When the Holidays Hurt: What It Feels Like to Be Incarcerated During the Holiday Season

The holidays are supposed to feel warm—full of lights, family, celebration, and the kind of joy that momentarily silences the rest of the world. But when you’re incarcerated, that season feels different. It hits you in a place you didn’t even know could ache. And as someone who spent holidays in the Rappahanock Regional Jail, I can tell you firsthand: the pain is real, the loneliness is sharp, and the memories stay with you long after you go home.

Life Moves On—Even When You Can’t

One of the hardest lessons I had to swallow was this: the outside world doesn’t slow down just because you went away.

They can’t. Life keeps moving. Families still have responsibilities. Loved ones still have bills, jobs, kids, and crises of their own. And when I was suddenly, unexpectedly gone, the people I cared about were the ones left to pick up the pieces.

Inside, time freezes… but on the outside, life keeps accelerating.

Accepting that truth was painful, but necessary for survival.

Inside, Your World Shrinks

When you’re incarcerated, your world collapses into a small pod or unit with a handful of strangers who quickly become your entire universe. The same faces. The same routines. The same walls. Time moves slow—painfully slow—and the people around you become your community, your family, your tension, your comfort… sometimes all at once.

And in the holiday season, those relationships are all you have.

We Made the Best of a Bad Situation

Even in the bleakness, we found flickers of humanity—because we had to. We needed something to hold onto.

We created our own traditions inside Rappahannock Regional Jail:

• We made Christmas cards by hand, coloring simple pieces of paper with dull inmate pencils. We wrote messages that carried more emotion than ink. Each card was a tiny attempt to remind each other that we mattered.

• We came together to create a “special meal,” something we called a flip. Everybody who could put in a commissary item did. And for once, we weren’t eating alone—we were eating together.

It was our way of making the season just a little less painful.

A flip might sound strange to anyone who’s never been incarcerated, but inside? It’s a feast.

Sausage meat was a luxury—one of the most expensive commissary items. If someone had it to give, that was love. Ramen noodles were always available because they were cheap. Crush in some cheese puffs, toss in diced pickles, mix it all together, and microwave it until it firmed up.

Then you flip it over like a casserole or a giant sandwich and divide it among the ones who contributed… plus a few who had nothing to offer.

Because even inside, we understood the power of compassion.

We topped it off with “honey mustard”—a mix of mayo, mustard, and a substitute sweetener packet.

And let me tell you, in a place where you feel less than human… a meal made with your own hands and shared with others can make you feel seen.

Humanity Feels Fragile in Jail

The way correctional officers treat you determines the temperature of the whole day. There were a few long-time officers who understood respect, but the new ones? They often walked in ready to prove a point.

They believed being stricter meant fewer problems, but in reality, the officers who gave respect were the ones who got it back.

The inconsistency was the hardest part—rules changed depending on who was on shift.

One day you could pass a Christmas card to another inmate.

The next day, that same card was considered contraband.

And nothing crushes your spirit like watching a heartfelt, hand-colored card—something you poured your emotions into—get confiscated and thrown in the trash. Especially during the holidays. Especially when you’re already fighting the feeling that your life no longer belongs to you.

The Bittersweet Highs and Lows

The holidays also brought a strange emotional rollercoaster.

There’s the bittersweet moment when someone gets released.

You cheer for them. You hug them. You say, “Don’t come back.”

But as they walk out the door, your stomach drops—because you’re still there.

Every day, someone goes to court hoping for bond or time served. Most return with a heavy walk, eyes lowered, shaking their head:

“No… not this time.”

And that disappointment cuts deeper in December.

It’s like watching hope walk into a courtroom and crawl back out.

And through all of this, you’re trying not to break in front of others who are trying not to break too.

Looking Back, I’m Grateful I Made It Out

When I think back on those years, especially the holidays spent inside, I feel a mixture of sadness and gratitude. Sadness for the woman I was—hurting, struggling, trying to hold myself together. But gratitude for the resilience I didn’t even know God was building in me.

Because today, that cycle is over for me.

Today, I get to tell the story instead of reliving it.

Today, I get to use what hurt me to help someone else heal.

And if you or someone you love is in that place right now, hear me clearly:

You are not forgotten.

You are not alone.

And your story is still being written.

A Prayer for Incarcerated Individuals and Their Families

Father God,

I lift up every person incarcerated and every family waiting, worrying, and loving from a distance. Be their peace in the uncertainty, their strength in the loneliness, and their hope in the heaviness of this season.

Remind those behind bars that they are not forgotten, not forsaken, and not defined by their worst mistakes. Surround their families with comfort and reassurance. Bridge the distance between them with Your presence, Your love, and Your protection.

Bring healing where there is pain, unity where there is separation, and hope where there is discouragement.

May Your light reach every cell, every home, and every heart connected to this journey.

In Jesus’ Name, Amen.