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75 First Date Questions

First dates can be as nerve-racking as they are exciting. After all, you don’t know that person super well yet, but that’s what dates are for! And when you’ve got plenty of questions to ask on a first date, there’s no need to be nervous because you know the conversation will flow. Lucky for you, I’ve got a whole list right here of good first date questions that will break the ice and help you get to know one another.

Tips for Asking Good First Date Questions

Imagine you’re on your first date. You’re naturally going to ask questions to get to know each other in between bites of pizza or sips of coffee. But what if you run into an awkward pause, or you’re nervous and don’t even know what to say after “hi”? Hey, not a big deal. Before you head out, here are five tips for starting a conversation on a first date.

Spend your first date somewhere you can talk and get to know each other.

The first tip for asking good first date questions is to choose a place that makes it easy to have a conversation! A theme park where you’re on roller coasters the whole time? Fun, loud and probably pricey. But eating an ice cream cone during a walk through the park together? Affordable, tasty and easy to hear each other. Perfect! The good news is, most date ideas that are great for conversations are also great for your wallet. It’s not about how much money you spend, but how you spend time getting to know each other!

Be curious, not judgmental.

When you’re getting to know someone, try not to make snap judgments about them when they answer get-to-know-you questions. Instead, be curious and ask some follow-up questions if something strikes you as different or unusual. You could learn something new or realize they have a personality trait that you really admire!

Let the conversation flow both ways.

A first date is way different than a job interview, guys! You don’t want to be the only one asking questions, and you don’t want to be the only one answering them either. Make sure you’re both taking turns in the conversation. And don’t be afraid of awkward pauses—use those quiet moments as an opportunity to smile and just enjoy the scenery! Remember, no pressure.

Tell the truth (in a positive way).

There’s a good chance you’ll ask someone one of these first date questions, and they’ll turn it right around back to you. Here’s a truth about dating: You never know what someone else might like—or not like. So if you’re honest about who you are and what you think and how you feel, there’s a chance someone might not jibe with that. But there’s also a chance that they’ll like everything about you. So do yourself (and them) a favor by being up-front from the start. This will set the tone for the other person to open up about who they are too. (Just don’t turn your date into a therapy session and let any crazy skeletons out of the closet . . . remember, good first date questions keep the conversation light and positive!)

Keep these questions light and fun!

If you hit it off and decide to keep going out, you can get into deeper questions to ask before marriage later on, once things get serious. But for now, there’s no pressure. You’re just two adorable people, sitting on a park bench overlooking the city, learning more about why he named his childhood dog Mr. Moose and why you think the only reason pineapple exists is to be added on top of pizza. When it comes to the best first date questions, just remember two words: Have. Fun.

75 First Date Questions

Hopefully you have a spot picked and the perfect outfit planned for your date. Once those very important details are taken care of, check out this list of 75 fun questions to ask on a first date to get the conversation going:

First Date Questions About Relationships

1. Who’s your best friend, and what do you admire about them?


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2. What are your family relationships like?

