When Rosa arrives at work wearing a pink shirt, nobody says anything to her as she scares them. Boyle, who is frequently the butt of their jokes, is annoyed at the double standard, but backs down from talking about Rosa's pink shirt when she intimidates him.

Captain Holt gives the squad a briefing on a joint investigation with the 93rd precinct. Jake is excited to hear Detective Dave Majors, the NYPD's best detective, will be joining them for the case. Holt assigns Amy and Jake to work the case with Majors. Later, Gina goes to Captain Holt's office to warn him a recruiter from a private security firm has just arrived. Having been chased by the industry reps for years, Holt is ready to bat away the recruiter, until he says he's there because Sergeant Jeffords reached out to him.

Jake and Amy excitedly wait for Det. Dave Majors at the crime scene. They're figuring out how best to impress Majors and, when he arrives, they try to out do each other at dazzling him. Back at the precinct, Gina attracts Charles's attention as Terry returns from his lunch with the private security recruiter. Terry admits to them that he is excited by the offer and all the free gear he received. Sergeant Jeffords says he's considering saying yes to the job offer.

As Jake, Amy and Det. Majors check out a van implicated in the crime, Majors invites Jake out for an after-work drink. At a secret and exclusive speakeasy, Majors tells Jake he's planning to ask Amy out after the case ends. The next day at work, Jake admits to Rosa that he still likes Amy, but he told Majors to go for it anyway.

When Holt asks to see Gina and Charles with questions over some of their requisition forms, they admit they're throwing a "Please Stay" party for Terry as they fear he's about to accept the job. Meanwhile, Jake arrives at the forensic lab where Amy and Majors are discussing the case. Jake asks to speak to Amy privately, but he has trouble getting to his point. Majors interrupts to say their criminal has struck again. Meanwhile, Boyle and Gina go to Terry's desk to win him over with homemade yogurt. Although he sees through their ruse, he's loving the attention all the same. Captain Holt, who didn't get the kindness memo, orders Terry to digitize old case records by tomorrow, disrupting his plans for a romantic evening with his wife.

Majors, Amy and Jake struggle to figure out the case in the evidence room. After Majors leaves to grab some coffee, Jake wants to tell Amy how he feels. As a tongue tied Jake tries to talk to Amy, he figures out how the robberies are connected and solves the case. Back at his desk, Jake talks to Rosa about his disappointment at solving the case before he had a chance to tell Amy his feelings for her. Rosa wonders whether Amy's done the "double tuck" with her hair that means she likes a guy. When Jake says Amy hasn't done it yet, Rosa says there's still time so Jake should go and ruin Amy and Majors night before anything happens between them.

In the records room, Gina and Boyle help Terry finish digitizing his files so he can go have dinner with his wife. When Holt arrives, he's angry that Gina and Charles did Terry's work for him. Holt orders Terry to spend all night digitizing more files, this time alone. Elsewhere, Jake struggles to gain access to the speakeasy. When he sneaks in, he's disappointed to see Amy, sitting with Majors, do the double tuck with her hair that indicates she likes a guy.

The next morning, when Terry returns from breakfast with the recruiter, he tells the squad he's not leaving. When Captain Holt celebrates Terry's decision to stay, Gina thinks Holt's changed his tune after trying to push him out. After Terry says Holt's the reason he's staying, he claims not to know what Terry's talking about, but he can't keep up the charade for long. Terry says Holt making him go through the case files made him realize how much good he's done as a police officer.

When Majors arrives at the precinct, he thanks Jake for his work on the case. After Jake asks how his date with Amy went, Majors says she wasn't in to it. On Rosa's advice, Jake goes to ask Amy why she said no. Amy tells Jake she has a new rule not to date cops after everything that happened with Teddy. Jake tries to be cool about Amy's rule and says he has the same idea. As Amy watches Jake leave the room, she does the double tuck with her hair.