Mohit Aggarwal 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
- Name it directly. Hinting drags it out; a clear, kind sentence ends the dread for both of you.
- Lead with the relationship, not the grievance (unless it's a pattern) — "I value us, and…" lowers defences.
- One ask, stated plainly. Bundling grievances muddies it; pick the thing that matters now.
- Own your part where it's real — a small honest acknowledgement disarms; a fake one backfires.
- 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?"