Ask the Bitches: How Do I Stop Myself from Judging Homeless People?

Ask the Bitches: How Do I Stop Myself from Judging Homeless People?

I have a question about maintaining empathy in this capitalist hellscape. I live in NYC and there are homeless people everywhere. I can remember being a kid and having huge amounts of sympathy for the homeless in my hometown; I always gave some of my allowance money if I walked by a homeless person, or asked a parent for a dollar to give. Now I’m 27, have lived in NYC for 2+ years, and have lost so much sympathy for the suffering of the homeless.

I know logically that I should be much more sympathetic to their situation, but I also can’t help but think they are such a nuisance. I almost never give them a spare dollar. I just can’t afford it. I loathe them for inconveniencing me with their shouting and their stench. I think that if they’ve reached the point of needing to beg strangers for help, they must have alienated all of their loved ones; I’d never be in that position. If the people who love them won’t help them, why should I?

But logically I know that’s not true. I could be in that place with just a few family tragedies. It’s this internal battle I deal with every day on my commute: I dehumanize these people, I feel guilty and logically know I’m wrong. I do nothing to help. I want to stop dehumanizing the homeless because I know it’s wrong, and because I know I can do better for them and society can do better for them. What can be done? How do I get over being annoyed and repulsed every time a homeless person inconveniences me?

This is an anonymous question about homeless people we received on our Tumblr. And… it’s a doozy.

It takes a rare person to be this self-aware, pragmatic, and compassionate. The last thing I want to do is submit this person for public shaming for finding homeless people “annoying” and repulsive. Instead, I want to applaud them for doing something rather difficult: staring straight into the heart of one of our collective societal failures and searching for a solution.

We tend to equate poverty with moral inferiority. And so it can be easy to look at homeless people and dismiss them as individual moral failures. They’re people who’ve fucked up so bad they have to live in a cardboard box, right? I want to challenge that dark individualism.

So let’s talk about homelessness.

It can happen to any of us

As John Oliver so eloquently explains in this clip, the vast majority of Americans are sooooo much closer to being a homeless beggar on the streets than they are to being on MTV’s Cribs.

And the numbers are only getting worse. According to’s 2022 report on homelessness in America, levels of homelessness are up among several demographics, including among students. In fact, 17 out of every 10,000 people experiences homelessness on any given night in America.

Our individual financial security is fucking precarious! That’s why we write this blog! Yes, you can build up an emergency fund and save six months of your income. But when you get right down to it, most of us are one major medical emergency away from bankruptcy.

And if you can’t recover from said emergency, if you don’t have a support network to get you out of that mess… that’s it. You’re done. You’re staring down the barrel of homelessness and getting judged by strangers on the street for your inability to stay clean and hygienic while you literally sleep under the overpass and rummage through the dumpster behind Au Bon Pain for day-old bread.

I’m hoping this stark reminder puts things into perspective. Most of us have more in common with the homeless guy at the park than we do with the Koch brothers.

Why are people homeless?

The knee-jerk reaction of the uninformed is that homeless people must’ve really fucked up to lose all support and end up on the street. Surely, someone like you could never end up there because you have people who love and support you, right? And besides that, you’ve taken care to build up your personal safety net. You’ve made responsible choices and Done the Right Thing. Homeless people can’t be anything like you—they’re just irresponsible!

That might be true for some. But a large segment of the homeless population doesn’t fit into that narrow stereotype.

Being homeless is not a fun game or even a choice for most homeless folks.

Mental health

A lot of homeless people are mentally ill. They are those who slipped through the cracks left by their caretakers and an imperfect system.

In fact, according to the Mental Illness Policy Organization, 20 to 25% of homeless people in our country have some form of mental illness. They report that the mental illnesses of homeless people disrupt their ability to perform essential parts of daily life: self-care, household management, and forming and maintaining stable relationships.

The result is that these people who desperately need the help of others end up pushing away or fearfully running from those who might otherwise be able to help them: caregivers, family, and friends.

Sadly, people with mental illnesses (read: sick people who need medical care) are more likely to experience homelessness than the general population.

Aging out of foster care

Others among the homeless population are young people who have aged out of the foster care system with no helping hand and no prospects for an education or career.

Think back to your eighteenth birthday. Were you expected to move out of your parents’ home the very same day? Manage your own finances? Support yourself? I’m guessing the answer is no.

Every year, 20,000 young people age out of the foster care system. They have no families, no safety net, no support network. And yet they’re expected to become functioning adults overnight.

Some of them are able to line up jobs and places to live right away. But a lot of them, through no fault of their own, end up on the street.

LGBT youth

Some homeless people are gay and trans youth who were literally kicked out of their homes and disowned by their families.

This is where things get really fucking dark. The Coalition for Homeless Youth notes that a staggering number of LGBT youth who wind up on the streets turn to prostitution to survive. Many of those end up contracting sexually transmitted diseases and becoming dependent on dangerous drugs. Oh yeah, and they get to deal with the joys of homophobia and transphobia on top of everything else.

According to the Williams Institute at UCLA, 40% of the nation’s homeless youth identify as LGBT. Of these, 46% are runaways who left because their families rejected their sexual orientation or gender identity. And 43% were forced to leave their homes by parents who would rather condemn their child to a life on the streets than have a gay or trans child.

I’m not a parent. But I’m hard pressed to imagine a more cruel and inhumane thing a parent can do to their child.

Substance dependence

Other homeless people are dependent on harmful substances in this great nation where we treat substance dependence like a crime rather than the public health crisis it is.

According to the National Coalition for the Homeless, “Substance abuse is both a cause and a result of homelessness, often arising after people lose their housing.”

If we consider substance dependence a public health crisis rather than a sign of moral failing, then homeless addicts are doubly fucked: trapped with a health condition that prevents them from living a normal, financially stable life, and cut off from the resources and support network that would allow them to recover.


Lastly, let’s not forget that many homeless people are veterans who have been totally abandoned by a broken and struggling VA. According to the National Coalition for Homeless Veterans, about 13% of homeless adults are vets.

Full disclosure, I am the daughter of a disabled veteran and that life experience has given me strong opinions on the VA. Like, strongly negative opinions. So while some might not think it’s fair to even partially blame the VA for the preponderance of vets on the street, I’m totes cool with that generalization!

The point is that a lot of people join the military to better their lives. Whether it’s to get out of generational poverty, become citizens after emigrating to the United States, pay for a college education, or to support a family, many service members view the U.S. military as a way out.

How tragic, then, when they’re discharged onto the streets and provided with little in the way of healthcare and transition assistance. Many veterans struggle with post-traumatic stress, which can lead to the kind of mental health issues and substance dependence problems discussed above.

Above all, compassion

Captain Hammer hates the homeless...

The homeless person you pass on the street could be a runaway, an addict, a mentally ill person, an abuse survivor, or a veteran.

Put even the most normal, patient, chill person in any of these situations, grind them down with bad weather, abuse, lack of nutrition and healthcare for months and years, and I guarantee they’ll get a bit surly.

When you meet a loud, annoying, unhygienic homeless person on the street, you’re meeting them at their worst. I defy you to act any better in their situation!

Let’s return to our anonymous question asker. Because I honestly don’t blame them for their feelings of discomfort and disgust in the presence of some homeless people! They’re not all saints, just like those of us who have homes. Some homeless people can be mean, belligerent, dirty, rude, or annoying. That’s not a pleasant person to deal with. Nobody wants to put up with an intrusion into their daily routine that makes them uncomfortable.

Our question asker shouldn’t feel bad for having an intensely negative reaction to difficult people. But what makes those people difficult is probably not their homelessness.

... ness problem that plagues our city.

Assholes come in all shapes and sizes

Kitty chiming in briefly to say: I once worked with a woman who was invisibly homeless. She held a good job in the tech industry, had a neat and professional appearance, seemed super put-together, and was genuinely sweet as pie. But she and her daughter slept in a car every night for several months, waiting for beds at a women’s shelter to open up. She spent all of her paychecks on lawyers to keep her physically abusive husband at bay. No one at work had any idea. Until one day when she was particularly stressed, and the truth came flooding out. Homeless, but not an asshole.

