what are some questions to avoid asking people you meet traveling?

You're overthinking this one but here's my 2 cents.
I've never had a problem asking travelers and home bums for advice. The very first time I had to sleep on the streets I just walked up to the guy who was asleep on the bench at a local school... (who I've now known for 10+ years and consider a friend) and asked him where was it safe to sleep. He gave me the advice I needed and we became lifelong friends. People can see through you and they know if you're legit. Develop those skills (takes time) but it will help you immensely in navigating this world. And always be kind. Leave situations that feel uncomfortable. It's something that definitely has to be honed. No one picks up a guitar and just knows how to play.
 
You're overthinking this one but here's my 2 cents.
I've never had a problem asking travelers and home bums for advice. The very first time I had to sleep on the streets I just walked up to the guy who was asleep on the bench at a local school... (who I've now known for 10+ years and consider a friend) and asked him where was it safe to sleep. He gave me the advice I needed and we became lifelong friends. People can see through you and they know if you're legit. Develop those skills (takes time) but it will help you immensely in navigating this world. And always be kind. Leave situations that feel uncomfortable. It's something that definitely has to be honed. No one picks up a guitar and just knows how to play.
Just pick a bridge near the tracks
 
From my experience, I try to get to know the person first and share laughs before I think to ask them harder hitting questions. Feel em out and make conversation first before trying to glean any particular information.
 
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