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I Learned How To Write Funnier

The cardinal rule of writing for new Gawker is to be, above all, funny. This was of some concern to me when I was considering whether or not to take this job, as I recognize that I’m not the most hilarious person around. Or at least in the way that I imagined Gawker would demand: acerbic, irreverent, probably a little mean.

But I said yes anyway because I thought it would be a good chance to learn and grow and be exposed to thousands of haters. Only I’ve run into some logistical issues. Writing a draft takes me at least twice as long as before, as I deliberate over each sentence, asking myself, “Is this funny enough?” before deciding no, it’s not, and then writing new jokes into it, which makes the whole thing sound forced and not even like me anymore, a mess of so much laborious overthinking that the strain shows through in every word. Here’s an example, the opening of a particularly discouraging draft of mine, written in the self-flagellating style of what I like to call “haha emo”:

On the internet, nobody knows you’re a dog. Actually, it would be great if I were a dog — presumably one with opposable thumbs and a working knowledge of digital platforms — because at least then I would be a fascinating dinner party guest. The truth is far more boring, as am I: I’m just a girl, causing permanent damage to my cervical spine constantly hunched over my phone, living with near certainty that I am worse in person than I am online.

No. Not good. No.

Every new job comes with its own obstacles, most of which are exponentially harder than being funny. Who cares if I write funny? Well, my boss, for one, as she is running an ostensibly funny website. Also the website’s readers a.k.a. you. Also maybe me, so that I can finally love myself? Ha… ha.

So I set off on a meta quest of self-improvement: learn how to write funnier. This was motivated partly by the desire to seek answers to fundamental questions such as: “Is funniness an innate gift or something that can be learned? Can the human spirit, through honest effort and a purity of heart, ascend to a higher plane of comedy? Nature vs. nurture, etc.?” But also, in part, by the fear that I could get canned if I don’t find a way to improve this situation. You never know. Media? In this economy? It’s so fickle.


If you Google the phrase “how to write funnier,” the first search result is an Amazon listing for a book handily titled How to Write Funnier: Book Two of Your Serious Step-by-Step Blueprint for Creating Incredibly, Irresistibly, Successfully Hilarious Writing.

My boss, who holds my employment in her hands, was nice enough to grant me permission to expense the book for research purposes. It cost $14.99, which seemed like an absolute bargain, considering the stakes (my livelihood). The author of the book is Scott Dikkers, whom comedy fans might know as a founding editor of The Onion. (Here I must disclose that I applied for an “apprenticeship” with The Onion when I was graduating from college, but I didn’t receive any response.)

It wasn’t long into the book before we arrived at the critical question. “What makes some writing funny and other writing fall flat?” Dikkers asked. The answer disappointed me: “Like a lot of editors and comedy professionals, I know it when I see it.” Thanks for the hot tip, Supreme Court Justice Potter Stewart.

At least some of the exercises had potential. One was to brainstorm a list of 10 joke ideas that could be expanded into comedy concepts. I sneered at the list of examples, which included the idea: “A man hanging up a picture can’t seem to get it to hang straight no matter how many times he tries.”

Trying to come up with my own list of ideas, however, was a humbling experience:

  1. Squirrel wearing top hat battling Mr. Peanut for survival?
  2. Tony the Tiger is a gangster boss (noir style)
  3. In helping make others clean, soap is the dirtiest object known to mankind (something about original sin?)
  4. “What about the boyboss?” — men complaining about girlboss as a cultural phenomenon
  5. Creating a hoax to convince gen Z (via TikTok) that Jessica Biel is a figment of our imagination
  6. Five Things Benito Mussolini Can’t Live Without, for the Strategist
  7. Man hanging up picture can’t get it straight????

Facing the growing evidence that whatever help I need couldn’t be found in these pages alone, I decided to turn to more drastic measures.


If you Google the phrase “how to write funnier,” further down on the search results page is a link to this article on Masterclass: “How to Make Your Writing Funny: 10 Tips for Writing Humorous Stories.” It’s one of those blog posts that’s optimized for SEO and mainly serves as an advertisement for the real product Masterclass is trying to sell: in this case, an online video course about storytelling and humor, taught by David Sedaris.

I have a soft spot for David Sedaris. He was the first humor writer I was ever introduced to, by a high school French teacher who had an annual tradition of reading that essay from Me Talk Pretty One Day about learning French. I own most of his books, and I even “met” (in the loosest terms) him at a book signing after a reading he gave in New York a few years ago. He made small talk with everyone and offered me a piece of flatbread that had come with the meal he was picking at in between signatures. Of course I said yes. To be offered carbs by a famous person is a beautiful thing.

Sedaris’s tutelage — filmed on what appears to be a stage, like a private reading between just me and him — was less action oriented than Dikkers’s “do this, do that” style, but seemed more suitable for the kind of thing I do, i.e., writing that uses humor as a tool instead of being structurally defined by it, e.g., personal essays and such. The difference between me and David Sedaris is that his work is published in prestigious magazines and bestselling books, and I write blogs for the internet.

