First Date Questions

Warm up Getting real Deeper

Warm up: easy questions with nothing to defend (58)

1. What was the best part of your week so far? Then ask: What made it land so well?
2. How did your day start today? Then ask: Is that a normal morning for you, or a strange one?
3. What do you do when you're not at work? Then ask: How did you get into that?
4. Are you a morning person, a night person, or neither? Then ask: What's the best hour of your day?
5. What's the last thing you watched that you actually liked? Then ask: Would you tell me to watch it, or is it a you thing?
6. Coffee, tea, or something else entirely? Then ask: What's your order, exactly?
7. What's a place in this city you keep going back to? Then ask: What keeps pulling you back there?
8. Where did you grow up, and what was it like? Then ask: What do you miss about it?
9. What does a good Sunday look like for you? Then ask: Is that what you did last Sunday?
10. What's something you're looking forward to this month? Then ask: Why that, of all things?
11. What music have you had on repeat lately? Then ask: What's it about that one?
12. What kind of food could you eat every week and never get bored? Then ask: Where do you get the best version of it?
13. Do you like your plans made, or do you like to wing it? Then ask: What's the last thing you did on a whim?
14. What's a hobby you picked up and actually stuck with? Then ask: What keeps you coming back to it?
15. Are you a cat person, a dog person, or a no pets please person? Then ask: Any pets right now, or pets growing up?
16. What was the last trip you took? Then ask: What was the best moment of it?
17. Where would you go if you had a free long weekend next week? Then ask: Who would you bring?
18. What's your favorite season, and why? Then ask: What's your perfect day in that season?
19. Do you cook, or are you more of a takeout expert? Then ask: What's your signature dish, either way?
20. What's the best thing you ate this year? Then ask: Where was it?
21. What do your friends come to you for? Then ask: Do you like being that person?
22. Are you a reader, a listener, or a watcher? Then ask: What are you in the middle of right now?
23. What app do you open most on your phone, apart from messages? Then ask: Is that a good thing or a bad thing?
24. Beach, mountains, or a city? Then ask: Where's the best one you've been to?
25. What's something small that always puts you in a good mood? Then ask: When did that last happen?
26. What's the most useless skill you have? Then ask: Can you show me right now?
27. What's a food opinion you will defend to the end? Then ask: Who disagrees with you the most?
28. What's the worst haircut you've ever had? Then ask: Are there photos, and will I ever see them?
29. Which fictional character would you want as a roommate? Then ask: Which one would be the worst roommate?
30. What's your karaoke song, even if you never do karaoke? Then ask: Is it a crowd pleaser or a deep cut?
31. What would your friends say is your most annoying habit? Then ask: Would they be right?
32. What's a trend you never understood? Then ask: Did you ever try it anyway?
33. If your life had a theme song, what would it be right now? Then ask: Has it changed in the last year?
34. What's the strangest job you've ever had? Then ask: What did it teach you, if anything?
35. What's your most irrational fear? Then ask: Where do you think it came from?
36. What's the weirdest thing you've ever googled? Then ask: What started that search?
37. Which emoji do you use way too much? Then ask: What does it mean when you send it?
38. What's a small thing people do that you secretly judge? Then ask: Have you ever done it yourself?
39. Would you rather always be ten minutes early or always ten minutes late? Then ask: Which one are you actually?
40. What's your go-to fun fact about yourself? Then ask: Is it actually true, or did it grow over time?
41. What's the most you've ever laughed at something that wasn't that funny? Then ask: Can you explain it, or is it a you had to be there thing?
42. What would your dating app bio say if your best friend wrote it? Then ask: Would they be kind?
43. What's a movie everyone loves that you couldn't get through? Then ask: Did you tell people, or did you nod along?
44. What made you say yes to tonight? Then ask: What were you hoping for?
45. What do you think people usually get wrong about you at first? Then ask: And what do they find out later?
46. What's your idea of a perfect first date, if this isn't it? Then ask: What would you never do on a first date?
47. Are you a good dancer, a bad dancer, or a fearless dancer? Then ask: Will I ever find out?
48. Which compliment have you never forgotten? Then ask: Who gave it to you?
49. What did you almost wear tonight? Then ask: What made you change your mind?
50. Are you more of a planner or a let's-see-where-the-night-goes person on dates? Then ask: What's the best unplanned night you've had?
51. Do you believe in chemistry, or do you think it grows? Then ask: Have you seen both?
52. What's your go-to move when you want to make someone laugh? Then ask: Does it usually work?
53. What's the most fun you've had on a night out? Then ask: Who was there?
54. What's something you're secretly hoping someone asks you about? Then ask: Okay, I'm asking.
55. What's the most charming thing someone can do on a first date? Then ask: Has anyone nailed it?
56. Would you rather be swept off your feet or do the sweeping? Then ask: What would sweeping look like?
57. What's your best feature, according to your friends? Then ask: Do you agree with them?
58. Which do you notice first: a laugh, a smile or a good story? Then ask: Why that one?

