Agent skill

Awkward Message Helper

by mohitagw15856 in mohitagw15856/pm-claude-skills

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.

MITAuto-check passed

Install Awkward Message Helper

skills CLI
$ npx skills add mohitagw15856/pm-claude-skills --skill awkward-message-helper -a claude-code

Project install by default; add -g for ~/.claude/skills/.

GitHub CLI
$ gh skill install mohitagw15856/pm-claude-skills awkward-message-helper --agent claude-code

Project scope by default; add --scope user for a personal install. Needs GitHub CLI 2.90.0 or later (public preview).

Manual copy
$ git clone --depth 1 https://github.com/mohitagw15856/pm-claude-skills.git skills-src && mkdir -p .claude/skills && cp -r skills-src/skills/awkward-message-helper .claude/skills/awkward-message-helper && rm -rf skills-src

Use ~/.claude/skills/ instead of .claude/skills for a personal install. The folder must contain SKILL.md.

Claude Code skills documentation · loads skills from .claude/skills/

Facts

Skill name
awkward-message-helper
GitHub stars
1.4k
Token cost
~887 tokens
SKILL.md length
485 words
Files
1
Skills in repo
1,348
Repo updated
First seen
Licence
MIT

At a glance

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.

  • Works in 5 steps: Name it directly. Hinting drags it out;… → Lead with the relationship, not the… → One ask, stated plainly. Bundling… → …
  • Asked to help send an awkward text
  • SKILL.md covers What This Skill Produces, Required Inputs, Framework: Honest, Not Harsh and Output Format, plus 3 more sections
  • Instructions only: no scripts, shell commands, URLs or credentials in SKILL.md

What it does

Awkward Message Helper is an agent skill from mohitagw15856/pm-claude-skills. 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.

Its SKILL.md is about 890 tokens, which your agent loads only when the skill is triggered. It is a single SKILL.md file with no bundled scripts.

The repository describes itself as: 1255 professional Agent Skills for Claude, ChatGPT, Gemini, Cursor & Codex — PRDs, postmortems, leases, medical bills, layoffs, go-bags, new countries. Plain markdown, MIT, in… The licence is MIT.

When your agent uses it

  • Asked to help send an awkward text
  • How to say something uncomfortable to a friend
  • Word a difficult personal message
  • Bring up something touchy

Example prompts

  • “/awkward-message-helper”

Workflow steps

5 steps, taken from the first numbered list in SKILL.md.

  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.

What it can do on your machine

Read from SKILL.md and the folder at commit 1cbf1f0. It shows what the files ask for, not the result of running them.

  • Tool permissions

    Pre-approves nothing: there is no allowed-tools line, so your agent's usual permission prompts apply.

    From allowed-tools in the SKILL.md frontmatter.

  • Runs code

    No scripts in the folder and no shell commands in SKILL.md.

    From the folder's file list and the shell code blocks in SKILL.md.

  • Network

    No URLs in SKILL.md.

    From URLs in SKILL.md, links to its own repository left out.

  • Credentials

    Names no API keys, tokens, secrets or passwords.

    From names ending in _API_KEY, _TOKEN, _SECRET, _KEY or _PASSWORD in SKILL.md.

Context cost

Awkward Message Helper loads about 887 tokens when it runs. Until then it costs about 123 tokens; SKILL.md has 485 words of instructions outside code blocks.

Always · name and description, kept in context so the agent knows when to use it
~123
When it runs · the whole SKILL.md, loaded when a task matches
~887

Estimates: characters ÷ 4, the usual rule of thumb; real counts depend on the model's tokenizer. Scripts and assets cost tokens only if the agent reads them.

Safety

Auto-check passed

The automated check found no risky patterns in SKILL.md.

Automated static check — not a guarantee. Review scripts before installing. It scans the text of SKILL.md for risky patterns (piping downloads into a shell, reading credential files, hidden Unicode, destructive commands); files beside SKILL.md are not scanned.

SKILL.md

The full file from mohitagw15856/pm-claude-skills at commit 1cbf1f0, republished under its MIT licence (© mohitagw15856). 485 words, ~887 tokens.

Download SKILL.mdSave it as .claude/skills/awkward-message-helper/SKILL.md (or your agent's skills folder).
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

Show full SKILL.md (206 more words)Show less
[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?"

© mohitagw15856, MIT. Rendered from Markdown: HTML in the file is shown as text, images as links, and headings moved down two levels. Raw file

Files

Just SKILL.md in skills/awkward-message-helper of mohitagw15856/pm-claude-skills.

