Compendium of Questions for Deep and Meaningful Chats


What are the three most important values in your life?

This offers a great way to get to know someone. Values represent what we stand for and can explain one's behavioural tendencies and motivations. It's also a great way to see if you share similar values

Similar questions: None

Tags: intimate

If you could choose a superpower, what would it be?

The choice of superpower represents what someone is interested deep-down. It's a fun question that can lead to a lot of interesting conversations.

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Tags: hypotheticals

Which of the seven deadly sins do you think you embody?

This question makes people think about their own flaws and fit them into the framework of the seven deadly sins. Even those who may consider themselves to be 'flawless' can be guilty of the sin of Pride.

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Tags: intimate

If you were made into a classical statue, what items would you be holding?

Subjects of statues often hold objects that are symbolic and representative of their characteristics, such as a sword for a warrior or a book for a scholar. This question pushes people to think about their most defining characteristics, and what they would like to be remembered for if they were to be immortalized.

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Tags: intimate, hypotheticals

Picture yourself in 10 years. What would be the worst case scenario?

This is a projection question that digs into people's fears and insecurities. You can vary this question by asking the best case scenario, which could be an alternative for understanding people's hopes and dreams.

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Tags: intimate, hypotheticals

What is your greatest fear?

This question pushes people to face their greatest fears, and forces them to talk about them.

Similar questions: Picture yourself in 10 years. What would be the worst case scenario?

Tags: intimate

Would you say you are prone to addiction? What is your biggest addiction?

This is a highly intimate question that pushes people to be honest about their vices.

Similar questions: What is your greatest fear?

Tags: intimate

What does art mean to you?

Each and everyone of us has a relationship with art, where it means more to some of us than others. But what does art mean exactly to you?

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Tags: art

What would be your spirit animal?

This is a fun question to ask and lighten the mood. It would also be a fun discussion to explore what 'spirit animals' mean for each person.

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Tags: fun, hypotheticals, ice breaker