3. What are you looking for in dating?

4. If you could have dinner with anyone from the past or present, who would it be and why?

5. Who’s influenced you most in life?

6. What do you think about love languages?

First Date Questions About Hobbies and Leisure

7. What does a perfect day look like for you?

8. If you could go on an all-expenses-paid trip tomorrow, where would you go?

9. What goals are you working toward right now?

10. How do you like to relax?

11. Do you have a hidden talent?

12. What’s a topic you could talk about forever?

13. Would you rather read a book or listen to a podcast? Why?

14. How do you like to learn new things?

15. What types of TV shows do you like to watch?

16. What simple pleasures bring you peace?

17. What’s something you enjoy that I would never guess about you?

18. What’s something fun you think everyone should try at least once?

19. What normal, everyday activity could you win a gold medal for?

20. Where do you like to spend free time outside of home and work?

First Date Questions About Imaginary Scenarios

21. If money didn’t matter, what would be your dream job?

22. If you could change an existing law or pass a new law, what would it be?

23. What city do you dream of living in?

24. If you could build or buy whatever style of house you’d like to live in, what style would you choose?

25. Would you rather spend one minute with your future self or past self?

26. If you never had to sleep again, how would you spend your extra time?

27. If you could time travel, would you go to the past or the future?

28. If you could be an animal for a day, what would you be?

29. Which actor or actress would play you in a movie about your life?

30. If you launched a YouTube channel or podcast, what would it be about?

31. Where do you see yourself five years from now?

32. If you added a new room to your home, what would you include in it?

33. What mystery would you love to solve?

First Date Questions About Personal Values

34. What do you want to be remembered for?

35. What helps you feel connected to your faith and spirituality?

36. As a kid, what did you want to be when you grew up?

37. What’s the best way to start and end your day?

38. What are you most grateful for in life?

39. What’s the best piece of life advice you’ve ever heard?

40. What’s a trait you’d like to develop in yourself?

41. How do you like to handle stress when life gets crazy?

First Date Questions About Life Experience

42. Would you like to be famous? Why or why not?

43. Do you prefer indoor or outdoor activities?

44. What’s something you’ve had to unlearn?

45. What’s getting better as you get older? What’s getting worse?

46. What’s something you’ve done that most people haven’t?

47. What does your dream retirement life look like?

48. Have you ever experienced a life-changing moment?

49. What accomplishment are you the proudest of so far?

50. What’s the most spontaneous thing you’ve ever done?

51. Have you ever experienced a plot twist in your life? How did it turn out?

52. What’s your favorite Christmas memory?

53. What takes up too much of your time?

54. What’s the toughest lesson you’ve had to learn?

55. What’s the funniest nickname you’ve ever had, and how’d you get it?

56. What’s the strangest thing you’ve ever experienced?

57. What’s something you’ll never do again?

58. What’s the luckiest thing that’s ever happened to you?

59. What’s the strangest food you’ve ever tried?

First Date Questions About Personal Taste

60. What kind of music do you like listening to?

61. You’re stuck on a desert island, and you have one book with you. What is it?

62. What’s something you like to do the old-fashioned way?

63. What’s your favorite holiday and why?

64. Who’s your favorite movie, show or book character?

65. Where’s your favorite place to vacation?

66. What do you enjoy most about living in this city?

67. What piece of clothing makes you feel the most confident?

68. What’s your biggest pet peeve?

69. What do you think is worth spending more money on (that other people don’t)?

70. What quality do you appreciate most about yourself?

71. What’s your favorite way to communicate long-distance: phone, texting, video chat or email?

72. What fad or trend have you never been able to understand?

73. What question do you really want the answer to?

74. What are you looking forward to right now?

75. What’s the most special part about the place where you grew up?

Keep the Conversation Going (On the First Date and Beyond)

Dating is a process, so if one first date doesn’t work out, don’t worry! Think of it as practice for the next one. It’s true what they say—there are plenty of fish in the sea. But if you and your date are really clicking, that’s wonderful (and probably because you’ve asked them great questions, wink wink!). If you’re looking for even more ideas to keep the conversation going during and after a first date, I hope you’ll check out my friend Dr. John Delony’s Questions for Humans conversation starters. These cards will give you tons of creative questions to keep getting to know each other, long after the first date.

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Rachel Cruze

About the author

Rachel Cruze

Rachel Cruze is a #1 New York Times bestselling author, financial expert, host of The Rachel Cruze Show, and co-host of Smart Money Happy Hour. Rachel writes and speaks on personal finance, budgeting, investing and money trends. As a co-host of The Ramsey Show, America’s second-largest talk radio show, Rachel reaches millions of weekly listeners with her personal finance advice. She’s appeared on Good Morning America and Fox News and been featured in TIME, REAL SIMPLE and Women’s Health, among others. Through her shows, books, syndicated columns and speaking events, Rachel shares fun, practical ways to take control of your money and create a life you love. Learn More.

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