Recipe №037 · writing

Write a tough message to a friend, kindly.

Draft a difficult personal message that says what you mean without saying it badly.

by mike·Jan 14, 2026·5 min read

① The goal

Send a message about something hard (cancelling plans, setting a boundary, apologizing) that sounds like you, not like a robot.

② The prompt

I need to send a message to a friend about something difficult. Here's the situation:

[describe situation]

Draft a message for me.

Rules:
- Sound like a real person, not a therapist.
- Be direct about the hard part in the first 2 sentences.
- Don't over-apologize or add filler warmth.
- Keep it under 100 words.
- End with something that leaves the door open.

③ How it goes

Try 1

"Help me write a message" gave corporate-empathy tone. Phrases like "I value our relationship."

Try 2

Added "sound like a real person." Better — but it buried the hard part in paragraph 3.

Try 3

"Direct about the hard part in the first 2 sentences" + word limit. Clean, honest, short.

④ Variations

Work context

Swap "friend" for "colleague" and add: "keep professional but not cold."

Family member

Add: "this person takes things personally. Be extra clear about what you’re NOT saying."

Follow-up

If they respond badly: "Draft a short follow-up that acknowledges their reaction without backing down."

Try the live version →

Generate your own recipe for a different goal.

Open the Recipe Generator →

The Saturday tab

One small AI experiment, in your inbox Saturday morning.

Plain English. ~4 minute read. One-click unsubscribe.

Subscribe free