10 Prompts for Deeper Conversations with a Friend or Colleague

Have you ever felt like you want to get to know someone better, but you just have no idea where to start?

In life, it’s safe to say we’re going to meet and interact with all different kinds of people…

On a few lucky occasions, we’ll come across a person that we get along with right away. Usually we know this because our interactions with this person provoke a feeling of trust or comfort. It feels almost effortless to get to know the person, and equally effortless to share personal details about our life…

On the other hand, there are times when we know right away that we are not compatible with someone. Maybe their core values or views conflict with our own, or maybe it’s as simple as their tone of voice just rubs us the wrong way…

But what about the people that we just simply want to get to know better? Maybe you have a hunch that you’d really enjoy someone’s company… but it’s hard to bridge the gap between the niceties of “Hey, how’s it going?”, “I’m fine. How are you?” to “Hey, did you end up deciding to take the day off to visit your cousin in the hospital? I’ve been thinking of you both…”

A client of mine actually reached out to me the other day asking for some ideas on how they can create deeper conversation with their colleagues on a weekend trip they were about to embark on…

And this got me thinking…

When looking to have a deeper conversation with someone, where do you start? Obviously you don’t want to scare anyone off by probing if they’re not very comfortable with you yet, but at the same time, maybe that’s the person who could really stand to gain from opening up about their life. What’s more, sometimes I find that it’s almost easier to confide in a person you don’t know very well, compared to confiding in a spouse or a family member.

In search of how to aid my client in their request, I came up with a list of 10 different ways to invoke deeper conversation with someone:

1) Have each of you make a list of the things that you’re most curious about the other person then take turns answering questions about their area of interest

2) Each of you shares one regret you have in life and what you learned from it (repeating as many times as you please)

3) Each of you writes down 5 answers on individual pieces of paper (answers that involve simple ideas or concepts) then, place each paper into a hat and take turns drawing an answer and trying to come up with the question that you think your answer is responding to.

4) Time Machine Time! Share something about who you were or what your life was like starting at age 5 and working your way up to your current age in increments of 5 years. (What was life like at 10 for you? 15? 20? And continuing on…)

5) Talk about the future you see for yourself and the future you see for your kids. What will the world be like for them and how might you help them prepare for it?

6) Talk about what you love about your romantic partners and what you want to learn to love and accept more of.

7) Discuss what you are most grateful for.

8) If you could change something about the way you were raised, what would it be?

9) Each of you choose one problem you are currently facing, then take the time to share, discuss and reflect on them together.

10) Throw all these questions away and simply ask in each moment what could I say that’s more true? What could we talk about that would matter more? What am I hiding or holding back? What if I shared more of my heart in this moment?

The beautiful thing about this process isn’t just that you’re about to gain a new friend! You also stand to gain from being vulnerable with this person, and will learn more about yourself through these conversations!

If you try any of these conversation-starters out, let me know how it goes!

Happy conversing!


Dear You,

 camera-man, dear you, open letter to humanity, uplifting letter, a letter to your heart, a letter of hope, a letter to you, a beautiful letter, believe in yourself, believe in yourself letter, inspirational letter to a son,  inspirational letter to a daughter,  inspirational letter to a friend,  inspirational letter to a teacher,  inspirational letter to a parent

Dear, You

I’ve been meaning to write, but I’ve struggled with what I wanted to say. 

In a way, I’ve known all along. But I wasn’t sure how to say it. And finally I decided that maybe I should just go for it.

So, here it is…

I love you.

I know you that might come as a surprise. I mean we hardly know each other. Then again, sometimes it feels like we never really know anyone. But no matter how well we know each other, it doesn’t change how I feel.

You know that feeling you had when you were young and you made a new friend. And everything about them seemed cool. And you felt this feeling of friendship and love for them. And you wanted to tell them, but you were worried it wasn’t cool or that it wasn’t the right time.

And sometimes you’d get so close, but then the moment would pass. And you regretted staying silent, but it was too late.

Well that’s how I feel and I just couldn’t hold it in any more. I couldn’t stand the idea of missing my chance to tell you I love you. So I did it, even though it may seem a little awkward.

