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.
When Jess insists on covering Robby's medical bill, she is stunned after finding out the total and goes to extremes to find a way to help pay. With Schmidt and Winston's help, Cece attempts to get her new modeling agency off the ground (and out of the loft), but is discouraged when her first client is inspired to change career paths. Meanwhile, Reagan puts off reading Nick's new novel.
Jess struggles to keep the loft's Secret Santa gift exchange afloat. When Winston believes his online gift order for Cece won't be delivered in time, he and Schmidt must endure going to an actual store to find a replacement gift. Meanwhile, Reagan surprises Nick, who helps makes Jess' Christmas one to remember.
It's Thanksgiving and Jess and the gang are determined to make this year's festivities a success. However, things don't go according to plan when Robby surprisingly shows up and Schmidt's dad arrives heartbroken. Meanwhile, Nick finds out that Regan is postponing her move-in date and Winston deals with his "heroic" injury.
Jess and the gang head to New York, where Schmidt believes he is being honored at his high school. Jess meets Det. Jake Peralta and helps him on a case, which leads her to Brooklyn’s 99th Precinct and a fateful encounter with Gina Linetti and Capt. Raymond Holt. Meanwhile, Nick and Winston scramble to make subway fare, while trying to impress Det. Charles Boyle, and Cece faces off with her new mother-in-law. The crossover starts on Brooklyn Nine-Nine S04E04 The Night Shift (I).