I don't mind milking the awkwardness! Rusty will probably be bold or direct in general, he knows what he wants and nothing stops him. Until it comes to some girl he thinks is cute and nice. Then it gets hard for him, which makes things fun since he'll be tongue tied or just awkward around her.  Though of course things developing would be good too, I wouldn't want it to just be pure awkwardness and obliviousness the whole way through, personally.