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I once dated a guy who was homeless at one point in his life

I once dated a guy who was homeless at one point in his life.

He told me he ran away from a perfectly good home (he found his mother too strict), at the age of 16. He lived on the streets for 3 years, did a lot of drugs, and it wasn’t until he woke up shivering on the sidewalk one day, crawling over to a grate for warmth that he said to himself: What the #$*#& are you doing with your life?

He said it was that morning that he.. “woke up”, and decided to get his life back on track.

Of course, this all ended well because he just had to go back to his mother who was more than willing to help him straighten his life out, and she housed him temporarily and helped him out until he could find a job in a factory, get clean and learn how to live on his own.

He was very lucky and admitted this to me.

He recounted stories of how he had to scrounge for food, look for odd jobs here and there to feed himself, but mostly he did it for the freedom of not having to listen to his mother.

He became a drug addict because of the people he hung out with on the streets who would introduce him to a hit of something, and then ask him to run errands if he wanted more.

I don’t remember much else from what he told me because he wanted to kind of forget all of that, and called it one of his dumbest periods in his life. He did say at one point that it was easier to be homeless than to be a working Joe, however.

He felt as though some people found it very difficult to wake up in the morning to go to work, cycle through 8 hours of work, come home exhausted, only to do it all over again 5 times a week just so they can pay for rent and food, and not much else. “It becomes depressing“, he said, “..and in some ways, being homeless is a kind of freedom from responsibility and life“.


There’s a post from Michelle a long ways back that talked about homelessness and what you would do if you became homeless.

“There is a war against those who are weakest in society and I have a theory about why. We are afraid that we will become them. 

So, we pretend like we don’t see the homeless on the street, we pretend that we don’t hear them.

We deny basic contact unless it’s Thanksgiving because usually that’s safe, there is no risk of anger.

There are people around and nothing bad can happen when you’re volunteering.

Recently though I find that I have to work hard on being compassionate. “

Read more of her post over at: Homeless versus The World

Michelle basically made all the points in her post, but I will just go over a few of them that rang a bell with me.


Never say never.

A lot of us don’t think we would ever be homeless but sometimes you can’t predict what the future will bring (knock on wood).

Being homeless is not simply the fact that you don’t have a place to go home to, there’s a whole psychological and emotional set of baggage that goes along with the fact that you tell yourself: I am homeless.


If you couldn’t stay where you were today, who would you call? I am sure you all have family, friends and others you can call on for help and they would gladly give you a helping hand any time you asked (the same courtesy you would extend to them, I am sure).

…but what if you didn’t have your network in place?

What if you didn’t have friends or family to call on? This actually exists as a situation — people who have family, but can’t go back to them for various reasons (maybe they’re the reason why they ran away in the first place), and perhaps their friends are also in a similar situation and aren’t really in a position to help you, let alone help themselves.

When you are alone, you are TRULY alone.



I don’t know if you are aware of this stupid game, but I remember hearing about high school students who purposefully dress and act like they’re homeless, but go home to a family every night. The worst of it, is that the kids I heard were doing this, were filthy rich as well.

They all attended private schools (although they cut class a lot to go “play homeless”), and had everything they could have asked for.

They spend their days and nights on the streets, hanging out with other homeless (perhaps fake homeless) kids, pretending to need money, food and assistance.


To them, it’s a game. A sick game, but a fantasy nonetheless that they can easily break any time they choose to.


I am not entirely sure giving money directly to homeless people helps them, because I do know that there are shelters available such as missionaries where they can go to sleep in a warm bed, and places like the Food Bank that will give them something to eat.

As I mentioned above, the guy I dated told me that he would just use the money for alcohol or drugs once he was addicted.

Sometimes, he’d use the money for laundry.

He said that he would just go to the Food Bank if he wanted food, which is an utter luxury compared to other countries where they don’t even have shelters or areas for people to go to, to find free food.

I think the best thing to do is to be open to helping homeless people find work (either by giving them such jobs) and to aid them up to a certain point, where they can then go on to support themselves.

It is not easy for them to find work because businesses think they’ll rob the cash register and run off, but there are those who are homeless, who genuinely want to better their life but can’t get a foothold out of the quicksand they are in.

If they don’t have a network of friends or family to turn to, who is going to trust them enough to give them a job?

