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75 Questions To Ask On Date For Memorable Conversation

There’s nothing more daunting than not knowing what to say on a date. Fortunately, I have a list of questions to ask on date, specifically on your first date! These questions to ask on date go beyond your typical ice-breaker questions. 

Rather, these questions to ask on date will help you get to know someone intimately. I’ve grouped these questions to ask on date based on relevant categories. 

I’ll also share advice on keeping the conversation flowing and, more importantly, how to help you feel calm and confident no matter the situation. 

Summary 

  • Family questions to ask on a date 
  • Friends & childhood questions to ask on a date 
  • Love & romance questions to ask on date 
  • Career & business questions to ask on date
  • Money & finance questions to ask on a date 
  • Religion & values questions to ask on date 
  • Play & relaxation questions to ask on a date 
  • Habits & lifestyle questions to ask on date 
  • Selfhood questions to ask on date 
  • Would you rather questions to ask on a date 
  • Post-date questions to ask yourself 
  • Frequently asked questions 
    • What are deep questions? 
    • How to not be nervous on a date? 
    • What are some tips on how to have a good first date? 
    • What to do when there’s an awkward silence? 
  • Conclusion 

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DISCLOSURE

Some of the links on here are affiliate links and I may earn if you click on them, AT NO EXTRA cost to you. Hope you find the information here useful! Thanks.

75 Questions To Ask On A Date 

If you’re overwhelmed by this list of questions to ask on date, scan through each section and select 2 of your favorite questions from each category. 

Chances are, your date’s answers will lead to follow-up questions that will keep the conversation flowing. 

Family questions to ask on a date

01. Do you have any siblings? 

02. What’s your relationship like with your siblings? 

03. What are your parents like? 

04. What’s your relationship like with your parents? 

05. What traits did you pick up from your parents? 

06. What’s your favorite childhood memory? 

07. What lesson did you learn from observing your parents’ marriage? 

08. Describe a memorable dinner

Friends & childhood questions to ask on a date 

09. How would your friends describe you? 

10. Are you still close with your high-school/college/university friends? 

11. What were you like in school? 

12. Was there a teacher that had a positive impact on you? 

13. Which friend do you call to bury a body? 

14. Which friend do you call for advice? 

15. Do you have a favorite memory with your friends? 

16. Name three friends that best represent you and why 

17. How important is friendship to you? 

Love & Romance questions to ask on date

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18. What has your dating experience been like so far? 

