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56 Personal Questions To Ask - Great Way To Know Your Boyfriend

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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 Dai ...
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by | | December 11, 2020


If you'd like to get to know someone new, you'll need to think of some great personal questions to ask them. These will help you to find out more about them and their life. Asking personal questions is a fantastic way to get someone to open up to you.

The most helpful are ones which let the person tell you about their thoughts, feelings, and experiences. If you're hoping to discover the most useful personal questions to ask, you'll find the best ones below. Simply jot down your favorites and use them the next time you're stuck for awesome question to asks.

Contents

11 Best personal questions to ask

The greatest questions to ask someone to help you get to know them better are ones that ask about their life experiences. Using these questions will assist you in really learning more about their life and their feelings.

Here are the 11 best personal questions to ask:

1. If you could go back in time and change one thing, what would it be and why?

This is a great question to ask if you want to know more about someone's past.

2. What was the best gift that you ever gave someone?

Instead of asking about the best gift someone has received, ask this instead - it will make them think much harder.

3. Where’s the next place on your travel bucket list and why?

People who love traveling will be able to think of a quick answer to this.

4. How do you deal with work stress?

We all have work stress so the answer can present a new way of looking at stressful situations.

5. What’s your idea of a perfect life?

Everyone has an idea of what they'd be doing if they could do anything.

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

Some people have a special place that they visit when they don't want to see anyone else.

7. What’s the best bad decision you’ve made?

This is a question which will certainly produce some very interesting answers.

8. What is something you wish you were better at?

Asking about things that someone likes doing but isn't very good at can be enjoyable.

9. What do you like most about yourself?

A nice positive question to find out how someone sees themself.

10. What one question can you ask someone to find out the most about them?

You can see what your answer to this one special question would be.

11. What is something no one knows about you?

The person you're speaking to might let you in on a secret when you ask them this.

10 Personal questions to ask to get to know someone

Meeting someone new can be exciting because you get to learn everything about them. But it can be hard to know the right questions to ask to find out more and bond with them. The questions below are exactly the type of thing you should be asking if you want to get to know someone really well.

Here are 10 personal questions to ask to get to know someone:

12. If you could become the number one expert in one niche field, what would it be?

Some people will be able to think of an answer to this question very quickly.

13. What’s the best piece of advice a family member has given you?

If you want to know more about the relationship that this person has with their family, this is a thoughtful question to ask.

14. What two things are you most passionate about?

Most of us love talking about our passions so this is a great question if you want to start a conversation.

15. How did you get into your hobbies?

Ask this question if you want to find out what someone likes to do for fun.

16. What one thing would you most want to save if your house caught fire?

Many of us have thought about what we'd save from a fire.

17. What do you consider your biggest accomplishment and why?

Asking positive questions like this can help someone to feel confident.

18. Which movie would you say resembles your life the most?

After a bit of thinking time, the majority of people can come up with an answer to this question, even if it's just something amusing.

19. What was the most historic thing you witnessed in person or took part in?

Although lots of people haven't taken part in big historic events, there will be something that comes to mind.

20. Have you ever successfully given up a bad habit?

Use this to discover the person's addictions and bad habits from the past.

21. What’s something that you love but feel embarrassed about?

It's always fun to hear about someone's guilty pleasures.

7 Personal questions to ask a guy

If you're hoping to make a new male friend, you'll need to ensure that you bond with them. Asking questions about their life is definitely the best way to do this. These personal questions to ask a guy are also great to ask when you're on a date as they help you to find out much more than the usual questions people ask.

Here are 7 personal questions to ask a guy:

22. What does friendship mean to you?

Guys have different ways of looking at friendship compared to girls so you might find a new way of viewing friends after chatting about this.

23. What’s the most useful skill you’ve ever learned?

Asking about skills can help you find out what he likes to do in his spare time.

24. What’s your idea of a really amazing date?

This can give you ideas for dates that you go on in the future.

25. Do you believe in soulmates?

Lots of people find their soulmate even though they weren't looking for one.

26. How much of a handyman are you?

Knowing a guy who is good with his hands can be really helpful.

27. Do you think that people can get along even when they have absolutely nothing in common?

Be ready to give your answer too when you ask this question.

28. What do you think is your ultimate couple goal?

This makes for a super fun question to ask on a date.

11 Fun personal questions to ask

Ensuring that the questions you ask are fun can make it easier for the person to answer them. They put the person at ease and let them know that you're genuinely interested in their answers and don't want to put them on the spot. Use these fun questions to ask if you're chatting to someone that you don't know very well and you're sure to get some interesting answers.

Here are 11 fun personal questions to ask:

29. What has been your biggest blessing in disguise?

It's very interesting to think about this in your own life too.

30. What was the best vacation you ever took and why?

If the person you're talking to likes to travel then you'll get a fantastic answer to this question.

31. What would be the first thing you'd do if you won the lottery?

This is a super fun question to ask because everyone would love to win the lottery.

32. What’s your favorite part of the workday?

It's unlikely that many people have been asked this specific question before.

