50 Intelligent Questions to Ask a Guy on Your First Date in 2024

There are a couple of intelligent questions to ask a guy on your first date, but some are exceptional, that is why we have to compile them for you.

If you have been having challenges with figuring out the best questions to ask a guy on a first date, kindly explore the next heading and make sure you take note of all the points listed.

 These questions usually come to some ladies as a dessert when they are on dates with the opposite sex. This is because men and women think in different ways. Let’s get started!

Questions to Ask a Guy on Your First Date

To get a conversation started, one needs to ask the right questions. Asking a guy the right questions will make the conversation interesting and go further to show the person how interesting you are.

We designed the right questions to ask a guy to get an interesting conversation started, and so some questions are a bit off the beaten track.

Remember, every guy is different, so pick which questions you think will work best for your guy, or pick questions that you really want to know the answers to.

The questions are:

1. What causes you to feel insecure? 

2. What do you hope to get out of a romantic relationship? 

3. Is there anything you can’t stand? 

4. What qualities do you admire in a woman? 

5. Do you have any expectations for yourself? 

6. What was the most memorable birthday you’ve ever had? 

7. Have you ever dressed like a girl?

8. Can you tell me about your family and friends?

9. What kind of music do you enjoy listening to, and where do you like to visit in the city?

10. What is one thing you can’t imagine your life without?

11. What is your most amusing high school memory?

12. What is it like to work for (company)?

13. What’s one item you’ve recently crossed off your bucket list?

14. If you could describe yourself with one word, which would it be?

15. What is your favorite food?

16. What is your favorite character from childhood?

17. What kind of animal do you love the most?

18. Would you rather choose to fish or hike?

19. Do you believe in God?

20. What is your all-time favorite film that you’ve seen a thousand times?

21. When you were a kid, what did you want to be when you grew up?

22. If money were no object, where would you travel on vacation if you could go anyplace in the world?

23. How would you spend a million dollars if you won the lottery?

24. What about a woman appeals to you the most?

25. What is your most outrageous ability?

26. What is one thing about you that everyone usually gets wrong?

27. How do you unwind after a long day?

28. Who do you look up to as a role model?

29. Which celebrity do you most wish to meet?

30. Is there anything you’ve never been really excellent at?

31. What is something you’ve never been good at doing?

32. What is the one thing you always notice first about a woman?  

33. What’s your favorite childhood memory?  

34. What have you done that you are most proud of?  

35. What have you done that you’re really not proud of?

36. What’s the scariest thing you’ve ever done?  

37. If you could be a pro at any sport, what would it be?  

38. If you could marry one celebrity, who would it be?

39. Why is your best friend your best friend?

40. What do you think the best thing about being in a relationship is?

41. What’s your favorite animal?

42. What’s something on your bucket list you really want to do soon?  

43. What’s something on your bucket list you think you’ll never actually do?

44. What’s the weirdest thing that’s ever happened to you on a date?

45. What do you always lie about on your resume?

46. What is the one thing about women that you despise the most?

47. Do you believe that dating has become more difficult or easier because of the internet?

48. Do you feel threatened by women who earn more money than you?

49. When you were a kid, who was your celebrity crush?

50. Do I make you jittery?

There are other intelligent questions to ask a guy on your first date, but the mentioned ones are the best you can ever think of. Always make use of the ones listed above and watch the difference manifests.