So, I really like
JD's/The Summit's idea about telling people all the nice things you think of them this week. Except...I'm kinda hesitant about it. Because for some reason most of the times I've tried to really encourage someone, tell them I appreciate them, tell them how awesome they are, etc., they've reacted like I'm some kind of creepy
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And about the other question: I'm not sure. I apologize if I've every reacted that way--honestly don't remember an instance--but I've seen it happen. idk. You're quite competent at nice and encouraging (one of the most sincere in my experience, might I add), so I'm not sure why it'd be received poorly. Spur-of-the-moment brainstorming [insert disclaimer here]: maybe people are taken aback by sincere encouragement, because it's so rare. Or maybe people come to expect snark from you, so when they see another side of you, they're confused. Or maybe we're all just wandering in the dark and it's the human condition.
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