The Challenge of Truly Getting to Know People.

We all have our routines when it comes to social interactions. We ask people about their jobs, their families, their weekend plans—safe and predictable questions that rarely lead to real discovery. But what if we flipped the script? What if we made it our mission to ask someone a question they have never been asked before?

This challenge requires a different level of curiosity and courage. It’s not just about coming up with an unusual question but about crossing an invisible line—gently pushing past the surface of routine conversations and into the realms of personal insight, forgotten memories, or unspoken thoughts.

But first, let’s turn the challenge on ourselves:

Has Anyone Ever Asked You This?

Before we go out and start asking others unexpected questions, let’s reflect on our own experiences. What’s a question no one has ever asked you?

For example:

• What is something you’ve always wished someone would ask you about—but no one ever has?

• If you had to describe your life as a movie genre that isn’t obvious, what would it be and why?

• What’s an unspoken rule you secretly follow that no one knows about?

The possible answers to these are fascinating because they break away from predictable narratives. They invite deep self-reflection and even surprise.

How to Ask Unasked Questions

If you want to truly get to know someone on a different level, your question needs to be:

1. Unique – It must not be something they hear all the time.

2. A Bit Edgy – It should challenge them, even slightly, without being offensive.

3. Personal but Inviting – The goal is depth, not discomfort.

Here are some examples based on how well you know the person:

For Someone You Just Met or Barely Know

• What’s the most unusual belief you hold that you rarely share?

• If you could live an entire day in someone else’s body, whose would it be and why?

• What’s something about you that people always get wrong?

For Someone You Know Casually (Colleague, Friend of a Friend)

• Is there a question you wish people would stop asking you? And if so, which question?

• What’s a risk you regret not taking?

• If your younger self met you today, what would surprise them the most?

For Close Friends or Romantic Partners

• What’s the one thing you never say out loud but wish people understood about you?

• When did you last feel truly free, and what was happening?

• What’s something you judge yourself for, even though you know you shouldn’t?

The Magic in Asking the Right Question

The power of asking these types of questions isn’t just in the answers—it’s in the way they shift the conversation. They break social scripts. They create new connections. And sometimes, they reveal something profound about a person—even to themselves.

So, here’s your challenge:

1. Write down some questions people never asked you and answer them.
2. Think about some questions you would be comfortable asking others. And go for it! Ask someone a question they have never been asked before. See what happens. You might just uncover a story no one else has heard.