Twenty-nine year old Leigh (Kristen Bell) has the realization that her life in New York is far from a fairy tale. Her boss, who is also her lover, trivializes her work and then to add insult to injury he gets engaged. With happiness surprisingly absent from her life, she returns to the safe haven of her childhood home in Connecticut. Her parents allow her to move back in, but insist she pull her weight and find a job. In her pursuit of a life of happiness, Leigh reverts to her teenage lifestyle and immediately reconnects with her high-school friends that never left town. Todd (Martin Starr) is her gay best friend who has never come out of the closet. Mel (Mamie Gummer) is in the process of trying to start a family with her husband. With Leigh leading the way, Todd and Mel slip back into their old teenage ways as well. Leigh regains the job she had a high-school student - lifeguard at a condo-complex. While there, she meets a group of troubled teenage boys, including sixteen year old Little Jason (David Lambert) with whom she begins an illicit affair. Little Jason and his friend Matt (Alex Shaffer) are determined to drop out of school and make their way to Vermont. Leigh, Mel, and Todd all urge the boys not to go, but there is no convincing them. Leigh's regression starts to take a toll on others. Enjoying the carefree life, Mel starts pulling back from the relationship she is in. Todd takes a cue from Leigh and eyes a young boy. When Matt is ready to go to Vermont, Little Jason backs out and asks Matt for more time. Leigh's father, who is fully enjoying having his daughter back home, starts neglecting other plans he had while her mother feels like she's picking up the slack for everyone. It is up to Leigh to find herself and get her friends and family back on their right tracks.