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For bell, should I pamper her, punish her, wait till she's done or does it matter, so far I did it 10 times and the event isn't  popping up, or is it once per day? or a bunch of times in one day then sleep and try again?

Just keep collecting milk from her!

as in not asking to milk her but asking for the milk she collected from her "co-workers"? And do you mean even when she says she's out do I keep asking for milk on the same day?

so just keep clicking "collect milk" or 

"ask to milk her"