Being homeless may not have even been their choice in the first place, but it was the only option available to them.

If no one ever takes a chance on someone who genuinely wants to have a different life, then over time I think “homeless” becomes something of a permanent badge that can be very hard to remove after years of being downtrodden.

Other ways to help would be to donate to the local Food Bank, which by the way, also feeds many families who are temporarily in need because they’re currently unemployed and trying to make ends meet.

What are your thoughts?


  • Michelle

    Thank you so much for sharing that post! It HAS been awhile since I wrote that one. I’m in the process of writing a new post after a particularly surprising experience in Hawaii. I’m still trying to process the whole thing. I am in L.A. right for the night and I’ve already told a guy off for making fun of a homeless man who was clearly mentally ill. I told him needed to have some compassion. He told me that the homeless guy was loud and that it was a public space and that he could make fun of him if wanted to. Dang. I told him he sounded like a fool. Yes, I did. Mind you, I had just gotten off a plane from Honolulu (SUPER turbulent flight) and had a free rum punch offered by the airline. I can’t believe that people don’t feel that it might be wrong to make fun of people. I’ve had people in my life who had family but couldn’t turn to their family for help-and I helped them. So, I’m very passionate about this topic. I donate money to food banks, clothes to charitable organizations, and will be volunteering at an amazing place called the Same Cafe. Basically, it’s posh food but everyone pays what they feel like paying in an envelope. Some people will slip in a $100 or $.25 Whatever they can pay. I am so excited to volunteer with this organization.

  • Cassie

    Oddly enough, I also dated a guy who was homeless in his late teens/early twenties. It’s a tough subject, because there’s no one correct answer for all situations. Some people are homeless by circumstance, and are struggling to try to get out of it and improve their life situation. Others are homeless by choice, because they’re comfortably with the lifestyle and don’t want to engage in modern society. I found the second concept kind of shocking when my ex told me that, but in some cases I can see how its true. Ditto with the fake homeless. I used to work on a large construction site where “homeless” men would panhandle when the traffic stopped. Every morning before rush hour, a black SUV would drop the men off at each corner. They would panhandle all day, then after the evening rush hour ended, the SUV would come back and pick them all back up. It was organized. If someone tried to panhandle on their corner, they’d end up getting in fist fights over their turf.

    I’m a proponent of supporting programs for people who are struggling, rather than giving money to individuals on the street. The food bank is my go to charity; I donate both food and money. That being said, I’ll donate money to musicians on the street regardless of whether or not they seem professional. There’s one guy near the big hockey arena in Edmonton who plays drums on old buckets at every game. He’s been doing it there for years, and I dare say he’s actually getting better. I’ll donate to them, because they’re putting an effort into trying to earn the money.

  • MelD

    Ouch. “Help” isn’t enough, even housing isn’t enough if there is no family basis, foundation or support. If you simply don’t know “how” to do things the normal way to live an independent life, the aids provided by the state or other helpful people are often simply not enough. If you have no education you don’t know how or where to get help, you can’t just write a letter. If you can’t do that, it’s hard to find a job, stay in a job, live a regular life, behave in a social setting. It gets hard to say “no” to things or people who are toxic when the network is so small you’re grateful to be alive. We are dealing with something similar at present with our daughter’s bf, it’s certainly teaching us a lot… and no end in sight, despite all we try to do to provide support, you can’t build when there’s no foundation, and putting in foundations afterwards is pretty hard. Right now I can’t really see a happy end.

    • save. spend. splurge.

      I once read a great ad in the metro that said: “Why can’t homeless people just get a job?”… and the list was just.. really eye-opening, covering a lot of points you’ve mentioned.

  • Erika

    Many of those who run away or become homeless are also at great risk of human trafficking. Yes, even in North America. I know that you have traveled extensively and I’m sure that you have seen all the “Roma” (gypsies) that beg on street corners. Most of it is an elaborate criminal network where children and the disabled are sent out to beg, but their handler is the one collecting all the income.

    • save. spend. splurge.

      Human trafficking is not at all surprising to me. I’ve heard some horrific stuff that has been happening in Canada right under our noses so to speak. I’ve also definitely seen those gypsies everywhere in Europe, and I am not at all surprised they aren’t the ones getting the money.

