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> What if all they need is one single person to say hi?

Then say 'hi'. By definition they're not going to seek you out nor are they going to be findable so you're only option is to say hi to everyone and hope one sticks.

edit: heh i hope you're not talking about me, i walk to the grocery store regularly by myself. It's how a take a break from work and get some exercise. i'm fine :)

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That's my point. How can I tell the difference?

One of my ideas was legitimately to just hold a giant sign that just says "hi"

I had this idea a few months ago, but never wanted to waste a whole Sunday on it. Maybe I should.

To me that seems like not saying hi, rather a device to shift the risk of engaging off of you. Don't be scared. Just say a few banal words to people you don't know every day and gauge their reaction, start a conversation if you like and they seem to be up for it.

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