Why Are People Homeless?

That's the big question, isn't it, but does it really matter?
When you talk with a person experiencing homelessness, it's the first thing you want to know, right?
Why?
Have you ever wondered why you want to know that? The answer to THAT question may be more important.
Don't worry. You aren't a jerk for wondering. It's natural. For some people, they want to know because they genuinely care and want to be intelligently empathetic. Others care because they want to fix the problem or be able to offer suggestions on what that person could do differently. Sometimes, the motivation is a sort of fore-warning because they are afraid it might happen to them.
You wonder simply because homelessness is so hard to understand in a country with so much opportunity, wealth, and happiness. America is not bound by a caste system, a totalitarian government, or rampant extreme poverty. Homelessness is strange to most of us. 
Before we can answer why people experience homelessness (my wording is on purpose), we need to understand our motivation for knowing. The reason? When you find out why, you will be required to respond and your response will make all the difference. It will also expose your true motivation.
What if you saw a man sitting on the side of the road with this sign, "Please give me money so I can buy drugs and alcohol."? Would you applaud his honesty or be appalled by his brazenness? What if the guy on the bench with the backpack and sleeping bag had a sign around his neck, "I just got out of prison."?
Or what if we tried to get rid of the signs and labels altogether?
The reasons for homelessness are as varied and unique as the individuals who are in the midst of it. One of the biggest reasons may surprise you.
When I spoke to Jay about why he was living on the streets, he told me that his parents and his siblings all had money, homes, and lives. Something broke down in their relationship, however, and Jay lost the most important thing that could have kept him off the streets. He lost his support system. Bridges get burned and it is hard to rebuild them. Shame, addiction, hurt, anger, and hopelessness all play into why someone would lose their support. They lose their safety net.
They can tell you exactly why it happened too. Jay takes full responsibility for his decisions. He knows why he is couch-surfing.
We can also talk about gentrification, mental illness, addictions, felonies, and other factors that answer the "why" question.
But, let's suppose for a moment that it didn't matter. Jesus said for us to love our neighbors. He then told the story of the Good Samaritan. A Jewish man was beaten and robbed and left for dead by the side of the road. The people that you would have thought would have been compassionate and would have stopped to help, didn't. Then along came a Samaritan. The Samaritans and Jews were enemies.  But this particular Samaritan didn't care. He tended to the wounds and even made sure he was cared for without asking anything in return. He didn't evaluate the situation to see if the man was worthy of his help. All he knew was there was a man who needed help. So, he helped. In the words of Jesus, let us "go and do likewise."