The summer after Audrey graduates from high school, her world is changed forever when an attractive young man named Mookie (Justin Long) moves in next door with his mother Mary (Gina Gershon) and her fiancée, Herb (Chris Mulkey). Knowing how much Calista longs for romance, Audrey encourages Mookie to ask Calista on a date. He obliges, and he and Calista soon become a couple. Audrey, however, finds herself developing feelings for Mookie, and as these feelings grow it becomes harder and harder to remain the dependable, selfless person that her father and best friend have always counted on her to be.

Dreamland is the story of a young woman who has taken care of everyone around her but ultimately learns to take care of herself. It is also the story of how those whose lives she touched must find the strength to let her go.