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75 Questions To Ask On A Second Date (To Keep Them Engaged) 

The first date went well and now you’re getting ready for your second date. If you’re uncertain how to navigate this, here are 75 questions to ask on a second date. 

Realistically, these questions to ask on a second date aren’t meant to be crossed off like a checklist. Rather these questions to ask on a second date are a source of inspiration. 

You can identify from this list of questions to ask on a second date which you prefer. They range from surface-level to deeply intimate. 

I’ll also share other tips to keep the conversation flowing and most importantly, how to help you know your date better! 

Summary 

  • 5 Types of questions to ask on a second date 
  • Family-related questions to ask on a second date
  • Friends and childhood-related questions to ask on a second date
  • Love and romance-related questions to ask on a second date
  • Career and business-related questions to ask on a second date
  • Money and finance-related questions to ask on a second date
  • Religion and values-related questions to ask on a second date
  • Play and relaxation-related questions to ask on a second date
  • Habits and lifestyle-related questions to ask on a second date
  • Selfhood-related questions to ask on a second date
  • “Would you rather” related questions to ask on a second date
  • Frequently asked questions 
    • What is the 3-date rule? 
    • How long should a 2nd date last? 
    • How to have a successful 2nd date? 
  • Conclusion

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DISCLOSURE

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5 Types of Questions To Ask On A Second Date 

The list of questions to ask on a second date helps initiate a conversation. But reflecting on your last date for ideas would also help sustain the conversation. Here are a few suggestions to consider. 

1. Ask any follow-up questions 

This image shows a couple on a date. It's used for the article "Questions to ask on a second date"

Credit: NadinShlyueva

A positive sign of a good listener is when they ask follow-up questions. Did your date confide in you about a work challenge? 

Or did they share a personal matter that they’re currently navigating? You can pick up where you left off by asking for an update on these matters. 

2. Ask any lingering questions 

Are there any questions you were keen to ask but didn’t get a chance to on your first date? Make a mental note of them and find time during your date to address them. 

3. Ask them to elaborate on their areas of interest 

Was there a hobby that they were excited to share? Or they sounded keen to explain a theoretical concept. 

Asking them to elaborate on their areas of interest will encourage them to talk. Of course, the caveat is that you must be intrigued enough to stay engaged. 

Otherwise, a helpful tip is to find a point in the conversation that piques your interest and ask a question about that point so you can pivot the conversation in that direction. 

4. Ask them to expand on a topic you’re interested to learn more about 

Are you curious about their family history? Did they mention a short stint working abroad? If there’s something about them that you’d like to know more about, then don’t hesitate to ask. 

5. Ask about their dating intentions if it’s not been made clear

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Credit: Pexels 

This is the most important question especially if you’ve entered the dating scene looking for a life partner. There might be tension in the future if your dating expectations aren’t aligned. 

I know it can be daunting, especially if you’re still getting to know each other but there is a way to approach this question carefully. Remember, if you’re dating to marry, your needs are of the utmost importance so find someone who shares the same vision. 

If you’d like to seek additional help navigating the dating landscape, you can consider reaching out to a licensed therapist or relationship counselor for advice. 

75 Questions To Ask On A Second Date 

As I mentioned in a previous article, if this list of questions to ask on a second date overwhelms you, pick two from each category. The conversation should naturally flow with follow-up questions. 

Alternatively, reflect on your last date and identify any topics you can launch the conversation. More importantly, be ready to answer these questions as it takes two to tango and keep the conversation engaging. 

I’ve arranged these questions into ten categories. Consider which questions you’re comfortable asking and what you’d like to know. Some of these questions are taken from the Best Self deck of cards. 

