What do I need to use Awkward Message Helper?

The situation; The relationship; Your goal; Your read.

Is Awkward Message Helper free to use?

Yes — run it free in the browser playground (no API key needed for the sponsored trial, or bring any provider key), or install it into Claude Code, Cursor, ChatGPT and more via npx pm-claude-skills. MIT-licensed and open source.

Awkward Message Helper

Q: How do I know the Awkward Message Helper output is good?

The skill verifies itself against its own 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.

🔵 Stable🕐 updated 2026-08-04 🔷 SkillSpec L3 pm-comms

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.

▶ Run it free — no key needed 📝 Grade your existing draft View SKILL.md ↗

🗣 Say this to your agent

“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?”

What to give it

▸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.)

✅ The bar it holds itself to

Every skill in this library self-verifies — these are this skill's own quality checks, straight from its definition.

✓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

⚠️ What it refuses to do

**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.

Install

npx pm-claude-skills add --agent claude   # or codex · cursor · gemini · hermes
# or one-line MCP (every skill, any client):
claude mcp add pm-skills -- npx -y pm-claude-skills-mcp

Related skills

🔌 Embed this skill

Drop this on your blog, docs, or site — it renders a "Run this skill" card:

<div data-pm-skill="awkward-message-helper"></div>
<script src="https://mohitagw15856.github.io/pm-claude-skills/embed.js" async></script>

💬 Discussion

Awkward Message Helper is one of 1078 open-source professional AI agent skills — all SkillSpec L3. Try them all in the browser · ⭐ Star on GitHub · Browse the full catalog