Deep questions to get to know someone will truly help you to get a peek into someone’s soul.
Once you open some big topics, there is no coming back. Especially if you’re trying to get to know better an introverted person.
If a person you’ve asked those questions pours out their heart to you, you’ll definitely know how you feel about them. Personal questions are the best way to learn more about someone.
What did the past relationship teach them, if they had all the money in this world, what would they do with it, and so on?
Such questions show how deep or let’s be real, trivial a person is. Such questions can be a relationship deal breaker at the very beginning.
In today’s article, we bring you some of the best deep personal questions. Learn more about people’s hidden thoughts and true feelings through 30 personal questions.
What Are Super Deep Questions To Ask Someone?
When getting to know someone better, you can ask them questions such as: Where is your favorite place in the entire world? What’s the key to keeping a good work-life balance? Do you believe in soul mates?
What is the biggest life lesson you’ve learned so far? Do you have recurring dreams? World today focuses on trivial relationships among people. But once you open these questions, you’ll feel like you knew this person for years now.
After these questions, you definitely won’t be strangers or just colleagues anymore. These questions are especially great when you’re trying to get a know an introverted person.
30 Deep Questions To Get To Know Someone
Are you tired of awkward small talk? Someone asked you out again but you’re not excited about your next date night?
You feel like you just don’t have a lot to talk about. If this is your greatest fear at the moment, we bring you a deeper level of communication with someone. Personal relationships can be tough, but once you open some topics, they don’t have to be.
These 30 questions are great conversation starters and we guarantee that you’ll enjoy learning about that other person this way. If you’re ready let’s start.
1. What Is Your Biggest Regret?
This question is one of the more difficult questions you will come across today. It opens up many painful memories from the past of those people.
Have they ever been unfair to a family member, did they do something bad in their last relationship, how did their relationship end, and do they regret it?
At the very beginning, you will get answers to some more painful questions and you will already have a little insight into the character of that person.
Of course, you will also see how honest and egoistic they are in this and every subsequent question.
2. What Did You Learn From Your Past Relationship?
The man or woman you’re talking to now ended their past relationship for a reason. If you are not interested in why this happened, ask this question as well. Each person learns from previous experiences.
A person should learn a lesson from a relationship, especially a long-term relationship. With this question, you can assess a person’s social and emotional maturity. They will either tell you the biggest lie ever or you will really learn a lot about your interlocutor.
3. What Is Your Biggest Fear?
No one walks through life bravely and we all have some fears. It is difficult, especially for men, to admit their fears. Then, in addition to that fear, they also fear the fact that they will turn out to be vulnerable.
Men don’t like it and avoid it. But there are also those who will open your heart and soul and answer the question without a doubt.
That person’s greatest fear will say a lot about the strength of their character and the way they see life and everyday life.
4. What Is Your Favorite Family Tradition?
Family traditions and memories from childhood carry with them the most cherished memories. Christmases with family, thanksgiving, birthday celebrations, and many other memories.
This is a topic that everyone can talk about long and wide because everyone remembers some funny events from these family gatherings.
Everyone has at least one embarrassing family photo, a funny story to tell, or something really heartbreaking but endearing.
When a person tells you a part of his childhood or reveals something about his vice, he gets an insight into another dimension of that person’s life. You will also see how close they are to their family and if they are close at all.
5. What Is Your Favorite Hobby And Why?
A personal hobby is something that everyone can talk a lot about. It is something ours and only ours.
If you are in the company of a creative person, she will surely relax even more when she starts talking about her hobby.
A hobby is something we do for love and pleasure, so even talking about it makes some people happy.
Hobbies are an excellent way to break the ice in a conversation, to start a conversation and of course to see how creative, ambitious, etc. a person is.
6. What Is Your Dream Job?
From the moment we were children, until today, we all have our dream job. It’s certainly changed over the years, but it’s interesting to talk about the work we’d like to do one day.
When you open this topic, expect the person to relax into the conversation because the topic is not black, it’s light and probably some funny stories will follow along the way. Especially when meeting introverts, this question is more than ideal to start a conversation.
7. How Would Your Friends Describe You?
From this question you can see how fun, confident and honest the person is. Someone will brag, but you will see the joke, while someone will be a bit immodest and praise themselves through the words of a friend.
