100 Interesting Questions To Ask To Connect Better With People

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If you’ve ever been in a situation where you had to break the ice, you understand that it can be challenging to develop interesting questions to ask when you meet someone.

You are not in an oral interview, so you don’t have to ask official questions. However, you want to know the person better, and you should ask personal questions.

That is how to know a person better; you may not want to hurt a person’s feelings by asking questions that might make them remember an unforgettable experience.

You can get to know them better through your straightforward queries and other things they may not share with anyone. Having a good conversation is not about making statements.

Asking questions, but not just questions for passing the time but rather interesting questions, will keep the conversation going.

There are various interesting questions you can ask. These questions vary with the occasion, circumstance, and environment, which demands certain answers.

Interesting questions are categorized into funny questions, questions from the great minds, pick-up lines questions that can lead to a relationship, and romantic questions.

Most of the questions I will share with you in this article require instant feedback. People will respond to your questions faster if they are engaging and interesting.

In addition, they like to say things about themselves. So, it is better to ask direct and straightforward questions.

Then, when they speak, be patient and listen. It’s easier this way for them to answer all the questions you have in mind.

I found it challenging to build relationships with people, and it’s not because I have low self-esteem. But, I didn’t know what to talk about. Then, I discovered that questions open conversations, fascinating ones.

So I came up with many interesting questions to ask people.

It became easier to start conversations, and I have known many people through this, thereby forming a connection. Today, we converse with people by chatting online.

It can be difficult to start a conversation; you need to have interesting questions to ask. Many of these interesting questions will result in some amusing answers, and some of them are fun to discuss.

Some might lead to an interesting deeper conversation, but those are few and far between. In this article, I will share lists of interesting questions to ask someone to know them better.


Interesting Questions To Ask Friends

interesting questions to ask

Do you think you know everything about your best friend?

Humans hide many things, and it takes a conversation to know them better. Knowing the questions to ask them will make you understand what made them – the experiences that shaped them.

If you want to create a bond with your friend, you have to know them better. Know who they are; from your questions, you can understand their hobbies, dislikes, and likes.

From there, you can understand their problems and proffer solutions if you can. We have to be careful when asking questions; some questions require intelligence.

You have to be aware of the exciting things to ask; some people might want to withdraw from responding to specific questions. Still, you can get them to respond by asking open questions in a way that makes them feel safe.

There is a mistake some people make when getting to know someone.

They ask questions out of context. You should ask questions that relate to them, and people prefer personal questions to general questions.

Therefore, personal questions should come first before asking their views and opinions. Even though many questions might sound general and may only lead to small talk, the responses are usually revealing.

They can give you a peek into a person’s true nature. Sometimes, answers to personal questions reveal an individual’s hidden attributes.

Suppose you want to know a person beyond the typical biographical information of their name, nationality, birth date, and hometown.

In that case, you need a list of deep but exciting questions to ask during conversations. Deep questions are not only tickets for getting to know others better.

You can use them to become aware of yourself. Especially if you are trying to find your purpose in life.

Of course, your best friend didn’t become close to you overnight.

However, knowing what questions to ask will make you cultivate closeness with everyone. That is why I have added questions that will help you create a bond with your circle of friends.

So, call your best friend, create a question and answer session with them with the list of interesting questions to ask below.

1. What embarrasses you the most and/or what has been your most embarrassing moment?

2. Who do you look up to the most, and what qualities do you love about that person?

3. What is your biggest fear?

4. What is your love language?

5. How do you like to be comforted when you’re sad or upset?

6. What is your all-time favorite memory?

7. Who was the last person to make you cry, and why?

8. Where do you hope to be five years from now? Ten? Fifteen?

9. When have you felt the proudest?

10. When have you felt the most challenged?

11. Have you ever been bullied?

12. Do you have any regrets? If so, what are they?

13. What is your earliest childhood memory

14. Out of all your family members, who are you closest to?

15. What do you do when no one else is around?

16. What is one thing most people don’t know about you?

17. What do you think happens when we die?

18. Do you want to have kids one day? How many?

19. What is the best present you ever received? Who gave it to you and why was it so special?

20. What is the worst you’ve ever been physically hurt?


Interesting Questions To Ask To Get To Know Someone

We meet new people everywhere and every day.

It is okay to walk up to them, start a conversation with them and ask a few questions to know them better. But, first, you have to read their countenance to see if they can listen to you.

When you meet someone for the first time, you want to know them. Ask questions that will make them want to talk to you more.

It might not only be a stranger you are trying to speak with, but it can be your neighbor across the street you want to know better.

If you want to know someone at your workplace, come up with interesting questions to know the person. When people share their details, it automatically forms a relationship between you and the person.

Asking profound questions will take you to an internal position, and they feel confident in sharing their details with you.

