Hi, thanks for the honest feedback!
The idea with the pudding is that the main character can recruit other characters but can't interact with items, while Dumbo (the 2nd character) can pick up items but won't interact with other characters, therefore - giving the pudding should be done by interacting through the main character. I agree that it isn't very clear at the moment, requires some experiencing and will be emphasized more in the next update of the game, once the voting period is over.
As for the core mechanic, to each his own I guess (: