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In addition to janitors & wait staff: you can chat with the homeless people, too. You don't have to ask them about "their situation" or offer to help them. Weather, sports, the traffic... just treat them like a person who's not invisible.

Before anyone jumps up & objects: yes, there are a lot of homeless who don't want to talk to you, or who are downright dangerous. You can avoid those.

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How do you pick out someone as being homeless? I'm in the UK and (accepting in the US it may be different?) there is a common misconception that people who sit in shop doorways begging for money are 'homeless' people when, in fact, they are usually just people who have a drug habit they need to continually finance.

The real homeless people are doing their best to blend into the background and not to look homeless.

[I used to be such a person]

If you like to talk to people with a drug habit who just want your money, be my guest. It might be a rather focused conversation, though.

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