10SEASON 2, EPISODE 23: "JOHNNY AND DORA"
Following a number of hurdles that included an undercover operation and ill-timed relationships, Detectives Jake Peralta (Andy Samberg) and Amy Santiago (Melissa Fumero) were both finally single when Santiago declared no more relationships with cops just as Jake was about to make his move.
They would then awkwardly go undercover as
newly engaged couple "Johnny and Dora," resulting in a couple of fake make-out sessions before Jake and May's first official kiss. This episode also featured an incredibly emotional moment from Detective Raymond Holt (Andre Braugher) who was forced to leave the Nine-Nine by his recurring nemesis Madeline Wuntch (Kyra Sedgewick) in order to save his squad from being split up.