Select Your Location

9 Tax Deductions You Wish You Could Write Off

By The Second City | Apr 15, 2014

April 15 marks Tax Day in the United States, the dreaded time of year when adults are asked to turn in their assignments — and show their work. Most hope for a refund, paying H&R Block or TurboTax to help maximize the number of deductions on a standard 1040.

In a modern, technically advanced economy, shouldn’t Americans be entitled to a number of other creative refunds? Here are 9 additional tax deductions we’d like to see:


Anyone who paid to see The Hangover Part III, Gangster Squad, or The Lone Ranger should be entitled to write off the full value of their movie ticket. Conversely, anyone who paid to see Movie 43 will be subjected to harsh penalties.

OkCupid, eHarmony &

Since time is money and sex is cheap, take the number of hours you spent crafting the perfect online dating profile and divide it by the number of seconds you could have spent finding immediate casual sex on Tinder or Grindr.

Home Ownership

Deduct the amount of home mortgage interest you paid in 2013. Please note that this deduction does not apply to millennials, who will never own homes.

Groupons You Forgot About

To offset the cost of your expired and unused deals for discount car washes or liposuction, take your number of unused Groupons and subtract the number of additional minutes it took the waiter to figure out how to save you six dollars on sushi.

Wedding Party Clothing

Unless the bride and groom have a themed funeral, you’ll probably never wear that dress or that suit again. Deduct the full amount of the clothing purchased, less the “value” of your bridesmaid or groomsman gift. (Gift value may vary; if a groomsman received yet another engraved flask, the value is zero.)


You knew you wouldn’t use it.

Your Friend’s Band

Oh, you’ve got a new bassist? Maybe the new-and-improved “Morning Evenings” is worth checking out on Tuesday at 11:30 on the other side of town. You’re going fourth? Even better! For this deduction, multiply the price of admission by the number of other terrible bands you have to listen to before the headliner you’re obliged to see because the guitar player is a friend of your roommate’s.


It snowed in Chicago nearly one month after the official start of spring. Divide your local amount of snowfall by the number of times you swore you were going to move next year to get away from it. (Both numbers should be the same.)

The Time You Spent Thinking About That Plane

Guys, it’s gone.


Greg Ott  is a writer, comedian and actor living in Chicago. Follow his pictures at


Hilarious Right? Follow the Second City For More