---
name: awkward-message-helper
description: "Draft the hard personal message you keep putting off — chasing money a friend owes, backing out of plans, checking in after a fight, following up on an unanswered text. Use when asked to help send an awkward text, how to say something uncomfortable to a friend, word a difficult personal message, or bring up something touchy. Produces a couple of calibrated options, the one line to open with, and the send/wait/call judgement call — warm, honest, and not a doormat."
---

# Awkward Message Helper

The message sits in your head for days because any version feels wrong — too confrontational, too soft, too much. This gives you a few options that are honest without being harsh, name the thing directly (avoidance makes it worse), and respect the relationship *and* your own position. It also tells you when a text is the wrong medium and you should call.

## What This Skill Produces

- **2–3 options** across a warm→direct range, so you pick the one that fits
- **The opener** — the first line that sets the right tone (most of the awkwardness is in how you start)
- **The medium call** — text vs. call vs. in-person, and why
- **The boundary line** — if you're being taken advantage of, the version that holds your ground kindly

## Required Inputs

Ask for these if not provided:
- **The situation** — what happened and what you need to say/ask
- **The relationship** — how close, and the history that matters here
- **Your goal** — get the money, exit the plan, repair the rift, get a reply — the message bends to the goal
- **Your read** — is this a one-off or a pattern? (Patterns need firmer.)

## Framework: Honest, Not Harsh

1. **Name it directly.** Hinting drags it out; a clear, kind sentence ends the dread for both of you.
2. **Lead with the relationship, not the grievance** (unless it's a pattern) — "I value us, and…" lowers defences.
3. **One ask, stated plainly.** Bundling grievances muddies it; pick the thing that matters now.
4. **Own your part where it's real** — a small honest acknowledgement disarms; a fake one backfires.
5. **Know when to stop typing.** Anything with real emotional charge is often a call, not a paragraph.

## Output Format

### [Situation] · to [relationship] · goal: [x]
**Best medium:** text / call / in person — why.

**Option A (warm):** …
**Option B (direct):** …
**Option C (holds the boundary, if needed):** …

**Open with:** "…"
**Don't:** [the move that would make it worse here]

## Quality Checks
- [ ] The message names the actual thing, no vague hinting
- [ ] Options span warm→direct so the user can match their read
- [ ] The medium recommendation fits the emotional charge (high charge → call)
- [ ] If it's a pattern, a boundary-holding option is included
- [ ] Honest without being cruel; self-respecting without being cold

## Anti-Patterns
- **Burying the point** in so much cushioning the person misses the ask.
- **Kitchen-sinking** every past grievance into one message.
- **Doormat mode** — softening to the point of giving up a fair ask.
- **Recommending a text** for something that clearly needs a voice.
- **A fake apology** to smooth it over — reads as manipulation.

## Example Trigger Phrases
- "How do I ask a friend to pay me back the $200 without it being weird?"
- "I need to back out of a trip I already said yes to — help me word it."
- "We had a fight last week; help me check in first."
- "He read my message and didn't reply — what do I send?"
- "My roommate keeps skipping their chores — how do I bring it up?"