When You Don’t Know What to Say at Christmas to the Homeless or a Loved One Who is Estranged

The joy of Christmas, for me, is real—gatherings, traditions, worship, gift-giving, the lights, the sounds, the smells… connection with loved ones.  It truly is my best time of the year.

Yet, alongside that joy, Christmas reveals a painful layer of my heart that many share.  It’s during Christmas that strained relationships feel heavier, distance feels farther, and the people we miss feel even more deeply missed.

This year, as I’ve been thinking about our blog series on “When You Don’t Know What to Say,” my thoughts keep drifting to something deeply personal…and to someone I miss every day—
our son, Lee.

The Gift Lee Gave Everyone

One of the things I miss most about Lee is how intentionally he connected with people—especially with us… his family.
He didn’t assume we knew he loved us.
He told us.
He showed us.

He made time, asked questions, offered appreciation, and spoke love out loud:

“Thanks, Mom and Dad.”
“I love you.”
“I appreciate all you do.”
“How’s your head and your heart really doing?”

Those weren’t rare moments—they were part of the way he lived.

And now, his words echo in my memory with a mixture of warmth and longing. I wish I had said more of those things to him. I wish I had asked more often how he was really doing. I wish I had expressed my gratitude more often instead of assuming he knew.

That regret has become one of my greatest teachers.

Because love unexpressed is often love unfelt. And many people—more than we realize—go through life aching to feel what others assume they already know.

People sometimes say, “I don’t need to hear it to know I’m loved.” But I don’t believe that anymore.

We all need to hear it.
We all need to feel it.

Because soul-to-soul connection doesn’t grow in silence—it grows through intentional, vulnerable, transparent love that is expressed.

And nowhere is that ache for connection stronger than in the hearts of those who feel alone, forgotten, estranged, or homeless during the holidays.

An Encounter With a Homeless Man: Seeing Beyond the Surface

Not long ago, I had an encounter that reminded me what true connection looks like.

I was going about my day when I noticed a man sitting on the sidewalk—hunched against the cold, clothing worn, face tired. And instantly that familiar inner debate started:

Should I stop?
Should I give something?
What if he misuses it?

But then a deeper question stirred in me: 

What if this moment isn’t actually about what I give… but about whether I truly see him?

I turned around, walked back, and simply said, “Hey, how’s your day going?”

He looked up, startled—like he wasn’t used to being addressed as a human being.

“Honestly? Not great. But thanks for asking.”

His name was James.

For a few minutes, we talked—not about money, but about life.
His story.
His pain.
His hope.

When I eventually offered him a meal, it wasn’t the food that mattered most… It was the connection.

Because in that brief encounter, James wasn’t invisible.
He wasn’t “a homeless man.”
He was a person.
A soul.

Someone God dearly loves.

And in those moments, I realized again—maybe this is what Jesus meant when He stopped for the blind beggar, spoke with the woman at the well, and touched the man with leprosy. 

Before He healed, He connected.

What We Often Get Wrong About Helping

We hesitate because we fear saying the wrong thing, being taken advantage of, or requiring too much of us.

But a soul-to-soul connection begins not with fixing, but with seeing.

This is what Jesus modeled.
This is what love looks like.
This is what Lee lived so naturally.
This is what we often forget to do with our own family.
And this is what the lonely and hurting miss most at Christmas.

Why Christmas Intensifies Our Need for Connection

The homeless man on the corner, the estranged daughter, the friend who doesn’t come around anymore, the adult child who rarely calls, the loved one whose absence is still unbearable… for all of them, Christmas sharpens the ache of disconnection.

In other words, we’re all longing for the kind of connection Lee gave so freely…someone to speak love and appreciation aloud to us.

How to Live-Connected in Moments When You Don’t Know What to Say

Here are simple—but deeply powerful—ways to bring healing connection this Christmas:

1. Say what you usually assume.

“I love you.”
“I’m proud of you.”
“I’m thankful for you.”
“You matter to me.”

Say it now, say it often, and say it before regret teaches you to say it too late.

2. Be curious about their story.

Ask questions that communicate value:
“How are you really doing?”
“What’s been heavy? What’s brought joy?”
“What’s something you wish someone understood about you?”

Curiosity communicates value and love.

3. Offer presence more than solutions.

With James, the meal mattered less than the conversation.
For many hurting people, solutions aren’t what they need most—presence is.

4. Pray for them, or with them.

Prayer is one of the deepest forms of connection because it brings two people together in the presence of God.

That day with James reminded me of something I often forget: 

Love is not measured by how much we fix, but by how deeply we see.

We can’t fix everyone’s problem.
We can’t meet every need.
We can’t heal every wound.

But we can change a moment.
We can change a conversation.
We can speak words that bring hope, gratitude, and affection.
We can make someone feel seen, valued, and loved—whether they live on the street or in our own home.

And sometimes, that is enough.  So this Christmas:

Look again.
Turn back.
Say the words.
Ask the questions.
Show up with tenderness.
See beyond the surface.

Because when we do, we don’t just change someone else’s day—we change ours too.

And we honor the way Jesus (Emmanuel) came to us at Christmas: with us, fully present, and full of love.