Winter is closing in, and with it comes a new set of problems. Ruby is afraid of the dark, and older brother Joe enjoys taking advantage of this by giving her scares whenever he can. The fabulous Holly points out that everyone is afraid of something. True as this turns out to be, it doesn't really help Ruby, especially when she discovers that her babysitter is even more afraid of the dark than she is!
On top of that, it's the school play and Ruby also has to confront her stage fright. And then, when things really can't get any worse, Joe is still going out with that awful girl, Tiffany. Why, oh why, won't he come to his senses, dump her and go out with the wacky, witty and wonderful Holly?