The Wednesday Wellness threads are meant to encourage users to ask for and provide advice and motivation to improve their lives. It isn't intended as a 'containment thread' and any content which could go here could instead be posted in its own thread. You could post:
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Requests for advice and / or encouragement. On basically any topic and for any scale of problem.
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Advice. This can be in response to a request for advice or just something that you think could be generally useful for many people here.
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You sound like you're getting "don't be irritating" muddled up with "talk to anyone and make them feel comfortable" and given your ruminations it appears the result is something that achieves neither.
Know why you're there. It's not for chitchat. Your grandfather might have been amiable and personable but that's no good if he's occupying the staff with rambling stories, holding up the queue and never getting to the point. A basic "hello, how are you, I'm fine too thanks" are all you need before you get down to business, whether that's stating your problem, placing your order, paying your bill or packing your shopping. If you feel rude not chatting then keep any chitchat superficial and connected to your purpose, eg "thought I'd try making [recipe] for a change" or "hopefully this choice will [achieve task]", not "hey haven't seen you here in a couple of weeks, where did you disappear to?". Also don't wait until you're at the front to get your shit together. You're at the bank to pay a bill, did you bring the bill and the money? You're on the phone to cancel your card, did you collect your account details before calling? You're at the bar to order, do you know what you want? Leaving aside blatant troublemakers like drunks and thieves the annoying customers are the ones who manage to both act over-familiar or over-confident while also performing as if they've never done this transaction before.
In the special circumstances where I've had a need to be charming (like phoning a call centre to ask for an anticipated but entirely justified fee to be waived) I stay polite, organised/timely, non-demanding (I'll phrase it as requesting a rare favour, not as a demand I'll escalate to their manager or as a threat that they'll lose a customer) and gracious.
One small tip for charming workers is to let them be the expert. It's like the opposite of mansplaining. Ask for their input on a product/service. If you're not sure about something own up to it, it gives them the opportunity to demonstrate their own expertise and value.
All this might be different in USA where depending on the context you might have the unspoken threat/promise of tips altering the dynamic. I've never worked a tip job so I can't speak about that.
Edit: I think you've fallen into the binary thinking that if you fail to create a rapport the only other possible perception is that you were irritating. So you end up trying to force a rapport, which in turn serves to be awkward and counterproductive. The solution is to stop worrying about being special and memorable (whether good or bad) and accept being normal and unremarkable. TLDR reduce your ego to the appropriate scale.
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