19. What have you learned about yourself from dating? 

20. What qualities do you look for in a partner? 

21. Were you in a relationship before? 

22. What did your last relationship teach you about love?

23. What’s a boundary you’ve set when dating or in a relationship? 

24. Best dating or relationship advice you’ve ever received? 

25. What are your expectations from dating right now? 

Career & business questions to ask on date

26. What do you do? 

27. What do you like about your job? 

28. What do you dislike about your job? 

29. Why did you choose this profession? 

30. What are your working hours like? 

31. Are there any ambitions outside of work that you’d like to achieve? 

32. How do you manage work stress? 

Money & finance questions to ask on a date

33. What’s good financial advice you’ve received recently? 

34. What financial habits did you pick up from your parents? 

35. Is there anything you’re currently saving up for? 

Religion & values questions to ask on date

36. Do you practice a religion?

37. How important is it for you to find someone who practices the same religion as you? 

38. Is there a social cause you feel strongly about? 

39. What’s one value that you live by? 

40. How do you practice this value in your everyday life? 

41. Is there any news headline that caught your attention recently? 

42. What would you do immediately if you were prime minister/president for a day? 

Play & relaxation questions to ask on a date

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Credit: HoangDongPhoto

43. What do you like to do for fun? 

44. Have you seen anything lately that’s good? 

45. What’s a TV show or movie that you always rewatch? 

46. What music do you listen to? 

47. Is there a hobby or activity you’d like to pursue? 

48. What’s your favorite cuisine? 

49. Is there anywhere you’d like to travel to? 

50. What’s a memorable holiday or travel experience? 

51. Is there anything you’d like to do outside your comfort zone? 

Habits & lifestyle questions to ask on date

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Credit: Pexels 

52. What does your ideal weekend look like? 

53. How do you decompress after a long day at work? 

54. Are you a morning or night person? 

55. What habit have you cultivated that you’re most proud of? 

56. What habit would you like to eliminate? 

57. What seemingly insignificant thing contributes greatly to your happiness? 

58. What makes you a good and bad person to live with? 

59. What do you do to stay physically and mentally well? 

Selfhood questions to ask on date

60. When do you feel most confident? 

61. What’s the best gift you’ve ever received? 

62. How do you take constructive criticism? 

63. What would you say is your best and worst quality? 

64. Are there any experiences that have shaped you? 

65. What’s an achievement that you’re proud of? 

66. How would you describe this chapter of your life? 

67. Who is someone, living or dead, that you’d like to have dinner with? 

68. How would you like to be remembered? 

69. How do you like to be consoled? 

Would You Rather questions to ask on a date

Credit: sasint 

70. Would you rather revisit the past or look into the future? 

71. Would you rather have the ability to talk to animals or speak in every language? 

72. Would you rather island-hop or explore the city? 

73. Would you rather be able to sing or dance well? 

74. Would you rather have universal respect or unlimited power? 

75. Would you rather explore the ocean or space? 

Post-date questions to ask yourself 

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Credit: terimakasih0

Besides questions to ask on date, consider taking time to reflect on the date by answering these questions. 

These questions will help you determine if you want to continue seeing this person. I believe it’s an important exercise especially when you’re dating intentionally. 

1. What was your first impression of this person? 

2. How did this person make you feel? 

3. What qualities do you admire about this person? 

4. What else would you like to know more about that you didn’t get a chance to on this date? 

5. Would you like to continue seeing this person? Why? 

If you need additional help navigating the dating landscape or need clarification on what your dating intentions are, you can consider reaching out to a licensed therapist or counselor. 

Frequently Asked Questions 

What are deep questions?

One that invites people to share their core values and what truly matters to them. For example, a deep question could be “What do you truly value in life and why?”

How to not be nervous on a date?

Focus on your date, not yourself. It’s easy to become too self-aware when you’re nervous, overthinking every word or action. Shift your focus on getting to know your date instead. Actively listen to them, ask questions, and genuinely be present in the conversation. 

What are some tips on how to have a good first date? 

Asking questions is a great way to have a good first date because it demonstrates an interest in getting to know someone. But here are some additional tips to enhance your dating experience even further. 

Embrace empathy

Empathy refers to the ability to sense other people’s emotions, coupled with the ability to imagine what someone else might be thinking or feeling.

Listening empathetically means listening to what emotion is being conveyed. For instance, if your date is describing a traumatic experience you cannot relate to, an empathetic listener would try to get a sense of what they’re feeling (for example, hurt) and will feel that emotion with them. 

By doing so, you’ll be able to generate a more appropriate response and subsequently feel more emotionally connected. 

Other ways you can practice being an empathetic listener: 

  • Nodding appropriately when they’re speaking 
  • Not interrupting or interjecting 
  • Asking questions to clarify their speech 

Be humble 

This is important especially when you’re navigating more sensitive topics like fundamental beliefs. If your date has a different opinion about something, give them a chance to explain their reasons rather than jump to conclusions. 

It’s important to hold space for these uncomfortable conversations. Perhaps they might offer an interesting alternative perspective. Ultimately, you’re on a date to genuinely learn who you’re dating and not project an image of them. 

Be curious 

It’s normal to find yourself in a situation where your date might be talking about something you’re not completely interested in. 

However, to avoid your thoughts from drifting as they ramble, cultivate curiosity. Find a point in the conversation that you’re drawn to and use that to ask a question. This will help you stay engaged. 

Eliminate distractions 

Staying fully present in conversation means eliminating any distractions. This includes silencing your phone and switching off notifications. 

Maintain open body language 

Creating a safe space for intimate conversations starts with non-verbal cues. How you position yourself plays a significant role in setting the tone of your date. 

So good non-verbal cues you can practice on your date are maintaining eye contact, nodding appropriately when they’re speaking, and aligning your body towards your date. 

What to do when there’s an awkward silence?

It’s normal if you encounter an awkward silence on your date. It takes time for the conversation to flow. 

If you notice a lull in the conversation, you can introduce the “Would You Rather” questions as they don’t require deep reflection and more of choosing one option over the other. 

Then you can follow up and ask why they’ve chosen their option. Alternatively, you can circle back the conversation to a topic that you notice your date was genuinely keen to elaborate on. 

Conclusion

Dating is daunting but it shouldn’t stop you from trying. One way to look at dating is it’s an opportunity to improve your conversational skills and to learn more about yourself and what you’re looking for in a partner. 

Shifting your perspective this way will allow you to have more fun on the journey rather than obsessing over the outcome. All the best!