Alone vs. Lonely Practice



alone vs. lonely practice alone vs. lonely practice alone vs. lonely practice

Deep Dive Discussions

When was the last time you had a meaningful conversation with someone? A time when you were able to share the depths of who you are, what you believe, and how you think? Nowadays it feels rare to find the right person, time, or level of interest needed to have this type of conversation. So the goal of this practice is to help you see that these interactions aren’t impossible. In fact, they are possible with nearly every connection we make.


In order to make a lasting connection with someone, it needs to be genuine. So what better way to achieve that than by being your genuine self? This means not only answering honestly, but asking questions that allude to your deeper thoughts and interests. No matter the person, there’s always an opportunity to dig a little deeper beyond the surface level of “polite conversation”. This doesn’t mean that every question or topic needs to be controversial. It just means that you’re willing to share and show a bit more of your authentic self with those you interact with.

But before you begin this practice, you must be willing to be brave and ask bold questions for either *beginner* a week or *advanced* a month. If you need help building up your courage, try one of the following RWY practices: List of Truth, Let Go of Your Ego, or Choose Change. Once you’ve gained some confidence, you can start shaking up some conversations.


The following are some examples of the types of deep dive discussion questions you can ask. Hopefully you’ll get a response that’s just as open and honest as you’re willing to be. If not, it may help to get the ball rolling by sharing your own answer first. Because believe it or not, people really do want to go beyond the small talk and engage in something more meaningful.

*  “How are you doing, really?”  *

This is a question many of us ask just to be polite, so what if we cared about the answer? We can ease into the process by using this question to set the tone. Once they see we’re actually interested, a deeper discussion can begin.

*  “When was the last time you (laughed, cried, felt like a kid, etc.)?”  *

These types of questions are perfect for when you want to dig a little deeper and peel back the layers. Since we aren’t asked these questions often, we don’t have a conditioned response. Thus the answer you’ll get is genuine. You should also choose a topic that you have a personal connection to in order to build mutual trust.

“Where do you want to be in 5, 10, or 25 years?”  *

Questions about the future tend to catch people off guard because either they haven’t really thought about it, or they don’t want to because they don’t think their life will change. So if you ask this question, come from a place of curiosity and encourage them to dream big. Perhaps you’ll light the spark that reignites their own curiosity, thus challenging them to confront their dashed dreams.


When we take the time to completely connect with someone, it benefits both of us. Through deep discussions we can reveal thoughts, beliefs, or dreams we didn’t know we had. So not only do we learn more about someone else, thus building our mutual bond, but we gain more knowledge about ourselves. This give and take is what binds us and creates a lasting companionship. 

A person diving deep into the ocean with fish swimming below

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