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I've been making a more conscious effort to say hi and make some small talk to people I walk by on trails. Being a sperg for most of my life, putting my head down in my phone or looking away when passing other people is habitual. Nowadays I take my headphones out and try and force myself to at the very least acknowledge people with a head nod when hiking. I tend to feel better as opposed to my usual habits.
Agreed that boomers are usually very receptive to a conversation. People my age or lower tend to be hit or miss.
