First dates can be nerve-wracking…

From not knowing what to wear to wondering if you’ll even get on and praying you don’t embarrass yourself. 

Oh, then there’s the small issue of wondering what on earth you’re both going to talk about. Because the worst thing is having way too many awkward silences right? 

That’s why we 100% believe in preparing beforehand by arming yourself with a selection of go-to questions to ask a guy on the first date. 


Well, firstly this ensures that the conversation flows and secondly it gives you an opportunity to get to know your date better.

Now the trick is to have a balance of light, fun questions mixed with more deep questions that may potentially let you know if there are any red flags you need to pay attention to. 

So without further ado, here’s a list of questions guaranteed to get your date chatting away…

55 Interesting questions to ask a guy

  1. What was your childhood like?
  2. What’s your love language? 
  3. Which celebrity would you marry in a heartbeat? 
  4. Where do you see yourself in 5 years? 
  5. What’s your dream job?
  6. What did you want to be when you were a kid? 
  7. How would you describe yourself in 3 words? 
  8. Which celebrity did you have your very first crush on? 
  9. Do you like PDA? 
  10. What’s your idea of the perfect date? 
  11. What’s your biggest pet peeve?
  12. What is your most memorable birthday to date?
  13. If you could only travel to one country, which would it be and why?
  14. Favourite song of all time? 
  15. Top three things on your bucket list?
  16. What would your last meal be? 
  17. If you could live anywhere in the world, where would it be and why? 
  18. Favourite restaurant? 
  19. Favourite T.V series of all-time? 
  20. Which movie scared you the most? 
  21. Which movie could you watch on repeat?
  22. Do you believe in God? 
  23. Do you have any role models or mentors? 
  24. How important is a woman’s physical appearance to you? 
  25. When have you been the happiest in your life? 
  26. First thing you’d do if you won the lottery?
  27. What scares you? 
  28. Most romantic thing you’ve done in a relationship? 
  29. Most romantic thing that’s been done for you in a relationship?
  30. Favourite book/author/ 
  31. What’s your worst movie of all time?
  32. Which one superpower would you choose to have?  
  33. What’s been your biggest achievement to date? 
  34. Do you have any weird habits? 
  35. If money was no object, which car would you buy today? 
  36. Would you go bungee jumping or skydiving? 
  37. What’s the one thing a woman could do that would impress you? 
  38. How long do you date a woman before introducing her to your family? 
  39. When and where did you have your first kiss? 
  40. Do you believe in love at first sight?
  41. How do you know when you’re in love? 
  42. Are you an early bird or a night owl? 
  43. If you could live in any other decade, when would you choose?
  44. Can you cook? If so, what’s your signature dish? 
  45. What piece of advice would you give your younger self? 
  46. Best piece of advice you’ve been given?
  47. Do you have any regrets? 
  48. Favourite quote? 
  49. Do you have any hobbies? 
  50. Have you ever been cheated on? 
  51. What’s your deal breaker in a relationship? 
  52. What’s your favourite fragrance? 
  53. Do you believe we all have a soul mate? 
  54. What’s your earliest childhood memory?
  55. What was the first thing you noticed about me? 

To conclude…

Now before we sign off, it must be said that you shouldn’t probe too much. If it seems like there’s a question that might have touched a nerve or if he’s looking a tad uncomfortable, then keep it moving. Change the subject, preferably to a more lighthearted question that’ll generate a couple of laughs.

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