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. "<line>"
2. "<line>"
3. "<line>"

## One self-aware opener
> "<line>"
**Why it works:** <one sentence>

## One absurd / specific detail to seed in the middle
> "<line>"
**Why it works:** <one sentence>

## Three sign-off candidates
1. "<line>"
2. "<line>"
3. "<line>"

## Risk flags
- <Anything that might land flat with this specific recipient — flag it>

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.