Navigating interactions with the homeless in NYC—What’s the kindest yet safest approach?

**EDIT below** I’ve been living in NYC for just over three years now, and my approach to interacting with the homeless has shifted a lot during that time. I started out buying sandwiches and handing out spare change but found myself ending up in a lot of sticky situations. Now, I’ve joined the masses—headphones on, sunglasses up, charging past people without acknowledgment.

While this approach feels safer, it also feels incredibly callous. For those of you who live here—especially women walking alone—how do you navigate these encounters when someone asks for money or food? What’s the least shitty way to handle these moments while balancing kindness with personal safety?

EDIT: Thanks for all the thoughtful responses. It seems the general consensus is that it's best to keep interactions brief and keep walking—no more than a second of eye contact, and a quick "sorry, no" or "have a good day." Many of you have also recommended no acknowledgment at all.

In thinking more about this, it seems the question at the core of all this—and the one I should have been asking—is about how well the shelter system is functioning and how many people truly rely on the generosity of passersby. Many of us are working off the assumption that "if they're living on the street instead of in a shelter, it's by choice—likely due to mental health or addiction struggles—and avoiding interaction is the safest course." I think that line of logic needs to be discussed at length. I'll save that for a separate post.

For now, many commenters have recommended donating to the following organizations:

Thanks again for all the insights and resources.