I am in Toronto for a conference and at an intersection while driving a homeless person came up to my window with a cup asking for change. I was shocked to recognize the man as an old high school friend. I had not seen him for 20 years and he has fallen on very hard times and he looks 15 years older than he is. He has alcohol problems but he is going to AA meetings and he became homeless 2 years ago after he split up from wife. Sadly he has 2 children that are no longer in his life. I excused myself from my meetings and spent the afternoon with him and it was a very difficult and emotional experience for both of us. He has asked me for help so he can rent an apartment and get some new clothes for job interviews and I said I would talk to my wife and think about it. My wife thinks that he will drink away any money that I could give him but other than give him money I am not sure what else I could do since I will be leaving the city after the weekend. How can I help him other than by giving him money? I also don’t want to put myself at serious risk of problems either, like by renting a place for him myself in my name.
It sounds like you have a lot of compassion for an old acquaintance. I believe we feel alive when we reach out to others in need. On the other hand, addicts (including alcoholics) can play on our heart strings in order to avoid facing consequences. This can cause a willing helper to end up in a co-dependent or enabling relationship with the person who is still struggling with addiction.
What can be done to avoid leaving the person "on the street?" I'm not familiar with the differences in Canada but most communities have some social safety nets, either through local government, or through religious organizations. Those are typically the best places to look in order to find available support services and connect a person with them.