That last sentence is a good example of one of the lessons I jotted down from Sedaris’s Masterclass: “Put yourself down, because you’re allowed to insult yourself as much as you want.” Is this improving the comedic levels of this piece? How about if I call myself too old to identify as gen Z, a wannabe Jia Tolentino, problematic? Do you feel more pathos with each self-deprecating joke I type, struck by pity or relatability or contempt or a combination of all three?

Other takeaways I noted: Allow weird situations to play out in life. A single incident does not make an essay. Sometimes things can be fudged a little for the sake of funny. But sometimes funny can be fudged a little for the sake of vulnerability or meaning. The difference between just talking about your feelings and revealing a larger truth is “peeling your skin off,” versus emoting like a cheap Hallmark card, which seems to be my specialty.

Do you feel more pathos with each self-deprecating joke I type, struck by pity or relatability or contempt or a combination of all three?

Sedaris also emphasized the importance of writing every single day. He rewrites a draft maybe 12 to 18 times before handing it off to an editor. That is another area where our differences show; he is a much harder worker than I am. Maybe that’s one of my biggest problems. I would rather do a stunt wherein I use trying to learn how to write funnier as an excuse to produce one more post for the content hamster wheel, rather than just, I don’t know, “honing” “my” “craft” every day until I become a funnier writer. Of course, that’s assuming the latter is even possible. Ha… ha.


After taking the Sedaris Masterclass, I felt it was time to call in a real expert, someone who could answer my specific questions and guide me like a Masterclass instructor liberated from the confines of whatever crystal prison the Masterclass masters have trapped him in.

I sent inquiries — each including some version of “I'm working on a story about how to write funnier, by way of trying to make myself write funnier, please help. I'm a fan!” — to three popular male Twitter comedians whose names I shall not utter because they said no (just kidding, I wish them all luck on their journeys to get jobs on SNL). Andy Borowitz’s agent’s assistant also politely declined my interview request; I assumed this was because Mr. Borowitz was busy supporting the New Yorker Union, for which I can’t fault him. My email to David Sedaris’s PR person, sadly, went unanswered.

Luckily, I finally caught a big fish: Jesse David Fox, a Vulture senior editor and podcast host who specializes in comedy so much that he’s writing a book about it. Within the first few minutes of our call, Jesse destroyed the Dikkersian assertion that you just know funny when you see it. “I don’t subscribe to that belief,” he said. “I think there’s such a diversity in terms of what people find funny, that to imply that there’s only one, and that there are things that are undeniably funny — it’s impossible.”

The belief that he subscribes to is called “play theory,” which, contrary to everything that common sense would tell you, has nothing to do with polyamory. The way he described it sounded very primal and sort of New Age-y, like the kind of thing that a hippie therapist would say: funniness is more of a state of being, a state of play, a state of fun, like animals or children frolicking together. To be funny is to make someone else feel like funniness is happening. As long as at least one other person finds you funny, then you’re funny. It’s a gentle, generous view of funniness.

But how can I become funnier to greater numbers of people, say, readers of this blog? “You can only do that by practice — and you can only do that by doing things to refine your understanding of what people find funny about you,” Jesse said. It could go something like this: you try out some jokes that you find funny in front of an audience, and then you see whether or not they also find it funny, and does that feel true to what you find funny?

At that point, the conversation started to veer into the territory of things I would discuss with my hippie therapist, if I had one. “I want you to leave this conversation believing that you’re funny. It’s my goal,” said Jesse, who is too kind to be in comedy. “Do you find yourself funny?”

Maybe, yes, no, sometimes? I think I’ve been kind of funny in tweets that I’ve mentally picked apart half a dozen times before posting, or when I’m messaging off the cuff with familiar friends. Hardly on phone calls, rarely on video calls, in person only with a lot of sweating and high blood pressure. That’s kind of the whole point of that dumb draft whose opening lines I shared at the top of this piece; I was trying to convey how much less funny I am in the flesh than online, only I ended up not being very funny there, too.

But here’s a core question I haven’t articulated yet: Why do I want to be funny?

The haha answer is that I think I won’t last long in this job if I can’t adapt. Sure, I can scrape by fine for a while, but eventually the concerted effort of going against my natural killjoy energy will wear on me until I have no choice but to quit. The more personal, haha emo answer is that some sense of my self-worth is tied up in the idea of making people type “lol,” a notion so sad that I must ask you to politely avert your eyes at this juncture.

But I digress. What you really want to know is: How do I manage to keep working here without losing my mind? Here’s what each of my mentors on this journey had to say in support of my efforts:

  • Scott Dikkers in How to Write Funnier: “[Writers] try desperately to inject as many joke beats in their pieces as they can, or use a jokey tone, forgetting that it’s the straight voice that creates the contrast for the jokes to work. These pieces come off as desperate.”
  • David Sedaris on Masterclass: “You need to do the best that you can do.”
  • Jesse David Fox on the phone: “To me, this piece is a very funny thing. It’s a funny thing to want. It’s inherently humorous.”

To which I must reply, respectively: “Okay!” and “I am!” and “Mission accomplished!”

Did you catch that? That was the rule of three, a famous humor writing technique known to scholars of comedy like myself. And if you still don’t find me funny, well, I suggest you free your mind and subscribe to the play theory. Or imagine a man trying to hang a picture, but he can’t quite get it straight.