The Challenge of Encouraging Random Connections

Why is it so hard to encourage connection among strangers as we go about our daily routines?

I assumed the problem was that we don’t have an easy way to break the ice and it’s still socially frowned upon to talk to strangers.

What if people had something that made it easier to spark conversation, like a SMILE card?

That was my motivation for starting GoingForSmiles and designing SMILE cards that are whimsical and encourage connection through a shared smile.

Few people pass along the card.

Many of them say they are waiting for the “right” person to share it with but end up holding onto it indefinitely.

At first, I thought this type of response would be the exception, but it warranted attention anyway, so I wrote, Random Acts of Kindness Aren’t As Random As We Think. Now, almost a year later, I sadly realize it is the norm.

  1. They are simply uncomfortable striking up conversation with strangers.


To try and understand if the “right” person exists, it would be helpful to understand what types of people are out there. There are many ways to evaluate the population, but for purposes of the topic we are exploring I believe there are three types of people in the world and kind gestures can have a big impact on all of them:

  1. Masked Crusaders — Invisibly Unhappy
    For people who are not comfortable being publicly vulnerable, it’s possible that a small gesture can move them to a path of healing, and later, to pay it forward. Considering that the ‘Masked Crusaders’ segment is probably the largest in our society, they can become a powerful change agent for this movement of kindness and connection.
  2. Kindness Lighthouses — Visibly Unhappy
    Being open about our vulnerability and need for support is often a risk in itself due to the associated stigma. But, often, society filters support towards people who fit certain criteria, which is why some people recognize that the benefits of showing vulnerability outweigh the risks of staying invisible.

Why are Masked Crusaders likely the largest segment of our population?

People respond differently to life’s complexities and conceal their emotions for a variety of reasons:

  1. Personality
    We all process information and show emotions differently, so people have different thresholds for what qualifies as a difficult situation.
  2. Social Norms
    There are certain social norms that require us to put on a brave face, even if in more private settings we are honest about negative emotions. Despite all the main-stream attention that mental health is receiving, society is still not ready for everyone to wear their emotions on their sleeve.
  3. Self-Help Industry
    It introduced the belief that we must be positive, that happiness is the goal, and achieving happiness or success depends heavily on our mindset.

Clearly there are several factors underlying our emotional masks which means there is no way of knowing if we are overlooking someone who does need a shared smile.

Though we may be tempted to ensure our finite energy is directed to people who absolutely need the help (i.e. “Kindness Lighthouses”), we can have a greater collective impact by extending our reach to a broader segment of the population, one that includes both “Masked Crusaders” and “Signal Boosters”.

That is why we need to share smiles and kindness with anyone rather than waiting for the right one.

Talking to Strangers

It’s always easier to comment that “people should look up from their phones and talk to each other more” rather than be the person who does the talking.

But, as with anything, it gets easier the more you do it!

It’s important to set expectations and recognize that there will be people who do not reciprocate your attempt to connect, but it has nothing to do with you. Once you are okay with that, then ask yourself: what qualifies as a connection?

The answer is simple: any kind gesture where at least one other person feels seen or heard.

There is no time minimum or setting requirement — it can take place over 60 seconds or 60 minutes. When you experience connections you’ll feel a surge of dopamine and see how truly random gestures can have outsized impacts on all people and society at large.

It just starts with individual choices made every day.

  1. Practice picking out a random person or two who you’d like to share a smile with or offer a kind gesture. Think about simple acts, like a compliment, letting someone go ahead of you in line, sharing a funny picture, carrying groceries, buying coffee (or, if you find one, passing along a smile card).
  2. Within the next 24 hours, follow through on at least one act of kindness, without discriminating based on appearance

Do you think we can break the cycle? Do you think you can share SMILEs with anyone, without waiting for a perceived “right” person?

If you would like me to send you SMILE cards to help you break the ice, you can email with the subject “Let’s Share Smiles.”

Emotional Health | Student Debt | Career Advice. Repaying my student loans w/ a proprietary method & helping others save tens of thousands too. Let’s talk debt!

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