--- name: fun-angle description: Finds the unexpected, dry, or self-deprecating angle that makes an email memorable. Turns "professional and polite" into "this person sounds like a real human." Use when a draft is technically correct but forgettable, when the user wants humor without slapstick, or when they need a subject line or sign-off with personality. Triggers on "make it funny," "more personality," "less corporate," "humor," "memorable subject line," "sign-off ideas." --- # Fun angle Source: `points/core-rules.md` rule 9 (warmth and humor), `points/cold-email-rules.md` rule 3 (subject lines), `points/examples-and-critiques.md` (the model letters that worked). ## Why this exists Kramon's class rule: *"Humor is non-negotiable. If you think there's too much humor, drop the course."* The emails that get answered have one moment that makes the recipient smile. Not a joke — a moment. A line, an image, a self-aware aside, a subject line that's slightly weird. This skill exists because most people are scared to be funny in professional writing, so they default to safe. Safe gets deleted. ## What works ### 1. Self-deprecation that doesn't beg for sympathy ✅ *"I spent last weekend reading your Substack instead of my OB pre-reads, and I'm not sure that was the wrong trade."* ✅ *"I open Google Docs and stare at it like it owes me money."* ✅ *"Collecting degrees like infinity stones."* What works: the joke is at the writer's expense, but it's confident — not "poor me," more "yes, I see it too." ❌ *"I know I'm probably wasting your time but..."* ❌ *"Sorry to bother you, I'm just a humble student..."* This is begging. Cut. ### 2. Specific, slightly absurd detail ✅ A specific shared object from your history with the recipient (a gift, a year, a place you both know), referenced concretely enough that the reader has to remember the moment. ✅ A specific sensory detail from your own past — what you wore, what was wrong with what you wore, what you held, what someone said — concrete enough to be unfakeable. ✅ A specific physical scene with a place name, a time, and one company-of-one detail (alone, with a friend, training, watching). What works: the detail is so specific it must be true. Specificity is funny on its own. ### 3. The unexpected juxtaposition The shape: an old identity + a current identity, in a five-to-eight word phrase, where the two don't usually co-occur in the same person. - *"[Unusual prior career] turned [current credential]."* The reader pauses on the gap between the two. That pause is your foot in the door. - *"[Current credential] who [unexpected current activity]."* Best when the activity is one a normal person would never combine with the credential. - *"Ex [elite endeavor that takes years]."* The "ex" carries the story without explanation. What works: two things you don't expect to coexist. Specificity does the rest. ### 4. Dry observational humor ✅ *"Anthropic recently launched Claude Cowork — chat is a conversation, Cowork is delegation."* ✅ *"Centaur writers and recovered consultants."* ✅ *"To centaur writers and recovered consultants,"* (sign-off) What works: doesn't telegraph the joke. The reader earns the smile by getting it. ### 5. The honest aside ✅ *"I was fortunate enough not to have to live on $4 a day while doing my MBA."* ✅ *"I'll be honest: I've never written a cold email I didn't second-guess."* ✅ *"I know that's a big ask, so no is a perfectly fine answer."* What works: a moment of honesty about the ask itself. Earns trust. ## What doesn't work - **Puns** — almost always groan-inducing - **Pop-culture references** — date your email; the recipient may not know the show - **Self-effacing humor that begs for sympathy** — see above - **Forced humor** — if you can't say it without straining, cut it - **Humor at someone else's expense** — even gentle ribbing of a third party is risky - **Exclamation points** — humor is dryer without them - **"LOL," "haha," ":)" or any emoticon** — undermines the line ## Where humor goes ### Subject line Highest-leverage place. The subject is what gets the email opened. Three subject-line shapes that work (see *unexpected juxtaposition* above for the underlying form): - Reference a specific shared object or moment between you and the recipient - Pair your unusual prior identity with the current credential - Name a small specific shared place or institution ### First sentence A self-aware aside that names the writer's own friction with the medium. *"I'll be honest: I…"* / *"I open Google Docs and stare at it like it owes me money."* The aside makes the rest of the email read as written, not generated. ### One line in the middle A specific physical detail from your past with sensory texture — what you wore, what was wrong with it, what someone said. One per email, dropped without fanfare. ### The sign-off The line that proves you're a human, not a template. - *"To centaur writers and recovered consultants,"* - *"From a fellow optimist about boring infrastructure,"* - *"With more questions than answers,"* Never: *"Best,"* *"Sincerely,"* *"Warm regards,"* *"All the best,"* ## Output format When invoked, take the user's draft (or context) and return: ``` ## Three subject-line candidates with personality 1. "" 2. "" 3. "" ## One self-aware opener > "" **Why it works:** ## One absurd / specific detail to seed in the middle > "" **Why it works:** ## Three sign-off candidates 1. "" 2. "" 3. "" ## Risk flags - ``` ## How to calibrate Match the humor to the recipient's tone. A line that lands with a startup CEO will not land with a litigator. Read the recipient dossier (from `recipient-research`) before suggesting humor. If the recipient is famously dour, dial it down to dry observational; skip the absurd detail. When in doubt: **one moment is enough.** A whole email of jokes is a comedy set, not an email. ## The litmus test Read the line aloud. If you slightly cringe, cut it. If you slightly smile, ship it.