Peter Desmond

Monday morning I wake up startled, but this is no dream: A tax client is ringing my doorbell. I look for the alarm clock, then remember that it broke and I threw it in the trash just yesterday. Dressed in my blue jogging suit, which I sleep in, I scramble out of bed, pull on my slippers, and sprint into the living room, where I find my equally startled ex-girlfriend Mary.

“I-i-it’s my 10 o’clock,” I stammer, as I grab the parking permit and race down the stairs. Mary had locked herself out of her next-door apartment last night and crashed on my couch. “I’ll slip out,” she answers. Since our breakup last summer she prefers not to meet my clients, though she stops by to use my spare computer almost every day.

Attempting to chitchat urbanely, I lead my client up the stairs and into the office. Perhaps she thinks I’m back from a morning run. (If only I had put on my Reeboks!) Perhaps she doesn’t hear the squeaking of doors and the creaking of stair treads as Mary furtively tiptoes out. My client may be in a world of her own: Opening the office window, she calls out to her dog, who is sitting in the passenger seat of her car below.

As our tax interview unfolds, though, the air of Restoration comedy thins and I begin to whiff the scent of Jacobean tragedy. She’s making good money as a self-employed writer, but no taxes are withheld, so we’ll need to rack up a lot of deductions. The pickings prove slim. Computer? Her main client provided it. Health insurance? That client took care of it. At least there’s the home office expense—we take off 10 percent of her rent and utilities. She has some receipts for supplies, for books, for tolls and parking, but halfway through the checklist I know she’s going to get socked.

Telephone? Her client paid for the line. Business trips? Again, her client footed the bill. She hesitates, then adds, “I had to hire a dog-sitter. I couldn’t have gone on the trip otherwise.”

I think of all the people who have asked me, half in jest, whether they could deduct their cat. But what she’s saying actually sounds legitimate. “I’ve never taken this deduction before,” I tell her, grinning. “How much did it cost?” I type in “Casual labor: $40,” and go on. When we’re through, I click on “Form 1040” and scroll down to the bottom line.

Swiveling in my chair toward her, I tell her what she owes. We look at each other, and she sighs. “I have the money,” she says, “but I was saving it for a down payment on a house.”

It takes a while for the bad news to sink in. And then the issue of taxes for next year comes up. She needs to make much larger quarterly payments. “If there’s a cash-flow problem,” I suggest, “you could delay the first estimated payment by a month. It’s really important to pay the full tax bill by the deadline.”

As I print out the return she asks, “Would it be better if I were an employee?”

“Then your costs would be itemized deductions,” I say as I sign her return. “Along with mortgage interest and real estate tax.”

“That’s if I ever become a homeowner.” Sometimes there’s just not much you can say. We walk down to the car together so that I can get back my visitor’s permit. The dog is curled up in the driver’s seat. “Oh, look,” I utter inanely, “your chauffeur is taking a nap.”

She gives me a big smile. Perhaps love does conquer all.

Illustration by Robert Neubecker.