15 questions to ask someone for deeper, more meaningful conversations

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Conversations are the gateway to revealing a person’s soul – they help us connect, understand each other, and grow together.

But I get it, sometimes it can feel like we only talk about superficial things, never digging deeper under the surface. 

So, without further ado, here are 15 questions to ask someone for deeper, more meaningful conversations…

Say goodbye to boring one-word exchanges – your interactions are about to get much more exciting! 

1) If you were to title the current chapter of your life, what would it be and why?

Want to get down to the nitty-gritty of how someone’s really feeling? 

This question goes beyond a casual, “How’s life treating you?”, and encourages the other person to reflect on how all the different elements of their life are progressing as a whole.

I remember once telling a friend that this chapter of my life is called “peace” because I was finally putting myself first and leaving toxic relationships in the past…

It sparked a great conversation about personal development and how we can learn from each phase of life! 

2) What’s one thing you’ve changed your mind about in the last year? 

One reason why I love this question is that it highlights the importance of adaptability and the evolution of beliefs…

And if you want a deeper, more meaningful conversation with someone, there’s no better place to start than discussing opinions or ideas that have changed over time!

I remember asking an uncle this question – he’s quite rigid in his beliefs. I was shocked to hear him explain how he’d changed his mind about certain concepts, mainly through getting educated and listening to other perspectives. 

Not only was it a pleasant surprise, but it got me thinking about my own limiting beliefs too…

3) What’s a risk you’ve taken recently, and what did you learn from it?

This question can reveal a lot about a person’s courage, decision-making abilities, and introspection levels. 

Rather than simply asking them what the scariest thing they’ve ever done is, you’re taking it to the next level and asking them to share what they learned from the process. 

This question can then lead to other interesting topics such as the importance of getting out of the comfort zone and past opportunities that may have been missed due to fear! 

4) When do you feel most alive?

You’re on a date, and you want to know what sparks the other person’s passion for life. 

Forget the typical line, “So, what are your likes and hobbies?”…I hate to break it to you guys, but you’re only going to get generic answers when you ask this! 

Instead, find out what makes the other person get out of bed in the morning. Discover what sets their heart on fire and what they live for. 

I promise the conversation will be much more interesting, and you’ll be surprised at how much you learn about them! 

5) What’s one piece of advice you’ve received that you didn’t take but wish you had?

The deepest, most meaningful conversations happen when two people can share their vulnerabilities. 

Not only will this question give you a glimpse into the other person’s past, but you’ll also get a measure of how much personal growth they’ve undertaken. 

It also sparks a conversation on regret and learning from past mistakes…and God knows we’ve all got plenty to say on that topic! 

6) If you had the power to solve one global problem, what would it be?

If you’re looking for a very current, trending conversation starter, this is the question for you. 

Get deep into how they view the world’s problems and what they see as potential solutions…encourage them to get creative with their answers and think outside of the box.

This will give you an insight into their thoughts on ethics, politics, and social issues. 

7) What’s a belief you hold with which many people disagree?

Now for another personal favorite…

I love this question because it often sparks a fascinating debate in which there’s usually never a clear-cut right or wrong answer. 

After all, we all have different beliefs, and learning about someone’s quirky, different ideas can be challenging, inspiring, and thought-provoking! 

Just make sure to keep things respectful and you’ll have a blast! 

8) What’s the biggest lesson you’ve learned from a mistake you’ve made?

Want to know how:

  • Humble 
  • Resilient 
  • Adaptable 

And introspective a person is?

Ask them what the biggest lesson they’ve learned from a mistake is! 

Not only are you getting them to open up about their past, but you’re also encouraging them to think about everything they’ve learned since. 

This question will tell you a lot about a person’s personal development and whether they value learning from their past experiences! 

9) What is the most transformative travel experience you’ve ever had?

As an experienced traveler, I can’t begin to tell you the number of times someone has asked me, “So, which country is your favorite?”. 

Sure, I can pick one and list a few reasons why – “The weather, the people, the food…”. 