Conversely, in my old neighborhood, a disheveled woman used to pester me for money on my commute home. She told lies about her situation to get kindhearted people to give her money. She’d spend that money on alcohol and drink it on the bench in front of my house. Then she’d pass out in a pool of her own piss, leaving bottles and cigarette butts everywhere. If you declined to give her money (and she was feeling feisty), she’d hit you with a big glob of spit, or cuss you out. Charming!

Here’s the thing, though… that woman was not homeless. She lived in the apartment building across the street from me, and was always too wasted to recognize me as her neighbor. Not homeless, but surely an asshole.

Non-homeless people can be massive fucking dicks on a regular basis, so why not the homeless?

Your bias is showing

Generalizing the behavior of a group of people by one trait they share is a pretty bad idea. That’s when you hear things like “women love tearing each other down.” Or “young people are too lazy to vote.” Or “white people can’t dance” because EXCUSE ME, I CAN SHAKE IT. Lumping all people together by their housing status is exactly as arbitrary as lumping them together by religion, or gender, or skin color. Especially when most homeless people don’t have a different choice.

There is a very thin line separating all of us financially stable people from the homeless. That alone makes them worthy of our compassion and respect. Basic human decency goes a long way. Especially to someone who gets alternately ignored and shat upon by most of the human race. You are not obliged to have perfect Christlike feelings towards everyone you meet in New York City. But your blanket contempt won’t improve their situation, and it won’t make you happier either.

Here’s s’more on why we should all cut the poor and homeless a break:

What can we do to help the homeless?

Here’s what you can do to stop feeling impotent, useless, and heartless when you see a homeless person and you can’t afford to give them money.


I personally very rarely give money to individual homeless people. But I do donate to a number of charitable organizations. These orgs help to alleviate the plight of the homeless and impoverished in my country. I also vote for politicians and policies that will improve life for those struggling to make ends meet.

I support policies and politicians who aim to get at the root of the homelessness problem. And not just systemic poverty, but inadequate mental health programs, lack of support for veterans and the disabled, and lack of protection for children suffering abuse or lacking stability in their home lives.

And if you ever doubt that your vote counts, just know this: there are some politicians and states that are going to drastic measures to help relieve homelessness! Take it away, Lloyd Pendleton, head of Utah’s Homeless Task Force:

Lloyd Pendleton, head of Utah’s Homeless Task Force.

I pay taxes in the hopes that my money will be used to stab the root problems of homelessness in the heart. When I see a homeless person on the street, I remind myself that I am making informed political decisions to help them. I remind myself that they are the reason I donate to charities and food banks. And yeah, sometimes if I can, I spare a dollar for their plight (though I rarely carry cash). But if I can’t in that moment, then I know that I’ve still done something on a broader scale.

A dispatch from the trenches

When this discussion came up on Tumblr, one of our followers wrote in about their own experience with homelessness:

I was homeless for six months because of laws in my state preventing me from signing a lease or getting a hotel. I think you’ve gotta be pretty entitled to assume that because someone’s homeless they did anything wrong. I got straight As in school, had a full-time job and a large savings account, and ended up in my car. My family wouldn’t take me because I’d ‘be an inconvenience.’ My friends wouldn’t take me in either. I did all the things the right way but got screwed by an unfair system. You want to help homeless people? Offer them a ride or some food or something tangible. That’s always what I needed. Even sitting down and talking would help. Homelessness is lonely.

Something as simple as a bureaucratic technicality made this person homeless. And the lack of a safety net or social support network left them hanging.

Yet what they longed for aside from the necessities of survival was respect. Comfort. Being treated like a goddamn person.

We clearly have a long way to go before we’ve solved the problem of homelessness in America. But in the meantime, remember that so little can do so much.

If you liked this article—or, to be more accurate, it bummed you out but motivated you to take action—consider sending a donation our way through our PayPal.

