On Brooklyn Nine-Nine Season 2 Episode 23, the season finale, Jake, Amy, Charles and Rosa are assigned to surveil an identity thief. Jake tries to get out of being assigned with Amy, and admits to her that he wanted to ask her out before she told him about her no-cops dating rule. They agree to work together without making it awkward.

However, during their surveillance, the suspect goes on a date to a fancy restaurant, forcing Jake and Amy to pose as an newly-engaged couple to get in. While following him around the restaurant, the suspect spots them, and they share a kiss in order to seem less suspicious.

They follow the suspect to a park where he drops off a briefcase, and are forced to kiss again when spotted. They catch the culprit, but things become awkward between them at the precinct.

Meanwhile, Rosa believes that Charles has helped Marcus plan a surprise birthday party for her, which she hates. However, Charles' plan, which was quite successful, was actually to get Rosa to a surprise private dinner with Marcus.

Back at the precinct, Captain Holt enlists Terry and Gina to help get a copy of an incriminating letter written by Chief Wuntch, which he intends to use as leverage to keep his captaincy at the precinct.  They locate the letter, but Chief Wuntch threatens to disassemble and disperse the entire 99 squad. Holt concedes, with his transfer to public relations taking effect immediately, and he says a heartfelt goodbye to the shocked precinct.

Jake and Amy, reeling from the news and dealing with their respective feelings of abandonment and shock, share a kiss in the evidence room. However, the moment is cut short when Boyle announces that their new captain has arrived.