Getting Unstuck: Funny/Not Funny

September 6, 2023

In our next Getting Unstuck, assistant editor Jen Dupree explores suggestions for incorporating humor into your fiction. “What’s funny to one person won’t be funny to another,” she says. But that’s okay! Take risks, put yourself out there, but consider the various advice offered in this essay when you do.


I think I’m funny—both in real life and in my writing—and I’m really drawn to other funny people, on and off the page. To me, humor is another way to get at what a story is really about. It can subvert expectations or act as a counterweight to more serious or tragic events. But what’s funny? And how can a writer render funny on the page?

What’s funny to one person won’t be funny to another. My husband loves Monty Python and, well, I don’t get it. On the other hand, puns elicit snorting laughter from me and a mere smile from my husband.  Humor differs across cultures, life experience, and general temperament. And so, while you’ll probably never make everyone laugh at the same scene, sentence, or character, there are a few things that hold true when trying to be funny on the page. In this episode of Otherppl with Brad Listi, Sloane Crosley, author of many funny non-fiction and fiction works, including one of my personal favorites, I Was Told There’d Be Cake, says, “I actually have to sort of prune the prose and make sure it’s not just like a cymbal-bashing monkey every paragraph. The selection of which darlings, or in my case, jokers, I need to murder, takes more energy and more effort. That is where the work comes in.” Even if individually the jokes are funny, piling one on top of another can feel too much like slapstick, which doesn’t translate well on the page. Crosley goes on to say that writing that becomes one punchline after another can end up being funny but meaningless and ultimately forgetful. Because funny without a counterbalance won’t make a story. And so, we have to figure out how and when to use restraint, when to pull back, when to not make that next joke or pun or include that ridiculous line of dialogue. What we ultimately want is for the humor to move the story forward, to make the story more meaningful, and to make the painful moments more poignant.

In this episode of Write-minded, David Sipress, cartoonist and author of the memoir What’s So Funny, has more to say about what makes funny resonate. Sipress says, “If you put something out there that people connect to but do it in a way that’s surprising…that kind of combination creates the laugh.” Especially in non-fiction, digging into funny missteps and personal stumbles can make a piece really relatable.  Host Brooke Warner further suggests that wry observation, a la Mary Karr’s The Liars’ Club, is a way to connect to the reader. There’s an appeal, Warner says, to “wallowing in the complete abnormality of your situation.” There’s a line here, though, between self-deprecation and wry observation being funny and becoming a pity party or mean and caustic. All of those emotions are fine to express on the page, but you don’t want them if you’re going for funny. Funny is one of the things I ask my writing group to gauge for me because I find it really difficult to know for sure on my own where my work lands.

So if you’re funny in real life, will you be funny on the page? In this episode of The Writing Life, writer and comedian Caimh McDonnell talks about just that. He admits that if you’re the kind of person who looks for the joke all the time, being funny on the page will be easier than if you don’t naturally lean toward humor. But writing humor is different than doing standup or being generally funny in real life, because funny writing requires the backdrop of a story the reader cares about. McDonnell says: “Funny lines come out of character.” He insists that a writer must develop characters, and that what’s funny comes out of how we relate to the character. A surface joke or pun will end up feeling cliché and won’t satisfy the reader. McDonnell insists that “[c]razy on top of crazy doesn’t work,” which is much the same sentiment as Sloane Crosley’s warning about monkey-clanging. McDonnell says that in order for something to land, “[y]ou have to understand context.” Moreover, “If something isn’t serving the story, it has to be gone.” That’s true with every part of the story, but it’s especially true with humor. Humor that doesn’t fit the story, or a joke that goes too far, or a pun that feels out in left field can really take the reader out of the story. Humor should feel effortless on the page, but that takes a lot of work. It takes editing and positioning and trying different scenarios. “Trust your instincts,” McDonnell says.

We see a fair number of submissions that are trying to be funny but fall short, either because there’s too much of it or because it’s not rooted in character or situation. Use restraint, use humor to leverage the story, and run it by at least one other trusted reader to see how it lands.

by Jen Dupree


At The Masters Review, our mission is to support emerging writers. We only accept submissions from writers who can benefit from a larger platform: typically, writers without published novels or story collections or with low circulation. We publish fiction and nonfiction online year-round and put out an annual anthology of the ten best emerging writers in the country, judged by an expert in the field. We publish craft essays, interviews and book reviews and hold workshops that connect emerging and established writers.

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