Ollie is an 11-year-old sixth grader who lives in the rural town of East Evansburg, Vermont. She has her father’s dark eyes and brown hair but inherited her adventurous spirit from her mother. Ollie is highly intelligent, with an eidetic memory and skill as a chess player. She also excels at softball. Since her mother’s death in a plane crash the year earlier, Ollie has retreated from her usual school activities and spends most of her free time riding her bike and immersing herself in books. She doesn’t want to deal with the loss of her mother and hates it when people show her sympathy.

During one of her solitary excursions, Ollie encounters Linda Webster trying to throw a book into Lethe Creek. When Ollie snatches the book away, she sets a chain of events in motion that lead to a supernatural experience with a fearsome figure called the smiling man. Once Ollie reads Small Spaces, she has the knowledge to navigate the alternate dimension where she and her classmates are being held prisoner. In the process, she begins reestablishing her connection to other people by befriending Coco and Brian and trying to rescue the other sixth graders.

Ollie’s refusal to deal with the loss of her mother makes her an ideal candidate for accepting an offer from the smiling man.