Personal questions to ask a guy aren't always easy to think of.

...And it got me thinking, why is that?

Well... personal questions in general can sometimes be a challenge to come up with but they're extremely useful in getting to know the person you're talking to on a deeper level.

So when you're in need of questions to ask a guy, look no further than right here.

Because let's face it...

When you run out of questions to ask, things can get real awkward real fast.

66+ Personal Questions to Ask a Guy (Over Text, Online, IRL)


13 Best Personal Questions to Ask a Guy

Our best personal questions to ask a guy are below and they've been hand-picked to help you be a better conversationalist.

Have a few of them handy the next time you're chatting with someone!

1. Does a relationship face negative changes after marriage, what would you do to avoid these changes?

Getting married is a big step in a relationship. Not all guys are excited to tie the knot.

2. What is that thing that you can spend some extra bucks to get the quality?

Every guy should own some buy it for life items.

3. What is a waste of money according to you?

Everyone justifies purchases differently.

4. What do you consider a wasted life?

A life worth living is a terrible thing to waste.

5. What simple change could you make in your life that would have the biggest positive impact?

I recommend making your bed and drinking a glass of water every morning. It's a productive and healthy way to start the day.

6. Who do you want to be more like?

We all have someone we look up to.

7. What are your biggest goals for your life? What progress have you made in attaining them?

You're doing better than you think. Keep at it.

8. What is the biggest lie you’ve ever told?

You shouldn't lie, but sometimes it's more beneficial to stretch the truth a little.

9. What is the lesson in life that you had to learn in the hard way?

It's never easy but sometimes it's necessary.

10. What are you most thankful for?

Appreciate the good things in life. You have clean water and decent internet.

11. What do you need to rant about or get off your chest?

It's always nice to have someone to confide in.

12. What do you judge people for that you probably shouldn’t?

You know they can't help it but it's just too easy.

13. Would you rather face your fears or forget that you have them?

It would be nice to forget your fears. But what if those fears are justified?

10 Personal Conversation Starters Questions to Ask a Guy

Starting a conversation is easier than it looks if you have conversation starters in your mental rolodex.

They're questions that are meant to get the other person thinking about interesting subjects, opening up a potentially fascinating conversation.

14. Do you consider yourself an introvert or an extrovert?

It's possible to be an extroverted introvert but it's not easy.

15. Where do you go when you want to be alone?

Where's your happy place?

16. What’s your nature love, Beaches, mountains, forests or fields?

For a little bit of everything, Acadia National Park is the place to be.

17. If you have the choice to name your kids, what name(s) would you choose?

I was either going to be Cory or Kyle. While my mom was still recovering, my dad told everyone I was Kyle.

18. How good are you in saving money?

He might have some tips.

19. If you were falsely convicted of a crime, how would you adapt to prison life?

Apparently the best way to survive prison is to mind your own business and don't get involved with troublemakers.

20. What activity calms you down and makes you feel at peace with the world?

You have to have a way to wind down after a tough day.

21. If you see a homeless person asking for money, do you give them any?

How can society eliminate homelessness?

22. Do you have any phobias?

All fear derives from the unknown.

23. What would you NOT do for 5 million dollars?

There's always a limit. Some just set the bar lower.

10 Personal Questions to Ask a Guy, that can also be used to Ask a Girl

Questions for everybody!

In reality, you should view guys and girls in the same light: As people.

Giving one special treatment over the other simply because one might get naked with you is disingenuous and fake.

But of course, if you like a girl, you're going to go the extra mile to get her to like you back so you should definitely have some personal questions to ask a girl handy. Being prepared is always important since questions to ask a girl aren't always easy to come up with.

So if you're in need of some questions that can be posed to both sexes, take a look below and memorize a few!

24. Do you think that every time a man should pay or they should split the money when needed?

Asking a man is conversational. Asking a woman might save you money!

25. What are the things a man should have in him when he is in a relationship?

Need some tips? This should help.

26. Do you prefer to spend more time with your SO, family, or friends? Why?

With whom are you happiest?

27. Who is the most important person in your life?

Who do you love most in this world?

28. What makes you feel accomplished?

Celebrate your little victories throughout your day. It's good for your confidence.

29. Who is that one person you can talk to about just anything?

Having a best friend is great. Having a therapist is also astoundingly helpful.

30. What are some things people have selflessly done to make your life better?

Who helped you navigate this wild ride called life? Who have you helped?

31. What was a random compliment that someone gave you that really stuck in your memory?

Give compliments often. It costs you nothing and makes someone else feel good!

32. What kind of people do you dislike?

Not those people again.

33. Would you rather be incredibly happy but alone forever or unhappy but with the love of your life?

This might be a good time to bring up codependence. Avoid these types of relationships and if you're in one, get out quickly.

7 Personal Questions to Ask a Guy to get to know Him

Get to know you questions are always useful in a conversation.

They're tailored to help you get interesting bits of information about the person you're talking to. Questions to ask a guy to get to know him are great, but personal questions to ask a guy to get to know him are better.

34. Have you ever done anything wild that you still enjoy when thinking about it?

When have you put it all on the line?

