A Real Human Being

How to Connect With People and Why You Should

It was a warm autumn afternoon in 2019 and I was driving to meet a girl for the first time. I mean, not meeting a girl for the first time in my life, but driving to meet this one particular girl that I had never met before.

It wasn’t a date.

We had become acquainted through Instagram. I had posted a question in my stories. I was looking for people to participate in a little experiment with me. I had made these conversation cards that were designed to help any two people connect on a deeper level and I wanted to test them out.

So I asked if anyone would be interested in trying them and this girl, Lauren was her name, said she would do it.

It was really brave of her. It wasn’t like she was super outgoing or anything. She just wanted to try something brave.

I really admire her for that.

Grab A Free Copy of my 50+ Questions to Connect With Anyone

I know she was nervous. In fact, I had tried to meet someone else for the same project a little while earlier that day but it fell through, and in communicating with Lauren I could sense her hesitation.

But she decided to do it anyway.

I didn’t blame her for her reluctance. I was actually a bit nervous myself.

As I mentioned in a previous post, I am an introvert. But it has gone beyond introversion at times throughout my life. I have been incredibly shy, even scared of people, from time to time.

Especially when I was younger.

I will chronicle some of my hilarious, if humiliating, misadventures in human interaction, especially with girls I have liked, in future posts. So stay tuned for that.

It has actually been really difficult for me. Really lonely and painful. As anyone who has experienced social anxiety will probably attest to, there is a lot of pain that comes with isolation.

But here’s the weird thing. I’m actually really good at connecting with people.

When I can get out of my head and into the moment, or get past the crippling anxiety of the initial interaction with someone, and especially if I can talk with someone who is interested in having a deeper conversation and making a meaningful connection, I am actually really good at connecting with them. I’ve always had this ability, since I was young.

It’s just getting past the obstacles that keep me from accessing it.

I am not one to just accept things as they are, though. If I am in a situation I don’t like or I am unhappy I usually try to find answers to help me understand why I am there and what I can do to make changes.

So I have done a lot of thinking about my social challenges. And I did a lot of thinking about what made for a good conversation and a deep connection between people. I thought about why I was so good at it sometimes, and so unable to access that skill other times.

At some point I came across this article talking about the 32 Questions to Fall in Love. Have you heard of it? It immediately grabbed my attention. I love love, for one thing. I am quite the romantic. But it also spoke to human connection in a way I hadn’t heard of before.

The theory was that basically psychology was simple enough, and human connection easy enough to manipulate, that any two people could fall in love given the right circumstances and the right questions.

Some really smart people came up with these questions, and the right sequence, that were specifically designed to gradually increase the intimacy and connection between people.

I read that there were two scientists, or social scientists, or some sort of scientifically-oriented people, who decided they wanted to test the theory so they followed the questions in the right sequence and ended up falling in love and getting married.

Now a couple of caveats. I think that these two were already actually at least marginally interested in each other romantically. So that’s probably a huge factor. I’ve actually seen several videos where they tested these questions on two strangers and most of them did not end in marriage. Although I think most of them did have a nice experience.

And that brings me to my takeaway from this whole discovery.

I thought if two people could fall in love with the right questions then certainly two people could connect in a meaningful way with the right questions.

So I set out to find, or create, those questions.

And I found a goldmine.

This post broke down 6 main pillars of human connection and how they help us connect.

Those pillars are:



Gratitude is a powerful human experience. It fills us with a sense of abundance instead of scarcity. It brings joy and enjoyment. And it invites in more to be grateful for. So when we experience gratitude in relationships, meaning that we feel grateful for, or do things that our partner might feel grateful for, we infuse those same elements into our relationship.

Gratitude helps to build trust and tends to help us look for the positive in each other. It also inspires us to return the favor. If someone does something nice for us, and we feel grateful for them, we often feel a desire to do something nice for them in return. This can create a cycle of positivity that builds on itself.



