How to Write a Sympathy Letter People Want to Receive

When you or someone you know loses a loved one, knowing what to say is one of the hardest parts of the experience. We don’t want to say too much. We don’t want to say the wrong thing and make it worse. So often, we either revert to tried and true messages — “I’m so sorry for your loss” or “My condolences” — that we can conveniently find placed on premade cards at the grocery store, or we simply say nothing . . . because isn’t saying nothing better than saying the wrong thing? Turns out, no. Saying nothing can leave the grieving feeling isolated and alone.

Grief is a journey that every human being will embark upon at some point in their lives. It is a universal human experience denied to no-one. As Helen Keller described it, those who are grieving “belong to the largest company in all the world — the company of those who have known suffering.” While it is a common inevitability for us, this does not minimize the immensity of it.  It is not always experienced and processed the same way. Grief journeys are as unique to the individual as the individuals are themselves. 

We know through much research that there are 5 stages of grief; denial, anger, bargaining, depression, and acceptance. Yet, these stages are not linear, meaning one may experience bargaining before denial or move through anger and depression only to find themselves back in denial again. There’s also no time limit for each stage. A person will move through this process in their own way, at their own pace. This is in part why our personal anxiety can rise when it comes to writing a card to someone. We don’t know where the person is in their grief journey, and so it’s hard to know what to say. 

Given the very personal and deeply painful experience of grief, Floracracy wanted to know if “playing it safe” in sympathy cards was perhaps the better option, or if people indeed wanted something different. After completing a small survey, we found that relying on those traditional phrases can hurt more than they help. When asked what helped after a loss, only 7% of individuals reported wanting traditional sympathy cards.

What did people want instead? 43% of individuals said they wanted someone to come and sit with them. Second to this, at 30%, were individuals who requested personalized positive letters or meaningful experiences that helped them both process their feelings and remember their loved one. In some age groups, the desire for a personalized letter was the highest. What’s interesting is that these two categories, in fact, are driving toward the same emotional need. Unpublished research shared by Matthew Lieberman in the book “Social: Why Our Brains Are Wired to Connect,” found that positive words written down actually change our body temperature to mimic what we experience with human touch. So when someone is asking for a personalized positive letter, they are actually asking to meet the same need as you physically being there: they are asking to experience someone being present in their grief. 

Likewise, if you cannot meet the desire to sit with someone, the next best thing is to send a deeply personal letter: It will make them feel like you are physically present. 

This is precisely the sense of intimacy that people do not feel they get from traditional cards. 

So when it comes to sympathy letters, the job to be done here is to send an experience that evokes the feeling of human intimacy, of a hand reaching out and holding yours. Our survey, as well as research, paints a simple (though possibly not easy) way to do this. 

If you want to write a sympathy letter that actually helps, whether it’s a letter to a friend who lost a mom or to someone who lost a spouse, here’s how: 

The Gift of Positive Words Through Funny Stories

In the Floracracy Grief Survey, we asked people what content in a sympathy letter helped them in their time of grief. The answer, across almost all age groups, was the same: funny stories. 

It’s not just “any” words written down that create that sensation of touch. It’s positive words, and no words are more positive than the ones that make us laugh. This is further backed up by research completed by trauma expert George Bonanno, which found that “those who exhibited genuine smiles and laughs while grieving, displayed less grief over time and evoked positive emotions in others.” The impact of funny, positive stories can change how some experience grief. 

Here are a few ways to share a funny story about someone  in writing: 

1. Consider sharing funny childhood antics of the deceased.

2. Focus on stories that capture the deceased in a positive light (this is not a roast)

3. Share memories of when the deceased “saved the day”.

4. If you cannot think of a funny story, or didn’t know the person well enough to have one, that’s okay. Stories that also ranked highly in our survey were ones regarding the deceased’s best qualities, surprising (positive) stories that had never been heard before, and stories of great acts of kindness done by the deceased. With these stories, as with before, you want to be as specific as possible. We’ll share more on exactly how to do that in the final section of this article. 

There are of course situations where there may be no stories. An example of this would be when a baby dies before birth.  There are no memories or moments to celebrate. Everything may feel taken away. In moments like this it’s important to acknowledge this truth because it is core to the grief. You can simply say something like, “It feels so sad to have such possibilities end before they’ve even begun.” or “My heart hurts so much for you. Please let me know how I can best support you through this.”

