The RelationshipQuestions
First date questions

First date questions

The ones that skip the small talk and actually tell you something.

A first date lives or dies on the conversation. The trick is knowing which question to ask when the small talk runs dry.

These move from easy ice breakers to the ones that quietly tell you who a person really is, plus a few red-flag detectors and the ones better left for date two.

First date / Fun and flirty

What is your idea of a perfect second date?

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Ice breakers

  1. 1How was your day before you got here?
  2. 2What almost made you cancel on me today?
  3. 3Did you have a whole outfit debate before tonight?
  4. 4What is the story behind picking this spot?
  5. 5Are you a planner, or did you just wing tonight?
  6. 6What is the last thing that made you laugh today?
  7. 7How do you usually spend a night like this?
  8. 8What is your go-to order at a place like this?
  9. 9Do you come to spots like this often?
  10. 10What is the best thing that happened to you this week?
  11. 11Are you more nervous or more curious right now?
  12. 12What do you do right before a first date to calm down?
  13. 13What is the last new restaurant you tried and loved?
  14. 14How far did you have to travel to get here?
  15. 15What made you say yes to this date?
  16. 16What is a question you wish I would ask tonight?

Getting to know them

  1. 17Where did you grow up, and what was that like?
  2. 18What do you do for work, and how did you end up there?
  3. 19What does a perfect Saturday look like for you?
  4. 20What is a hobby you have picked up recently?
  5. 21What is the last trip you took that you would repeat in a heartbeat?
  6. 22Who is the first person you call with good news?
  7. 23What is something you are really good at that has nothing to do with work?
  8. 24What is a skill you are currently trying to learn?
  9. 25What show or book has actually stuck with you lately?
  10. 26What is a place you could go back to again and again?
  11. 27What do your weekends usually look like?
  12. 28What is something people are always surprised to learn about you?
  13. 29What is a version of your life you almost lived instead of this one?
  14. 30What do you do when you need to clear your head?
  15. 31What is on your bucket list that you are actually planning?
  16. 32What is your relationship like with your siblings?

Getting real

  1. 33What does a meaningful life look like to you?
  2. 34What is a belief you hold that not many people share?
  3. 35What is the best advice anyone has ever given you?
  4. 36What are you looking for right now, if you know?
  5. 37What is something you are working on about yourself?
  6. 38What is a risk you took that changed your life?
  7. 39What do you value most in the people close to you?
  8. 40What is something you learned the hard way?
  9. 41What does home mean to you?
  10. 42What is a moment that changed how you see the world?
  11. 43What are you most afraid of losing?
  12. 44What do you want more of in your life right now?
  13. 45What do you wish more people understood about you?
  14. 46What is a goal you are chasing that scares you a little?
  15. 47What is something you wish someone had told you this year?
  16. 48What is something you are proud of that most people would not guess?

Fun and flirty

  1. 49What is your idea of a perfect second date?
  2. 50What is the most impulsive thing you would do tonight on a whim?
  3. 51What is a talent you have that would actually surprise me?
  4. 52What is the boldest thing you have ever done to get someone's attention?
  5. 53What is your type, and am I anything like it?
  6. 54What would you order for me if you had to guess?
  7. 55What is a compliment you are fishing for right now?
  8. 56What is the most charming thing anyone has ever done for you?
  9. 57What is the cheesiest line you would actually try on me?
  10. 58What would make you actually want a second date?
  11. 59What song instantly puts you in a good mood?
  12. 60What is the last thing that gave you butterflies?
  13. 61What is your love language, and did you have to look it up?
  14. 62What is a green flag you are noticing about me so far?

Red flag detectors

  1. 63How do you usually treat people who cannot do anything for you?
  2. 64What is something you argue about with your family?
  3. 65How do you usually act when a plan falls through?
  4. 66What is your relationship like with your ex these days?
  5. 67How do you handle it when you find out you are wrong?
  6. 68What is the last thing that made you lose your temper?
  7. 69How do you feel about staying friends with an ex?
  8. 70What is your honest take on splitting the bill?
  9. 71How do you handle conflict with someone you are dating?
  10. 72What does a bad day usually look like for you?
  11. 73How would your friends describe the way you handle stress?
  12. 74What ended your longest relationship?

Questions not to ask on a first date

  1. 75How much do you make a year?
  2. 76Could you see yourself marrying someone like me?
  3. 77How many kids do you want, realistically?
  4. 78Why did your last relationship actually end?
  5. 79Are you completely over your ex?
  6. 80Why is someone like you still single?
  7. 81What is the most traumatic thing that has ever happened to you?
  8. 82Where do you see this relationship going long term?

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