Scenario: The other day I was downtown and needed to let my toddler daughter out of the stroller to stretch her legs before putting her back into the car (it had been hours). The only green area/park for her to walk around in often has what appear to be homeless people in it (they don’t live there, but they hang out there on the benches and talk). Maybe transient people would be a better word? Or beggars (not PC term, sorry!) But there were cops present making conversation with them and so I felt like it was fine to let her walk around a bit to stretch her legs (while holding my hand). Note that this is not an unsafe area. People from downtown regularly walk through this park constantly, farmers markets are held there, and it’s in a town with a very low crime rate, mostly like a hippie town kind of. Anyways, two or three of these people eventually came up to talk to me and my daughter. We made small talk, and a couple of them asked her for high fives (she obliged two out of three).

My dilemma is this: I want to raise a child who doesn’t judge people by things like being homeless or what not. But I also want her to have street smarts about what’s a safe or potentially unsafe situation. One of the men who wanted a high five had a visibly dirty hand. I cringed internally but didn’t want to be rude to this man who was being nothing but kind to my daughter and I. In the end, my thought process was that a dirty high five isn’t going to hurt my kid. I want her to be respectful of other people and their feelings and also be safe at the same time.

What are your thoughts? Am I crazy for letting my daughter high five a stranger with a dirty hand? Was I crazy to even let her walk around there? How do I raise a kid who respects others for wherever they are in life but still stays safe at the same time? I don’t want her to think the homeless/beggars are yucky people that aren’t worthy of a smile or conversation. But I want her to be safe too.