Fred Savage's real-life brother Ben plays the seventh-grader who delivers the Valentine to the wrong locker. Danica McKellar's real-life sister, Crystal, also reprises her role as Becky Slater.
The title is based on the mob hit called The Saint Valentine's Day massacre concerning the death of seven people as part of a Prohibition Era conflict between two powerful criminal gangs in Chicago, Illinois, in the winter of 1929.