If you simply don’t know any stories, you can refer to the person to whom you’re writing. “I remember when you donated all the money in you and your sisters piggy banks to Crafters for a Cause, and the impact it had on others. I imagine your mother played a central part in you being so generous.” What this does is invite them to fill in the blanks. “Yup, she truly was the most generous woman I ever knew.... but actually I got grounded for a year for that.” Which may make them laugh. That’s the power of a story: when delivered with thoughtfulness and positive intentions, you can be wrong. Stories aren’t statements. You’re not telling them what to think or how to grieve. The secret, the gift, is just to be there. 

How To Write A Thoughtful Sympathy Letter

To write a thoughtful sympathy letter, there are three main parts. Each plays a significant role. These steps completely take you out of the traditional sympathy card sphere, and help you to write a grief letter of love: intimate, meaningful, and impactful. 

Step 1: Context

In writing your letter, it helps to begin by giving the reader a bit of context of where you are. This lets them visualize you, creating more intimacy. It also helps you begin to move into the letter. Here are some examples: 

1. I’m sitting at my kitchen table, where we’ve had so many talks together.

2. I was in the middle of a busy workday, but I couldn’t stop thinking about you. So, I’m sitting here, writing to you.

3. I know I just saw you, but I got home and couldn’t stop thinking about how much we’re both missing mom.

These can be longer and more or less personal. They do the same thing that a classic ‘once upon a time” does. They lead you into your message or story. They also avoid the kind of statements people do not like: My deepest sympathies; My condolences, I’m thinking of you (in a way that doesn’t feel sincere). 

The one kind of statement that you can use here is, “I”m so, so sorry for your loss.” If you do this, it helps to acknowledge that the situation is painful, that you know it’s changed their life, or that their grief is probably beyond bearable right now. 

Step 2: Tell a Story 

Once you and your recipient are led into your letter with your context, it’s time to share a story. It might be a funny story, a story that shares the impact the person had on the world, a story that’s never been told before or a story that captures their best qualities. All stories have the same attributes: character, struggle, a hero, an outcome.  

In this situation, it’s helpful to include a few strong details. The color of the sky the night of the funny event. The way something smelled. The exact time something took place. It really doesn't matter what it is, details make something real and help the imagination work, which is what builds that intimacy. 

Also, remember that stories do not need to be long if the idea of writing one feels overwhelming. A phrase shared between two people so many times you know implicitly what it means is a story too. It can be a simple sentence like, “I’ll never forget the way your mom would dress up in those tall boots and her wild red hat to play along with all of our stories as kids.” That one sentence says it all. The details about the tall boots and hat are enough to take the reader right back to her mom. 

This piece can feel the most difficult, and you can get help finding a story (and writing the rest of the letter) using Floracracy’s 1:1 personalization support with their concierge team. 

Step 3: How to End a Sympathy Letter

On the internet “how to write a sympathy letter” is searched a lot. But within that category, the question that most comes up is how to end a sympathy letter. What do you say when the ending is grief? How do you make that okay? 

The answer is you don’t even try. In our survey, 57% of the participants actually don’t even think you can end a sympathy letter. People do not want to hear “my condolences” or “I’m praying for you.” 

A loss is not an end. It is a beginning. With that in mind, the best way to end a sympathy message or condolence message is to acknowledge your love for the person to whom you’re writing and, if appropriate, the person who has died. 

This again is the power of focusing on a story and making it personal.  

The ending can be as simple as why that story mattered to you. What did it mean? How did it change your life or make you laugh? Here are some examples: 

- Jane truly was the most awe-inspiring person. When she did X, she taught me personally the power of never giving up.

- I have never laughed so hard as I did that day, and I still find incredible joy when I go back to that moment.

- I always thought you were the luckiest person alive to get to have that experience with X. 

These endings are different from “my condolences” in a big way. They aren’t actually endings. They name emotional experiences about why someone was significant in a way that lasts. You aren’t trying to put a cap on a loss and tuck it in the ground. You’re letting the person live on in your memories and in stories, in joys and regrets. This kind of ending lets people grieve and feel a way forward. It’s an ending that acknowledges a new beginning. 

You call conclude your letter then with simple statements like this: 

- I love you and am here for you through this.

- I’m having food delivered tomorrow night for you.

- I will always love X, and I will always love you.

A letter that shares a positive message through stories that make us laugh and cry is a letter that changes lives. It builds an intimate experience, bringing a person away from loneliness to the experience of a loving touch. It supports the grief process and validates the loss. 

It’s also something you can give yourself. So often, in grief and in life in general, we think that these powerful messages have to come from someone else, and often it’s a person or situation that is gone. This is where those feelings of “if only…” become so strong. 

The gift of a “grief letter of love” is one that you can also write and gift to yourself. You can share the stories or messages. You can record for yourself the memories. You can tell yourself what you need to hear. There is no better moment than now to give yourself the gift of love through the healing process of writing.

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