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awkward-message-helper

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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.

skills/awkward-message-helper/SKILL.md

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Nov 10, 2026
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# 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

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