Nick becomes irresponsible with the money from his late father's estate, so Jess uses some of the money to pay Nick's unpaid bills, behind his back. With Nick's improved financial situation, Winston feels its finally time to ask Nick for the money he owes him.

Jess is ready to paint the town purple when a chance encounter finds her and best friend Cece invited to a once-in-a-lifetime mansion party thrown by music legend Prince. Not wanting to miss out on the fun, Nick, Schmidt, Winston and Coach are determined to crash the festivities, building toward an Unforgettable ending.

Jess and Nick invite the gang along with them on a cruise they booked while still together as a couple.

When Coach's liaison with the school nurse gets messy, vice principal Jess must enforce a new, "no fraternization" policy among the teachers. But the tables soon get turned when she finds herself attracted to the hot new science teacher. Meanwhile, Nick is enjoying being Schmidt and Winston's secretary, after the loft gets a new home phone

Nick and Coach become concerned when they meet Winston's new training officer; Jess uses Schmidt in hope of influencing a councilwoman to stop the night construction taking place outside the loft.

Fawn takes Jess to a charity golf tournament, but the Vice Principal lands in the sand trap in her attempts to make a good impression. Meanwhile, Winston meets a beautiful woman and must lie about being a cop.

With Jess sequestered at jury duty, Nick turns the loft into an airbnb in order to help pay for Schmidt's upcoming bachelor party. Meanwhile, Winston asks Cece for help when he suspects KC is cheating on him.

Nick's cousin and his wife visit with a very special request, which prompts Schmidt to offer Nick a glimpse into the future. Meanwhile, Winston and Cece shop for a wedding dress.

Schmidt enlists Nick to help him earn the respect of his difficult house contractor. Meanwhile, as Jess and Robby test the limits of their ability to be in a casual relationship, Winston and Cece debate the pros and cons of not being single.

As Jess continues to stay with her dad in Portland, they unexpectedly help one another with their love lives. Meanwhile, Nick turns to a reluctant Aly for help with his relationship with Reagan, and Schmidt contemplates using his first name.