In many parts of the city (especially downtown) a homeless person may approach you to purchase a newspaper. Usually, this newspaper contains articles concerning the homeless. This is a successful system where the poor buy the newspapers and then resell them with a profit. This opportunity gives them more dignity, as they are selling something useful rather than just begging. I do believe that this is a wonderful system. I always feel good when I purchase from them. I am not lecturing you what to do should they approach you, as that is obviously your decision. I will, however, suggest that you be amicable with them. One of the agreements of this system is that they must be polite. Throughout my years in Toronto, I found this to be 100% true. They are extremely friendly and are definitely not troublemakers at all. I cannot find any reason why I should not be friendly back at them.
Please remember that most homeless have some sort of mental illness such as schizophrenia and they are not mentally aware of certain things. Please treat them with respect and dignity, they are still human beings after all. If you don't want to give them money, give them your left overs or buy them food.
In Toronto it's rare to see any violence occur on the part of homeless people. Unlike some other large cities, you won't be looked at stragely if you speak to or help a homeless person. Toronto being the safe city that it is, the homeless do not expect to get into arguments and will often be polite to you.
Most of them have psychological problems, and since the government does embarrasingly little to assist them, spare some change while you're in Toronto.
'e che c'hai cento lire?' was the usual sentence you heard in Italy from drugs addicts begging you for a few coins and most of beggars anyway have done a job of it more than asking for a real need so at first I must admit I didn't pay too much attention to beggars on the street BUT after seeing one of them putting all his small cent coins at a counter for a hot soup, I felt really terribly thinking of me on holiday and enjoying the town shops and I began to give always some of my coins for another soup or whatever because if even later on I was explained by a Canadian that these people often 'choose' to live in such a way, I think there must not be very happy reasons beyond it...
...if you feel like, to be continued in my travelogue
In downtown Toronto, you're guaranteed to encounter a few homeless people, especially close to street corners and traffic lights. You don't have to give them money if you don't want to, the ones I saw didn't pester people for spare change.