Sometimes when you meet someone, you might click. You feel like you’ve been best friends your entire life and can’t believe there was a time when you didn’t even know who they were.

But, other relationships need a little more work—i.e how it feels like pulling effort to know about your brother-in-law. While you might never be best friends with your brother-in-law, there is a trick you can use to get him to open up a little more.

You just have to ask him exciting questions to make him see that you’re genuinely interested in knowing him better.

No matter the occasion, these interesting questions to ask will help you connect better with people you meet. You could even use a question in a social media post to engage your followers.

You might learn something about them simply by asking one of these interesting questions.

It can be difficult to come up with questions to ask someone to know them better. You might decide not to respond to a stranger, because one can never be too careful.

This is why you should approach them in a friendly manner to get the information you need. I will help you with a list of interesting questions to ask someone below.

1.  What is your favorite thing about your career?

2.  What is your biggest complaint about your job?

3.  What is your proudest accomplishment?

4.  What is your child’s proudest accomplishment?

5.  What is your favorite book to read?

6.  What makes you laugh the most

7.  How would your friends describe you?

8.  What are your hobbies?

9.  What is the best gift you have been given?

10.  List two pet peeves.

11.  Where do you see yourself in five years?

12.  If you were a superhero, what powers would you have?

13.  What would you do if you won the lottery?

14.  If you could go back in time to change one thing, what would it be?

15.  If you could share a meal with any four individuals, living or dead, who would they be?

16.  What is the worst gift you have received?

17.  Aside from necessities, what one thing could you not go a day without?

18.  What is your favorite zoo animal?

19.  How many pairs of shoes do you own?

20.  What is the best present you ever received? Who gave it to you and why was it so special?


Interesting Questions To Ask Students

As a teacher, you must know your student better to understand how to relate with them. You have to ask students; it is not like questions you ask your best friend or a guy you met at a bar.

You should ask questions that concern their upbringing, schooling, and ambitions.

Teachers are expected to ask ice breaking questions; these questions should build a rapport and create a more relaxed environment where students can participate fully.

With time, you certainly will uncover information about them.

One way to get to know them faster is to have students use a couple of minutes on the first day of class to answer some interesting questions in the classroom.

Instead of asking the questions on the first day of school to students aloud, you can give them a sheet and tell them to write out their responses.

You will be amazed at what you learn about them by asking these questions. Some students won’t answer you verbally. They may hold back some answers or be dishonest in their responses.

Some students need the luxury of time to put their thoughts together – when they stand in front of the new class, it can be challenging to organize their thoughts.

At that moment, they might forget the answers to some of the questions. Evaluation is different from asking students questions to know them better.

First, you have to ask them questions that make them feel heard and included.

There are some interesting questions to ask students. Students are easier to ask questions, and they may feel shy to respond to others; you can consider asking everyone in the classroom.

Everyone in the classroom comes from different backgrounds, and they differ in experience and knowledge. So, you have to understand them separately as a teacher.

This will help you know them when they do anything absurd or good, and you can correct it immediately since you know them.

In this part of the article, I will dive into exciting questions to ask students. The questions will help you know them better and help everyone in the class know each other a little better.

1.  What are your hobbies or interests?

2.  If you were someone who influenced society, what would you do differently?

3.  What is one thing that made you laugh recently?

4.  If you could ask your favorite celebrity one thing, what would you ask?

5.  If you were invisible for a day, what would you do?

6.  What is your favorite sport to play?

7.  Tell me about the pet(s) you have or the pet you wished you had.

8.  What is your favorite ice cream flavor?

9.  What instrument(s) do you play or want to learn?

10.  What is your favorite YouTube channel?

11.  Which cartoon character do you wish was real?

12.  What is the weirdest thing you have ever eaten?

13.  What is your favorite thing to do when you are alone?

14.  Do you have any hidden talents?

15.  How would you spend a rainy day?

16.  Who is your favorite superhero?

17.  What is your favorite line from a movie?

18.  What is the most unusual thing in your school bag right now?

19.  What is the most meaningful gift you have ever received? OR What’s a meaningful gift you have given?

20.  What was your favorite book you read this summer? OR What is something that you learned how to do this summer?


Interesting Questions To Ask A Guy

Starting a conversation isn’t always easy; this is why there is small talk. For example, when you are on a date with someone you like, discussing the weather is the last thing you will talk about since it is boring.

There are a lot of questions you can ask a guy to keep the conversation interesting between both of you. Striking up interesting discussions is an essential part of building great friendships.

But it can be difficult to find the right things to talk about, especially when you don’t know a lot about them. It’s even more complicated when chatting with people online.

Conversations can be in any form, either physical or on the net. This means of communicating can make you know someone when you convey exciting questions.

Having great conversations will be super easy if you use the guide of interesting questions I’m about to share with you. You will find all the best ways to have meaningful conversations with someone through exciting questions.

