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Drippy is assertive. He tells Ollie to get over it because he believes that Ollie can save his mom so all hope is not lost.
Besides, later in the game he gets a skill called Tidy Tears which he'll use at random (usually not at a useful time though in my experience) which heals the whole party and puts a barrier up around them so he's not totally useless. Plus he'll sporadically throw glims into the battle field.
My theme song: http://www.youtube.com/watch?v=SBjQ9tuuTJQ Most people think they are the odd one out but never truly are. I am that one who actually is. :D
I could see where he might get annoying after about 30 or 40 hours, but right now,at maybe twelve hours in, I'm finding him very entertaining. I like the little bits of "business" he does in the background in some scenes where Ollie is having talks with NPCs, like when he's trying on a lady's hat while Ollie is talking to Myrtle and her Dad. I actually LOL'd at that. (well, more of a giggle, really)