You need to know about the right deep personal questions to ask because they will definitely be of help to you when you are trying to get to know someone.

The deep questions to ask are those that will not only make your conversation longer but also those that will make the other person open up to you more. After all, you ask questions because your ultimate goal is to have a better idea of who they truly are.

Having said these, it might sound like finding out which questions to ask is not a walk in the park. Well, that's true. But what's also true is that we are here to help you, so you don't have to worry.


7 Best deep personal questions to ask

The best deep personal questions to ask are those that are not out rightly intrusive, but those that are genuinely and purely inquisitive. Choose one of these and you'll be sure that you're going to get the answers you are looking for.

1. What would the perfect you be like?

This is a great way to ask about their insecurities without being direct.

2. What does your ideal relationship look like?

This is like asking how she or he wants you to be when you are in a relationship with them already.

3. What has been the biggest change you ever made that made you the most proud of yourself?

This question will give them the chance to tell you what their greatest personal accomplishment is.

4. What is the greatest struggle you’ve overcome?

Overcoming struggles is a great show of strength.

5. What are the three things you value most about a person?

A subtle hinting of what you should pay attention to.

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

Sometimes being in solitary means being able to breathe at last. Find out where his mind wanders.

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

Does he have that one true friend?

10 deep personal questions to ask to get to know someone

These personal questions to ask to get to know someone will come in handy if you want to go up close and personal with another person. With the right timing and mood, you'll definitely be able to get to know just about anyone you want to with these questions.

8. What is the strangest thing you ever did?

This will give you a peek at their wild, adventurous side.

9. If you had a task to ask a person just one question, what would it be?

Find out what he's curious about.

10. What movie influenced you the most?

The kind of movie he enjoys tells a lot about him.

11. What book influenced you the most?

His taste in books also speaks volumes about his personality.

12. How do you cope with stressful situations?

They say that the ultimate test is when a person is under stress.

13. What are you passionate about in life?

Oh, and passions are an important aspect of every person's being.

14. What is your biggest irrational fear?

Ask this and you just might be surprised, or amazed, or maybe both.

15. What qualities do you admire about your parents?

How they look up to their parents is something you might want to pay attention to if you're in it for the long run.

16. Which parent are you closer to and why?

Parent-child relationships aren't always easy, they can be complicated too, learn about theirs.

17. What’s your philosophy in life?

Talk about deep, huh?

10 deep personal questions to ask a guy

Now, if you are wanting to know a guy, then these are the perfect questions to ask a guy. They're not that complicated and not too simple either. They're just the right kind of questions to get closer to a guy.

18. What childish thing do you still enjoy?

We all have that thing we have never grown up from.

19. What video game do you wish life was more like?

Ah, deep questions and video games, quite the combination, right?

20. Who or what is your nemesis?

It is surprising how you can know people through their nemesis.

21. What did you think was silly until you tried it?

Who knows, maybe that thing is now a regular habit already. Look who's silly.

22. Do you believe in soulmates?

And then maybe ask as well if you are anything close to their idea of a soulmate. That's smooth.

23. What keeps people in unhappy relationships?

This might be an eye-opener.

24. What is a definite turn off for you?

Now, we're talking.

25. What do you think about love?

The most profound conversation is about to begin.

26. What's the best way to resolve a fight?

You need to know this because fights are inevitable.

27. What's the weirdest thing you've seen while driving?

But first, do they drive?

12 fun deep personal questions to ask

When we think of personal questions, we usually think that these questions are so serious and really thought-provoking. But, did you know that you can also have some fun while diving deep into one's personality? Take a look at these fun questions to ask to see what I am talking about.

28. Do you think you could endure the pressure of being famous?

Well, you might be famous tomorrow, for all you know.

29. If you could be someone else for a day, who would you be?

This can be anyone, dead or alive.

30. What is the best gift you have been given?

For future reference, you know.

31. When was the last time you slept outdoors?

Oh, this could be fun!

32. If you were given a million dollars today, how would you spend it within three days?

Yup, you can get to know someone by their spending habits.

33. What is your favorite part of a house, and why?

Bedroom? Living room? Garage?

