When the Holidays Hurt: Navigating Christmas After a Loss

The holiday season is often portrayed as the most joyful time of year, but for many families it can also be one of the hardest especially when a loved one has passed away or when someone has recently moved into a retirement home.

Homes hold decades of rituals and memories: the dining room table where everyone gathered, the garland hung on the banister for years, the decorations we may not even want to keep yet still feel attached to. When the person at the centre of those traditions is no longer there, Christmas can feel unsteady, painful, or even empty.

As an estate specialist, I see this every year. Sorting through a home in November or December often brings up an added layer of emotion because the house itself carries the imprint of Christmases past.

One of the most helpful strategies I share is this:

If recreating the old tradition feels too painful, change the tradition even temporarily.

For some people, keeping the exact same routine is grounding. It helps them feel connected and held.

For others, trying to duplicate “the way it always was” intensifies the sense of loss.

And it’s okay to choose something different.

A Personal Example

In 2008, after my mother passed away, my family faced our first Christmas without her. It was a very difficult year, and due to various logistical reasons, we couldn’t gather the way we always had.

So we changed the plan completely.

We took our girls to the Eaton Centre. Gave each of them a little money, we wandered, we talked, we looked at the lights, we had dinner out, and we let the day unfold without pressure or expectation. It was nothing like our usual Christmas and it was exactly what we needed.

We ended up repeating that for two or three years, and it became its own gentle, healing tradition.

Small, Simple Shifts Can Help Too

You don’t need to reinvent the holiday entirely.

Even small, intentional changes can ease the ache:

    •    If your dad always sat at the head of the table, choose a different seating arrangement.

    •    If your mom’s chair feels too empty, place flowers there or at both ends as a symbol of presence and love.

    •    If a particular ritual feels too sharp this year, soften it or skip it.

    •    If certain traditions bring comfort, keep them.

The key is to make choices on purpose, not out of guilt or obligation.

There is no “right way” to do Christmas after a loss only the way that helps your family move gently through a tender season.

My Wish for You

I wish everyone a very Merry Christmas and a warm, comforting holiday season.

May you feel close to your family, supported by your traditions (old or new), and surrounded by the love that truly defines this time of year.

With all my best,

Caroline