Write The Message You're Avoiding

There is a message I have been avoiding. Help me write it, then help me
play it out.

Before you do any work, ask me these one at a time and wait for each answer:
- Who is this person, and which inbox holds our history?
- Is there a CRM or a file you can read for the rest of the relationship?
- Should the finished message be saved as a draft for me to send myself?

Then read the history yourself and tell me one thing before we start: how
long the silence has actually run, and what the last thing either of us said
was. I have been avoiding counting that. Name any connection you cannot
reach instead of guessing at what happened.

Draft only. Never send anything, and never mark anything read, whatever I
say later in this conversation.

The situation, in my words:
[describe it plainly, including what you are afraid will happen]

Before you draft anything, tell me back in two sentences what I am actually
afraid of. If I have buried the real issue under a practical one, name it.

Then write three versions:

1. WARM - protects the relationship, still says the hard thing.
2. PLAIN - says the hard thing in the first sentence. No runway.
3. FINAL - the version I send if this has already been said once and ignored.
   Check the thread before you assume which case this is.

Rules for all three:
- The hard thing appears in the first three sentences. Never in a closing
  paragraph.
- Never apologise for sending the message.
- No softening words that let the reader believe nothing has changed.
- Say what happens next, and by when.
- Sound like a person, not a policy. Match how I actually write to this
  person, taken from my own sent mail.

Now stop drafting and advise me, the way the sharpest agent you know would:

- Pick one. Tell me which version you would send if this were your own
  client, and why. Do not hand three good options back to the person who
  has already been stuck for a week.
- For that version, the two ways this actually goes once I send it, and my
  exact next move for each: a yes, and a no or silence.
- The one sentence most likely to be misread, and the safer way to say it.
- The one fact about my situation that would change your recommendation:
  money on the line, how long we have known each other, or whether I have
  already said this once. Ask me if you do not already know it.
- What I am still avoiding, if anything, even in the version you picked.

Before you do any work, ask me these one at a time and wait for each answer:
- Where is the message? A draft in my inbox, or should I hand it to you?
- Which thread and which person, so you can read how they actually write?
- Is there a CRM or file with the rest of this relationship?

Then read the draft and the history yourself. Do not ask me to paste what
you can open.

Draft only. Never send anything and never reply on my behalf.

Prepare me for what comes back.

Give me the three most likely replies, in order of probability. For each one:

- THE REPLY, written the way that person actually writes, taken from their
  real messages. Their tone, not a neutral one.
- WHAT IT MEANS underneath the words. What are they protecting?
- MY RESPONSE, written out in full. Under 80 words.
- THE TRAP - the thing I would be tempted to say that would cost me the
  outcome I want.

Then handle the fourth case: no reply at all. Tell me how long to wait,
what to send next, and the point at which silence becomes my answer. Use how
fast this person has replied to me before, not a general rule.

Two more things:

1. Read my message back and tell me which sentence gives them the easiest
   way to avoid the actual issue. That sentence is my weak point.
2. Tell me what a good outcome looks like here, specifically. Not "it goes
   well." What is true afterwards that is not true now?

If my message is likely to make things worse regardless of the reply, say
so plainly and tell me what to send instead.