But be that as it may, you will be able to see what they tell you through the rest of the evening or your writing if you are not at the meeting in person.
8. Why Is Him/Her Your Best Friend?
I firmly believe that you can have many friends in life, many close ones, but only one very close and best one.
Even if it is two friends, you will always be favored by more than one friend. For someone to be that person in your life, they must have good qualities.
Through this question, you will get to know the assessment of the character of the person you are talking to and you will see what is really important to them in people. However, it is not easy to answer this question just like that, give them a moment.
9. How Do You Imagine Your Dream Life?
For some people, the dream life means a lot of money, and luxury and they will never be fully happy until they have that.
But for some people, happy life is getting married, having your own children, a home, a job, and doing everyday things in life, but being happy doing them. The priorities that this person presents in his life will tell you a lot about that person’s character.
10. Who Was Your Favorite Teacher?
Each of us had a favorite teacher, especially because he/she loved us a lot. We remember such people as role models throughout our lives and remember them with a lot of love.
When people talk about memories from their younger days, it’s proven to relax them, give them the motivation to continue the conversation, and ultimately make them happy, of course.
11. Are You A Dog Person Or A Cat Person?
This question is of great importance to some people, believe it or not. Although I secretly believe that you can change these things in a person (I did and now they sleep together haha!).
If you have pets, and your preferences still match, you will surely be even happier when you find out.
12. What’s The Weirdest Thing You’ve Done?
Growing up, we all had a bunch of challenges that we did with our friends. A really strange thing would happen here and there, sometimes funny, sometimes just weird. But these are all things we recount today at parties, meetings, reunions, etc.
We suggest this question when you want the conversation to go in a lighter, funnier, and more relaxed mood, especially with introverted people.
13. What Was Your Best Birthday?
Oh yes, we all remember that one special birthday. We remember the smell, the cake taste, the gifts we received, and some naughty boy who blew your candles, but the birthday remains remembered. That’s what everyone likes to talk about.
Especially about that important gift that we really wanted and finally got from our parents. This question brings back happy memories and is a good idea to use when you think the person is a little nervous.
14. What Is Your Biggest Pet Peeve?
Each of us has at least one little pet peeve. It’s funny to talk about them because we are all different and each of us is animated and triggered by a different thing.
This is also a great question if you want to go in a humorous direction with the conversation.
15. Do You Have A Bucket List/What’s On Your Bucket List?
That famous bucket list! I have had them since childhood until today. Everyone has one, even with one item.
Talking about the things we want to do, but most of which we are partly afraid of or are very difficult to achieve awakens enthusiasm and an adventurous spirit in us.
These questions are also great if you want to learn more about a person’s hobbies and interests in an indirect way.
16. What Would Be Your Perfect Vacation?
This a great way to find out if this person is a city lover like you or prefers the countryside. Does he prefer skiing or the sea, which you simply enjoy?
And why that place? Personal interest in a place can bring with it an interest in history, other cultures, etc.
This question indirectly asks more about the person’s character. The question is a great conversation starter. Especially if you’ve both had a busy work week.
17. If Your Three Wishes Could Come True, What Would You Wish For?
We all know the story of the goldfish and the three wishes. Just imagine if you had that possibility.
If the person responds to you honestly, you will easily find out what kind of character he is. If they lie, when will they find out that this question was answered dishonestly?
Three wishes, or any, is a strong and good question, so we suggest them for an advanced part of the conversation.
18. If You Win Lottery Tomorrow, What Will You Do With The Money?
This question is very similar to the three wishes question. Finding out that overnight you got more money than you can imagine…opens up many questions.
What to do with that money, how to spend it? A fairly simple question can make your interlocutor either a generous person or a self-centered person. Of course, if they are honest.
19. Who’s Your Favorite Fictional Character And Why?
We would all love to hide behind an avatar or a fictional character for at least one day. We would like to be brave, daring, creative, and powerful like them.
The choice of such a character will reveal the interlocutor’s deep desires and you will know what they actually long for and what they would like to be.
This question definitely deserves a place at the beginning of the conversation because it is a simple question that can be a little funny.