Family-related questions to ask on a second date 

01. Tell me something you believed as a child that makes you laugh now. (best self) 

02. Is there a scent that reminds you of a childhood memory? 

03. What good traits have you adopted from your parent(s)? 

04. What bad traits have you adopted from your parent(s)? 

05. What value(s) did your parents instill in you when you were younger that you practice today? 

06. What belief do you have about yourself that resulted from childhood? (best self) 

07. What’s your relationship like with your extended family? 

08. Do you come from a big family? 

Friends and childhood-related questions to ask on a second date 

09. What role do you play in your friendship group? 

10. How often do you see your friends? 

11. Which friend do you confide in the most? 

12. Have you gotten in trouble before with your friends? 

13. How did you spend your free time when you were younger? 

14. What aspect of your childhood did you take for granted? 

15. Do you do any group activities with your friends? 

16. What advice would you give your younger self?

17. What do you miss about your childhood? 

Love and romance-related questions to ask on a second date 

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Credit: sasint 

18. What lessons did you learn from your previous relationship? 

19. What are you currently looking for in dating? 

20. What’s a turn-off for you in a partner? 

21. Describe a quality that turns you on. 

22. How do you like to be shown affection? 

23. What’s a surprising quality you look for in a partnership? 

24. Have you ever been rejected when dating? How did you navigate it? 

25. What’s the worst date you’ve been on? 

26. Were you ever involved in a toxic relationship? 

Career and business-related questions to ask on a second date 

27. Do you attach your self-worth to your job? 

28. Is your job your vocation or just something that pays the bills? 

29. What are the working dynamics like at your current job? 

30. How do you overcome challenges at work? 

31. Would you like to pursue anything else outside of work? 

32. Do you have a dream job? What is it? 

33. What’s preventing you from chasing this dream job? 

34. What else have you gained in your current work other than financial rewards? 

Money and finance-related questions to ask on a second date 

35. What’s something frivolous you don’t mind spending money on? (best self) 

36. What’s an investment that you don’t regret?

37. What’s a financial habit you wish you’d practiced sooner? 

Religion and values-related questions to ask on a second date 

38. Did you grow up in a religious or conservative household? How did that shape you? 

39. What do you have absolute faith in? (best self) 

40. Was there ever a period when your beliefs were challenged? How did you navigate this? 

41. What is the most damaging modern industry and why? (best self) 

42. Do you think higher taxes or more philanthropy will solve the world’s problems? (best self) 

43. What’s your definition of success? 

44. Do you think it’s possible to be “self-made”? 

Play and relaxation-related questions to ask on a second date 

Credit: CHENA

45. Is there a piece of art (i.e. music, painting, movie) you constantly revisit? 

46. What movie would you have liked to star in? 

47. What’s your go-to karaoke song? 

48. What song reminds you of high school? 

49. What’s a hobby you’d like to master in? 

50. Is there an instrument you’d like to master? 

51. What holiday destination would you like to be transported to now?

Habits and lifestyle-related questions to ask on a second date 

52. Do you have a mantra or positive affirmation that keeps you going?

53. How often do you exercise? 

54. What habits do you practice that makes your life easier? 

55. How messy do you think you are, on a scale of 1-10? 

56. How do you avoid feeling burnt out? 

57. How do you handle negative self-talk? 

58. What act of self-care has become a non-negotiable in your life?

Selfhood-related questions to ask on a second date 

59. What’s currently a highlight and lowlight of the year? 

60. What’s been your biggest blessing so far? 

61. What have you read that has profoundly impacted you? 

62. When was the last time you cried? 

63. When did you feel the most loved? 

64. What makes you angry? 

65. When do you feel insecure? 

66. If you could attain a skill, what would it be and why? 

67. What’s one thing you wouldn’t change about yourself? 

68. What’s one of the best decisions you’ve made? 

“Would you rather” questions to ask on a second date 

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Credit: IqbalStock

69. Would you rather be an extra in an Oscar-winning movie or lead a box office bomb? 

70. Would you rather have a third nipple or an extra toe? 

71. Would you rather have super-sensitive tastebuds or super-sensitive hearing? 

72. Would you rather be able to teleport anywhere or stop time? 

73. Would you rather hear a comforting lie or an uncomfortable truth? 

74. Would you rather have an annoying song stuck in your head or an itch you can’t scratch? 

75. Would you rather be a great chef or repair person?

Frequently asked questions 

What is the 3-date rule?

According to the three-date rule, it is best to wait three dates before becoming physical with a potential partner. This rule helps daters navigate the dating landscape, specifically when to be intimate. 

How long should a 2nd date last?

2-5 hours is a good rule of thumb. First dates can last 1-2 hours but a second date should last slightly longer as you want more time to explore more intimate details about each other. 

How to have a successful 2nd date?

Here are a few tips: Pick the right venue, preferably one that encourages conversation like a café. Avoid loud or formal places. Be present by putting away your phone and giving your date your undivided attention. 

Conclusion 

Navigating a conversation on a second date can be tricky. No exact script or formula can accurately tell you what you should say. While these questions to ask on a second date may get the ball rolling, we cannot truly predict how your date will receive them. 

Ultimately, ask yourself what you’d like to know about your date. Use these questions as a guide, not a checklist. Most importantly, let the conversation flow naturally. 

If you encounter any awkward silences, know that it’s normal. Bring the conversation back to an area of interest or have those Would You Rather questions on standby. All the best!