33. What's your favorite way to spend time with your family?

Watching movies or having dinner are the usual answers to questions about family time, but you might hear something new each time you ask this.

34. When was the last time a stranger made your day?

Even the smallest thing can feel big when coming from a stranger.

35. What would be the absolute best pet to have?

While most people like cats or dogs, some people would prefer to have a more exotic pet.

36. How would your 10-year-old self react to what you do now?

Although it doesn't directly ask about the past, this is a wonderful query to help find out more about someone's childhood.

37. If you could only eat one food for the rest of your life, what would it be?

Who doesn't love to talk about their favorite food?

38. What do you own that a lot of people comment on?

An obscure question but one which will definitely make people think.

39. What song always gets you out on the dance floor?

Lots of people love to dance so this is a great question to ask if you want to make the person smile.

9 Funny personal questions to ask

Funny questions are always useful to have up your sleeve. They can help to break the ice or fill a lull in the conversation. Not only do they make the other person think hard about their answer, but these questions also encourage them to come up with an amusing answer. Write down a few of these funny questions to ask and see what kind of responses you get when you ask them.

Here are 9 funny personal questions to ask:

40. What game do you always lose at?

Be sure to remember the answer to this question for the future.

41. What’s the best $5 you’ve ever spent?

You might get some amusing responses when you ask someone this.

42. Do you and your family have any nicknames for each other?

Lots of families have nicknames for the kids and it can be fun to hear these.

43. Would you take a trip to outer space?

Not everyone would want to go outside the earth's atmosphere.

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

Spontaneous people will love answering this question.

45. What’s the weirdest thing you’ve seen while driving?

If you live near the countryside it's likely that local people might have seen some strange things.

46. If you were a ghost, who would you haunt?

A super fun question to ask if you want to hear about someone's grudges.

47. What's the best joke you've ever heard?

Everyone has at least one joke up their sleeve.

48. What’s the weirdest thing you used to eat as a child?

You might think that you didn't eat anything weird but if you consider it for a moment you'll realise that you know how some unusual things taste.

Personal deep questions to ask

If you have known someone for a little while but don't feel like you know much about their background or the way they think, you can get to know them better by asking deep personal questions. These questions delve into the person's experiences and help you find out more about their outlook on life. Choose your favourite deep questions to ask and try them out the next time you're chatting with a friend.

Here are 8 personal deep questions to ask:

49. How can a person become truly successful?

Success is not always about power or money.

50. What’s the biggest doubt you have?

This is a deep question because it encourages the other person to open up to you.

51. How often do you feel overwhelmed?

We all feel overwhelmed sometimes so it's interesting to hear someone else's point of view.

52. What are you most grateful for in your life?

Getting someone to think about this can help them to feel thankful for what they have.

53. Where do you go when you need some inspiration?

This is a fantastic question to ask creative people.

54. Who do you look up to in life?

If you want to hear about someone's heroes, this is the best question to ask.

55. What quote has always stuck with you?

Quotes can be very powerful when people ponder on them.

56. If there’s one thing you could change about your personality, what would it be and why?

Although we all have things we would like to change, some people have thought about this more than others.

How to Pick the Best personal questions to ask

Once you have taken a look at the queries above, you might be wondering how to choose between them so that you can pick the most useful ones. By asking yourself the questions below, you'll be able to decide on the most helpful questions to ask.

Here is to pick the best personal questions to ask:

1. Who are you asking?

Thinking about who you're asking these questions to can be really useful in being able to sort the most useful questions from the less useful ones. For example, if you are asking someone that you know well then you can choose deep questions. However, if you are speaking to someone you've never met before then you might want to ask more basic questions about their life.

2. How well do you know the person?

Considering how well you know the person is important because you want to make them feel that they can trust you with their answers. Not only this, but you might already know the answers to some of the questions above. If you are asking someone like your boyfriend or a family member then it's likely that you already know a good deal about him, so choose more obscure questions.

3. When are you planning to ask the questions?

This can help you pick the best personal questions to ask because you want to make sure that the question is appropriate for the time and place. A good time to ask personal questions is when you're having dinner together or watching TV because the other person will be relaxed and happy to chat.

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

Asking questions is one of the best ways of creating a connection with someone new. Asking about the person helps them to realise that you're interested in how they think and what they say. If you're hoping to come up with some awesome things to ask, the questions below will be a great help.

  1. Texting with someone you like can help you to come up with ideas of things to talk about in person. So finding out the answers to your questions is a good way to form topics. These questions to ask a guy over text will help you find out more about the guy.
  2. Speaking with your crush can be super exciting. But that thrill can sometimes make your mind go blank so you can't think of anything to say. Taking a look at these questions to ask your crush will ensure you always have an interesting query to put to them.
  3. Do you want to feel a deeper connection with your boyfriend? By using these questions to ask your boyfriend you can get to know everything about him and find out more about his past.

In Conclusion

By picking the most relevant and interesting personal questions to ask, you can help people open up to you. You'll be able to learn about their thoughts and experiences while having memorable conversations.

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