Dear Liza,

Help! My boyfriend won’t pay his taxes. It’s been six years since he had a full-time job, and ever since he went freelance in 2010, he has not been able to complete his 1099s. 


There are a few reasons for this. For one thing, he feels somehow that he’s getting cheated, because his quite sizable reimbursements required for his job have been lumped in with income. (I’ve explained to him that he just needs to write off these expenses, but he won’t listen.) Also, he struggled with a pretty heavy alcohol addiction that, thankfully, he finally took care of about six months ago. And now he owes so much (over $10,000!) that he’s just overwhelmed by the whole thing and can’t bear to face it. I’ve tried pleading with him, nagging him, offering to do his taxes myself, etc., and also tried pleading/nagging/yelling to get him to see a psychotherapist, to no avail. (He quit drinking all on his own, miraculously.)


We don’t have any shared accounts, so I’m not personally responsible in any way, but I’m just so fearful about what bad things might happen if he doesn’t take care of this problem that I don’t know what to do. —Fearing the IRS


Dear Fearing,

Taxes force us to confront our relationship to money. No wonder they’re overwhelming! Our feelings about money can stem from our upbringing; perhaps your boyfriend’s parents were stingy, or else obsessive about household budgeting in ways that felt controlling.

If we’re political, taxes may also ignite our rage at the state, especially the American system. I stare at my pile of 1099s and wonder: Why are my tax dollars funding war and destruction? How about decent schools, clean energy, and ending hunger?

Also, freelancers’ taxes are a pain in the ass. Not only must we track our expenses, but the system feels rigged against us: In New York, for example, the self-employment tax is brutally regressive. Freelancers in Germany and Holland tell me that, in those countries, the process of paying taxes is no better for self-employed workers, perhaps even more onerous. But like other middle-class people in Europe, they find their tax dollars returned to them in the form of universal public services. This eases the pain of paying. Julie Phillips, an American freelance writer who lives in Amsterdam and is married to a Dutch freelancer, explains: “You get a lot back [for your taxes] here. Good schools. Affordable university. Democratic socialism works.”

Still, your boyfriend will make his life—and yours—much easier by taking care of this. Like alcoholism, chronic indebtedness can be a pathological pattern. And also like alcoholism, it’s one that he can overcome.

First, he should join Debtors Anonymous. He may resist, having quit drinking without such a program, but do your best to get him to a meeting. Although I always recommend psychotherapy, understanding why he doesn’t want to pay his taxes won’t actually put those returns into their stamped envelopes. Debtors Anonymous members—people who have suffered from such problems themselves—will not only help him figure out why he engages in this self-destructive behavior, but will sit down and help him, step by step, to file and pay his taxes and to figure out how he can avoid this problem in the future. They will set goals with him and follow up, even daily if necessary.

Some practical points: The IRS will help your boyfriend develop a payment plan, so he won’t have to come up with all the money now. He should also investigate whether his state has a voluntary-disclosure program, says Jonathan Medows, a New York–based CPA for freelancers; if so, he may be able to get the penalties waived. Medows also stresses that your boyfriend should start paying 2016 quarterly taxes now, so he won’t get behind again.

Above all, says Medows, with the tough-love exasperation of someone familiar with freelancers and our many neuroses, “He needs to stop bellyaching, suck it up, and move forward.”

* * *

Dear Liza,

I live in a mostly gentrified neighborhood in Brooklyn that still has pockets of poverty. Low-income housing developments are a couple blocks away; a few blocks in the other direction are multimillion-dollar townhouses. There’s a lot of racial and class tension. Recently, a group of mostly brown and black teenage boys (maybe 14 or 15) have been harassing the neighborhood. I know they live in the area because I see them walking to school in the morning. They’ve thrown bottles, rocks, auto parts, and, inexplicably, a bocce ball at me on my way home. I’ve been followed, taunted, and menaced routinely. I don’t think I’m being especially targeted, and it has also happened to my neighbors. I’m a lifelong New Yorker, so my ingrained attitude is to ignore and walk on—don’t engage. But that doesn’t seem to be working. I don’t think these kids actually want to physically injure me, and I don’t think they are violent felons! That said, having large rocks thrown at you at least a few times a month isn’t nothing. What do I do? If I call the cops, I worry that there will just be increased policing, and given that stop-and-frisk-lite is still the norm, I worry that these kids will have their lives ruined. On the other hand, I want to be able to walk home without dodging slurs and bottles. Personally confronting them doesn’t feel wise.—Abused Gentrifier

Dear Abused Gentrifier,

How scary! Yet I agree with your reluctance to involve the police. I’ve called the cops myself, before the stories of Tamir Rice and so many others burned the racist criminal-injustice system into white consciousness. I’d be less likely to do so today. Slate’s Emily Bazelon has written, “if I have a choice about whether to involve the police in the life of a black person, I will try to choose not to.” If you’re in physical danger, you must call 911. But as Bazelon points out, most situations are more ambiguous than that.

You’re still in this gray area, Abused (though the rocks worry me). Please avoid walking on the block alone at night. At least text a friend or partner when you are heading home, and agree to text or call again when you arrive safely indoors.

But as Sue Yacka of New York City’s Anti-Violence Project points out, you can also keep yourself safer by fighting gentrification, and improving life for your low-income neighbors. Join groups working on this—a good one in Brooklyn is Families United for Racial and Economic Equality (FUREE)—and get to know the other nonprofits, community groups, and service agencies in your neighborhood. Such engagement won’t shield you from bocce balls tonight; after all, the wayward youth aren’t hassling you for failing to be an upstanding member of your community. But addressing the inequities caused and revealed by gentrification can ease racial tensions and violence in the long run.

You don’t say whether you are a person of color, queer, or whether these “slurs” are homophobic. If so, the Brooklyn’s Audre Lorde Project could be an excellent resource. Its SOS (Safe OUTside the System) Collective works to address both police violence and homophobic violence, by helping communities of color build the capacity to address and prevent hate without involving police. The SOS Collective has open meetings the fourth Tuesday of every month; such a meeting might be a productive setting in which to discuss your situation, as well as find out who else in your neighborhood is working to ease tensions over sexuality, race, and class—and how you can join them.

Have a question? Ask Liza here.