Here's a suggestion, ask the person how they ended up where they are?
I grew up in a middle class family in a rural area, my dad owns his own business, and my mom works in healthcare. Just before my 18th birthday, I was rearended. I had a promising career ahead of me in welding, and because of my dad's connections I would have been making 100 grand a year in a short while. Because of this accident, I was no longer able to work in my desired profession, and I'm limited to mostly paper work and light duties now. Three years after the accident, I finally recieved my insurance settlement, which was about half of what I'd be making a year now. Since I couldn't work for a while as my injuries have gotten in the way, it barely covered my debt from the time between the accident and my settlement. Now my predicament is that my parents make too much money to get a loan for school, and i'm too messed up to work a labour job that would let me save for school. If it wasn't for the fact that my parents are willing to help me out, my only option would be to make money through illegal means. Right now, my life completely sucks. I pretty much make just enough to to eat, and for a place to live. I haven't gone out in two months, my clothes look like shit, and now i'm in a situation where my income won't be enough to cover next months rent. So now I have to swallow my pride, and move back in with my parents, and I'll likely be declaring bankruptcy this year. The worst part of failing, is the seemingly endless depression I've had for the last three years as a result of losing everything I had going, which has all but killed my motivation. Some days I just stay in bed, cause I have nothing to look forward to that's worth getting out of bed for. And i'm not stupid or anything, infact I actually have a very high IQ, which gets me even less sympothy.
Many homeless people are homeless for the sheer reason that unlike me, they don't have a family willing to take them in.