Conversation Skills, Deux: Going Deep

A few days ago I wrote a post about conversation skills. It was my most popular post ever. I take that as a sign that I should write more about the topic.

The idea for this post came to me from a special place in my heart, an expression of the Muse herself. So if you like the post, do me a favor and share the exercise with a friend.

In my last post I informed you that your individual words and actions are not important in forming relationships. They are an illusion that hides the real variable. What matters is how you make them feel.

I gave you simple questions to use as a starting point in conversation with a new person. I’ll expand on proper use of them in a later post. (For now, the summary is “Expand on their answer with another question, don’t just skip straight to the next one”.) But right now I want to go deep.

We all understand that asking someone about their pet will produce a pleasant feeling in their mind. There are probably a lot of humorous associations there.

But how can we get at some stronger, more personal associations — and therefore connections?

What can we do to get into a conversation that will produce strong feelings of trust, compatibility and understanding?

My experience with friends is that conversations are usually about topics like gossip, activities, and light hearted humor. We rarely step into the territory of our private inner thoughts, momentary joys and sacred memories. I mean specifically the internal stuff that other people cannot be aware of.

Our private life is just that — private. So there is a lot of potential there for associating feelings of trust and connection. The inaccessibility of these thoughts’ private dwellings are what make art so special. It is a physical manifestation of the artist’s inner life given form (albeit with imperfections). So if you can direct a person’s internal attention towards their private inner life, you get privileged association with their true self.

Imagine a therapist’s office. This space houses stronger catharsis than any other space on the planet. But our friends, and even our closest loved ones, never know these things (in my experience) because we never share them. I imagine much fear of rejection is involved — and we do all have dark, empty places in our minds. Just different ones.

This inner life is something I often wonder about but rarely discover. I would really like to.

I am suspicious I know why these conversations don’t happen. As I said, people fear rejection. There needs to be trust involved.

But people don’t go straight from “Oh, you like Galantis too? How many times have you seen them?” to “What was your earliest happy memory of your parents?” and “What are you scared you won’t be able to do before you die?” That’s miles away from most friendships.

So if you want to get there, you need a bridge. Nudge your questions slowly into a more personal area, and you will begin to associate more feelings of connection. Thankfully, somebody already figured out a path for us. We just have to walk it.

I now invite you to take a moment to choose a friend who you are already close with, but would like to get to know better.

Got them in mind? Ok.

Your exercise is to read these questions to each other.

Note that this article (and other manifestations of it) always fail to note the mechanics of how this works. That’s the real lesson here for you. But try the exercise with a friend or me if you’d like and let me know how it goes.

I’ll write my own questions if this one performs well. This is a two way street! Share my article with a friend so I know you liked it, or tell me directly.

I’ll conclude this post with a song that, for me, tunnels right to the warm feeling of connecting with friends.


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