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56 Best Deep Personal Questions – Spark deep conversations.

56 Best Deep Personal Questions – Spark deep conversations.

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When you want to find out more about someone, deep personal questions can be really useful. These questions really help you to understand how someone thinks and feels, meaning you can get to know them better. You might be scared to ask personal questions at first but once people open up to you, it will become much easier.

Using the fantastic examples of deep personal questions below, you can learn more about friends, family members and loved ones. If you’re looking for the best deep personal questions, just keep reading.

Contents

7 Best deep personal questions

If you want to ask the most interesting and meaningful questions, look no further. These questions are the ones most likely to help you really find out new things about someone you know. This could be a friend or family member or perhaps someone you have started dating.

Here are the 7 best deep personal questions:

1. What’s the one thing you would like to change about yourself?

Everyone has something that they don’t like about themself.

2. Are you religious or spiritual?

This is a great question to ask people that you don’t know well.

3. What kind of parent do you think you will be?

In the right context, this is an interesting question to ask.

4. Are you confrontational?

It might be interesting to ask this if you already know the answer.

5. When have you felt your biggest adrenaline rush?

Be ready to share the daredevil things you’ve done in life, too.

6. What’s your favorite hobby to do alone?

Everyone has things that they really love to do by themselves.

7. What would your best friend say is your best quality?

It can be interesting to think about how your friends see you.

6 Deep personal questions to ask a girl

If you have just started dating a girl or you want to find out more about one of your friends, deep personal questions are a great place to start. These personal questions to ask a girl below are perfect for getting a response from a girl.

Here are 6 deep personal questions to ask a girl:

8. What or who would you sacrifice your life for?

Most people would sacrifice themself for their family but the person you ask might have another answer.

9. What lies do you most often tell yourself?

This is a deep question that will make both of you think hard.

10. What do you hope you grow out of?

A great question for someone young.

11. What belief do you have that most people disagree with?

This is a nice question to ask a girl because it helps you understand her better.

12. What dumb thing did you believe for a really long time?

A funny question like this can help to lighten the mood.

13. What brings you the most joy in life?

A lovely question to ask someone, no matter who they are.

6 Deep personal questions to ask a guy

It can be notoriously difficult to get guys to talk about their experiences or feelings, but these personal questions to ask a guy are a great place to start. By using these questions, you can get guys to tell you more about their life and the things that have happened to them.

Here are 6 deep personal questions to ask a guy:

14. When was the last time you really panicked?

This question could have a serious or funny answer depending on who you ask.

15. What seemed normal in your family when you were growing up, but seems weird now?

This is a good question because most people have things that only their family does.

16. What is a controversial opinion do you have?

Most of us have some kind of opinion that seems to divide people.

17. Where do you see yourself 10 years from now?

Would you be able to answer this question if someone asked you?

18. What do you think—can enemies be friends?

It’s nice to learn about whether someone can easily forgive and forget.

19. Do you lose your temper easily?

Lots of people lose their temper but some more easily than others.

5 Deep personal questions to ask your girlfriend

No matter how long you have been with your girlfriend, it’s likely that there is much more that you can find out about her. Questions to ask your girlfriend are great because they help you to share things with one another that neither of you already knew. Asking your girlfriend these deep personal questions can help you both to bond.

Here are 5 deep personal questions to ask your girlfriend:

20. What is something that you’ve never told anyone?

This can be a very big and interesting question.

21. What is your biggest regret?

Learning about your girlfriend’s past will bring the two of you together.

22. Is there anything you’ve wanted to do for a while, but need help with?

If you are able to give help to your girlfriend then this can be a nice way to show it.

23. Who was your crush as a kid?

A fun and lighthearted question which will make your girlfriend think back to her past.

24. What skill did you master when you were younger that you’ve forgotten since?

Many of us have a skill that we used to be great at but now we’re useless.

6 Deep personal questions for couples

Questions for couples can be really useful because they help two people to share things and bond with each other. Instead of just asking your significant other a question about themselves, you can ask questions that relate to your relationship. You’ll then get to know how the other person feels.

Here are 6 deep personal questions for couples:

25. Were you nervous during our first kiss?

This is a fun question to ask because lots of people get nervous about first kisses.

26. When and where did you go on your first date ever?

It might be hard for some people to remember their first-ever date.

27. Do you believe in true love or love at first sight?

This deep personal question will help you find out whether your other half thinks that you can fall in love as soon as you meet someone.

28. What do you look forward to experiencing with me?

You can use this question to help make plans with each other for the future.

29. What is your favorite memory with me?

Couples have lots of experiences together so it can be fun to think of your favorite memories with each other.

7 Deep personal would you rather questions

Would you rather questions can often be weird, humorous or disgusting, but there is also a great deal of deep and personal questions which can be asked. Instead of giving funny answers, the person you’re asking can think about the question and answer honestly.

Here are 7 deep personal would you rather questions:

30. Would you rather be able to read someone’s mind or control their mind?

Find out what kind of person someone is with this question.

31. Would you rather be the person who flips the switch during executions or be the judge who decides who should be executed?

You might think the answer to this question is simple but it might take a bit of thinking.

32. Would you rather be 4 years old your entire life or be 90 years old your entire life?

Would you know the answer to this question if someone asked you?