Getting real: stories, plans and what matters (57)

1. Do you believe in first impressions? Then ask: What was your first impression of me?
2. What does your work look like on a normal day? Then ask: What part of it do you secretly enjoy?
3. If you could switch careers tomorrow, with no risk, what would you do? Then ask: What stops you in real life?
4. What's something you're proud of that you rarely get to talk about? Then ask: What did it take to get there?
5. Are you close to your family? Then ask: Who are you most like?
6. Do you have siblings, and where do you land in the order? Then ask: Do you think it shaped you?
7. Who's the friend you have known the longest? Then ask: How did you meet?
8. What's a skill you want to learn in the next year? Then ask: Who would you learn it from?
9. What's something you changed your mind about in the last few years? Then ask: What changed it?
10. What are you better at than most people? Then ask: When did you notice?
11. What's a tradition you love, from your family or your friends? Then ask: Would you keep it going?
12. What's the best advice you ever got? Then ask: Do you follow it?
13. Where do you see yourself living in five years: here, or somewhere else? Then ask: What would make you move?
14. How do you recharge after a long week? Then ask: Is that alone time or people time?
15. What's a book, show or podcast that changed how you think? Then ask: What stuck with you?
16. What's a place you've been that you'd go back to tomorrow? Then ask: What would you do first?
17. What do you do when you can't sleep? Then ask: What's the strangest thing you've done at 3 am?
18. What's the most spontaneous thing you've ever done? Then ask: What made you say yes in the moment?
19. What's the worst date you've ever been on, without names? Then ask: What did you learn from it?
20. What's the funniest way a date has ever ended for you? Then ask: Did you see it coming?
21. If we were on a game show right now, which one would we win? Then ask: And which one would we lose badly?
22. What's something you're weirdly competitive about? Then ask: When did you last win at it?
23. What's the pettiest reason you stopped liking something? Then ask: Do you stand by it?
24. What would you do with a completely free day and 500 dollars that you had to spend? Then ask: Who would you call first?
25. Which family member would you send to represent you on a reality show? Then ask: Would they win?
26. What's the most embarrassing thing that happened to you in public? Then ask: How did you recover?
27. What's a rule you follow that nobody else seems to? Then ask: Where did it come from?
28. What's the best thing you've ever found or won? Then ask: Do you still have it?
29. What app or gadget could you not live without, and which one should you delete? Then ask: Would you actually delete it?
30. What does a really good day look like for you, start to finish? Then ask: How many of those did you have this year?
31. What are you most curious about right now? Then ask: What got you into it?
32. Who has had the biggest influence on who you are? Then ask: What did they get right?
33. What's a goal you're working toward right now? Then ask: What's the hard part?
34. What does home mean to you, a place or people? Then ask: When did you last feel that?
35. What's something you do that makes you lose track of time? Then ask: When did that last happen?
36. What's something you value more now than you did five years ago? Then ask: What changed?
37. How do you like to be cared for when you're sick or stressed? Then ask: Do people usually get it right?
38. What's a risk you took that paid off? Then ask: Would you take it again?
39. What does friendship look like for you as an adult? Then ask: Has it gotten easier or harder?
40. If money were no problem for a year, how would you spend your time? Then ask: What would you miss about your life now?
41. What's your love language, if you believe in that kind of thing? Then ask: What's a small way someone got it right for you?
42. What's something you find attractive that's not about looks? Then ask: Who taught you that?
43. Do you get nervous before dates? Then ask: How nervous are you right now, out of ten?
44. What's a green flag that makes you want a second date? Then ask: Have you seen any tonight?
45. What's the best date you've ever planned for someone? Then ask: Did it go to plan?
46. Would you rather have a fancy dinner or a picnic with no plan? Then ask: What would you bring to the picnic?
47. What song would you put on in the car with someone you like? Then ask: Would you sing?
48. What's a small gesture that wins you over? Then ask: When did someone last do it?
49. Are you a hand-holder, a hugger, or an arm's length person? Then ask: Does it change with the person?
50. Where would you take someone to impress them, in this city? Then ask: What would you order there?
51. What's your favorite thing about the neighborhood you live in? Then ask: What would you change?
52. What's a trip that went completely wrong? Then ask: Was it fun looking back?
53. What do you think makes a first date go well? Then ask: How are we doing so far?
54. What's your idea of the perfect second date? Then ask: Too soon to plan one?
55. What's the most romantic thing you've ever done on a whim? Then ask: How did they react?
56. Do you like being flirted with, or do you prefer to flirt? Then ask: Which are you doing right now?
57. What's a cheesy date idea you secretly love? Then ask: Should we do it?

