Day 55: Ask a Stranger How Their Day Is Going—and Genuinely Listen

The Idea:

Today’s challenge is to strike up a brief conversation with a stranger by simply asking, “How’s your day going?” Then—really listen. It could be someone working at a café, someone waiting in line, or someone walking their dog.

Why It’s Good:

This might sound simple, but it’s scary for many—especially in a world where small talk is rushed and strangers are seen as off-limits. You’re choosing to step outside your bubble, to connect without an agenda, and to show someone they’re not invisible.

That one moment could lift their whole day—or yours.

How to Do It:

1. Look for an Opportunity: A cashier, a fellow walker, someone waiting alone.
2. Ask with a Smile: “Hey, how’s your day going?” or “Has today been treating you well?”
3. Be Present in the Moment: Even a 10-second exchange can be meaningful.
4. Respond Warmly, Then Carry On: A kind word and smile go further than you think.

Relevant Quotes:

On unexpected kindness:

“Too often we underestimate the power of a touch, a smile, a kind word… all of which have the potential to turn a life around.”

~Leo Buscaglia

On human connection:

“You can’t hate someone whose story you know. And most people are only one good conversation away from being seen.”

~Fred Rogers

On the magic of listening:

“Being heard is so close to being loved that for the average person, they are almost indistinguishable.”

~David Augsburger

Takeaway:

Asking a stranger how they’re doing might feel small—but it’s a radical act of humanity in a disconnected world. And the courage to care, out loud, is how you make life—and the world—a little better.