The original source of this is by Sarah Fader of betterhelp.com and can be found here
1. What is the One Thing That People Always Misunderstand About You?
When was the last time someone asked you what's commonly misunderstood about you? Most of us have something that we wish people would realize even though they don't. Finding this out can help you understand an important fact that that person wants you to know about them and clear up a common misconception.
2. What's On Your Bucket List This Year?
Finding out what is important to them and what they want to accomplish in life before they kick the bucket is a way to get an idea of them as a person. If they want to go skydiving, they may be more adventurous. If they want to go back to school, maybe they enjoy learning.
3. Do You Believe in Second Chances?
You have to be careful in your approach for this one. You don't want them to think that you're looking for "if I screw up will you forgive me?" It's actually about how they feel about mistakes and if they believe someone can make a mistake and overcome it.
4. What Makes You Feel Accomplished?
Getting to know someone is finding out what is most important to them and learning what activity or accomplishment makes them the proudest. Is it being a parent? Being a supervisor at their job or being a good friend?
5. What's the One Thing You Would Like to Change About Yourself?
Everyone would change something about themselves whether it's a physical attribute or a skill they wish they could master. It can be something like "I wish I wasn't so nervous in public," or 'I would like to be able to make friends more easily." This can tell you a lot about them.
6. Where Do You See Yourself after Five Years?
This is a common interview question for a reason. Learning where someone wants to be in five years tells you what type of goals they're setting for themselves.
7. If You Could Live Forever, How Would You Spend It?
What would they do if time were not an issue? Something fun about themselves? Something good for others?
8. How Would You Want to Be Remembered?
What's the one thing (or few things) that you would like someone to remember about you when you die? Do you want to be remembered as the fun aunt who always played with her nieces and nephews or the hard worker who always gave their all to their job or something else entirely?
9. If You Could Master One New Skill, What Would It Be?
Find out the things they already may be good at and the things they would enjoy trying out. Maybe it's a skill you could teach them or a skill you could learn together.
10. What Would Your Perfect Day Look Like?
Everyone has an idea for a perfect day. So what things would make them happy? This can help you get to know what things they like best. Maybe you can use that ideal day as a model and schedule some adventures like this in the future.
11. What Makes You The Happiest?
Picking one thing or one person or one activity that makes you the happiest can be difficult. But, it's also a way to learn things about someone. If they say money it means they put a lot of stock in wealth. If they say being with someone special, it shows they care more about the simpler things.
12. Who's Your Biggest Hero?
Getting to know their heroes can help you understand a person because it shows you who and what they admire most and that's important to their personality.
The original source of this is by Ryan of mantelligence.com and can be found here
Guys
Girls
Funny
Don't ask these upfront until there's some connection/rapport
The original source of this is by Ivana Kiki of lifehacks.io and can be found here
Can find out if:
Examples
Screen and learn about their past/emotional baggage.
Even if they do not want to answer some questions a little personal, that will also give you information. You know it’s impossible not to communicate, their silences also speak … It means that it is a reserved or shy person.
See a person's jobs, dreams, future aspirations
Personal deep questions. Not to be asked right away.
The original source of this is by Stephanie Kirby of betterhelp.com and can be found here. Don't ask these serious questions too soon until some intial trust and rapport is built.
1. What are you the most proud of?
What does this person value? Some people might consider their job performance to be their biggest achievement. Others might put more value on relationships with friends and family.
2. What are you the most ashamed of?
This question requires an honest look at someone's mistakes, as well as the sincerity of their efforts to improve themselves.
3. If you could go back and change one decision in your life, what would it be?
The answer will tell you how this person has changed over time, and how her values and beliefs have shifted.
4. What is your biggest dream in life?
Where does this person want to go in life? And can you see yourself being part of that?
5. What difference would it make in your life if you felt completely safe, accepted, and loved?
This tells you about the challenges a person is facing, and how these challenges affect him.
6. Do you think your parents did a good job raising you while you were growing up? Why or why not?
A person's childhood says a lot about who they are…but not nearly as much as their feelings about that childhood.
7. What's one thing that you wish people understood about you?
Sometimes appearances are deceiving. This question brings out hidden personality characteristics.
8. What is your biggest flaw?
When answered honestly, asking this question can protect you from unpleasant surprises further along in the friendship. It also reveals what personality qualities your new friend values.
9. What event in your life has shaped you most as a person, and how did it do so?
This offers valuable insight into the person's past. It may explain many decisions and behaviors as the friendship progresses that would otherwise be mysterious.
10. Have you ever treated a person in a way that you regret?
And related to that: What would you do differently if given a chance?
The answer will reveal much about what she considers to be right and wrong ways of treating others, and tells you what you can expect in the course of the friendship.
11. Do you think it's possible for men and women to be "just friends?"
Especially in cross-gender friendships, it's helpful to know exactly what the person's friendship goals are…or are not.
12. Would you rather be rich and lonely or financially destitute with lots of great family and friends? Why?
This is another question which speaks volumes about this person's priorities. It gives you an understanding of how much he may be willing to give to make a relationship or a friendship work.
13. Tell me about something you did when you were drunk that you've never confessed to anyone.
Often, the loss of inhibition leads us to show our true colors. But what exactly are those true colors? You can either wait until the next time she drinks a little too much…or you can just ask straight out.
14. If you could change one thing about yourself, what would it be and why?
Like the question about what you're ashamed of, the answer to this one speaks volumes about a person's weaknesses, and what he is trying to do to conquer them.
15. If you knew you would die tomorrow, how would you spend today?
Whether it's seeing a longed-for tourist landmark or just spending the day with a group of closest friends, nothing says more about you than how you choose to spend your time…especially when that time is limited.
16. Are you truly happy?
And why or why not?
This is useful for gauging how positive and upbeat your new friend is. Is she a glass half-full kind of person? Or does he have a tendency to ruminate about negative things? And what triggers her happiness or unhappiness?
17. Have you ever been in love?
And how do you know? What was it like for you?
Love can seem like a moving target. Everyone has different experiences and different ideas.
18. When you're home alone, and nobody else is around, how do you like to spend your time?
Who is your friend when no one is watching? That's the person that he is likely to become once he is more comfortable around you.
19. What do you want people to say at your funeral?
This shows you what a person wants to accomplish in her life, as well as the kind of impression he hopes to make on others.
20. If you could have a conversation with anyone living or dead, who would it be and why?
Buddha? Elvis? A deceased parent? Whatever the response, you can discover who your new friend admires the most, revealing the attributes that he values above all.
21. Do you think you're a genuinely good person?
And why or why not?
This question is helpful in sorting out your friend's standards of human worth. What does she consider good? Is everyone innately good, or are most people deeply flawed?
22. How did you choose your current profession?
Are you happy with your job? Would you rather be doing something different?
Asking this question helps you understand whether this person is content with his path in life. Is she making steady progress towards her goals, or is he ready to mix things up at any given moment?
23. If money were not an issue, how would you spend your time each day?
We can all safely admit that the business of earning a living gets in the way of many a hope and dream. Learn about the hopes and dreams your friend may hide underneath the daily grind of existence.
24. Tell me about your political leanings.
Have they changed? How were they developed or influenced?
In some situations, you will prefer the friendship of a person whose political convictions are similar to yours. But if there is open-mindedness, you can have some engaging discussions.
25. What's one thing that you do on a regular basis that you hate doing, but nobody knows that you despise doing it?
This is a unique way to discover someone's likes and dislikes, as well as how much they are willing to give up for others or for a necessary cause.