There might be affiliate links on this page, which means we get a small commission of anything you buy. As an Amazon Associate we earn from qualifying purchases. Please do your own research before making any online purchase.
One of the best ways to get to know someone better is by asking open-ended, deep questions.
Even though many questions might sound generic and it may only incite small talk, the responses are usually very revealing. They give you a glimpse into a person’s true nature. Sometimes, answers to personal questions will even reveal what an individual often hides from others or is afraid to tell most people.
Sounds heavy, right?
But really, if you want to get to know a person beyond the basic biographical information of their name, birth date, and hometown, then you need a list of deep questions to ask during conversations.
Deep questions are not only ideal for getting to know others better; you can also use them to become better acquainted with yourself, especially if you are searching for your purpose in life.
So with that in mind, this post contains 371 deep questions that will help you:
- Get answers to reveal a person’s core values and true character
- Discover their short- and long-term goals.
- Understand their capacity for humor (or lack of humor)
- Gauge their intelligence
- Learn about their level of compassion
To simplify things, we have broken down this post into four basic categories. You will discover deep questions to ask:
- A girl
- A guy
- Your family or friends (or people you’d like to turn into friends)
(Sidebar: If you want to use deep questions to spark the interest of someone you're interested in, then you should also check out these two resources: For guys, there are 3 text message that can get a girl interested in you. And for girls, there is a concept known as a “devotion sequence“ that can attract the long-term interest of a guy.)
Remember that although these questions, like this or that questions, are great for getting the conversation going, you must be attentive to the answers and ask for details when necessary. As much as possible, even with the more serious questions, keep the “interrogation” light and lively. (Which is why we highly recommend you focus on the practice of mindful listening.)
OK, let’s get to the questions you can ask someone…
What You Will Learn
91 Deep Questions to Ask a Girl
If you’re looking for ways to know a girl better, these get-to-know-you questions can help you dig further and reveal more about her personality.
These questions help keep your conversation going, and at the same time, allow you to discover more about her. With these questions, you’ll learn about her life’s story and how it has shaped her in the present, what her tastes are, and how she views other people, among other things.
You can use these more personal questions to start up new conversations instead of revisiting the same old conversations again and again. New topics will lead to learning how someone really feels about something, and this small talk can ultimately lead to a deep and meaningful conversation that can lead to a healthy relationship.
90 Deep Questions to Ask a Guy
As with the get-to-know-you questions for a girl, the following list questions has the potential to reveal the true personality of the guy you are talking to.
Ask follow-up questions to the answers given to you. Learn to read between the lines in his answers, as sometimes the things that are being said are colored by the things you want to hear.
(If you want more questions to ask your partner, here's a list of 43 questions that can start a deep conversation.)
92 Deep Questions to Ask Your Friends
Asking deep, get-to-know-you questions can often strengthen the bonds of friendship.
Although you may already know them at a certain level, their answers to some of these questions may surprise you and bring you closer together.
100 Deep Questions to Ask Yourself
One of the benefits of answering deep questions is that you get the chance for self-reflection.
Self-reflection points out exactly where you are right now in your emotional landscape. It can also remind you about the goals you’ve set for yourself and force you to acknowledge whether you’re fulfilling them or not.
It would be a good idea to write down your answers in a journal.
Bonus Round! A Few Questions to Ask Kids
While some of the above questions are deep and meant to spark a more meaningful conversation with someone, it is also always fun to talk to kids. Maybe they have a favorite movie they want to tell you about, or they have an embarrassing moment to share.
The following questions for kids are great conversation starters. They are interesting questions, funny questions, personal questions, and good questions to ask a younger audience.
If you're in the mood for more, check out our compilation of deep philosophical questions and would you rather questions. Or if you prefer something lighthearted, here are some funny yes or no questions.
Final Thoughts on These Deep Questions to Ask Someone
Well, that’s a wrap!
The answers to these questions will hopefully surprise, inspire, and move you.
Before we part, I’d like to leave you with this reminder.
In asking these deep get-to-know-you questions, there are two essential things to consider:
- Your sincerity – Is your purpose for asking these questions truly to get to know the person better?
- Your confidentiality – Some, if not most of the answers to these questions will be sensitive, and they will be given to you by the person in confidence. Remember to keep their answers private.
Hopefully you picked up a few great questions to ask during your next conversation, and hopefully, the responses will help you build a deeper connection with someone. (If you're looking for more, here are some questions to make you think, some hypothetical questions to start a fun conversation, some challenging logic questions, and a list of conversation starters for texting.)
Finally, if you want to use deep questions to spark the interest of someone you're interested in, then you should also check out these two resources: For guys, there are 3 text message that can get a girl interested in you. And for girls, there is a concept known as a “devotion sequence” that can attract the long-term interest of a guy.