Doesn’t mean someone isn’t struggling somehow in some way. It was clear to me at the time that she wasn’t doing well in some way. But I agree with you, she just wanted money and harassed me for it.

Trying to give someone the benefit of the doubt, but I hear you. Probably not the case

I once had a woman directly approach me at North Station, look me dead in the eye and go:

“Can you buy me a ticket to Portland”

Me, unable to leave the situation: “No, I’m sorry no cash”

Her: “The ATM is around the corner. Please? It’s not even that expensive!”

Me: “I’m sorry, I’m not going to get cash from an ATM for you”

Her: “Aw come on half? I’ll walk with you to buy it”

Me, very annoyed: “Look, I said no, please stop harassing me”

Her: “I’m not harassing you! Just buy me the ticket”

Me: “I said no, please get out of my face”

Her, walking away “Nobody wants to help a old fucking grandma”

I don’t want to be critical of this woman as I’m sure she is/was struggling, but I was really just trying to go home and wanted to listen to music. As a society I truly believe we should be doing more for these people, I am not the right person to find a solution but I do know having them on the street is a bad deal for everyone. Especially those who are experiencing homeless on these cold winter nights.