
Charles tried to get close to Rosa, but she made it clear she only thought of him as a friend. In the beginning, Charles had a crush on Rosa, even though she did not feel the same way about him.

He admitted to her that he would have liked something to happen between them, romantic-styles, if she wasn't already in a relationship. When Jake agreed to lead an undercover mission for the FBI, Jake said goodbye to Amy in the precinct's car park. Seeing Amy and Teddy together in a relationship, Jake threw himself into his work, obsessing about a supposedly "unsolvable" case. It looked like Jake would finally ask Amy out, but he aborted the plan when Amy mentioned she was back together with Teddy. When Jake wondered why Amy was with Teddy, Boyle told him it's because he actually asked her out. Seeing Amy with Teddy, Jake started to confront his feelings for her. Amy had only broken up with Teddy because he was stationed in Queens, so she never got to see him. When the squad attended a training course at a tactical village, Amy ran into a fellow police officer, Teddy Wells, who she used to date. Despite Jake's attempts to make it a horrible date, Amy described it as "good" because they caught bad guys. Jake and Amy successfully caught the criminals together. When the Captain called Jake and offered to send in a relief squad, Jake turned it down. Jake and Amy bonded as they watched over the drop site. Unable to reschedule his date, Jake took Amy with him on the stakeout. During the date, the Captain ordered Jake to go stake out a drop site. Charles could see that Jake's huge effort was more than just a childish joke and that Jake clearly liked Amy. He had an elaborate evening planned which included renting a tiger cub, hiring a youth choir, and going to a photo studio. Jake promised to take Amy on the worst date in the history of the world. Jake and Amy rushed to get as many arrests as possible before their bet ended. According to the terms of the bet, if Amy won she would get Jake's Mustang, while if Jake won he would get to take Amy out on a date in said car. Jake and AmyĪt the start of the series, Jake and Amy were competitive colleagues who had an ongoing bet over who would solve the most cases. The show's early episodes focus on Captain Holt, whose ambition to have his own precinct has finally come true, trying to fix up the precinct and improve its performance.

The strict new captain clashes with the precinct's star cop, Jake Peralta, whose great detective skills are let down by his immature and care-free attitude.

Brooklyn Nine-Nine begins when a new captain, Raymond Holt, is assigned to the ninety-ninth precinct.
