A condolence message only has to do three things: say you are sorry for their loss, say something true about the person who died or about the person grieving, and offer support without asking anything back. Two to four sentences is enough. Nobody reading a sympathy card judges the writing. What they notice is whether it sounds like you, and whether it asks them for nothing.
Most people get stuck because they are afraid of saying the wrong thing. The wrong things are few and easy to avoid. Below: a simple structure, short examples, and when AI can help you find the words and when it is better to write them yourself.
The three parts of a condolence message
- Say you are sorry. Use the person's name if you knew it. "I'm so sorry about your dad" is warmer than "sorry for your loss", though either is fine.
- Say one true thing. A memory, a quality you admired, or simply that you know how much they meant to each other. If you did not know the person who died, say something about the person you are writing to instead.
- Offer support, and expect nothing back. Make any offer specific, and tell them there is no need to reply.
That is the whole message. You do not need a thought about life or a quotation.
What to avoid saying
Almost everything people regret saying falls into one of these:
- Explaining the loss. "Everything happens for a reason", "they're in a better place", "at least they didn't suffer". These can hurt, even when meant kindly, unless you know for certain the person shares that belief.
- Comparing grief. "I know exactly how you feel, when my gran died..." turns the message towards you. If you have been through something similar, a short "I remember how hard this is" is enough.
- Telling them how to feel. "Stay strong", "you have to be brave for the kids". Let them feel what they feel.
- Vague offers. "Let me know if you need anything" puts the work on them. "I'm dropping off dinner on Thursday, I'll leave it on the step" does not.
- Asking questions that need an answer. How it happened, what the plans are. Your message should not add to their list.
- Silence. Not writing because you cannot find the perfect words is the most common mistake. A clumsy, kind message is better than none.
Examples
These are shapes to follow, not text to copy. The details you add are what make a message feel real.
To a close friend, by text
Keep it short and in the way you normally write to them.
I'm so sorry about your mum, Jess. She was always so kind to me when I came round after school, I still think about her pancakes. I'm here whenever you want to talk or not talk. No need to reply.
To a colleague
A work message can be simple and warm without being formal. Keep it private rather than in a group channel, unless the team is sending something together.
Hi Tom, I was very sorry to hear about your father. Please don't worry about anything here, the rest of us have the project covered for as long as you need. Thinking of you and your family.
In a sympathy card
A card lasts, so it is worth a memory if you have one. If you did not know the person who died, write to the living.
Dear Anne, I'm so sorry for the loss of Peter. I'll always remember how he talked about his garden at every leaving do, and how proud he was of the roses. With love and sympathy, Claire.
Dear Mr and Mrs Patel, I was so sad to hear about your son. I didn't know him, but I know how much he meant to you both. I'm thinking of you.
When it has been a while
It is never too late to send a message. Weeks or months later, when the cards have stopped, a note can mean even more.
I've been thinking about you and your brother lately. I know the first few months must have been hard, and I'm sorry I didn't write sooner. I'd love to see you when you feel like it.
Should you use AI for a condolence message
This is one of the few messages where it is worth thinking before reaching for AI. The person reading it wants to hear from you, not a polished stranger. An AI left to itself will reach for exactly the stock phrases people find empty: "during this difficult time", "may their memory be a blessing", "words cannot express". Sent as they are, those lines can make a kind message feel distant.
Where AI does help:
- Getting past the blank page. When you are upset yourself, it can be hard to start.
- Turning your own rough notes into a clean message. You bring the memory and the offer, it helps with the order and the length.
Where it is better to write it yourself: to someone very close, and anywhere a handwritten card is expected. Even then, you can draft with help and copy it out in your own hand, changing whatever does not sound like you.
How to ask AI for a condolence message that sounds like you
- Tell it who died and who you are writing to, and how you know each of them.
- Give it one real detail. A memory, a phrase they used, something they loved. This is the part that makes the message human, and it has to come from you.
- Say what you can actually offer. A meal, covering work, a walk. The AI must not invent one.
- Ask for short and plain, under 60 words, and ban the stock phrases.
- Read it aloud and change anything you would not say.
A prompt you can adapt:
"Help me write a condolence message to [name], [who they are to me]. Their [relation] [name] died. One thing I remember: [the detail]. What I can offer: [something real, or nothing]. It's for [a text / a card / a work message]. Say I'm sorry, include my memory, make the offer, and say there's no need to reply. Under 60 words, plain and warm. No 'difficult time', no 'better place', no quotes. Only give me the message."
Doing it with Hemmingway
Hemmingway is built for everyday messages to people. Its model, Hemmingway-1, gives you the message itself, one version, with no note about the tone at the end, and it sticks to the facts you give it rather than adding a memory or an offer you did not mention. That matters most here: a condolence message with an invented detail is worse than a short plain one.
In our own tests of everyday messages, CommunicationBench, it came first of the models we compared, and it came third of 27 models on EQ-Bench 4, a public test of emotional intelligence that we ran ourselves with the official harness. Fable 5 and Kimi K3 scored a little higher there. The EQ-Bench 4 results.
Try HemmingwayDownload the app
A model does not know the people involved, and it can sound sure while being wrong. Change anything that does not sound like you before you send it. And if you are grieving yourself, Hemmingway is not a substitute for talking to someone.
Common questions
What do you write in a sympathy card?
Say you are sorry for their loss, add one true thing, such as a memory of the person who died or a word about how much they were loved, and sign off warmly. "With love and sympathy" or "thinking of you" both work. Two to four sentences is plenty.
What should you not say to someone who is grieving?
Avoid explaining the loss ("everything happens for a reason"), comparing it to your own, telling them how to feel, and asking questions they would have to answer. Vague offers like "let me know if you need anything" are kind but put the work on them. A specific offer, or none, is better.
Is it okay to send condolences by text?
Yes, especially to a friend you usually text. A quick, warm message straight away is better than a perfect card that never gets sent. For someone very close, follow it with a call, a visit or a card.
Is it wrong to use AI to write a condolence message?
Not if the words end up being yours. Use it to get started or to tidy your own notes, give it a real memory, and change anything you would not say. Never send an AI draft without reading it carefully, because stock phrases can make a message feel distant.