After a game of Never Have I Ever, Carly fears she is boring and sets out to prove to Harper that she can hold her own on a wild night out on the town. Spencer finds new office space for Freddie's app at the old Groovy Smoothie location.

Carly hires a matchmaker to help Spencer find someone to settle down with, but when he falls for the matchmaker instead, Carly must convince her that Spencer is her type. Freddie is ready to move out on his own, but it won't be easy.