Having an arsenal of interesting random questions to start conversations is important. Guys may not answer questions directly; that’s why you have to come up with interesting questions to ask.

You should know someone you want to befriend, especially if you have plans to marry him. If you don’t know him, you will be surprised when you see strange behaviors.

However, these behaviors shouldn’t be odd if you ask the right questions. It is okay if, after asking him questions, you don’t want to be with him. At least, you know him, and he’s not your choice.

These questions are still great to ask within a month, and if you’re still trying to know them. You can keep these questions in mind for a while in case you can’t find anything to talk about.

This way you can get to know each other better. Some of these questions are flirty, while some of them are deep. So here’s a list of interesting questions to ask a guy when you’re feeling stuck.

1.  What makes you insecure?

2.  What do you expect from a love relationship?

3.  What’s the one thing you can’t tolerate?

4.  What do you find attractive in a woman?

5.  What expectations do you have of yourself?

6.  What was your most memorable birthday?

7.  Have you ever worn a girl’s clothing?

8.  Who are your family and friends?

9.  What kind of music do you like and which places in the city do you want to go to?

10.  What is the one thing you can’t live without?

11.  What is your funniest memory of high school?

12.  If you could ask your favorite celebrity one thing, what would you ask?

13.  What is your favorite character from childhood?

14.  What kind of animal do you love the most?

15.  What is one thing that made you laugh recently?

16.  What is one item you’ve recently crossed off your bucket list?

17.  If you could describe yourself with one word, which would it be?

18.  What is your favorite food?

19.  If you were invisible for a day, what would you do?

20.  What is something you would never spend money on?


Interesting Questions To Ask A Girl

I’d like to tell you the faster way to know a girl and start a conversation with her. When you meet a woman you like, you first go on a date and hopefully have a good time. But what happens next?

Your emotions open, and your mind takes over. All your insecurities will be exposed, but you will want them to go. They don’t. You are drawn to a girl, and you want to know her.

This is where exciting questions to ask a girl can help. You can think of these questions I’m going to share as a shortcut to know a girl better, but the girl has to give good answers to make them less boring.

Girls find people who ask them questions about themselves attractive. You will always run out of topics no matter how social you are. This is why you should have an arsenal of topics, and a girl will find you more interesting.

Listening skills, humor, and romance are attractive qualities, and you can show them in your questions to her.

In addition, you should try to get in the mix of the conversation by sharing your experiences because you don’t want the conversation to be like an interview.

There is a chance that you have stumbled on a topic they’re passionate about. People love talking about their passions.

So if you’re the one who gets her to talk about the things that interest her, she will always tell you about those positive feelings.

If she’s passionate about traveling, you will know how to start conversations with her. If you’re both well-traveled, you have gotten a bowl of topics to draw from.

If she hasn’t traveled much but wants to, and you are well-traveled, you can be her own international guide.

Tell her about where you’ve been and encourage her to visit places she wants to see.

If she’s not the travel type, reconsider talking about traveling. Know that you can get this information about her by asking her. I’m confident that if you can memorize some of these questions, you will see an improvement in your interaction with girls.

Now, these questions aren’t your common everyday questions. Instead, it puts both of you in a vulnerable state and forces you into an internal position.

This way, you are accurate and become personal by sharing each other’s details. So, let’s look at interesting questions to ask a girl.

1.  What is your ideal dream date?

2.  Are you a troublemaker?

3.  What are the craziest things you’ve ever done with someone else?

4.  Where do you like being touched the most?

5.  What is the craziest thing you’ve ever done?

6.  Who is your celebrity crush?

7.  If you could have dinner with anyone in the world, past or present, who would you choose?

8.  What skill would you like to become a master at?

9.  If you could play a role in any movie, what person would you want to be?

10.  What is your favorite photograph of yourself?

11.  What is the best present or gift you’ve ever received from someone?

12.  If you could live anywhere in the world, where would it be?

13.  What is your favorite and most treasured memory?

14.  In four minutes, tell me your life’s story.

15.  What things or person has influenced you the most?

16.  Who do you think knows you the best?

17.  What is your favorite childhood memory?

18.  What is the most extraordinary thing someone could genuinely say about you?

19.  What is something you stressed over that ended up being no big deal?

20.  Have you ever had a crush on someone who didn’t like you back?

Have a lover and wondering what kind of questions can help strengthen your relationship? Here are some questions that can strengthen your relationship with a loved one, click here to read.



With this article, it’s easier to ask exciting questions when you meet anyone. Be direct with your questions and listen to the response patiently. On the other hand, don’t be shy to ask a question.

If you want to know someone better, engage them with questions. I hope you can put these questions into practice and build a relationship!

Save this for later!


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Author: Afam Uche

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