40 First Date Questions That Always Work

Phase 1: The first 10 minutes

These questions are key primers, the ones to ask after you’ve said hello, and settled in somewhere comfortable.

  1. What do you do, and how long have you been doing it?
  2. Where are you originally from?
  3. Where did you go to school?
  4. What was your major?
  5. Where exactly do you live in [insert your city or town here]?

Phase 2: After the first drink arrives

What are his likes and dislikes, what do you have in common, what does he do in his spare time?

  1. What do you like to do when you’re not working?
  2. Are you more of a TV person, or do you prefer movies?
  3. Depending on the above answer, ask what they’re watching, or what they’ve seen lately.
  4. What type of music are you into?
  5. Have you traveled anywhere cool lately/do you have any trips coming up?
  6. Have you read any good books recently?

Phase 3: Things are starting to get comfortable…

Some of these questions may seem silly at first, but they can be very telling. They’ll also further loosen the two of you up and can lead to some funny, entertaining conversation.

  1. Are you a cat person or a dog person?
  2. If you could only eat one thing for the rest of your life, what would it be?
  3. Do you have any nicknames?
  4. If you won the lottery tomorrow, what’s the first thing you’d buy?
  5. Do you have any siblings?
  6. If you could be any person for a day, who would it be?
  7. What’s your biggest pet peeve?
  8. Coffee or tea?
  9. Where else would you consider living?
  10. Are you as tired of KimYe as I am?
  11. Do your parents still live in the house you grew up in?
  12. What’s on your bucket list?
  13. Are you a morning person or a night person?
  14. Do you ever cook?
  15. Do you like your job? What do you want to do next?
  16. What’s your social life like? Do you have a big group of friends?
  17. Do you consider yourself career-driven?
  18. What are you most passionate about?
  19. When’s your birthday?

Phase 4: Sign Me Up for a Second Date 

Time to seal the deal– the last few minutes of a date are crucial to make sure he asks you out a second time. If you think the date went well, don’t be afraid to let him know. The final questions should easily transition you out of the date while subtly implying that you’d be down to meet up again.

  1. Can I split the check with you? Okay, can I at least leave the tip?
  2. How is work looking for you this week?
  3. Did you like this place?
  4. Do you have any fun plans for the rest of the weekend?
  5. Do you have a busy week coming up?
  6. How are you getting home?

Phase 5: Let’s Keep the Date Going

  1. There’s this cool bar I know around here, want to go grab a drink?
  2. Want to get coffee/dessert after this somewhere else?
  3. My friend’s actually having a party a few blocks away, do you wanna stop by?
  4. What are we doing after this?