After volunteering to participate in a crossword solving competition with a new supercomputer, crossword puzzle editor Tess Harper finds herself swept up into the investigation of the bizarre murder of the tech CEO.

Fired from her job as a reality TV host, Natalie (Lenz) returns home for Valentine's Day only to find herself running the town festival's auction with her ex-fiancé (Macfarlane) thanks to two scheming mothers.

Dave returns to his hometown on the Massachusetts coast for his father's funeral, where his reunion with two old friends provides a healthy dose of reality.