Nostalgia invites us to revisit cherished memories from the past, fostering a sense of warmth and connection. As we reminisce on shared experiences, we deepen our understanding of each other’s journey and cultivate empathy. By embracing nostalgia in our relationships, we weave a tapestry of shared history that strengthens our bond and enriches our connection.


Giving & Asking For Advice

Engaging in the exchange of wisdom and vulnerability, giving and seeking advice fosters a culture of support and trust within relationships. It signifies a willingness to be honest and open, nurturing intimacy and understanding. By offering guidance and seeking counsel, we deepen our connection and cultivate a sense of mutual reliance, laying the groundwork for a resilient and supportive partnership.


Vulnerable Sharing

Vulnerable sharing is the cornerstone of intimacy in relationships, inviting authenticity and acceptance. By bravely revealing our fears, insecurities, and past experiences, we create space for empathy and understanding to flourish. Through moments of vulnerability, we forge deeper connections, fostering emotional closeness and strengthening the bond of trust between partners.


Learning Preferences

Exploring each other’s preferences and values is a journey of discovery that deepens our connection and appreciation for one another. By actively seeking to understand our partner’s likes, dislikes, and communication styles, we cultivate empathy and mutual respect. Learning preferences fosters a sense of validation and understanding, nurturing a deeper bond grounded in appreciation for each other’s uniqueness.



Discovering shared interests and experiences creates a sense of unity and belonging within relationships. Celebrating commonalities fosters a connection rooted in mutual understanding and shared purpose. By bonding over shared passions and experiences, we cultivate a sense of camaraderie and solidarity, enriching our relationship with a shared sense of joy and connection.


My Own Attempt to Fix Loneliness & Disconnection

After reading and pondering this post I started compiling my own list of questions that were developed specifically to fit one (or sometimes multiple) of these pillars and thereby help any two people to connect more deeply with each other. I used some of the questions from that blog post, found some from other sources, and made some myself.

In the end I came up with a list of 50+ questions. I pulled out my trusty Photoshop skills and went to work designing some cards, which I then had printed through a custom playing card printer, and voila!

I now had my own custom deck of conversation cards ready to help address one of the most pervasive, and devastating, plagues of our time:

Loneliness and disconnection.

See, I think that now more than ever in history we are starving for connection. Like, real, deep, profound connection with other human beings.

We’ve never been more technically connected and yet more emotionally isolated it seems. I have a lot of theories about why that is, but I’ll save those for another post. Suffice it to say that I think a large percentage of people are desperate for connection.

Brene Brown said in her book Daring Greatly:

“Connection Is Why We’re Here. We Are Hardwired To Connect With Others, It’s What Gives Purpose And Meaning To Our Lives, And Without It There Is Suffering.”

I think there is a lot of suffering going on in the world today. I know I have experienced plenty of it myself.

Why did Lauren push herself past some nervousness to find a way to try to connect someone she had never met before? Well, I suppose I can’t speak for her, but I know why I did it. Connection is one of the most beautiful and fulfilling experiences I have ever had the pleasure of experiencing. It brings such joy and peace into my heart. There is such a big emotional reward when connecting with another person beyond just a surface level.

And without it I have suffered. 

In loneliness and isolation I have struggled.

So I was really desperate to find ways to alleviate that pain.

And to invite more joy into my life and the lives of others.

My conversation with Lauren was so fun. And so rewarding.

You can watch it here:

What a lovely human that I never would have had the chance to connect with if I had not pushed myself past some fear. And if she had not done the same.

I invited all of you to try to find a way to connect with another person in a vulnerable and meaningful way. Explore that possibility. Discover what is holding you back. And find ways to bring more connection into your lives.

It will reward you in ways you probably can’t even imagine. This world certainly needs us to see each other more as friends and fellow travelers and less as avatars on a screen.

Truly I think more connection can help the world heal in ways it really needs.

If you want a free copy of my connection questions, you can find that here!

And if you are interested in grabbing a deck of my Connect Cards, go here and sign up to be notified when they are available!

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