awkward-message-helper

name: awkward-message-helperdescription: "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?"