50 Personal Questions To Ask A Guy

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50 Personal Questions To Ask A Guy

Whether it’s your boyfriend, an old friend, or someone you’ve just met, get to know them on a deeper level and feel more connected to them thanks to these personal questions to ask a guy.

personal questions to ask a guy

I’m sure you will love these personal questions to ask a guy as much as I do. Yes, it’s nice to ask funny or flirty questions while spending time together, yet nothing will bring you as close to him as asking more personal questions. You can save your favorite ones on your phone as an inspiration whenever you feel like quitting the small talk and getting a little bit more personal with a guy or with your boyfriend.

50 Personal Questions To Ask A Guy

Maybe you feel like it’s time to strengthen your bond and deepen your connection with that one guy.

Go for it, when if not now? You don’t want to end up wasting your time on meaningless conversations and feel like you don’t know the guy even after spending several weeks or even months together.

There is a time and place for everything and I’m sure you’ll find the perfect moment to create a warm and safe atmosphere to ask more personal questions.

Just make sure you’re also ready to answer them yourself! It’s not an interrogation nor an interview so he might ask you some deep questions in return as well.

What personal questions can I ask a man?

I suggest you set the tone of how deep and juicy you want the questions to be.
Don’t be afraid to set boundaries and hold off with answering certain questions.
Likewise, accept if he’s not willing to answer some of the personal questions that you’ll ask him. Don’t take it personally, try again another time if knowing the answer to that particular questions is that important to you. Just be kind and understanding.

So what personal questions can you ask a guy? Check out the list below and save your favorite ones in your phone’s notes!

If you’re looking for flirty, cute, or funny questions to ask a guy you will find these below as well. Or do you want to make it even more fun? Then a game of truth or dare questions for crush might be just what you need!


Just a few more tips on asking your crush some more personal questions.
Depending on the setting, where you are, and how well you already know each other, make sure to first actually ask if you can indeed ask him a personal question.

Make sure his privacy is being respected, so it’s better when others can’t overhear your conversation. Establish an atmosphere of trust where he can open up, be vulnerable with you, as well as feel heard and respected.

If he’s a decent guy he will certainly appreciate you being curious about him and being a great listener. I’m sure he loves to discover more about you but at the same time might feel very flattered that you’re putting the focus on him and are trying to get to know him, at his core.

It’s a win-win and a great way to build a strong foundation for a relationship… or to find out that you don’t fit together. Which you better find out sooner than later.

50 Personal Questions To Ask A Guy

  1. What is your biggest fear?
  2. What makes you laugh the most?
  3. What are you most grateful for in life?
  4. What do you consider your core values?
  5. What do you think your role is in this world?
  6. What’s your biggest regret?
  7. What’s something that worries you these days?
  8. What’s your favorite childhood memory?
  9. How would you spend your last day on earth?
  10. Do you give people second chances?
  11. What is something that gives you hope?
  12. Have you ever told a lie that you regretted?
  13. Do you believe in God?
  14. Do you believe in true love?
  15. How do you describe commitment?
  16. What’s your biggest insecurity?
  17. Are you afraid of death?
  18. When was the last time you cried?
  19. Did you ever get your heart broken?
  20. Do you want your own family someday?
  21. What makes you feel nostalgic?
  22. What’s the best gift you’ve ever received?
  23. What is your favorite family holiday tradition?
  24. Do you consider yourself to be an introvert or an extrovert?
  25. What do you consider the most beautiful quality in a human?
  26. What’s your favorite thing about being a man?
  27. Who do you admire most and why?
  28. Have you ever had a nickname? 
  29. Do you believe in marriage?
  30. What is the biggest compliment you can give someone?
  31. What five words would you use to describe yourself?
  32. What do you like them most about yourself?
  33. What did you want to be when you were little?
  34. What’s the most important quality in a friend for you?
  35. What’s the most important quality in a partner for you?
  36. How do you hope people describe you?
  37. Do you have the desire to be famous?
  38. What’s one of your goals for the upcoming year?
  39. Do you have a favorite memory?
  40. Who or what inspires you?
  41. What’s a dealbreaker for you in a relationship?
  42. What are you most proud of in life?
  43. What is a skill you’ve always wanted to learn?
  44. What is something that makes you really angry?
  45. What’s the toughest conversation you’ve ever had to have?
  46. What is your most terrible memory?
  47. Do you remember your first kiss?
  48. What is your dream vacation?
  49. How do you react when you’re upset?
  50. What’s the most spontaneous thing you’ve done lately?

You can spend a lot of time with someone yet still don’t know them too well.
Asking the right questions can make the whole difference.
So next time you’re spending time with your guy make sure to ask him a few of these personal questions and see your relationship get deeper and stronger than ever.

Personal Questions To Ask A Guy

50 Personal Questions To Ask A Guy