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.”