Holiday Writing Prompts For The Difficult People In Your Life

By Caitlin Kunkel | Dec 16, 2016

It seems like the list of people you have to buy presents for gets longer and longer every year: coworkers, distant family members, people you stay in touch with on social media who really should have drifted out of your life by now. What do you do when you’ve run dry on money–but still have people remaining on your obligatory holiday gift list?

Hey, you’re a comedy person, right? You can write them all an original piece of holiday comedy just for them! Here are holiday writing prompts for all those hard-to-buy-for individuals in your life.

For the aunt who tends to overshare

Each year, your aunt loves to send out her annual big, long holiday letter filled with exhaustive details about everyone in her family. Well, it’s your turn to write one for her! Take her favorite art form and transform it into a ten-page long parody letter. Make sure to include any and all details of any medical procedures, Facebook disputes or sexual encounters you had in 2016.

For a particularly “enthusiastic” coworker

You know, that person who marks everything as “urgent?” Let’s just call them “Melissa.” For the Melissas, write a compendium of truly urgent holiday emails, including things like:

“The tinsel in the conference room is on fire!”

“We’re going to play Russian Roulette at the company holiday party this year!!”

“The copier has become sentient while OH MY GOD HELP ME MELISSA IT’S EATING ME!!!!!!”

For a second cousin who lives in Canada

When you don’t know someone that well, the beauty of writing is that you can let your imagination fill in all the pertinent details. Imagine your distant relation in the Great White North as a trusted business associate of Santa’s. Write a series of long, increasingly testy memos describing the supply chain problems for this year’s hottest holiday toy. Will your cousin and Santa ever fix their working relationship? Up to you!

For a friend’s child

For those of us whose friends have begun having children, it can be a challenge to know what to buy the unfamiliar offspring. Luckily, every young kid loves alternative comedy! Using horned folklore holiday figure of Krampus as your guide, write an interactive children’s book with “right” and “wrong” answers designed to make three-year-olds question their choices all year long. They’ll love reading it AND learn something about being an ethical citizen of the world.

For a former significant other who just got married

What could be more festive and fun than an imagined account of the couple’s divorce? After all, it’s a personalized piece of fiction, righ? Include all the gory details as you see them going down exactly a year from next, during the 2017 holiday season. Mail the short story anonymously to their house. After all, the holidays are all about the spirit of giving, so no need to take credit for your creation!

For a boss who had a really rough year

After a long 2016, who wouldn’t want to look back on their life as a whole? Cheer your boss up by writing their obituary for them. Make sure to include all their personal ups and downs (and find ways to work in your requests for a raise as well) while critiquing capitalism and their role in it. The totally impartial look back on their time on Earth will be sure to get them in the mood to conquer 2017.

For a huge group of improv buddies

You need to break out all the stops for all your best comedy buds. Write a 1200-page science fiction novel about a dystopian universe where the holidays have been abolished and people can only say NO to one another. What could possibly be more horrifying to a group of people whose friendship is founded on “yes, and?”

Bonus: You can then ask them to help you improvise plot points for the sequel.

Got writer’s block? The Second City Training Center has a Writing Program to help you with that.


Caitlin Kunkel (@KunkelTron) is a comedy writer, director and producer based in Brooklyn, NY.

Hilarious Right? Follow the Second City For More