Surviving Tax Season with Uncle Bobby: A Sassy Guide to Filing Taxes

Dear Uncle Bobby, It’s Tax Day, and I’m still not done with my return. I’ve got receipts in a shoebox, half a form filled out, and no idea what “adjusted gross income” even means. Should I panic, file for an extension, or just fake my own death and move to the woods?

Yours in Receipt Chaos,,
Filing and Flailing

Oh, Flailing, welcome to the most patriotic day of the year: The Annual Government Math Contest, where the rules are vague, the instructions are written by demons, and the prize for winning is… absolutely nothing. Now first off, don’t panic. Filing taxes on time is a suggestion—not a hard rule. That’s why the IRS invented the “extension,” which is fancy code for “I’m not emotionally ready to deal with this.” Just slap that request in and boom—you’ve bought yourself six more months of not doing your taxes, but with paperwork! And let’s be honest, no one actually understands taxes. Not even the IRS. I mean, if they did, they wouldn’t need you to tell them how much you owe. They already know. They’re just sitting back, watching you guess, like some cruel financial game show. “Oooo, I’m sorry, Carl—looks like you forgot Line 32-B. That’ll be a fine and a soul tax.” As for deductions? Make it up. Everyone else does. - Did you “occasionally” use your living room for “business meetings?” Home office. - Bought a stapler in 2021? Still depreciating that bad boy. - Drove past a client’s house on your way to Arby’s? That’s a business trip, partner. Now, if the IRS ever comes knocking, just remember: 1. Be confused. 2. Be pitiful. 3. Offer them a cup of coffee and pretend you thought “audit” was a dance. And don’t worry about where your tax dollars are going. The government’s got it under control—probably buying tactical printers, funding studies about shrimp on treadmills, and constructing roundabouts in towns with no traffic. You’re not contributing to waste—you’re investing in national confusion. So relax, Flailing. File something. File nothing. File a strongly worded letter. Either way, we’re all in the same sinking boat, just using different forms. Happy Tax Day! And remember: if you round confidently, it’s basically math.