Deeper: late in the date, or on the second date (57)

1. What's something you want more of in your life right now? Then ask: What's in the way?
2. What did you learn about yourself in the last year? Then ask: Was it a good surprise or a hard one?
3. What's something that always makes you feel understood? Then ask: Who does that for you?
4. What do you think makes a relationship work long term? Then ask: Where did you see that?
5. What's a belief you hold that most people around you don't? Then ask: How did you get there?
6. What are you most grateful for this year? Then ask: Who do you thank for it?
7. What would you want to be remembered for? Then ask: Are you on track?
8. When do you feel the most like yourself? Then ask: How often do you get that?
9. What's a fear you've gotten over? Then ask: How did you do it?
10. What does a good partner do on a bad day? Then ask: Did someone do that for you once?
11. What's something you're still figuring out? Then ask: What would help?
12. What's a lesson you had to learn twice? Then ask: Do you think you have it now?
13. What did your last relationship teach you about what you want? Then ask: What would you look for next time?
14. What's the kindest thing a stranger has done for you? Then ask: Did you ever pay it forward?
15. What part of your life are you most proud of building? Then ask: Who helped you get there?
16. What did you learn about love from the people who raised you? Then ask: What do you want to do the same, or differently?
17. What does a happy life look like to you, in one sentence? Then ask: How close are you to it?
18. What's something you wish more people asked you about? Then ask: Can I ask you about it now?
19. What's a dream you haven't told many people? Then ask: Who was the first person you told?
20. What do you do when you feel stuck? Then ask: What got you unstuck last time?
21. How do you think about money: safety, freedom, or something to enjoy? Then ask: Where did that come from?
22. What's a cause you care about? Then ask: What got you into it?
23. What's a moment that changed the direction of your life? Then ask: Would you change it?
24. How do you show someone you care, without saying it? Then ask: How do you like it shown to you?
25. What's on your list for the next few years: places, skills, adventures? Then ask: Which one comes first?
26. What would your perfect weekend away look like? Then ask: Who plans it, you or the other person?
27. What's something you've always wanted to try but haven't yet? Then ask: What would it take?
28. How do you want your life to feel a year from now? Then ask: What's one change that gets you there?
29. What kind of home do you want one day: city flat, house, van, farm? Then ask: What would be in it?
30. What's a small daily ritual you'd never give up? Then ask: When did it start?
31. If we had to plan a trip together right now, where would we end up arguing? Then ask: Who would win?
32. What's a dealbreaker that sounds small but isn't? Then ask: Has it ended something before?
33. What's the most romantic thing you've ever done that went wrong? Then ask: Would you try it again?
34. What would you name a boat, a dog and a band? Then ask: Which one first?
35. What made you laugh the most tonight? Then ask: What's the funniest thing that happened to you this week?
36. What's something about tonight you didn't expect? Then ask: A good surprise?
37. What makes you want a second date with someone? Then ask: Is it the talk, the laughs, or something else?
38. What's the most romantic place you've ever been? Then ask: Who were you with?
39. What's a date idea you've always wanted to do but never have? Then ask: Should we?
40. Do you like being asked out, or doing the asking? Then ask: Who asked who tonight?
41. What do you notice first about someone you like? Then ask: What did you notice tonight?
42. What are you hoping for in the next year of dating? Then ask: Is that something you say on first dates?
43. What's your favorite way to end a good night? Then ask: Late snack, a walk, or straight home?
44. What's something you're better at now than you were at 20? Then ask: What taught you?
45. Who do you call when something good happens? Then ask: And when something bad happens?
46. What's a compliment you find hard to accept? Then ask: Why that one?
47. What's a city you could see yourself living in one day? Then ask: What would your life look like there?
48. What's a hobby you'd take up if nobody could see you do it? Then ask: Is it too late to start?
49. What's something you'd want to show someone you're dating, in your own city? Then ask: When would you take them?
50. If tonight were a movie, what genre would it be? Then ask: Who would play us?
51. What's the worst gift you've ever given someone? Then ask: Did they ever find out how you felt about it?
52. What would your perfect day look like if it had to include something ridiculous? Then ask: Where does the ridiculous part come in?
53. What's a small thing you're irrationally proud of? Then ask: When did you last bring it up?
54. What's a skill you'd love to teach someone? Then ask: How long would it take to learn?
55. What would you do with a whole week off next month? Then ask: Would you stay home or go somewhere?
56. What would make tonight a ten out of ten? Then ask: Is it still possible?
57. If we went somewhere after this, where would you pick? Then ask: Want to try it sometime?