Finding the Funny, Writing the Truth

How to craft humorous personal essays without bad puns, limericks, or unexpected knock knock jokes

Once, when I was emceeing the open mic portion of a funeral (I have a very, very strange niche as a comedian), an organizer informed me that everyone who had signed their name on the clipboard to speak had already done so.

“Can you check if there’s anyone else?” she whispered.

I stepped to the podium and began, “So, um, for the first time in queer history, um, running early.”

The attendees were broken-hearted. And because of the circumstances surrounding the person’s death, many were also mad. Really mad. At the deceased and also—again, because of some very specific circumstances—at each other.

Nevertheless, they laughed.

They laughed because they needed to.

And that is precisely why a little humor in a personal essay is often a gift for the reader.

Write First, Make Jokes Later

One of my first paid writing gigs was at Au Courant, a sadly deceased Philly gay paper, where I wrote a weekly humor column I had (hilariously, it seemed at the time) named Trippin’ Out.

It was the 90s. Eighty-seven percent of all public queer culture had a moniker that paired a gerund with the word “out.”

Because Au Courant was printed on actual paper with actual space limitations, Trippin’ Out had to be within a dozen words of the 500-word count I was permitted. It also had to match the theme of the periodical that week—sometimes a controversial issue, but more often a local event.

Almost every Thursday afternoon, I would call my best friend (who, by the way, had no relationship to the paper; she was just being a good friend) in a panic I tried to cover with hyperbolically feigned casual conversational intent: “So, um, the Devon Horse Show. I’m just wondering if there’s anything funny and, um, gay about it.”

The patient and caring editor once returned what was apparently a particularly hacky piece of writing with the note: “Kelli, you can’t base an entire column on one joke.”

That sounded like a dare to my twenty-something ears. Column after column came back to me with similar sentiments. After a year of spending my Thursdays writing and my Fridays rewriting, I realized: Oh, should I maybe start with a point instead of a funny line?

The answer is an unqualified yes.

For example, in my essay for Open Secrets, “Ashes to Ashes, Trust to Trust“, which chronicles the journey my chest tattoo—filled with the ashes of my dead partner—has taken me on, I have collected dozens of hilarious reactions to my admittedly dubious choice to posthumously Borg in this way. But when I tried to construct the essay around the funny (and mostly not thrilled) comments, it pulled focus from the emotional takeaway I wanted to communicate in the piece. I wanted to celebrate the comfort that comes with having a failsafe filter: If you can’t handle this, you can’t handle me permanently emblazoned above my heart.

Writing first and making jokes later allows humor to serve the story, not overshadow it.

Observation, Not Creation, Is the Easiest Road to Humor

In my “Ashes to Ashes” essay, my partner Heather and I were discussing how to make our long-distance relationship a short-distance relationship because she was dying.

Practical conversation, this—but not hilarious.

But as we sorted through the particulars and considered whether someone might foster my feline companions rather than traumatizing them with a cross-country move, Heather responded, “It’s not like it's a long-term commitment.”

This was not a joke I could have written—or at least not in good taste. But all I had to do was listen when Heather spoke.

Heather was indeed a funny person sometimes. But the truth is, most people will occasionally make a hilarious comment (sometimes intentionally, sometimes not) when things are terrible, because even the WASPiest people become more blunt under pressure.

In Liz Alterman’s “Coming to Terms With My Misguided Job Snobbery,” she molds a dyad of unpleasant topics (underemployment, confronting one’s own emotional shortcomings) into a funny essay. At one point, her father provides the humor:

“My dad had reduced our exchanges to sentences like this: ‘You’d better do something because I didn’t pay for you to go to college so you could sit around all day watching Love Connection.’”

Although Alterman is herself a celebrated humor writer, she still brings in the words of others to produce additional hilarity, in this case, at her own expense.

Once you start actively looking for stolen humor to add to your writing, keep out your notebook or your notes app, because I promise you, you’ll find it everywhere.

Feelings Are the Fuel

Even if the people in your life aren’t considerate enough to say funny things under pressure, you can inject humor into almost any piece of writing by enthusiastically following emotion wherever it might lead.

In Siham Lee’s “The Romanticization of the Organic Meet Cute,” Lee writes about not wanting to date a neighbor because if they break up, “we’re doomed to run into each other at the local pharmacy while looking like I might be carrying the plague with me.”

Lee describes a feeling—“Ugh, I don’t want to run into exes”—which is, in itself, very relatable. But then Lee exaggerates the feeling for comic impact, jumping to “doomed.” The humor is enhanced (as it often is) by schadenfreude. As readers, we can laugh and say, “Sometimes I’m a mess, but at least running into former lovers doesn't feel like a literal zombie apocalypse to me.”

Adding humor to first-person narrative work isn’t about forcing a joke onto the page—it’s about finding the humor that’s already there. It’s also about being comfortable with holding the tension between comedy and tragedy, which is often an absurdly fine line.

An additional benefit of the search for humor to add to your essay is that fine-tuning your humor antenna doesn’t just help you find humor; you’re actually opening your internal creative process to being more honest about your feelings. And like the classic Saturday Night Live sketch in which Christopher Walken’s character demands “more cowbell” be added to a music production, personal essays can almost always be enhanced by adding more feelings.

When the people in your life know you’re taking careful notes, sometimes they behave just a little better. No one wants to be the villain in a well-crafted punchline. Or if they don’t behave better, at least you’ve got the material. Either your art or your life will benefit from your humor search.

Even if you’re writing about very serious subjects, harnessing the humor found naturally within some of life’s most challenging events can support the reader to engage with material that might otherwise feel too emotionally difficult. Fine-tuning your humor-wielding abilities in turn, widens potential subject matter. Some topics ask for laugh or two, but others demand humor to keep the reader (and perhaps the writer) from sinking into a pit of existential despair. I’m looking at you, climate change. Pitching an editor a humorous take–or a serious take enlivened with humor can also light up your pitch.

In a world drowning in heavy headlines, a pitch with humor is like a life raft—editors, and ultimately readers, will grab on.

Kelli Dunham is the nonbinary ex-nun nurse storyteller comedian so common in modern Brooklyn. Kelli has appeared on the Moth Mainstage, Showtime’s Penn & Teller Bulls**t, BBC’s Religious and Ethics Hour, the Discovery Channel and is the author of seven hilarious nonfiction books about extremely non-humorous subjects.