And I know what you’re wondering.

You’re thinking, “Why do you love me?”

Well I’ll tell you. I love you because you’re beautiful. And I’m not just talking about your heart but every part of you.

Every time I see you walking down the street, or I see a picture of you, or I read the words you write, or when you stop by to read a post, I’ve thought, Wow! Sooo beautiful!

And I bet you probably don’t get it.

Maybe a lot of people have told you you’re not beautiful.

Maybe they said you were ugly, or dumb, or fat, or dorky, or had a funny looking face. Or maybe they told you your dreams are meaningless and that you don’t matter.

Well, I feel sorry for those people. Because they don’t get it. They don’t really see you. And that’s their loss.

Because I appreciate every little thing that makes up ‘you.’

Your scars, your stretch marks, your wrinkles, and even that oddly placed mole you’ve never liked. All of it just makes me love you more.

Because those little details make you real
and human
and flawed
and breath taking.

See you have to understand that when I see pictures in magazines I know they’re a lie. When I see reality TV, I know it’s just a show.

But your image, your words, and your life are different.
It isn’t some manufactured fiction. It’s special.

It’s special because it contains so much real joy and suffering.

If I could hook you up to a computer and download your experience it would make me weep, and laugh, and feel completely overwhelmed. Because I know that in just one day of your life, there is so much beauty and depth.

And it’s that beauty and depth that makes me love you.

And I wouldn’t change any of it.

Because without it, you wouldn’t be here. Without it, you wouldn’t be reading these words.

And I know that some of it was probably unfair and hard. And I know you may wish it was different. But I just appreciate it, because I appreciate you.

OK I know that was a lot to handle, but before I go I just want to tell you one more thing.

It’s something that I wish I could tell you everyday, but I know that I can’t. So I’ll settle for telling you once. And I’m afraid you won’t believe me, but despite that, I’m going to tell you anyway.

(Deep Breathe)

You are so much more powerful than you could ever imagine. When I look at you, I see so much unbelievable potential for wisdom and compassion.

I can tell that for too long people have told you what you aren’t and what you can’t be and that you should just be realistic.

But I want to tell you that they‘re WRONG. They don’t know you and they don’t love you. They’re scared of your light and humbled by your power.

They couldn’t see their own light, so they put you down to make themselves feel better.

Well I hope you won’t listen to them.
In fact, I hope you won’t listen to me either.

I hope that you won’t listen to anything except for that strong soft voice in your core.

The voice you used to hear when you were little.
The voice that told you what you were meant to be.
The voice that called you to love other people.
The voice that made you stare with wonder at spider webs, or the setting sun, or at the face of a crying friend.

I hope that you will find that voice and listen to it.
I hope that you will have faith in it and follow it.
Even if what it asks is hard.

Because I know that if you find that voice and follow it, then it will lead you somewhere amazing. And I’m not talking about wealth or fame, because those things don’t last.

No the place I’m talking about is something that lives deep inside and also right in front of your eyes. It’s been yours all along, but you didn’t realize it.

But don’t take my word for it. Listen, be still, and search with all your heart.

Because I know when you do anything is possible. I know that when you do, you’ll be a huge benefit to yourself and the world. In ways that no one can fully comprehend.

I hope you will wake up tomorrow, take out a piece of paper, close your eyes, and listen for that voice. And when you hear it, you’ll start writing and not stop until you are done.

I hope you’ll do this tomorrow and the next day
and the next
and the next.

I hope you’ll do it until that voice rings in your ear with every breath.
Because if you do this one simple thing, you will be on your way.

I can’t promise that the path will be easy, but it will be worth it. Because deep satisfaction is waiting for you. It’s there, if you only have the courage to look.

Ok that’s it. I’ve said my peace; the rest is up to you.

Thanks for everything . . . really.

My life would be so dull and empty without you.

I feel so grateful that you are here to teach me and show me what I need to know.
Without your guidance, I would be lost.

Thanks again. And I hope to see you soon.

I can’t wait to see what you’re going to do.


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