Deeper Conversations Lead to Even Deeper Connections

By: Jeffrey Craig
When was the last time you felt understood by someone? I mean REALLY understood. Like they could see directly into the darkest corners of your soul and knew every secret, every painful trauma, everything that you want no one to know. When was the last time you were able to show that side of yourself to somebody?

For me, it had been a long time since I had that kind of connection with someone. Life got in the way I guess. Just like many people, I got wrapped into presenting a life of perfection to others. Life had become a competition of who is doing it better. I had no time to allow someone to really understand me. Hell, I didn’t even understand myself. I was too preoccupied with showing people what a fantastic life I had to care about being understood.

Ever since a young age, I have had a passion for motivating and inspiring others to do great things. I remember when I played Little League Baseball growing up, the coach would tell my parents that I was uplifting to many of the players. When someone would strike out, I was there to encourage them and lift their spirits. In my teenage years, I played the roll of a youth leader at my local church. I would encourage my peers to make morally sound choices and be there in times of struggle and pain. Even in college, I joined a fraternity where many of my brothers would confide in me for support or advice.

I have spent my whole life focusing on improving the lives of others, but what did I have to show for it? When I moved to Orange County four years ago, it became more clear than ever.

As a new guy in an unfamiliar place, I met new people on a daily, or nightly, basis. But what I didn’t realize then, is the relationships I was creating were shallow and would eventually become meaningless

As time went on, my list of friends grew to the point that any time I went out, I was guaranteed to run into someone I knew. This sounds like the dream, right?

Have you ever been in a crowd of people and still felt like you were all alone? It’s a strange concept, but hear me out. We have all been by ourselves before at one point or another. That is not the same. I am talking about being in a crowd of people where no one understands you, the REAL you. It is the loneliest feeling on the planet.

I had people surrounding me who liked me, but only the me they knew. They accepted the Jeff who was funny, outgoing, and goofy. There was no way they could accept me after seeing my dark side. The side of me who felt inferior, unworthy of love, scared, and lost. If they saw that side of me, I would lose the whole perfect image I had worked so hard to build. I would become a fraud and they would discard me like Monday garbage. So, instead I chose to sit in my lonely despair with the hope something would change.

Eventually something did change, me. I realized that I was tired of living a lie. I was exhausted from doing the same song and dance every single day and getting nothing out of it. I began looking back at the times where I had formed the deepest connections with others and times I have witnessed other people form deep connections.

I remembered when I was playing Little League and one of my teammates would strike out. In that moment of shame and failure, I was always at the front of the dugout ready to give them a hug and assure them that they would get on base next time. I remembered my time as a youth leader when one of my peers told me about his battle with depression because of his parents’ divorce. I recalled the time when one of my fraternity brothers just needed another man there for him as he mourned the loss of a close family member.

As I looked back at times when I have witnessed the greatest connections were made, I began to notice a trend. Certain aspects of a conversation or situation stood out as defining factors in building a solid connection.

Safe Space

One important factor in forming a deep bond with another person is making sure we are in a safe space to do so. Although not impossible, it is far more difficult to have deep, meaningful conversations at a bar, work, or social event.

The situations I recall building the strongest bonds usually occurred in a quiet, more private place. It was not a situation where our focus was placed on another task. We had the time and the space to be with one another.

By creating a safe space, we allow the opportunity for meaningful dialogue to start and deep bonds to form.

Meaningful Dialogue

I would be lying if I said I didn’t love talking about Game of Thrones, but I know it doesn’t really contribute to any deep connection with another person. When it comes to forming deep connections, I have found that meaningful dialogue is a good way to get the ball rolling.

We all have interests that we love talking about, but it is all very surface level. There is a completely different level of ourselves lying deeper within us. Meaningful dialogue is the “Why” to the “What” of a conversation. It evokes emotion from us. It ties in the subject to how it relates to its meaning in our lives.

For example, I love to travel. And I often have conversations about travel with many different people. However, this topic is quite surface level. A deeper, more meaningful dialogue would be about WHY I love to travel. How it impacts my life in a meaningful way.

When we are able to have a meaningful dialogue with another person, we feel that they not only see us, but they understand us in the context of our reality. Through this understanding, deep bonds are formed.

Loving Honesty

When I look back at all the shallow relationships I’ve had, I notice that there is an extreme lack of honesty. Not only honesty with the other person, but honesty with myself. We live in a world where we are afraid to tell the truth because we might offend someone. We might hurt someone’s feelings, but we forget to take in account our own. We would be willing to sacrifice our own happiness simply to ensure the happiness of someone else.

Now, when I look at relationships with honesty, I see something very different. I see trust, understanding, and change. Sure, the truth can hurt, bad. But if we can swallow our pride and allow the other person to be heard the way we would want to be heard, we open ourselves up for healing and positive change.

It is important that when being honest, we do so with a loving heart. Honesty is not meant to be malicious. By framing our truth from a place of love, we are more likely to be heard and trusted. 

Sharing Pain

One of the biggest mistakes I’ve made is believing that everyone else is perfectly fine while I was the only one suffering. I was afraid to share my pain, my failures, and my fears with anyone because I felt they would look down on me. Looking back at times when people have shared their pain with me, I saw something very different. I never looked down on them. If anything, I gained more respect and admiration for them.

It takes an immense amount of courage to share our pain with another person. Something amazing happens when pain is shared. When we hold in our pain, it weighs us down. It’s like a wound that refuses to heal. But when we share our pain with another, it is like pulling the knife from the wound. It can be difficult, but the healing can finally begin.

When pain is shared, we feel a stronger bond with the other person. They have seen the worst and they are still by our side. Trust is formed and we are granted the comfort of knowing we never have to hold in that pain again. 

Bonds are formed through a safe environment, meaningful dialogue, loving honesty, and expression of pain. It’s not easy. Being emotionally vulnerable with another person is probably one of the scariest things we can do. But the rewards are so worth it. If we can open up to another person on a deeper level, the bond we form with them will be greater than any surface level relationship we can have.

Listen, the truth is, none of us are perfect. We all experience pain, sorrow, and anger. But we don’t have to sit with it. When we open ourselves up to another person, we are released from the burdens of our lives. We are no longer alone.

I have come to realize that perfection is not in the cards for me. I am a flawed human and always will be. But I now have deep bonds with individuals who have convinced me that despite all my imperfections, I am still a pretty cool guy.


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