Weekend Wanderer: Tax Season Has Turned into Tax Year


weekend wanderer

Willie — oh, Willie. 

Willie hasn’t filed a tax return. 

In years. 

And I’m not going to lie. I started this whole thing with good intentions but now I’m kind of hoping Willie goes to jail. 

January 2023 morphed into April 2023 and still Willie hadn’t made an appointment with her accountant. 

So I made the appointment.  

Rather than letting Willie rideshare to the accountant and handle the taxes herself, I went with her. 

In part — yes — to make sure she filed her tax return. 

But also out of sympathy. It can’t be easy, filing a tax return as a new widow. I offered to keep Willie company, to take her for Starbucks afterward. 

“What are we doing today?” Willie asked when I picked her up. 

“Ooh!” she said when I told her. Which is more excitement than I think is warranted for tax returns but — hey. We all have our things. My husband recently told me he loves how excited I get about tea. 

So I wasn’t about to judge Willie’s enthusiasm for taxes. 

But then Willie ruined it. 

“What year?” she asked. “What year are we filing tax returns for?” 

“What year do you need to file tax returns for?” I asked, a little nervous. 

Willie thought at least 2022 needed filing.  

Also 2021.  

And maybe 2020. 

I said we could ask the accountant. 

That’s what I said. 

But what I thought was that this column would just about write itself. 

I’m a horrible person. 

Which is probably why we didn’t get an answer about Willie’s taxes that day.  

The accountant’s door was locked, nobody answered when we knocked, and nobody picked up the phone when we called. 

I don’t think the universe does that to good people. Good people have accountants, who, you know, are actually present for appointments. 

Not accountants that call two hours later and ask why you didn’t show. 

I can’t even sometimes. I just can’t even. 

I’d have to figure out when Willie last filed a tax return — without the accountant’s help. Then I’d have to assemble tax documents for all those years.  

Then find a new accountant. 

Do you see why I find jail so appealing?  

It was after April 15, so there was no point in rushing to tackle this project. I decided to wait until Willie took her annual trip to Cape May with her sister so I could go through her files in peace. 

While I waited for July to roll around, I gave some serious thought to just ignoring the whole problem. If the worst that could happen was a little “Shawshank” for Willie, could I just let this go? 

But then I thought of all the stuff I was still handling in the wake of Indy’s death.  

Stupid stuff.  

Like getting a tax identification number because no, you can’t just use Indy’s social security number for the bank account you have to open because in fifty-plus years of marriage Indy and Willie never got around to putting Indy’s Maryland property in both of their names so now that you’ve finally — finally! — sold it, no one is entitled to the money until the bank is sure that everyone isn’t entitled to the money. 

Yeah. Still angry. 

Can you imagine the postmortem paperwork for tax returns that haven’t been filed? 

That’s a whole other kind of jail. 

So with Willie in Cape May, I took my Starbucks and a podcast to the Temple of Doom and sorted through Willie’s files. 

This was not easy because one, Willie holds onto every bit of paper that comes her way. I found uncashed checks from a long-shuttered consignment shop. Volunteer schedules from a church Willie no longer attends. Repair receipts for a car she owned two cars ago. 

Two, Willie’s folders might read “Taxes 2017.” But what they contain are pharmacy receipts from 2012. Or return address labels for a house long sold. Or invoices from the business Indy owned in the late nineties. 

And three, Willie is one of those people who thinks she’s organized when in reality she and organization live on different planets. 

In different galaxies. 

At different times. 

So although Willie told me I only had to pull each year’s tax folder to look for the corresponding tax returns in order to identify which years she was delinquent, that’s not what happened. 

What happened was that I had to sift through every piece of paper in the Temple of Doom. Papers in the filing cabinet. Papers on the desk. Papers shoved in a grocery bag along with a photo album and broken umbrella. Papers piled on the windowsill with Good Housekeeping and newspaper circulars. 

Hours later, I had three piles — definitely tax-related, possibly tax-related, and I-don’t-give-a-word-my-editors-won’t-let me-use. 

I spent the subsequent weeks sorting the paperwork. Ultimately, the best I could figure was Willie had last filed taxes in 2017. 

I seriously considered jail again. 

Because, well, I was at a loss. What do you do when you’ve just spent two and a half years selling a property that wasn’t yours, five years caring for a Parkinson’s-riddled father, seven months filing postmortem documents, and now there are five years’ worth of back taxes? 

I’ll tell you what you do. 

You leave it for another day. 

And that’s what we’ll do with this story. 

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