AI prompts for the messages you don't know how to start
Published

Short answerGive the AI the real relationship and one specific memory or detail, not just the occasion. A message built from one true detail always reads better than a polished message built from none.
Some messages are hard to write not because the words are complicated, but because the stakes feel high and a cliché is always sitting right there, ready to use instead of something real. "They're in a better place." "Sorry if you felt that way." These are the lines people reach for when they don't know what else to say, and they usually land worse than silence.
AI is well suited to this kind of writing, as long as you give it the one thing it can't invent: a real detail about the person or the situation. The prompts below are built around that detail, not around finding fancier words.
1. A condolence message that isn't a cliché
The hardest part of a condolence message is usually the opening line, and most of the common ones ("they're in a better place", "I know how you feel") do more harm than good. The condolence prompt asks for a specific memory instead:
Help me write a message of condolence to [NAME], whose [RELATIONSHIP] [NAME OF PERSON] has passed away. My relationship with them: [RELATIONSHIP] A memory or quality I want to mention: [MEMORY] Cultural or religious considerations: [NOTES] Write a short, sincere message of three to five sentences. Avoid clichés such as "they are in a better place" and offer one specific way I can help.
Offer something specific, like bringing a meal on a named day or picking up their kids from school that week, rather than "let me know if you need anything". A concrete offer gives a grieving person one less decision to make, while a vague one puts the work of asking back on them.
Mention a specific memory; it means more than general words of comfort.
2. Writing a eulogy without a blank page
A eulogy carries real pressure, both to get it right and to get through delivering it. The eulogy prompt is built to pull the material out of you gradually, rather than expecting a finished set of memories in one go:
Help me write a eulogy for [NAME], my [RELATIONSHIP]. Ask me for stories one at a time first if I have not given enough. What I have so far: - What they were like: [PERSONALITY] - Stories and sayings: [STORIES] - What they taught me: [LESSONS] - Tone: [GENTLE / UPLIFTING / WITH HUMOUR] Write a draft of about [MINUTES] minutes when spoken, with a warm opening, two stories, and a closing line.
Read the draft aloud and time it, rather than judging it on the page. Most eulogies land best between three and five minutes, and a line that reads well silently can sound completely different, often too long, once you say it out loud in the room you'll actually be standing in.
3. A get-well message that doesn't force cheerfulness
Get-well messages often swing too far toward forced positivity, which can feel hollow to someone who's actually unwell. The get-well prompt asks for three different versions so you can match the tone to the relationship:
Write three get-well messages for [NAME], who is recovering from [ILLNESS OR SURGERY]. My relationship: [RELATIONSHIP] Tone: [WARM / LIGHT / RESPECTFUL] One thing I can offer: [OFFER] Make one a short text, one a card message and one a longer note. Avoid forced positivity and do not give medical advice.
Again, offer something concrete, such as a meal, a call at a set time, or picking something up for them. "Let me know if you need anything" is the line everyone writes and almost no one actually uses to ask for help.
4. An apology that doesn't undo itself
Most failed apologies have the same flaw: they slip in an excuse, or they ask the other person to do the forgiving in the same breath as the apology, which undercuts it. The apology prompt is built to avoid both:
Help me write an apology to [PERSON]. What I did: [WHAT HAPPENED] How it affected them: [IMPACT] Our relationship: [RELATIONSHIP] What I will do differently: [ACTION] No excuses, no "sorry if you felt that way". Name what I did, acknowledge the impact, take responsibility, say how I will fix it. Give a text message version and a longer letter version.
Notice what the prompt leaves out on purpose: there's no line asking for forgiveness, and no "but" to soften what you did. A real apology does not ask the other person to forgive you in the same message; it just names the thing, owns it, and states what changes.
5. A note to a neighbour that doesn't start a feud
A note about noise, parking or a shared fence can easily read as hostile even when you didn't mean it that way, and a badly worded first message can turn a small issue into a long-running feud. The neighbour note prompt gives you a friendlier opener plus a backup for later:
Write a polite note to a neighbour about [PROBLEM, e.g. loud music late at night]. When it happens: [TIMES] How it affects me: [IMPACT] What I would like: [REQUEST] Give me a handwritten-note version, a text message version and an escalation letter to send later if nothing changes. Keep the first two friendly, assume good intent and stay factual.
Start with something that assumes good intent, such as a compliment or a shared interest, rather than leading with the complaint. Most people respond far better to a neighbour who seems to like them than to one who opens with a list of grievances, even a fair one.
Common problems
The message still sounds generic. Add a more specific detail, a particular memory, a shared joke, an exact time something happened. Generic input produces a generic message, however good the prompt.
It's too long for a text message. Ask for the same message cut to under 300 characters without losing the one specific detail, rather than trimming it yourself and risking cutting the part that matters most.
You're not sure about the cultural or religious tone. Say so directly in the prompt and ask the AI to flag anything that might read as insensitive for that context, then check with someone close to the situation before you send it.
Where to go from here
Writing a goodbye message for a colleague instead of a loss? See AI prompts for resignation and farewell messages. For the broader skill of saying a hard thing clearly and kindly, AI prompts for setting boundaries covers related ground. These prompts live in the chat and writing prompts collection, and the prompt builder can adapt any of them to your own situation.
Quick checklist
- Give one real, specific detail; it does more work than any clever phrasing.
- Offer something concrete instead of "let me know if you need anything".
- Read a eulogy or speech aloud and time it before the day itself.
- Keep an apology free of excuses and don't ask for forgiveness in the same line.
- Open a difficult note by assuming good intent, not with the complaint first.
- Check tone with someone close to the situation before you send anything sensitive.
Prompts to try
Write a condolence messageChatGPT · Gemini · Claude
Write a eulogy from your memoriesChatGPT · Gemini · Claude
Write a get-well message that is not a clichéChatGPT · Gemini · Claude
Write a sincere apology messageChatGPT · Gemini · Claude
Write a polite note to a noisy neighbourChatGPT · Gemini · Claude



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