Hilarity With a Side of Heartbreak

Katie Love, first place winner of WD's 2023 Personal Essay Awards, shares how she walks the line between comedy and tragedy in her writing.

- MORIAH RICHARD

A man and woman meet on a dating app. They see each other for a few months. Then an argument over politics reveals that the man is a convicted felon who served 24 years for murder.

You'd think it were fiction if it wasn't entered in a personal essay competition. And more surprising than the plot twist is that the essay-titled "Killer Punchline: Comedy-tragedy in the Dating World"-is funny.

A lifelong writer, Katie Love's résumé features a good many years as a corporate copywriter and freelance journalist, as well as a screenwriter and memoirist. She has explored the ins and outs of storytelling from every angle and has a feel for when something will reach out and grip an audience with both hands.

So, a year after that ill-fated romance ended and Katie found herself bursting into tears retelling the story to a fellow comedy writer, she thought, Maybe there's something here.

"When I think about my very early writings, from English class in, you know, seventh grade, the hero always won, but wow, did they have a tough time!" Love says, "... so I've always written from a place of comedy-tragedy. Those two balls are always in the air."

She acknowledges that there's a delicate balance between writing a funny essay about a disastrous relationship and honoring the fact that this man is a real person with a real past, no matter how complicated, and that there was a very real victim. She discusses how she overcame her fear of upsetting those she was writing about while she drafted her memoir, Two Tickets to Paradise: From Cult to Comedy.

"You have to be extremely careful about writing from a narrative place that would live inside someone else's heart, someone else's experience, someone else's mindset," she says.