32 thoughts to “Ask the Bitches: How Do I Stop Myself from Judging Homeless People?”

  1. Ah homelessness, yet another way our inability to deal with mental health issues in this country is biting innocent people in the ass.

    I agree with you that the question-asker is showing remarkable self-awareness, so kudos to him/her on that at least. Even if his/her feelings have devolved into the slightly heartless. I think it’s something a lot of us struggle with, so the post is a good reminder to all of us to keep these people’s humanity in mind. And to remember just how close most of us are to the same plight.

  2. I used to work for a housing nonprofit that advocated for low income rental housing (National Low Income Housing Coalition) and it was heartbreaking to see how quickly one can become homeless because of the lack of affordable housing. Not being able to afford rent in a shitty apartment and then getting evicted leads to a vicious cycle in which it is nearly impossible for someone to get back on track. Matt Desmond’s book Evicted illustrates how much people profit off evicting tenants and how easy it is to lose one’s home. Statistically, the people who need the most housing assistance in order to not become homeless are senior citizens, disabled people and veterans, all groups who tend to have a fixed income. It’s shameful that we can’t provide better care or services.

    1. I JUST read “Evicted” and I fucking loved it. By which I mean it depressed the hell out of me and made me want to burn it all down. Such an eye-opener. I would compare it to Michelle Alexander’s “The New Jim Crowe” as a companion piece, as they look at opposite sides of the same racist policy coin.

  3. Donate to your local shelter organization or other entities that are providing crucial services for the homeless. I live in an area of the West where there is A LOT of white guilt and therefore much of the population here gives money to panhandlers – not all of whom are truly homeless (read: lots of young punks who are “traveling”). While I understand the intention of giving directly to an individual, it is much better to support the organizations that are providing basic needs to these folx as well as getting mental health services to those that need it. My husband is a librarian at the public library and has cultivated personal relationships with many members of the homeless community – our urban public libraries unofficially double as day shelters for these folx (sans the needed funding and social services training for library employees) and there’s a lot you can do to support your library in this way as well.

    1. Alternatively, a lot of homeless people can’t get support from shelters, as many shelters will exclude people with substance addictions, or they’re too damn full, or people can’t keep their belongings, or they’re more dangerous, or a myriad of other reasons. Sometimes giving directly to people is the better option – they know what they need, and being given money can help them get it.

      I’m not saying that you should only give to homeless and not organisations, I’m just saying that giving to organisations isn’t necessarily better than giving directly to individuals.

    2. This is excellent advice, and I’m so thankful you’re sharing it here. Yet another reason I will lay down my life to protect the public library.

  4. Fuck, this post is so good.

    As for smaller things to do in the meantime before we burn our current system to the ground, they exist even if you don’t want to/don’t feel comfortable with handing people money. A few weeks ago as I was coming out of the grocery store, a woman asked me for help so she could buy groceries for her family. I turned right back around to go back into the store and bought her a gift card; she was incredibly grateful for something that cost me a few extra dollars and five extra minutes of my time, and that was sobering. One of these months I’m going to buy a few $10 grocery cards so I can hand out one a week. If I have an extra granola bar or something with me, I’ll offer it to anyone who asks me for money. I hate single-use water bottles, but those are a good idea to pass out to people in the summer.

    At the very least, people experiencing homelessness deserve to be treated like the humans they are instead of being ignored. Even if it’s to tell them I don’t have any cash (which is always true), I make an effort to acknowledge people instead of walking right past them like I used to.

  5. I recommend checking out the YouTube channel “Invisible People”. They interview homeless people from all over the country, and just hearing different people’s stories is enough to really open your eyes to how difficult it can be to dig yourself out of that situation.

  6. Thanks for an interesting post and also for not judging that original Tumblr poster, as most of us who live in a big city can relate to them.

    I always get annoyed when people tell me the reason I should empathise with homeless people is that I’m just 1/2/3 paychecks away from being homeless. Because that just doesn’t ring true to me. I have a pretty healthy 6 month emergency fund and I have a shit load of income insurance many would say is over cautious. I have a kind, supportive family who would always let me live with them, and failing that, plenty of friends who would rather me sleep on their sofa than sleep rough. I have no mental health issues and/or drug addictions that would change this. I should should also point out I’m in the UK where we have universal health care.

