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If you really want to help and it makes you feel good, go ahead. But don’t let people pressure you.
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Ugh I’m sorry that happened to you!
I live in a city and do a fair amount of outreach to the homeless. Many of the people who are street homeless are in that situation because shelters have rules about who they cannot accept (sex offenders, violent criminals, etc). If you really feel guilty, give to an organization and not directly. It’s unsafe and will likely just have them harassing you more (esp. with digital payment)
FWIW whenever I see anyone give money to people on the street my opinion of them goes up 1000%
I basically swoon when my boyfriend does it.
As a New Yorker, whenever I seen anyone give money, my brain just jumps to “naive tourist”
In Nashville where I live there’s a program where homeless people can sell a newspaper called The Contributor. I know there are some program requirements and they also give them other assistance. I buy from these people every time I see them and sometimes get them a coffee or fast food meal. They accept Venmo and I know the money goes to people truly in need. I think it’s a really cool program and wonder if other places have something like it.
I never give out money directly to people, you don’t know what they’re doing to do with it. If I feel like I want to, I look up local organizations to donate to instead. I also always give away leftovers from eating out (pre pandemic anyway)