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Clearly you've spent cycles thinking about this. I just do whichever happens first. If I go first, I anyway order a coffee and sit. If we go together, I offer to get it for both but if the other person offers over it, I just cave. Also, I feel no obligation to match the coffee or whatever later because I walk around thinking that the conversation itself is interesting / entertaining / fun in itself that it paid for the coffee 😂

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