Jess invents a male alter ego, "Jeff Day," in order to buy a new car from a sexist salesman, but her plan backfires when both Nick and Sam arrive at the dealership pretending to be him. Meanwhile, Schmidt and Cece panic when Winston decides to bring his new prankster girlfriend, Rhonda as his plus one to their wedding.

When Jess gets nervous about starting her new position as principal, Nick and Schmidt decide to take her on a relaxing day trip to Solvang, which quickly goes "sideways." Meanwhile, with Cece's help, Winston tries to finalize his divorce from Rhonda, but finds that he and Aly are caught in a series of never-ending pranks.