But if you want to get into a meaningful conversation, ask them about a travel experience that changed them for life. 

Not only will you hear a great story, but you’ll get a glimpse into how the other person values and learns from such experiences! 

10) What was the last thing that made you genuinely laugh?

Now, just because you want to dig deep and have a meaningful conversation, it doesn’t mean it has to be serious and stuffy! 

That’s why this question is a great way to lightheartedly get to know what tickles the other person and what type of humor they have. 

It’s also great for creating a relaxed atmosphere that can then lead to deeper, more vulnerable conversations! 

11) What is one thing you would like to do or achieve in your life that you haven’t yet?

Want to know where someone is going in life? 

This question will delve deep into a person’s aspirations and goals. But it’ll also force the topic of regret, fear, and overcoming limitations. 

And if this doesn’t make for a deep, meaningful conversation, I don’t know what does!  

12) What is the most challenging thing about growing older for you?

One thing we’ve all got in common is the process of aging. It’s inevitable, but each of us has a unique experience with it. 

So, if you want to find out how someone is coping with such changes occurring in their body and life, this is a great question to ask. 

Especially if you want to know about:

  • The other person’s acceptance of things they can’t change 
  • Whether the other person has embraced or rejected personal growth 
  • The wisdom they’ve built up over the years to reach this point 

Ultimately, it’s a vulnerable conversion that will reveal their challenges, but will also highlight their resilience and adaptability! 

13) If you could relive one day from your past, which day would it be and why?

If you really want to send someone down memory lane, this is the question for it!

And the reason why it’s such an emotional conversation starter is that you’ll find that most people don’t have grand, extravagant memories to recall. 

It’s usually something seemingly simple that forms their happiest memory. The day their dad took them out of school to go on a road trip. 

The day they met their partner. 

The last day they spent with their mother before she passed away.  

It’s these little moments that can actually lead to the deepest of conversations, revealing all sorts of beautiful emotions! 

14) Which experiences have shaped you into the person you are today? 

I don’t know about you, but I love finding out why people are the way they are. 

But it’s a heavy question to ask and one that can be a bit overwhelming. 

That’s why breaking it down into experiences makes it easier for the other person to reflect on the impactful changes in their life. 

With this question, you’ll learn more about a person’s past, but also how it has shaped them into the person they are today! 

15) How do you define success, and do you consider yourself successful?

How a person defines success says a lot about them, and that’s why this is an excellent question if you really want to dig deep! 

You’ll learn about what benchmarks they see as important, and how they define contentment and success in life…

And let’s be honest, this looks different for everyone! 

So, now you’re armed with 15 questions to ask someone for deeper, more meaningful conversations – have fun with them and remember that for these conversations to happen, there needs to be respect and understanding on both sides. 

And be prepared – you’ll have to open up when the questions are directed back at you! 

Lost Your Sense of Purpose?

In this age of information overload and pressure to meet others’ expectations, many struggle to connect with their core purpose and values. It’s easy to lose your inner compass.

Jeanette Brown created this free values discovery PDF to help clarify your deepest motivations and beliefs. As an experienced life coach and self-improvement teacher, Jeanette guides people through major transitions by realigning them with their principles.

Her uniquely insightful values exercises will illuminate what inspires you, what you stand for, and how you aim to operate. This serves as a refreshing filter to tune out societal noise so you can make choices rooted in what matters most to you.

With your values clearly anchored, you’ll gain direction, motivation and the compass to navigate decisions from your best self – rather than fleeting emotion or outside influences.

Stop drifting without purpose. Rediscover what makes you come alive with Jeanette Brown’s values clarity guide.

 

Kiran Athar

Kiran is a freelance writer with a degree in multimedia journalism. She enjoys exploring spirituality, psychology, and love in her writing. As she continues blazing ahead on her journey of self-discovery, she hopes to help her readers do the same. She thrives on building a sense of community and bridging the gaps between people. You can reach out to Kiran on Twitter: @KiranAthar1

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