  • Alicia

    My fiance and I grew up in two VERY DIFFERENT situations. Without going into too much detail, he knows a lot more hardship than I do. And he’s much more aware of these sorts of things being not all that far away than I do. It’s more real to him. I have started to understand it more, but having not experienced it… it’s very different to be told, and to have lived it.

    At this point we are dealing with a family member whose network isn’t catching him. Me and my fiance are trying our best to catch him, but I could easily see him ending up somewhere like homeless or a shelter if we weren’t keeping him from toppling over that edge. It’s hard to watch, and it’s killing me heart. And then I think about all the other people I don’t know (unlike this family member) and I realize how much I’ve overlooked in the past. I’m not proud of it, but it hadn’t touched me personally so I just didn’t realize… I was in my own little world.

  • ArianaAuburn

    I worked in a homeless shelter and the reality is that what blew me away was how much food was served to each person who showed up for the food bank. Lack of food was not the problem: it was lack of shelter. After 2 hours after a meal was served, everyone was kicked out into the cold.

    Lack of affordable housing is the real problem. A lot of the people who show up at the shelter have jobs, yet because of the high rent, they can’t afford to rent privately. Section 8 housing has a long list and priority is placed for families with children.

    Homelessness can happen. It is really a dividing line in class warfare. The truth is you are the only one who can create your own safety net because you can be denied the same social services you pay for while working your butt off.

  • Annie

    I’ve been homeless in the past and have known several who were homeless themselves at one point. The stories they shared were tragic.

    Many organizations that cater to the homeless offer a handout but not a hand up. They impose rules that would prevent or discourage working (arrive at a certain time to get a bed even though you have to be at your job until much later, for example). My friends who were homeless told me of choosing to live on the street and keep their jobs rather than give them up to stay at the shelters.

    I’ve even known professional panhandlers who lived in vehicles and begged for money. One person told me it paid more and was a better life to live in a car and beg (doing odd jobs when they appeared) than it was to live in an apartment on the minimum wage jobs they qualified for. I’ve never tried it so I can’t say.

    In this nation (US) we have have a serious issue with the poor and especially the homeless. Many believe that they aren’t trying hard enough or that they are lazy. Many are everything but.

    • save. spend. splurge.

      The thing is more how do we transform them and integrate them back into society? I almost think like a buddy system where 3 families take on one person to help him out would be a good thing.

  • Taylor Lee

    You can help by donating to shelters, writing to your local legislature against anti-vagrancy laws and ceasing other microaggressions against the homeless (e.g. creating benches that have a rail in the middle that prevent homeless people from sleeping), volunteering at an adult education center, offering to buy a homeless person food (if you are against giving them money), supporting youth LGBTQ groups (many homeless teens in the US are gay/queer/other and have been kicked out of their homes), or just generally advocating for improved social services to help build a safety net to keep ’em off the streets.

  • marilyn

    Speaking as someone who is living in a homeless hostel and existing on disability benefits and child support ,its very easy to think it would never happen to you.but believe me it can.i once had a job,house,family.following my ill health my husband left and then I couldn’t support myself due to my ill health .housing is too expensive here in the UK for me to live by privately renting.i was evicted when my landlord wanted his son to live in his family didnt offer to support me in any way and would have seen me on the streets had the local council not stepped in and considered they had a proven duty of care for me as I have what they consider a priority need,and so now I share a tiny room with my son who has autism and learning don’t go thinking it wont happen to you there is no guarantees your marriage is going to succeed forever and you maybe one day will have something happen to you which means you cant work.

  • Revanche

    Sigh. I started to respond and it became an off topic novel.
    It’s always felt like that was the next step down if I didn’t find a way to survive on my own merits. We had no safety net, it was all on me, so I’d never ever think it couldn’t happen to us. But I don’t know what the answer is, as the obvious answer (“help”) is not at all obvious when you try to figure out how. I’m doing my part in keeping two more people off the streets but I don’t know what I can reasonably do for those already there that truly is help.
    For some I guess it’s more a matter of just letting live because short of housing and supporting them entirely, they’re not going to be able to survive more than day to day. For others, they just need an opportunity to make it out of there. I don’t know how we tell the difference in the few seconds we have to assess random encounters. But in the end, except for those rotten rich kids, I have to feel like they deserve to be treated with basic human dignity.

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