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First date questions that aren't an interview

The problem with first-date questions is that they sound like screening. A choice doesn't — "window or aisle" is play, and play is how people actually relax into being known.

Steal these, or send them as a challenge from Games we Play and compare answers properly.

1.What's the perfect date-night vibe?

2.Would you rather: South of France or Italian coast?

3.What should date-night dinner be?

4.Would you rather: St. Barth or Turks & Caicos?

5.What's your first-round order?

6.Would you rather: Aspen or St. Moritz?

7.Movie night — what are we watching?

8.Would you rather: Niseko powder or Courchevel?

The other 42 are better with your person.

On Games we Play you both answer, both guess each other, and the reveal is scored.

Play free on iPhone

The full list

  1. 9. After dinner, where does the night go?

    💃 Keep going — music, dancing · 🌙 Long walk, big talks · 🍨 Second location: dessert · 🏠 Home while it's still perfect

  2. 10. Would you rather: Tulum or Mykonos?

    🌴 Tulum · 🪩 Mykonos

  3. 11. It's midnight and we're still out. What's the move?

    🍕 Late-night slice, obviously · 🥃 One more bar — a quiet one · 🪩 Dancing till they close · 🌃 The long walk home

  4. 12. Would you rather: Ibiza or Saint-Tropez?

    🎧 Ibiza · 🥂 Saint-Tropez

  5. 13. Where's our first weekend trip?

    🏙️ A city neither of us knows · 🛖 Cabin, fireplace, no signal · 🏝️ Somewhere warm with water · 🚗 Road trip, playlist matters

  6. 14. Would you rather: Paris or London?

    🗼 Paris · 🇬🇧 London

  7. 15. How do you feel about surprises on a date?

    🎁 Love them — don't tell me anything · 🗓️ Surprise the what, tell me the when · 📋 Tell me everything, I'll act surprised

  8. 16. Would you rather: New York or Los Angeles?

    🗽 New York · 🌅 Los Angeles

  9. 17. How much PDA on a date?

    💑 Hand-holding, the works · 🤝 Low-key — an arm, a look · 🚪 Save it for the door

  10. 18. Would you rather: Miami or Palm Beach?

    🌺 Miami · 🌴 Palm Beach

  11. 19. Live-music date — what's the show?

    🏟️ Stadium pop, scream the words · 🎷 Tiny jazz bar · 🎧 DJ set till late · 🎸 Indie band in a small room

  12. 20. Would you rather: Tokyo or Seoul?

    🗾 Tokyo · 🇰🇷 Seoul

  13. 21. Cheesy date ideas — mini golf, aquarium?

    ⛳ Yes. All of them. Immediately · 😏 Fun ironically… then actually fun · 🙅 We're better than mini golf

  14. 22. Would you rather: Maldives or Bora Bora?

    🐠 Maldives · 🌺 Bora Bora

  15. 23. How do we order for the table?

    🥢 Everything shared, order together · 🍽️ My plate is my plate · 👨‍🍳 Let the chef decide

  16. 24. Would you rather: Safari or Yacht week?

    🦁 Safari · 🛥️ Yacht week

  17. 25. Sudden downpour mid-date. That's…

    🌧️ A movie moment — dance in it · 🍸 The universe saying: bar, now · ☔ Reschedule. Hair exists

  18. 26. Would you rather: Positano or Capri?

    🍋 Positano · ⛵ Capri

  19. 27. Photos on dates?

    📸 Document everything, golden hour · 🤳 One good one, then phones away · 📵 No phones, live it

  20. 28. Would you rather: Santorini or Amalfi?

    🇬🇷 Santorini · 🍝 Amalfi

  21. 29. What made you swipe right, honestly?

    📸 The photos. Obviously · 😂 The bio made me laugh · 📊 That match percentage · ✨ Pure vibes, no notes

  22. 30. Would you rather: Monaco GP or Cannes?

    🏎️ Monaco GP · 🎬 Cannes

  23. 31. How nervous are you about actually meeting?

    🫠 Already rehearsing openers · 🦋 Good butterflies · 😎 Cool as a cucumber

  24. 32. Would you rather: Après-ski or Beach club?

    🍷 Après-ski · 🏖️ Beach club

  25. 33. First thought when we matched?

    😳 “Out of my league” · 😏 “Oh no, this is trouble” · 🛋️ “Why is chatting this easy?” · 🙌 “Finally, someone interesting”

  26. 34. Would you rather: Lake Como or Lake Tahoe?

    🚤 Lake Como · 🌲 Lake Tahoe

  27. 35. Who have you told about this match?

    📱 Best friend, immediately · 💬 The entire group chat · 👩 Mom (don't judge) · 🤫 Nobody — keeping it close

  28. 36. Would you rather: Dubai or Singapore?

    🏙️ Dubai · 🦁 Singapore

  29. 37. What almost made you NOT swipe?

    🫣 Photo #3. We need to talk · 📝 One suspicious bio line · 📍 The distance · ⚡ Nothing. Instant yes

  30. 38. Would you rather: Sardinia or Sicily?

    🐚 Sardinia · 🍊 Sicily

  31. 39. Pre-date research level?

    🔍 Full deep-dive, 2019 posts · 📄 Respectful skim · 🙈 Going in blind

  32. 40. Would you rather: Big Sur or The Hamptons?

    🌉 Big Sur · 🦞 The Hamptons

  33. 41. Your profile pics — honest verdict?

    📸 Accurate — that's really me · 🎯 My best angles, strategically · ⏳ Slightly outdated, still cute · ✨ Honestly? Better in person

  34. 42. What should the first date be?

    🍸 Drinks — easy exit, easy extend · 🍝 Dinner — commit to the night · 🎳 Something to do — games, mini golf · ☕ Coffee walk, classic

  35. 43. What energy are you bringing to date one?

    😌 Calm and unbothered (fake) · 🎤 A thousand questions · 😏 Full flirt from minute one · 🫶 Charmingly awkward

  36. 44. Biggest surprise so far?

    😂 Funnier than the profile · 🌊 Deeper than expected · 📱 How much I check my phone now · 🤓 Secretly a huge nerd

  37. 45. Dessert plan?

    🍮 One dessert, two spoons · 🍰 Own dessert. Boundaries · 🍦 Walk somewhere for gelato · 🍸 Skip it — another drink

  38. 46. Where do we sit?

    🛋️ Corner booth, side by side · 🍹 At the bar, watching the shakers · 🪟 Window table, people-watching · 🌙 Outside, even slightly too cold

  39. 47. It's midnight and the place is closing. We…

    🏡 Head home — perfect ending · 🚶 Long walk, no destination · 🍸 Find one more open bar · 🍟 Late-night greasy food

  40. 48. Who plans the perfect date?

    📋 Me. I love the planning · 🎁 You — surprise me · 🤝 We plot it together · 🎲 Nobody. We wing everything

  41. 49. Dancing comes up. I…

    💃 Am already on the floor · 🥂 Need two drinks first · 🌹 Slow songs only · 🧥 Hold the coats, happily

  42. 50. Ideal anniversary shape?

    🔁 Recreate the first date · 🥂 Big night, dress up, splurge · 🧳 A night away somewhere · 🕯️ Quiet, homemade, just us

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