How To Go Out With Your Tax Preparer


Be a fairly typical lady in her mid-20’s who frequently makes vague references about “how broke you feel this weekend” while still going ahead and buying the $50 shoes or $12 grass-fed hamburger. Do things like pay rent and your monthly phone bill without too much trouble, but the idea of understanding taxes makes your brain freeze up with terror that only a recently graduated newbie adult can understand. You feel 14 again, back in Geometry class while realizing that you’ve never actually succeeded in doing a single proof correctly. You shake your fist angrily at the heavens and ask god WHY do writers have to do taxes?? Why do such cruel jokes exist??? And yet, like the rest of the math-stunted Liberal Arts world, you always find a way to sack up and get them done (geometry though–never quite tackled that hurdle). #worsethingshavehappened

You finally make the very adult decision that this year you’ll just pay someone to wrangle the government for you. You ask your good friend, where are you doing your taxes? And she’s all, well, I know a dude. He’s cheap, and seems real down-to-earth. You think, worth a shot right? Friends don’t let friends screw up their taxes. After Googling said tax dude, you observe that his website is a) user friendly, b) smart with just the right amount of clever and c) tax dude is CUTE. Two minutes later, you’ve set up an appointment, and strangely enough, instead of dreading your tax day like any normal red-blooded American, you’re actually kind of looking forward to it. After all, how many cute tax preparers do YOU know?

Your tax day arrives. You get up early, hop a train, and knock on Tax Man’s front door. He-llooo nurse! Tax Man is even cuter in person than he is in his promotional video, but it’s in no way your initial objective to hit on him. You intend only to hand him your 1099s, count off the number of deductible business lunches you’ve had during your time as a freelancer, and pay the man. But gosh, he’s nice. Somehow Tax Man is able to carry on witty date-like banter while delving into the contents of your social security number, act sweetly sensitive to your incredible lack of financial knowledge, and jokingly suggest that you two get a drink sometime around your respective workplaces. You discover that you have a mutual affection for endless banter, not to mention mutual New Jersey-based bar and bat mitzvahed upbringings. You peer into Tax Man’s bright green eyes, and feel charmed. After the appointment, you float back to the subway, call the friend who had recommended him, and say “I think I just made a date with the tax man?!” Cue girlish squealing. “He must get hit on / hit on customers constantly,” you surmise. But after way too many uncomfortable Internet dates, you suddenly feel like you’ve won the lottery (or gotten a huge tax return, which you didn’t).

Spend the next couple of days scheming about how to best follow up. Force your Girl Brain to behave and attempt to think like a rational human being. Fortunately, no scheming is necessary on your end–Tax Man calls a few days later with a few questions for you, one of which being “So what are you doing next Sunday?” Within a few minutes you’re back to feeling on top of the world. Your impending Tax debt? Who cares? You’ve got a date with the cutest accountant in town.

Arrive at the bar a small bundle of nerves. Think to yourself how financially naked you feel in this very moment. This dude’s seen how much you made in the last year, and has probably stared at your checking account balance for much longer than you’ve ever managed to in the entire seven years you’ve been pulling money out of it. Decide to compensate for your weak finances like any writer-type would: with big words and puns.

Much unlike your first meeting however, the once polite Tax Man seems to be forgetting his manners. After sitting down with your drinks, his hands keep finding reasons to snake up your inner thighs. Feeling surprised, you launch into some small talk to distract yourself from feeling awkward (aka turn bright red and RAMBLE like a teenager). “So tax season’s almost over,” you say. “What are you going to do with yourself after the 1099s run out?” “Hmm…sleep,” Tax Man says. “And masturbate.” “OH!” you say, laughing nervously. “You couldn’t just do that in the shower?”

As the date wears on, Tax Man’s sexual innuendos grow more pronounced, his body language more handsy, and your desire to feel better about this whole thing more intense. Feel like you might have imagined your entire first encounter. Was the “Sensitive Accountant” persona all an act? You attempt to downplay the sexual innuendos by asking more questions. “Where did you go to college?” “Where did you grow up?” “So you’re also an actor / comedian with a math brain??” you ask, only to be met with short-form answers that curve slyly into another sex joke. You feel like you should have recognized this earlier: “this” being the nonsensical back-and-forth as most obvious illusion of discourse before two people find an excuse to collapse into bed–a routine most often reserved for house parties and crowded Friday night bars. Feel fairly certain that you didn’t sign up for that, as it’s only 10pm on a Sunday.

And this is how you accidentally banter your way into toplessness. Tax Man has promised you a classy ride home, and you intend to hold him to it, especially since you’ve hauled ass halfway across Brooklyn for this date. About an hour and a half into your drinks, Tax Man stands up and puts his coat on without so much as announcing what he’s going to do or where he plans to go next. You awkwardly follow suit. But instead of walking you to his car, Tax Man walks you straight up the stairs to his apartment. Began seeing red flags. “Want to watch some TV?” he asks. You think, wait, are you even going to offer me a beverage? A snack? A f*#*$ing Altoid? Realize it might not be a good idea to stick around, but still want to give Tax Man the benefit of the doubt. Approximately one Netflixed episode of My So Called Life later, you end up sloppily making out on Tax Man’s couch with your shirt halfway around your neck, bra almost completely undone, and he’s going for more, all in under 10 minutes. “Hold on, hold on,” you gasp. “Let’s pace ourselves.” Tax Man meets your request with a Blank Stare. ::Does Not Compute:: Feel yourself finally give up on this would-be mensch. “I should probably go soon,” you say.

A few Blank Stares, some forced dick-touching (you know the ol’ hand push), and uncomfortable adolescent-style breast-squeezing later, Tax Man finally lives up to his word and drives you home. You feel less than amused, and frankly pretty grossed out. Now not only has he seen the underside of your checking account, he’s also gotten a pretty decent look down your pants without so much as a “does that feel good?” For someone who was so considerate in letting you pay him in installments, feel rather shocked at Tax Man’s complete lack of sexual etiquette.

Decide it’s worth the extra $200 to visit H&R Block next April.

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image – John Morgan