
  • Financial situation
  • Family drama
  • Past trauma
  • Future plans (marriage, kids) - too soon!

    • Too Serious

  • Politics (unless you both enjoy it)
  • Religion (unless it's important to you both)
  • Controversial topics
  • Complaints about exes
  • Work stress (keep it light)

    • Too Boring

  • "What do you do for work?" (okay, but overused)
  • "Where are you from?" (fine, but basic)
  • "What's your favorite color?" (too simple)
  • Yes/no questions (kill conversation)

    • Making Your First Date Memorable


    Do's


    āœ… Be yourself: Authenticity is attractive

    āœ… Listen actively: Show genuine interest

    āœ… Share your own answers: Create reciprocity

    āœ… Have fun: Enjoy the moment

    āœ… Be present: Put your phone away

    āœ… Ask follow-up questions: Show you're engaged

    āœ… Laugh together: Humor creates connection


    Don'ts


    āŒ Don't interview them: Make it a conversation

    āŒ Don't talk only about yourself: Balance is key

    āŒ Don't check your phone: Be present

    āŒ Don't overshare: Keep some mystery

    āŒ Don't be negative: Keep it positive

    āŒ Don't force chemistry: It either exists or it doesn't

    āŒ Don't have expectations: Just enjoy the moment


    First Date Conversation Tips


    1. Start with observation: Comment on something around you

    2. Ask open-ended questions: Avoid yes/no questions

    3. Share your own stories: Create reciprocity

    4. Find common ground: Build on shared interests

    5. Use humor: Laughter creates connection

    6. Be curious: Genuine interest is attractive

    7. Listen more than you talk: Show you care


    Conclusion


    Great first dates are about connection, fun, and getting to know each other. The right questions can help you achieve all three. Remember to start light, go deeper gradually, and always read the room.


    Want to add some fun to your first date? Try playing [Truth or Drink](/game) together! Our AI bartender will provide personalized questions that make first dates more interactive and memorable.


    Most importantly, be yourself, have fun, and let the conversation flow naturally. The best connections happen when both people feel comfortable and can be authentic.


    Good luck on your first date! šŸŽ‰

    Ready to Play Truth or Drink?

    Put these tips into practice with our AI-powered game featuring personalized questions and multiple bartender personalities!

    Play Now

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