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Presuming we are not referring to a grocery bill then no. Its a bit extravagant to spend on one person's meal, rather than a group. With people starving every day that's money that could be put to better use than eatting pearl caviar one afternoon at Masa.
Ever heard of Luts dolls before I just mentioned them?
No, I will not remind somebody constantly. I will remind them once or twice. If its very specific like directions or an order then I will put it in writing and give it to them so they can consult it if they forget a detail. If that's not enough then this person is probably not reliable so I would probably not entrust anything to them.
Have you ever received a note from a secret admirer?