Write a Compassionate Sympathy Card with ChatGPT


I find writing sympathy cards to be pretty nerve-wracking. It feels too easy to write the wrong thing, and that moment when the pen touches paper feels kind of perilous.

Woman with writer's block.

Photo by Ivan Samkov

I doubt I'm alone in this. And I suspect that plenty of others, like me, have responded by putting off these messages to later. The problem with later is that it can become never, and the worst sympathy card is the one you never send. 

Our mission at Here For You is to make it easier to show up when it matters most. Anything that increases the odds of that card dropping in the mail is a win. 

I have found that with the right prompting, ChatGPT does a very good job of organizing the message and keeping the tone appropriate. It is more than up to the task of being your sympathy card copilot. 

Try our Sympathy Card Copilot chatbot

We have created a free sympathy message chatbot that will guide you through a series of questions, and then produce a draft message for your friend or loved one.


Sympathy Card Copilot

Is it wrong to use AI for something so personal?

No, it's not. The irony of sympathy cards is that they are a constrained form of writing that make it harder to fit in genuine feelings.

The foundation of most sympathy cards is a slew of safe refrains:

  • "I'm so sorry for your loss..."
  • "I wanted to offer my condolences..."
  • "Holding you close in thoughts and prayers."
  • "May you find solace in the love of those around you."

There's nothing wrong with this convention – of course we want to avoid offending the people we care about. But these generic formalities take effort to come up with and organize.

The good news is that ChatGPT is really good at generic writing. That is why my recommendation is to let the bots spare you the time on the structure and tone of your message. They'll also help you keep your foot out of your mouth, so that you can focus on what you actually want to say.

Build your own sympathy card chatbot with this AI prompt

For those without a ChatGPT Plus subscription, the prompt below draws from on our in-depth card-writing tips. It can be used with any generative AI service, including regular ChatGPT, Google's Bard, and Anthropic's Claude. Please edit and adapt the prompt according to your situation, and add in details where indicated.

ChatGPT-assisted message
Photo by cottonbro studio


/---- Prompt: Personalized Sympathy Message ----/

INSTRUCTIONS: Please draft a 300-500 character sympathy card message based on the inputs below. Take into account the following writing guidelines:

1. BE SINCERE AND SHARE HOW I AM FEELING WITHOUT OVERSHADOWING THE BEREAVED'S GRIEF. Example of sharing pain in an appropriate way: "Desi was such a positive light in my life. His humor brought me so much joy over the years. I will miss him terribly." Example of overshadowing the bereaved's pain: "This is the saddest thing that's ever happened to me — I don't know how I will get through this.”

2. INCLUDE A REFERENCE TO THE FOLLOWING MEMORY OR IMPRESSION OF THE DECEASED. It can be especially beneficial to include a memory the receiver has never heard before.

3. SHARE HOW I WILL CONTINUE TO REMEMBER AND HONOR THE DECEASED. People want to be sure that a loved one will not be forgotten, or that they will be carried forward even if they are no longer physically here. Sharing things like, "We will toast Susan on her birthday every year," or "I know Jacob felt most at peace at the beach. Whenever I visit the coast, I will take a moment to remember him."

4. AVOID USING PLATITUDES. Here are some common grief platitudes that are best to be avoided: "Everything happens for a reason," "I can't imagine what you're going through," "They're in a better place," "You wouldn't be given you more than you can handle," "They are watching over you," "Stay strong," "God needed an angel," "It could be worse, at least.."

5. INCLUDE A SPECIFIC OFFER OF HELP. If you can make a commitment, do it. Avoid (at all costs) 'call me if you need me' - this puts the burden of action on the person you are trying to help. Instead say, 'I will bring you dinner next week', or 'I can watch the kids for you on Friday morning' and follow up on your offer. If you are in a position to offer ongoing support, tell the person. For example, "I am home every Sunday afternoon. I would love to host your kids any week that you need a break."

Depending on how close the sender is to the recipient and/or deceased, they may or may not have specific memories to share, and plan for honoring the deceased, or an offer of help to provide. For any of the input fields below that are left blank, please omit their mention in the message.


- Card recipient: {add name + your relation here}

- The deceased: {add name + relation to recipient here}

- Memory or impression of the deceased: {add input here}

- How I’ll remember and honor the deceased: {add input here, if any}

- Offer of help: {add input here}

- Sender’s name: {your name}

/---- End Prompt ----/

Sample AI-drafted sympathy card

I copied and pasted the prompt above word-for-word into ChatGPT-4 with the following details: 1) Recipient: "My coworker Olivia." 2) The deceased: "Her mother, Julie." 3) Memory: “Julie gave me the warmest welcome when I visited your home last year. We spoke for about 10 minutes." 4) Offer of help: "I'd like to get you a meal next week."

    Here is the result:

    Dear Olivia,

    I was deeply saddened to hear about the loss of your mother, Julie. I remember when I visited your home last year, she gave me such a warm welcome. Even though we only spoke for about 10 minutes, her kindness and warmth left a lasting impression on me.

    I understand that words can't make the pain go away, but please know that I'm here for you. To help in any small way I can, I'd like to get you a meal next week. Please let me know a day that works best for you.

    Sending you strength and comfort during this difficult time.


    Not bad! I wouldn't send this without some considerable editing, but this is a great start.

    Which generative AI service to use?

    At the time of this writing, I recommend ChatGPT, and specifically GPT-4, over other popular generative AI services. I ran the same prompt through Anthopric’s Claude and Google’s Bard, with weaker results. Both services far exceeded the character limit I requested. They also included several platitudes and/or awkward statements. But these services are always improving. I'm also sure that a follow-up prompt or two would have given a great result. So don't let this dissuade you from using these other services – they're still quite good.


    There is no longer a need to get stuck — or worse, delay — when the next occasion to write a sympathy card arises.  

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