25 Interesting Questions to Start off an Interesting Conversation

25 Interesting Questions to Start off an Interesting Conversation

25 Interesting Questions to Start off an Interesting Conversation

We human beings are social creatures and communication is the key. We often find ourselves at places, in groups with nothing to talk about. The right questions placed correctly can stimulate interesting discussions.

Here are 25 questions that are not only great conversation starters but also gives you an insight into the person you are speaking to and help create a more personal bond.

1. How Did The Two Of You Meet?

how did u met

When talking to a couple ask this question and learn more about their happy memories. It is a fun way to create ease and have a natural discourse.

2. Who Do You Admire The Most In Life?

Generally, people tend to emulate the person they admire. Thus by giving them a chance to talk about their role model is a great way to get a deeper insight into the character of the person.

3. What Does Love Mean To You?

While talking to your partner this is a good question to understand what makes them feel loved and what their idea of it is. The attitudes, words, actions that make them feel loved is what you can expect when they themselves expresses love.

4. How Would Your Friends Describe You?


Talking about themselves from another person’s perspective helps people to talk more honestly thus leading to authentic conversations. This is also a fun way to break the ice as often we end up sharing fun things are friends say about us.

5. How Do You Spend Your Free Time?

Any one feels great to talk about their hobbies and interests. And if you share an interest or at least show interest in knowing about them, expect an enthusiastic and stimulating conversation.

6. How Would Your “Perfect Day” Be Like?

This is a safe, feel good question that invokes memories that are close to their perfect day and takes the person to a happy place. Consider the ice broken and find yourself engaging in some happy, spontaneous discussion.

7. What Are Your Top Five Favorite Books And Why?

Discussing favorite books gives you a common ground of interest and sharing your likes and your dislikes makes you understand each other more. Add to it the “why” part to get a deeper understanding of her/ his thought process.

8. What Is Your Favorite Music?


There is rarely a person who does not like music. The choices may vary from one to the other but they do like something.  Their choice reflects their attitude and dreams and hopes. Start discussing them. Your interest in knowing about their likes opens them to you and you end up having a great conversation.

9. What Is The Best Memory From Your Childhood?

Again, a happy question leading to a fun discourse. Reminiscing and talking about childhood always brings a smile and opens up a person.

10. Who Was You Favorite Teacher In School And How Did She/ He Impact Your Life?

As a continuation to a previous question, this helps them delve deeper into childhood memories and talk of fond situations that led to the woman/ man they are today. 

A person never forgets the person who played a key role in helping them realize their passions and who they want to be. People who inspired them believed in them and helped them towards their goal are often people who they respect and admire.

11. What Do You Feel Most Proud Of?

Bragging is a bad habit and people do not get much chance to share their achievements. When someone shows interest, it gives them a perfect opportunity to talk about them as they feel that you are truly interested in knowing them better. This also helps you get a great insight into how that person thinks and what they value most.

12. If You Could Travel Anywhere, Where Would You Go And Why?

You get to know what sort of a traveler they are. Are they the luxurious, resting type or adventure all the way type? Sharing travel anecdotes can be a fun way to begin a friendship.

13. If You Won The Lottery, What Would You Do?

o lottery facebook

Money is a crucial factor. So you actually get to know what sort of a person they truly are if you take money out of the equation. Winning a lottery means that you can have anything your heart wants, the sky is the limit. (I personally would build be a huge library!)The answer to this fun conversation starter reflects their innermost desire and help you to know them better.

14. If You Could Only Keep Five Possessions, What Would They Be?

Knowing that we are mere mortals and we leave the world with nothing, human beings are very materialistic. This question will make the person dig deep to figure out what they value most deeply.

15. What Was One Of Your Most Defining Moments In Life?

Talking about a life defining moment shows the person’s vulnerable side and guarantees a deep, meaningful discussion on life.

16. If You Had A Second Chance For At Life, What Would You Change?

A question aimed to make the person share their deep-rooted regrets and unmet desires, this helps to gain a better understanding regarding them.

17. What Do You Want Your Tombstone To Say?

Though morbid, you can turn this into a fun discourse and talk about what legacy you want to leave behind.

18. Why Did You Choose This Profession?


The reason, motivation, ambition, interest behind someone pursuing their career can give you a great view into the type of person she/ he is.

19. What Scares You Most?

Though it would be hard to make someone talk about their pain or vulnerabilities at the very beginning, you may end up having fun with it even- scared of ghosts, spiders, darkness, lightning, snakes. What people are afraid of often gives a glimpse into their psyche.

20. What Age Do You Feel Right Now And Why?

You are as old as you feel at heart and not what your birth certificate says. Talking about how old the person feels and the reason behind it is a great way to know someone better.

21. If You Could Witness Any Past, Present Or Future Event,What Would It Be?

A sure shot starts to a gripping and long discussion, this question unveils a person’s character and desire.

22. What Was Your Most Embarrassing Moment?

Show empathy if this turns sour which would be rare. Mostly what you will get out of this will be a laughter-filled, humorous discourse full of funny anecdotes. A perfect ice-breaker.

23. What Is Your Strongest Personal Quality?

lauri lyster2 photo rod matheson

Modest people might find this question difficult to answer but deep within we like talking about it and getting recognized. Share yours to create a mutual positive bond.

24. What Is A Skill You’d Like To Learn And Why?

Most of us have something new that they are yet to learn- be it as a hobby or for self-development. Talking about them gives a chance for them to analyze why they have not done it yet and a chance for you to get to know them and their aspirations better.

25. What Is The First Thing You Would Do If You Were President?

Might be a storm-in-a-teacup sort of discussion, but a great way to share your political views and opinions on current affairs. Definitely more intellectually stimulating than talking a sentence or two about the weather.

Everyone wants some attention and asking questions, showing interest about them and their lives help people to open up more and gradually helps build a connection between you.