Every summer, I hear from clients who are caught off guard by grief.

Not because they’ve experienced a recent loss. In many cases, the loss happened years ago. What catches them by surprise is the calendar.

A birthday approaches. Father’s Day appears on the horizon. An anniversary pops up in a social media memory. Graduation season arrives. Wedding season begins. Suddenly, emotions they thought had settled feel remarkably close to the surface again.

If you’ve experienced this, you’re not imagining it, and you’re certainly not doing grief “wrong.”

In fact, researchers have long recognized what is often called an anniversary reaction – the resurgence of grief, sadness, anxiety, or other emotions around meaningful dates connected to a loss. The experience is common enough that both the American Psychological Association and trauma researchers have studied why significant dates can reactivate memories and emotions, sometimes years after an event.

I’ve lived this reality myself. For years, summer has held Richard’s birthday and Father’s Day. Those dates have never been just another page on the calendar. They are reminders of a man I loved deeply, a life we built together, and a future that changed overnight.

This year brought another layer.

After walking through the loss of my father, I find myself experiencing these summer milestones differently once again. Grief has a way of reshaping familiar dates. What once carried one memory now carries many.

And that’s one of the most important things I’ve learned about loss: Grief doesn’t move in a straight line. It evolves because our lives continue to evolve.

Why Do Birthdays, Anniversaries, and Holidays Trigger Grief?

People often assume grief is tied primarily to the date someone died. In reality, that’s only one type of grief anniversary. Often, the harder dates are the ones connected to life itself.

• A birthday
• A wedding anniversary
• Father’s Day
• Mother’s Day
• A family vacation tradition
• The first day of school
• A holiday meal

These occasions remind us not only of who is missing, but also of the role they played in our lives. They highlight an absence that may feel less noticeable during ordinary weeks.

Researchers describe grief as an ongoing process of adapting to loss while maintaining a meaningful connection to the person who died. Modern grief theory has moved away from the idea that healthy healing requires us to “let go” entirely. Instead, evidence suggests many people continue an internal relationship with their loved one through memories, traditions, values, and rituals.

That perspective resonates deeply with me. I don’t spend my life trying to leave Richard behind. I carry him with me. I carry my father with me, too.

Not every day looks the same, but neither relationship ended simply because their lives did.

The Hardest Dates Are Often the “Would-Have-Beens”

Some grief anniversaries appear on a calendar. Others exist only in our hearts. I call these the “would-have-beens.” The birthday they would have celebrated. The retirement they should have enjoyed. The grandchild they never met. The family photo where someone is missing. The anniversary that would have marked 30 years of marriage.

These moments can be surprisingly painful because nobody else knows they’re happening. The world keeps moving. Meanwhile, you’re quietly calculating what should have been.

One of the mistakes many grieving people make is judging themselves for these reactions. They tell themselves:

“It’s been years.”

“I should be past this.”

“I shouldn’t still think about that.”

But grief isn’t measured by a stopwatch. Love leaves a permanent imprint on our lives. When a milestone highlights that imprint, emotions naturally follow.

How I Approach Difficult Dates

People often ask me how I handle Father’s Day or Richard’s birthday. The answer has changed over the years. What works one year may not feel right the next. But I’ve learned not to ignore these days. Pretending a meaningful date is unimportant rarely makes it easier.

Instead, I choose to acknowledge it intentionally.

Sometimes that means setting aside quiet time to reflect. Sometimes it means sharing stories. Sometimes it means looking through old photographs. Sometimes it means simply allowing myself to feel whatever emerges without trying to manage it or fix it.

I’ve also learned that grief doesn’t require a grand gesture.

Many people believe they need an elaborate ritual to honor someone they’ve lost. In reality, some of the most meaningful acts are remarkably simple. A favorite meal. A handwritten note. A walk in a place that mattered. A conversation with family members. A donation to a cause they cared about.

The goal isn’t to create a perfect tribute. The goal is to create space for remembrance.

What Should You Do on a Grief Anniversary?

There is no universal formula, but I often encourage people to ask themselves three questions:

• What do I need today?
• What would feel meaningful?
• What expectations can I release?

That last question is especially important.

Many people enter birthdays, anniversaries, or holidays believing they should feel a certain way: Strong, happy, grateful, at peace.

The reality is often more complicated. You might laugh and cry on the same day. You might enjoy a family gathering while also feeling the weight of someone’s absence. You might be perfectly fine one year and unexpectedly emotional the next. All of those experiences are normal.

The emotional intensity of grief anniversaries often has less to do with how much healing you’ve accomplished and more to do with where you are in your life at that moment.

What I’ve Learned About Love and Loss

If loss has taught me anything, it’s that healing and remembering are not opposites.

For a long time, our culture treated grief as something people were supposed to finish. I hear from people in the Bishop Life community often who talk about being told to “move on” or “get over it.” But that’s not what I’ve witnessed in my own life or in the lives of the countless people I’ve coached.

The healthiest grieving people I know aren’t the ones who forget, they’re the ones who learn how to carry both joy and sorrow at the same time. They make room for memory without allowing grief to define every part of their future. They continue living while remaining connected to the people who shaped them.

It reminds me of a favorite quote I read from time to time:  

“You will lose someone you can’t live without, and your heart will be badly broken, and the bad news is that you never completely get over the loss of your beloved. But this is also the good news. They live forever in your broken heart that doesn’t seal back up. And you come through. It’s like having a broken leg that never heals perfectly — that still hurts when the weather gets cold, but you learn to dance with the limp.” – Anne Lamott 

This June with Father’s Day and Richard’s birthday both glaring on my calendar, I find myself thinking less about letting go and more about gratitude. Not for the loss; I would never romanticize that. Gratitude for the relationship and that love leaves a mark substantial enough to be felt years later.

If an anniversary, birthday, holiday, or “would-have-been” is approaching for you, my encouragement is simple: Don’t measure your healing by whether the day hurts; measure it by how honestly you’re willing to meet the day.

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