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Does Lily gain more weight? I have reached where I take help from Jamie but after that, Lily does not gain weight at all. Can anyone help?

Im pretty sure thats the stage where you have to wander in the park and then purchase a vat of ice cream for the vendor, then you see lily afterwards to feed it to her.

What about after that, do I have to keep feeding her for next couple of days

If I remember correctly you keep feeding her the vats of ice cream and there should be an event after like 3 or 4 times