35. What has had the biggest impact on your political beliefs?

Politics should be discussed with care. If you don't agree, you should discuss and try to understand the other person's position.

36. What issue do most people think is black and white but you think there is a lot nuance to?

There's no shortage of such issues in today's world.

37. Do you have any enemies? How do you handle them?

We can't get along with everyone.

38. Who has completely lost your respect?

And sometimes it's very hard to forgive.

39. Who are some people you only met once but they left a big impression on you?

Some people just have that effect on people. Try to be like those people.

40. What was fun to do once, but you’ll never do it again?

I thought I would love skydiving (no tandem) but almost two years later, I still don't know how I feel about it. You should definitely try it though.

9 Personal and Random Questions to Ask a Guy

If you want to be quirky and fun, random questions are a great bet.

We've already thought up some random questions to ask a guy but here are some personal and random questions to ask a guy!

41. If you could fit your whole life into one picture what would it look like?

How do you picture your life?

42. What do you think about when you’re by yourself?

Or what keeps him up at night?

43. What’s a piece of advice that you wish everyone would take to heart?

What small thing could make the world a better place?

44. What happens more often than you’d like?

Life would be so much easier if that thing stopped happening as often.

45. Would you rather be ignorant and happy or be knowledgeable and never fully content?

Ignorance is bliss.

46. What is your most prized possession?

What's the one thing that you could never live without?

47. What are some of the things you consider unforgivable?

We all have our limits on forgiveness.

48. What is important enough to go to war over?

Human rights violations? Oil? Power?

49. If you could have complete knowledge of any 5 things, what would you want to know?

A fun question that will open up a whole new conversation.

7 Personal, Interesting Questions To Ask A Guy

Interesting questions are perfect to ask when you want to sound interesting (and why wouldn't you?)

Start with interesting questions to ask a guy for some ideas, then get more personal with the questions below.

50. What event would you rather die than live through?

An interesting take on a classic question.

51. How would you react if there was irrefutable proof that God doesn’t exist? How about if there was irrefutable proof that God does exist?

Furthermore, how would humanity as a whole handle either scenario?

52. If you died today, what regrets would you have about your life?

Regret is a terrible weight we all end up carrying from time to time. Let it go while you still can.

53. What are the experiences that have made you, who you are today?

The big experiences are the most memorable but the small ones we hardly remember also have a strong impact on us.

54. Do people underestimate or overestimate you?

Always under-promise so you can over-deliver.

55. Ever felt that no one relates to you?

You're not alone. What you see on social media is a highlight reel of people's lives. Talk about it.

56. What does ‘The American Dream’ mean to you?

A house with a picket fence? That's so 1955.

10 Personal, Deep Questions to Ask a Guy

When the conversation is on the verge of becoming existential, you might want to try some deep questions to ask.

They dig deep and focus on our deepest, most personal thoughts and feelings.

57. Do you think lies are necessary to have a long relationship or honesty is the best policy?

Is a white lie here and there beneficial to, or terrible for a relationship?

58. What are some of the morals you live by?

Every man needs a moral code.

59. Do you believe in second chances?

Is a break up really a break up because it's broken? Or can things work out in spite of underlying issues?

60. What are you tired of hearing about?

What do people really need to let go of?

61. Till what age would you like to live and why?

The older you get, the more your body deteriorates. What if we could eliminate aging?

62. How's your life lately?

This question has the power to get any guy to open up about all sorts of things in his life, good or bad.

63. Are you happier single or in a relationship?

Relationships take work but you should also constantly be working to improve yourself.

64. Would you rather be forgotten or hatefully remembered?

We all die three times. When it happens, when we're put into the ground, and when we're forgotten.

65. What will people say at your funeral?

What legacy will you leave behind?

66. What is the best thing that you have done, just because you were told you can’t?

Sometimes our best work comes from our limitations.

Downloadable and Printable List of Personal Questions to Ask a Guy

Here is a downloadable and printable list of personal questions to ask a guy (right click the image and select Save Image As...):

How to Ask Personal Questions to Ask a Guy

Personal Questions to Ask a Guy - How To Ask Personal Questions To Ask A Guy 3 Steps.jpeg

Unsplash / Amanda EdwardsenThere are a few rules to keep in mind asking a guy personal questions.

1. Be casual

It's not a job interview. You're just getting to know a guy, so be cool, calm, and don't put him on the spot.

2. Switch it up!

Don't only ask personal questions. He might think you're coming onto him.

3. Buy him a drink

If the conversation is interesting and you're both enjoying it, offer to buy him a drink! You might make a new friend.

More Great Questions To Ask

You shouldn't always ask personal questions. It makes people uncomfortable. Try some of these instead!

  1. When you want to know more about the ones closest to you, our questions to ask friends are perfect.
  2. In the mood for a compelling conversation? Interesting questions are a great place to start.
  3. For non-stop fun, would you rather questions are a must!

In Conclusion

Hopefully this article has helped you find some great personal questions to ask a guy.

Use them properly and the next time you're having an interesting conversation with a guy, you'll be all set to potentially make a new friend.