25 Questions to Make Conversation with on a First Date

We’re revisiting this classic Autostraddle piece on queer dating as we get back to dating basics in partnership with HER’s Queer Dating 101, a series of live edutainment events that brings in concrete how-tos, insights, experts and some of your favorite Autostraddle personalities to help you find love (or whatever you’re looking for) in the time of corona. Check out the event on Nailing the First Date, complete with a live first date followed by a loving critique, TONIGHT 1/19 at 6pm PT | 9pm ET!

It can be tough to figure out conversation for the first date — something in between the first ten minutes of establishing where you both work/how totally fine this small-plates place is and delving into all your childhood trauma. A relatable icon for adult dating is Real Women Have Curves‘ Ana García bringing index cards of conversation topics to her first date. To that end, here are X open-ended yet casual, chill questions to get to know your date better without it feeling like a job interview or summer camp icebreaker.

1. Is your job now what you imagined doing when you were a kid? What was?
2. What’s the farthest trip from home you’ve made?
3. How did you meet your best friend?
4. What’s your comfort show/book/album?
5. How did you get into doing [hobby]?
6. What superpower would you most like to have?
7. What absurd thing did you believe was true about how the world worked as a kid?
8. Do you have any superstitions?
9. What’s your favorite thing to shop for?
10. Do you have a guilty pleasure TV show or movie?
11. What’s your favorite thing about where you work/live?
12. What’s your karaoke song?
13. What were the urban myths where you grew up?
14. What’s your favorite holiday to celebrate?
15. Who in your life could you put up with being trapped on a desert island indefinitely?
16. Do you believe in ghosts?
17. What TV character do you most relate to?
18. What would your dream house look like?
19. What did you grow up thinking was universal because your family did it, and then realized later it wasn’t?
20. Where have you always wanted to travel to?
21. What ending to a TV show did you hate?
22. What was your clique in high school?
23. Were you a group projects person or do you hate them?
24. Do you believe in astrology? (Lol)
25. What’s the best sandwich you’ve ever eaten?

What questions do you like best for getting to know new people? (Also would love to hear your answers! Especially to 8 and 16.)

Want to learn more? Register for Nailing the First Date tonight, 1/19/2021 at 6pm PT | 9pm ET!