Former prom king Scott returns home for Thanksgiving break and gets dumped by his long-term girlfriend. With his world turned upside down, Scott strikes an unlikely friendship with former classmate Tori, an ugly duckling who blossomed in her first semester of college, and they embark on an outrageous adventure through their hometown. But when Scott and Tori start falling in love, they realize that a few months away may have changed them more than they realized.

Leigh, feeling unfulfilled, quits her reporter job in New York and returns to the place she last felt happy: her childhood home in Connecticut. She takes a job as a lifeguard, regresses into adolescent behavior, and begins a dangerous relationship with a troubled teenager, leading to consequences for everyone involved.