20. If You Knew You’ll Die Tomorrow What Would You Do Today?
Great tomorrow. But this time it’s not coming and you know it. Finding out what a person would do if it were their last day on earth is really interesting, especially if you are just getting to know that person.
If the person honestly admits these things to you, you might laugh, and you might cry. But these questions certainly connect people.
21. What Is Your Favorite Season?
This is one of the simpler questions, but it still carries the reasons behind it. Why does someone like winter or autumn, why do they see so much specialness in a certain season?
That is what you are looking for in this question. You can place it at the beginning of the conversation or some already heated part of the conversation.
22. Have You Ever Broke Someone’s Heart?
Definitely save this question for the part of the conversation where the person feels relaxed and you see that they are ready to talk about something more serious.
If this really happened, be understanding. It is not easy to talk about our mistakes, especially painful ones from the past that we cannot fix.
Introverts will find this especially difficult to admit and talk about, but don’t force anything. Let the person say how much they want to say.
23. What Would Be Your Perfect Date?
This is a sweet and charming question, much more than a deep question. However, through this question, you will find out if a person is romantic, how much effort they are willing to put in for a perfect night with someone they care about, and the like.
If you want to have something more with that person, then this question is very important.
24. Do You Believe At Love At First Sight?
This follows the previous question. It is an excellent question if you want to find out if a person is a hopeless romantic or if they are tired of unfulfilled romances.
But I believe that introverts are much more romantic people and that you will get a positive response from them in any case.
25. What Do You Find Important In The Opposite Gender?
When it comes to this question, this is one of the more important questions if you are looking for something serious with this person.
Making sure that a person is interested in character, ambition, humor and other special features in addition to looks are more than important today.
In the age of social media, it’s really refreshing to come across a person who really cares about what kind of person you are.
But it won’t be bad if they list some things that attract them to a person because we all have preferences after all. In any case, you will find out in a few sentences whether you meet the requirements.
26. What Is Your Favorite Thing About Yourself?
One of the proverbs says that a person who does not love himself cannot love others. If a person is full of insecurity and constantly points out their flaws, that person’s mental health is a bit shaken and then you should act as a friend instead of continuing the questioning.
But if a person reveals your favorite thing about them, it would be good if you point out that thing here and there and flatter them that way. A simple and cute move, right?
27. When Do You Feel The Biggest Adrenaline Rush?
In this way, you will find out what actually moves a person. For some people, adrenaline is a happy thrill, for others, it’s just excitement.
But anyway, we all like a little adventure in life. Finding out what makes a person tick is a somewhat private matter, and now you are privileged to know it too.
28. What’s The Craziest Thing You’ve Done?
Storytime! I’m very sure that every person has craziness from their childhood or teenage years.
When you share such things with other people, you share positive emotions and laugh together. Laughter connects people very quickly.
You will always rather remember the people you laughed with than the ones you kept silent with. This is a great question for introverts, one of those that will really put them at ease.
29. What Is Your Favorite Personal Embarrassing Moment?
Another interesting question and super funny story time. It is usually associated with childhood.
You must have seen in the movies how people laugh secretly and remember embarrassing moments.
But they are also an integral part of life and that is their charm. Afterward, they are a great story to tell when you meet people.
30. What Is The Most Important Lesson You’ve Learned So Far?
The most important question of all is the definitive question of life lessons. What have you been through so far, do you feel stronger now, did you grow up because of circumstances and similar things?
This is definitely one of the first questions you should address when you start talking seriously. You will certainly learn the most about the person this way.
Wrapping Up
Deep questions to get to know someone truly unlock a whole new level of learning about someone. Before your relationship ends, try some of our questions.
You might make the biggest mistake of your life before you give this a shot. We also hope you’ve found an answer to a big question why do introverts love being alone too?
The thought process you unlock with these questions will be a great way to learn more about people, especially those quiet types of people. Favorite songs, political beliefs, and favorite movies, that is not even close to asking what they expect from life, what is their biggest regret and so on.
These questions bond people and you learn about them in mysterious ways. If anything, you’ll be sure if you want to stay close to those people. Since you enjoy reading about introverted topics, introvert quotes might be your cup of tea as well.
Thanks for reading us!