34. Presented with the opportunity to be immortal would you take it?

Immortality is both a blessing and a curse, right?

35. If you could be President of your country for an hour, what is the one thing that you would change?

The crazier, the better!

36. If your life was a movie or a book what would be the title to it?

Ah, just as long as it isn't The Unfaithful One, you're good.

37. Who is your greatest hero?

We all have heroes, right?

38. If past lives are real, what was yours?

Be sure to be ready to answer this back because he's gonna want to know yours as well.

39. When have you felt your biggest adrenaline rush?

Was it a medical emergency or something more interesting?

8 random deep personal questions to ask

Who says you need to plan everything out when wanting to get to know someone? You can actually use these random questions to ask because sometimes, it's the randomness that makes things more meaningful.

40. Which activities make you lose track of time?

You'll get to know what he enjoys, that a good piece of information to have.

41. What would you do differently if you knew nobody would judge you?

Whether we admit or not, we hold back on doing some things because of what others might think.

42. What can you do today that you were not capable of a year ago?

This will show how much they've changed in a span of a year.

43. Why does society place such a high value on beauty when it serves no functional purpose?

Great, great question and conversation starter.

44. Do you think human morality is learned or innate?

Talk about deep.

45. What do we do now that will be looked at as primitive and backwards in 100 years?

Maybe snail mail?

46. What do you think is humankind’s greatest invention?

Call me shallow, but video call is a great contender here.

47. Do you think that humans are doing more harm than good to the planet?

Well, people really have different opinions about this.

6 deep personal interesting questions to ask

Deep questions are bound to be interesting. So, these interesting questions to ask are great if you want to know someone better.

48. What’s your dream job?

Did you know there's a job where your only task is to hug a person?

49. What’s the most inspiring thing you saw someone do?

What inspires them will reveal deep things about them.

50. Have you ever cried tears of joy?

They say real men cry, right?

51. What song makes you unconditionally happy?

His taste in music is also another window to his soul.

52. What’s something you can’t go a day without doing?

His habits are what makes him himself, so you can discover many things with this question.

53. What are you most thankful for?

Gratefulness is a very good thing to have.

How to Pick the Best personal questions to ask

Getting up close and personal is something that lots of people want to accomplish, and asking the right questions will definitely help. But really, how do you go about picking which questions to ask?

Here's how to pick the best personal questions to ask:

1. Know where you're at with the person

Did you just meet, or are you on your third date? This is critical because not all personal questions can be asked anytime. Some questions require an existing relationship before being asked, and some are okay to be asked to a completely new acquaintance. Choose accordingly to avoid awkward conversations.

2. Know where you're are at, literally

Personal questions, especially the deep ones, are better asked in private rather than in a public space where someone can overhear your conversation. Now, depending on where you are, you should weigh in your questions. If you're on a date in a high-end restaurant, then you can probably ask questions that are more on the getting-to-know side and you better shy away from questions that might elicit an emotional response. Reserve the emotional questions when you're out camping or when you're enjoying the warmth of a bonfire.

3. Test it on yourself

The ultimate test when picking the best deep personal questions to ask is to actually put yourself into the shoes of the person you're asking. How would it make you feel? Is there a chance you'll get offended? If there is the slightest chance that you would feel a negative emotion from a question, it is better to choose another question that you think is safe and you'll never go wrong.

Downloadable and Printable List of Personal Questions To Ask

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

More Awesome Questions to ask

If you ever find yourself need more questions other than the ones found above, we have them.

  1. If you want questions that would interest a guy in particular, head to our list of questions to ask a guy and you'll absolutely find what you need.
  2. Now, if asking questions is how you want to go about making your crush like you, then these questions to ask your crush are the ones for you.
  3. If you are already in a relationship and you still want to get to know your boyfriend better (which I think is awesome), then you should see our picks of questions to ask your boyfriend.

In Conclusion

Choosing deep personal questions to ask might seem tricky but if you have lots of questions to choose from, then the chance of you not being able to find the best questions to ask is extremely low. Go ahead and choose one of these deep questions to ask now and see how it'll go.