33. Would you rather lose all your teeth or lose a day of your life every time you kissed someone?

These are two random things but it’s difficult to choose between them.

34. Would you rather give up cursing forever or give up ice cream for 10 years?

This is a funny question to ask a friend or family member.

35. Would you rather lose all of your friends but win the lottery or keep your friends but you don’t get a raise for the rest of your life?

For some people, money is more important than people.

36. Would you rather have a lot of mediocre friends or only one really good friend?

The answer to this question might seem simple to you but someone else might not feel the same.

7 Deep personal questions to ask friends

Deep questions don’t have to be limited to boyfriends, girlfriends and dates – you can ask your friends personal questions too. These brilliant questions for friends let them answer honestly so that you can really get to know them well.

Here are 7 deep personal questions to ask friends:

37. Do you usually follow your heart or your head?

We all have friends who follow their heart and others who follow their head.

38. Would you put your family or your friends first if you had to choose one?

Some of your friends might choose one option, while some might choose another.

39. What is the craziest thing that you’ve done with someone?

This is can be a super fun way to find out more about your friend’s experiences.

40. What is the best advice you’ve ever been given?

Who doesn’t love great advice?

41. What was your favorite romantic moment and why?

We have all experienced romantic times in our lives.

42. How long does it take you to really trust someone?

A serious question like this is good for friends that you’ve known for a while.

43. If you knew that you only had one year to live, what would you change in your life?

People might need to think for a minute before they can answer this question.

5 Deep personal questions to ask your best friend

How well do you really know your best friend? Even if you’ve known them for years, there is likely to be lots of things that they haven’t told you. This can be particularly true if you haven’t known them since childhood and don’t know everything that they’ve been through in their life. These questions to ask your best friend will help you to understand your friends better.

Here are 5 deep personal questions to ask your best friend:

44. Would you ever take back someone who cheated?

Most of us have thought about this so it can be interesting to hear someone’s perspective.

45. How do you feel about sharing your password with your partner?

Does your best friend trust their partner?

46. What’s your philosophy in life?

It can be nice to hear about someone’s take on life.

47. What’s the one thing you would like to change about yourself?

Finding out what someone else doesn’t like about themself can help to put things into perspective.

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

If you’ve never asked someone this then it can be super fun to hear their answer.

8 Deep personal insight questions

Deep questions aren’t just good for asking friends and family, they can be used in other situations too. For example, they make awesome interview questions to find out about the candidates’ personality. These Personal insight questions can be incredibly useful.

Here are 8 deep personal insight questions:

49. In what scenario, if any, is it okay to lie?

You can find out a lot about someone by their answer to this question.

50. If you could change one thing about your character, what would it be?

Asking people about their negative points can be a good way to learn how they see themself.

51. What do you see as your best character trait?

People will be able to pick one of their traits easily.

52. When were you the proudest of yourself?

Hearing about someone’s achievements can allow you to understand them better.

53. In what ways are you contributing to the world?

This is a good question to ask yourself as well as someone else.

54. What was the last piece of constructive criticism you received and how did you react to it?

Knowing how someone responds to criticism is useful in the workplace.

55. Do you think crying is a sign of weakness or strength?

When people answer honestly it can help them learn about themselves.

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

You will get some unusual answers when asking this.

How to Pick the Best Deep Personal Questions

When faced with a lot of questions, it can seem daunting trying to choose the best ones to ask, but this doesn’t need to be the case. If you ask yourself the questions below, it will take no time at all to choose the most suitable deep personal questions.

Here is how to pick the best deep personal questions:

1. Who are you asking?

This is the most important question to answer because you will want to ask different questions depending on who you’re talking to. For example, you might ask a boyfriend or girlfriend questions about their romantic history, but you’re unlikely to ask this when talking to a family member.

2. How well do you know them?

How well you know someone can have a big bearing on the questions you ask. If you don’t know them well, you might go for more general questions about the person’s personality, achievements or their dreams. If you know someone well, you can ask them deep and meaningful questions without them feeling like you are being too full-on.

3. How long have you known them?

Some deep personal questions are great for asking strangers – you could pose the question to anyone and you’d be able to find out more about them without making them uncomfortable. This is particularly true of personal insight questions, which you can ask to someone if you have only known them for a few minutes, for example in an interview situation. If you have known the person longer, especially if you know them well, you can ask them more probing questions.

Downloadable List of Deep Personal Questions

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

More Awesome Conversation Tips

Asking deep questions can be a great way to get to know someone, but there are other fantastic ways of starting conversations and being an interesting person to chat to. Check out the conversation tips below for useful hints on talking to others.

  1. Beginning a conversation can be a really difficult thing to do, but once you have some pointers, you’ll find it much easier. If you’re wondering how to start a conversation, these tips will really help.
  2. Truth or dare isn’t just for kids – it’s a super fun game that people of all ages can play. These truth or dare questions for adults will certainly prove that.
  3. If you want to get really deep with someone and really make them think, these existential questions are all that you need.

In Conclusion

When you’re hoping to find out more about what someone thinks and how they feel, you should be sure to use these fabulous deep personal questions to help you.

About The Author

Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on Marriage.com, iHeart Media, Elite Daily, and The Urban List. Jasper lives in Georgia with his new bride.

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