From Shy to Social: How I Learned to Engage Wisely and Avoid Heartbreak

A personal take on when to say hi and when to walk by

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Welcome to another edition of Beyond Self Improvement! If you missed it, here’s last week’s article: Productivity Is Not a Substitute for Love.

Today’s essay will explore my journey of learning to connect with strangers.

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Would you strike up a conversation with this guy?

Dear Friend,

Engaging with strangers can take many forms, from cautious avoidance to open-hearted connection. Through personal experiences and reflections, I’ve discovered the profound impact of how we choose to interact with others. In this newsletter, I want to share my knowledge and insights on connecting with people and what it has meant for my life.

My Path of Connection

As a kid, I felt alone, so I longed to connect with people. The desire to be seen, heard and understood was so strong that I developed qualities like people-pleasing and co-dependency. My moods fluctuated with others’ moods. Yet I was painfully shy, which meant I spent much time alone, often feeling like an outsider looking in. I had a love-hate relationship with people but still managed to have a few close friends. When I tried to connect, my efforts often were not reciprocated.

Most of my attempts to bond with people, whether men or women, ended in disappointment. Women didn’t share my affection, and as a shy and sensitive guy, I struggled to relate to more masculine, extroverted men. This inability to connect deeply with others persisted until my mid to late 30s, mainly because I hadn’t yet learned to befriend myself.

The Turning Point

It wasn’t until I lived in a town where I went for daily walks that I finally felt the full sting of my lifelong dilemma of wanting to connect but not being able to. Every time I went for a walk, I would say hi to strangers on the street—partly for my benefit but also for theirs. I know how lonely life can be, and I don’t want others to feel lonely, so I say hi.

However, a surprising number of people didn’t say hi back. This left me wondering: Did they not hear me? Were they ignoring me? Or simply too shy or awkward? These thoughts plagued me. One day, it occurred to me that my heart broke a little bit each time someone didn’t return my hi. To my horror, I realized this heartbreak had been happening my entire life.

I began to question my need to connect. Was I genuinely wanting to bond, or was I lonely and seeking validation? My motivation to say hi stemmed from my sincere yearning to connect, societal pressure to be nice, and trying to use strangers to meet my emotional needs. In the process, I risked my heart daily to feel validated. It never occurred to me that I had a choice in this interaction—to say hi or not. Of course, I say hi to my fellow humans. Why wouldn’t I? While I wouldn’t say I liked the idea of ignoring people, I decided I needed to be wiser about how I engaged.

If someone had friendly energy from a distance, I would say hi to them. If not, I would ignore them. I quickly discovered most people, at least where I lived then, did not have friendly energy. They were what I would refer to as material-first people, not people-first. This meant I had to start disregarding a lot of people. Initially, it felt awkward and uncomfortable. I felt bad for anyone I may have ignored who wanted to connect like me. But I needed to take care of my heart, and this was the best way to do it.

Eventually, not feeling compelled to say hi was a relief. Now, I could walk down the street and not engage people who didn’t have friendly energy. After all, it wasn’t my job to cheer them up. One day, as someone approached in the distance, I crossed the street to avoid the discomfort of looking past them on a narrow sidewalk. Now I finally understood why people walking toward me occasionally crossed the street—for the same reason I did.

Three Ways of Engaging with People

While it was one thing to be selective about who I engaged with, I still wanted to bond with strangers. After all, talking with people I don’t know consistently enriches my life. Through my experiences, I realized there are three approaches to engaging others:

1. Ignore everyone: This approach ensures you’re never disappointed but never get to connect with strangers, either. Most people follow this path.

2. Engage everywhere, get hurt often: This was me in the past. I engaged with people wherever I went, frequently failing and repeatedly feeling hurt. Such people tend to need connection but are constantly disappointed.

3. Engage everywhere, be surprised: This is where I am today. I engage with people and have fulfilling conversations wherever I go. This approach leads to ongoing meaningful and enriching conversations.

The difference between my past experiences of getting my heart broken and my current fulfilling interactions comes down to three key factors:

My way of being: I’m secure, feel good about myself, and am comfortable in my skin. This is reflected in my whole way of being and how people perceive me.

Not trying to get anything from anyone: In the past, I tried to extract validation, acceptance, or affection from others. Now, I engage without trying to get anything from anyone. I connect because I genuinely enjoy the interaction, not because I want or need something in return.

Not being attached to a particular experience: I am no longer attached to any specific outcome. I enjoy seeing what shows up, and whether the person responds positively or not, my sense of self-worth remains intact. I engage with others because it enriches my life, but my well-being is not dependent on their response.

I love connecting with people wherever I go. When I buy something at a store, I ask the clerk how their day is going, and the exchange is satisfying even when they say the most common phrase, “Busy, but I’d rather be busy than bored.” I talk to the passenger next to me when I'm on a plane. Standing in line at a coffee shop or bakery, I chat with the person beside me. Without fail, when I talk to a stranger, I’m happier and more fulfilled than if I ignore them, put on my headphones, and work on my laptop.

Of course, sometimes I need to prioritize rest or getting stuff done. But I almost always regret missing an opportunity to speak to someone and learn about their lives, including the grandmother on the last flight who spent an hour talking about how amazing her granddaughter was.

Taking the Risk

Human interactions have been declining for decades. Smartphones and headphones have allowed us to control our environment at the expense of the well-being of social interactions.

Like all things, engaging with people requires intention. Find the right approach that protects your heart while allowing you to experience the joy of connection. By being selective and discerning, feeling good about yourself, not trying to get anything from others, and not being attached to the outcome, you can create meaningful interactions that enhance your life. Occasionally, you will disappointed.

So, the next time you reach for your phone or headphones, ask yourself, “What do I need more: alone time or life-giving human connection?”

Keep engaging strangers,

Ryan

Thank you for walking beside me on this path, my friend. I’m glad you’re here.

My biggest passion is working 1:1 with readers like you.

Whenever you’re ready, I can help you stop waging war with yourself and start being your best friend. Schedule a free, 45-minute discovery call now.

Virginia, aka “The Queen,” who looks down on lesser dogs