    Anyway, that sounds like I’m being dismissive of your post when actually I think you’ve hit the nail on the head. The “trick” with changing attitudes to homeless people isn’t trying to convince people “this could be you”. But rather, convincing people that the only reason it isn’t them is through luck. I wasn’t born into a super wealthy family but I was born into a family that was stable and (I guess) middle class. I have no underlying mental health issues and am straight, white and cis.

    That has led me to the “almost inconceivable she could end up homeless” position I’m in now. And that’s what I try and remind myself any time I too get annoyed with being hassled for money.

    1. This is a great way of looking at it. I also feel like there’s a lot to be said for just… having compassion for other human beings, even if you have nothing in common with them. Which seems to be the attitude you’d come to.

  7. At some point in the future, my sibling will likely be homeless because he has MI, won’t allow anyone to help him, and won’t accept medical aid. He was a selfish jerk *before* this happened but when the MI came into play, it became impossible to manage him or get him in a position to help himself.

    Even though we had a terrible relationship, I still feel horrible about that near inevitability. We donate to the local support systems for the homeless but I know, I KNOW that one day, he’s going to end up on the street because I cannot and will not take him in. (I lived with him for 20+ years and he was nearly impossible then, before the MI. I cannot allow him near vulnerable children and animals in my home now.)

    A dear friend who lost both parents and a sibling in a terrible tragic situation then lost her other sibling to the trauma of those losses. He ended up on the street and later died on the streets.

    Another dear friend is watching their only child dissolve under the pressure of MI that is difficult to treat consistently and cannot do anything to help because when unmedicated (thinking they are well) the child has abused their trust repeatedly and it’s not safe for them to help.

    All of them are people and no one could know their situations at a glance.

    1. I’ve really… enjoyed isn’t the right word, but I’ve been reading your blog posts about your brother and dad and I’m really, really glad you came to comment today. These are exactly the situations I wanted people to think about when I was writing.

  8. Great post, and an important reminder to try to better understand a problem; to try to empathize with people. I’m guilty of making all sorts of presumptions when I see (or just assume) someone is experiencing homelessness.

  9. Great post. Homelessness (for both people and animals) are the causes I support the most. Totally agree with so much that has been said here. It’s sad how easy it is to become homeless. Think about someone who is down on their luck, miss some bills, credit score goes down…then they can’t get a job because employers run credit checks and can’t get a place to live because landlords run credit checks. It’s like debtor’s prison. The biggies are mental health and drugs, which unfortunately often go hand in hand. The opioid crisis is making this worse as well. For people who want to help, donate time or money to an organization that helps. I cook dinner occasionally for a local shelter and have the opportunity to talk to the residents. They are people just like all of us. This doesn’t excuse bad behavior though and being rude or violent. It’s such a tough problem and hopefully local governments will step it up and help. Thanks for discussing this issue with class.

  10. I love this! I lived in my car for four months senior of college because I wasn’t making enough to rent a room out of someone’s house. I had friend’s who would let me spend an occasional night at their house but lease laws couldn’t allow me to crash indefinitely, and my family lived in TX. I managed to put my life back together, but it was so hard listening to callous conversations about homelessness that my peers had with me (I went to a hoyty-toyty, rich kid college) when I was the one sleeping in my car at night. Recognizing the broader spectrum of homelessness and working on ways to fix it (voting, donating to orgs, personally, I’m applying to get my master’s in Urban Planning with an emphasis on Social Justice) is so important to the fabric of society, and it’s a much better way to approach the problem than generalized stereotypes.

    1. I’m so glad you’re doing better now! That must have been awful listening to your classmates when they had no idea how fucking insensitive they were being to one of their own.

  11. I don’t eat out often, but when I do, and I can’t finish my meal (what’s with the serving sizes on steroids?!), I ask to have the left over food wrapped up and then offer it to a homeless person on my way to the subway. I describe to them what the left over food is and I ask them if they would be interested in having it – ie I try my best to be respectful of them.

