55 Best First Date Questions That Will Get Them Talking

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Let’s face it, first dates can be awkward. While some people get lucky and click with a person right away, the fact is that getting to know someone takes effort — especially when it comes to the conversation.

After getting over the humps of brainstorming first date ideas and what to wear, keeping the conversation flowing is the next step. If you’re a planner, choosing first date fun dating questions ahead of time can help you to relax into conversation more easily and avoid those uncomfortable silences. Of course, you don’t want to just fire off questions at them as if you’re interviewing them — instead you might consider having a couple of questions or topics in mind for if the conversation does slow.

Tips for first date conversation:

  • Show genuine interest in your date. Having some topics and ice breaker questions in mind can ease your anxiety ahead of the date, but asking questions that show you’re genuinely interested in getting to know the person will make the conversation flow.

  • Keep it light. This is a first date after all, it should be fun! Sticking to topics and questions that are fun, flirty, and not too heavy can help you gauge just how much the other person is willing to open up.

  • Be sure to share about yourself, too! If the other person isn’t asking as many detailed questions, there could be a lot of reasons for this. But it’s always okay to insert some fun facts about yourself as you’re asking your date questions too. That way, you can share interests and find commonalities.

If you’re still nervous about the date, we’ve come up with a list of questions to ask on a first date that are lighthearted and flirty, yet can tell you a lot about a person and their dating potential. Maybe save some of the harder hitting questions to ask your crush, like do they fall in love easily or the state of their mental health, for future outings. For now, think of a first date as playing the classic 21 questions game and simply enjoy the company of this new person with some prompts that will spark laughter and nostalgia and hopefully have them reciprocating with some fun questions of their own!

  1. If you could drop everything right now and travel, where would you go?

  2. Are you more of a morning person or night owl?

  3. What are you currently watching on TV?

  4. What’s something good that happened to you this week?

  5. What do you like most about yourself?

  6. Who are some of your favorite musical artists?

  7. Who do you usually go to for advice?

  8. What movie can you quote beginning to end?

  9. Are you more introverted or extroverted?

  10. What’s your family like? Do you have siblings?

  11. How do you like to relax at the end of the day?

  12. Do you have any hidden talents?

  13. Do you have a dream job?

  14. If you could relive one day, what would it be?

  15. How important is it for you to have a routine to your day?

  16. Have you read any good books lately?

  17. Do you have any bucket list items for the year?

  18. If you’re having a hard day, how do you usually turn it around?

  19. What’s your favorite type of cuisine?

  20. If you didn’t live here currently, where could you see yourself living?

  21. What do you look for in a good friend?

  22. What’s something people might find surprising about you?

  23. How long is your longest friendship?

  24. What’s the worst movie you’ve watched?

  25. What topic could you talk about for hours?

  26. What do you like to do on your days off?

  27. What skill would you like to learn?

  28. Who makes you laugh the most?

  29. Who are you closest with in your family?

  30. Were you a Disney Channel or Nickelodeon kid growing up?

  31. What’s your favorite thing to do on a Sunday?

  32. What’s your go-to dessert?

  33. When is the last time you tried something new?

  34. Sweet or savory breakfast?

  35. What celebrity do you get told you look like?

  36. Did you play any sports in high school?

  37. Do you have tattoos?

  38. What’s the first concert you ever went to?

  39. What’s a fun fact you can’t shut up about?

  40. Who are your top 3 favorite musicians?

  41. What’s a country you’d love to live in for a year?

  42. What’s the last movie you watched?

  43. What’s the last TV show you binged?

  44. Are you a planner or more go with the flow?

  45. Were you shy as a kid?

  46. Are you a relationship person or more comfortable being single?

  47. How long have you lived here?

  48. Is there something you were embarrassed to like growing up?

  49. Do you have a nickname?

  50. What’s your biggest pet peeve?

  51. What did you study in college?

  52. Did you grow up with pets?

  53. Who was your celebrity crush growing up?

  54. How do you deal with stress?

  55. What’s your favorite season?

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Want more from Teen Vogue? Check this out: 168 Questions to Ask Friends That Are Fun, Personal, and Deep

Originally Appeared on Teen Vogue