7 questions to ask someone for deeper, more meaningful conversations

Have you ever found yourself craving a conversation that delves beyond the usual small talk? 

Welcome to the club — I’m someone who relishes deep, meaningful conversations. 

Now, I know we can’t just dive into the depths from the get-go; these things take a gentle build-up, a natural progression. And not every conversation is meant to be deep either. 

But I’ve learned that guiding a conversation into more profound territories isn’t as hard as it seems. It’s about asking the right questions at the right time. 

When the moment feels ripe, these questions can open doors to thoughts and stories that linger long after the conversation ends. 

1) “What’s on your mind today?”

This first question is like a deeper version of the routine “How are you?” or “What are you up to today?”

But people are practically primed to answer those two typical questions without any depth — “fine” and “not much”. At best, you might find out the person is tired, and that they had a salami pastrami for lunch. 

But “what’s on your mind?” reframes the question in a way that invites people to go deeper. 

And most of us have something on our mind all the time. (Though I did once meet a guy who claimed he could think about “nothing”.) 

If they’re willing to share, you might find out that they’re worried about their exams, or wondering what gift to buy their partner. Or they might even dive into some deeper territory with you.

And who knows, you might just be the perfect person to help them with something they’ve been struggling with. 

I’ve received some excellent advice from people who I least expected it from when I opened up to them about things I was really thinking about. 

Not to mention, some excellent conversations that helped us both get to know each other on a much deeper, and much more satisfying level. 

2) “What’s been the highlight of your week so far?”

I’ve found this question often elicits a thoughtful expression and long pause. It seems people often are not even aware of what the highlight of their week is.

It’s a little sad, considering how quickly they’re able to answer if you ask them about their problems. 

But this is a totally natural result of our mind’s tendency to focus more on the negative.

And that’s precisely why I love this question so much. It helps people turn their focus to the positive, and look for the good stuff — because even a terrible week has some silver linings. 

At the same time, you can find out what the person values and appreciates in their life. You might learn about their hobbies, a goal they’re working on, or the relationships that are important to them. 

You can also ask about the highlight of the day rather than the week — but I like to give a longer time frame to give the person more room to choose what they’d like to share. 

Just make sure you’re patient. As I mentioned, it can take people a few seconds to remember their favorite part of the week. But if you can resist the urge to fill the couple seconds of silence while they think, some real gems of conversations can come as a result. 

3) “Have you read or watched something interesting lately?”

Here’s a question most people will have an answer to, as most of us love to either read or watch series, or both. 

If not, then they might still volunteer what they do spend their free time doing instead.

And truthfully, this question can lead to a riveting, deep and meaningful conversation, or it can come to a total standstill after just a few sentences. 

It depends on the dynamics of the conversation, and also whether there are points in common uncovered.

I’ve found a good way to steer the conversation more towards the deep end is to make yourself really curious about whatever it is they’re reading or watching — even if it’s not really your vibe.

What is it about the book or series that captivates them? Do they find the characters realistic? How has the storyline and quality evolved since the beginning? 

Because every story has some deep elements to it — if only you’re interested enough to uncover them. 

I’ve had chats about books and movies turn into discussions about what is genuine friendship, whether or not people can change, and how to find real purpose in life. It’s pretty hard to get deeper than that! 

4) “What led you to think that way?”

This question is different from the first three shared in the sense that it’s a follow-up question rather than a conversation starter.

It’s also clear you can only use it as a response to certain types of comments. It might be about a decision they made or an opinion they’ve shared.

I tend to use it only when I have genuine curiosity to learn more about what the person just shared — otherwise it can come across sounding a bit fake or forced.

Of course, there are many variations of this question — a very simplified one is “Why?” 

And depending on the situation, you might also use “What are the reasons behind that?” 

The most important thing to remember with this question is having a judgment-free and friendly tone and frame of mind. 

Because the purpose is not to try to change their mind — it’s just to understand and get to know them better. 

And this question can certainly reveal a lot about a person’s way of thinking and values, if they’re willing to share. 

5) “If you could be doing anything right now, what would it be?”

This question can be a fun conversation starter even with strangers. 

You both get to fantasize about the ideal world, where you might be lounging on a beach chair listening to rolling waves, or riding a camel through the Marrakech desert. 

Or on the other hand, maybe someone would love to be taking a nap in bed, or spending time with a loved one. 

The conversation might stay fun and lighthearted, or it can take a turn into deeper, more meaningful territory. 

You might find out, for example, that they’ve been having a particularly stressful time at work and really need some rest, or have a sick relative whose side they’d love to be at right now.

In more positive possibilities, they might share that they’ve started a new hobby they feel obsessed with, or have started a new business that they can’t wait to dive back into. 

Either way, you will find out more about the ideal life they’d like to be living — or at the very least, something fun they like to do. 

6) “I’ve been struggling with XYZ. What would you do in my shoes?”

Now we come to a question that can lead to surprising depths. Many people think it’s uncomfortable to ask others for advice — that they’re bothering the person, or asking for too much.

But if forums like Quora and Reddit have taught us anything, it’s that people love giving advice and telling people what to do — especially to strangers. 

Think about it — when someone asks you for help, don’t you automatically feel more useful, and proud that you’re able to help someone?

What’s more, getting someone to help you actually brings you closer together — a tactic known as the Benjamin Franklin Effect.

Be sure you only ask this question if you’re okay sharing about this particular struggle with others. Especially since if you don’t know the person well, you can’t be sure that they’ll keep it to themselves. 

Through their answer, you may learn about how they think, or they may relate to you in some way if they’ve gone through something similar. 

Plus, you might get some excellent advice from them, or at least a new perspective to think about. 

7) “What’s something you’d like to know about me?”

Lastly, here’s a question that actually turns the tables — and invites the other person to be the one to ask a question. 

This obviously works best with people you know already on some level, or where both of you have an understanding that you’d like to get to know each other. 

For example, when you’re spending time with a new friend, on a first date, or getting to know a new colleague. 

In my experience, there’s almost always something people may wonder about you, but hold back on asking — perhaps because they don’t want to be intrusive, or there hasn’t been a good opportunity.

Just think about the people in your life that you know — surely there are things you’ve wondered about them but haven’t asked yet.

Be prepared that their question might end up being something you’d prefer not to share. If you’re someone who really values privacy, this question might be best avoided. 

If you do go for it, inevitably you’ll both learn something interesting about each other, as you bounce back ideas, opinions, or experiences you can relate to. 

Creating meaningful connections through conversation

We’ve explored a variety of questions that can transform everyday chatter into something more profound and meaningful. 

Always remember, the key is not just in the asking but in the listening and responding with genuine interest. 

When you do that, you’ll be sure to have conversations that not only pass the time but also enrich your life.