    What a great topic to see on an FI blog. Well done.

    1. Thank you so much! I’ve given leftover pizza away before, but I never thought to make it a regular practice. I like your respectful methods.

  12. Thank you for this great post! Some more data that helps us better understand homelessness:
    The typical person experiencing homelessness is not the “dirty, crazy, annoying” guy living on the corner that you may think of. For most people experiencing homelessness (~75%) it’s temporary (meaning lasting less than one year) and not chronic. And many people experiencing homelessness are “sheltered” (e.g. in shelters, crashing on friends couches, paying extortion-level rates for weekly hotels, etc). As Kitty and Piggy rightly pointed out, that could be almost any one of us for any number of reasons.

  13. I live in London, which also has a massive problem with homelessness, and to be honest, before I moved here, I was fairly callous in my approach to homeless people. Yeah, not anymore. I’m not sure how much these would apply to American cities, but in London, all the below are really good pointers:

    – If you want to give to a homeless individual, give money rather than things (which was super counter-intuitive for me; my family taught me to buy things for homeless people if I wanted to help them, but never hand out money). One, cash in hand might mean a warm night in a hostel. Two, money buys warm food and drinks. Warmth is important in this climate, and warmth can be bought with cash. That’s not to say giving things is useless, but I’d say the golden rule is, it’s better to give cash than things, but better to give things than nothing. I often don’t have cash on me, but I’m a snack monster, so I often carry around easy-to-share food.

    – Acknowledge them. Don’t pretend you can’t see them when they ask for stuff. Just act like as if a well-dressed guy asked you what time it is, and you don’t have a watch, either. Just look at them when they ask and say “I’m sorry, I don’t have any cash on me” before you walk away. They usually say “Thanks” and move on. I started doing this when I read somewhere that one of the worst homelessness-related experiences was that you become invisible to people, and I realized, holy shit, we do this so stupidly. There is nothing inherently different or removed about a homeless person asking for money. They aren’t a special category of people — they are like any stranger asking for a favor. You’re the one making the whole interaction awkward by pretending that you don’t see them. Remove the awkwardness by acting like it’s any other request you unfortunately can’t fulfill, but at least you’re polite about it.

    – Look into buying from social enterprises that focus on hiring homeless people. Maybe there is a shop in your city that trains homeless people to be bakers, or to repair computers, or to make coffee? Look into that next time you need to order an office lunch for 20 people, fix a gadget, or organize an outing. Bonus: those businesses are often sustainable and local, and just tick all the boxes for us bleeding-heart, avocado-munching special snowflakes ;).

    – If you’re not sure where to donate to alleviate homelessness specifically in your area, look up your local Community Foundation. Odds are, they will be working with some tiny organizations that are doing great work locally, and they’ll have wide enough reach to allocate resources where they’re most desperately needed.

    (Also hi, I’ve been reading this blog every evening for the past week, and I bow to your collective thrifty wisdom. Carry on being stingy!)

      1. Hiii, sorry, I only just realized that you responded! I’m not sure I count as a proper Londoner, what with being a fairly recent and *undesirable* immigrant, but thank you, I will take it! 😉

  14. When I interviewed several homeless people in Montana, I found that a lot of them avoided shelters because of the disease and sexual abuse rampant there. I think lice/mites were deterrents as well. I wish there was more support in place to fix broken systems but also broken help. If the “help” is dangerous and unsanitary, it prevents people in need from accessing support networks or changing their situation. One other huge issue- at the food bank- is people who think they’re not “poor enough” or they don’t deserve help. Or that they “deserve” to be miserable.
    I ended up volunteering at the food bank for several months, but then found myself having to take more hours at work instead and use the food bank’s services to eat at all. Fortunately, when the medical crisis was averted, life went back to “normal” but “normal” was still beneath the poverty line.
    It is crazy just how fast you can find yourself scrambling no matter where you come from.

Leave a Reply

Your email address will not be published. Required fields are marked *