Open the folder on GitHubat commit 1cbf1f0

Compare with similar skills

Awkward Message Helper next to the 5 skills that share the most tags, products or categories with it. Stars are the repository's; “used in” counts other GitHub owners with a copy.

Awkward Message Helper compared with similar skills
SkillStarsUsed inTokensAuto-checkLicenceRepo updated
Awkward Message Helper this skillmohitagw15856/pm-claude-skills1.4k—~887Automated safety check: PassMIT
Messages Opsaffaan-m/ECC276k1 repos~724Automated safety check: PassMIT
Channel Message Flowsopenclaw/openclaw392k—~306Automated safety check: PassMIT
Commit Message Storytellergithub/awesome-copilot40k1 repos~1.3kAutomated safety check: PassMIT
Personalize MessageOthmane-Khadri/YALC-the-GTM-operating-system318—~1.3kAutomated safety check: NotesMIT
Agent Messagingdavila7/claude-code-templates33k—~807Automated safety check: PassMIT

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Questions about Awkward Message Helper

What does Awkward Message Helper do?

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. Awkward Message Helper is an agent skill from mohitagw15856/pm-claude-skills. 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.

When should I use Awkward Message Helper?

Awkward Message Helper fits situations like: asked to help send an awkward text; how to say something uncomfortable to a friend; word a difficult personal message; bring up something touchy.

How do I install Awkward Message Helper in Claude Code?

Run `npx skills add mohitagw15856/pm-claude-skills --skill awkward-message-helper -a claude-code`. Or copy the skill folder (skills/awkward-message-helper in mohitagw15856/pm-claude-skills) into .claude/skills/awkward-message-helper in your project. Claude Code loads it when a task matches its description.

How do I install Awkward Message Helper in Codex?

Run `npx skills add mohitagw15856/pm-claude-skills --skill awkward-message-helper -a codex`. Or copy the skill folder (skills/awkward-message-helper in mohitagw15856/pm-claude-skills) into .agents/skills/awkward-message-helper in your project. Codex loads it when a task matches its description.

Can I use Awkward Message Helper in Cursor, Gemini CLI or GitHub Copilot?

Cursor, Gemini CLI, GitHub Copilot and OpenCode also load SKILL.md folders. With the skills CLI, run `npx skills add mohitagw15856/pm-claude-skills --skill awkward-message-helper -a cursor` (or -a gemini-cli, github-copilot or opencode for the others). To copy it by hand, put the folder in .cursor/skills/awkward-message-helper, .gemini/skills/awkward-message-helper, .github/skills/awkward-message-helper and .opencode/skills/awkward-message-helper in your project.

What does Awkward Message Helper need to run?

SKILL.md names no scripts, command-line tools or credentials: Awkward Message Helper is instructions for the agent only.

Does Awkward Message Helper access the network?

SKILL.md contains no URLs. Any network use would come from the scripts or tools the agent runs. This is read from the text; nothing was executed.

Is Awkward Message Helper safe to install?

Our automated static check of SKILL.md found no risky patterns, such as piping downloads into a shell, reading credential files or hidden Unicode. It is not a guarantee. Review the folder before installing.

What licence does Awkward Message Helper use?

Awkward Message Helper is published under the MIT licence (the repository's licence). It allows redistribution, so the full SKILL.md is shown on this page.

How many tokens does Awkward Message Helper use?

About 887 tokens (SKILL.md is roughly 3.5k characters). Agents keep only the skill's name and description in context until a task matches; then they load SKILL.md in full.

What are the alternatives to Awkward Message Helper?

Skills that share tags, products or a category with Awkward Message Helper: Messages Ops (affaan-m/ECC, 276k stars), Channel Message Flows (openclaw/openclaw, 392k stars), Commit Message Storyteller (github/awesome-copilot, 40k stars) and Personalize Message (Othmane-Khadri/YALC-the-GTM-operating-system, 318 stars). The comparison table on this page puts their stars, adoption, token cost, safety result and licence side by side.

Who maintains Awkward Message Helper?

mohitagw15856 (a GitHub user) maintains it in mohitagw15856/pm-claude-skills, which has 1,434 GitHub stars. The repository holds 1,348 skills in this directory. The repository was last updated on October 9, 2026.

Source: mohitagw15856/pm-claude-skills on GitHub. Facts on this page come from the repository at the commit we read; the author's words are quoted as theirs.