- Jake makes a terrible first impression on Holt and is forced to repeat his robot voice. Holt notes it was terrible and tells Jake he wants him to wear a necktie.
- Holt calls Jake "meep morp" in reference to the robot voice.
- Holt mentions Jake's "overdoing it with the manscaping" when he pulls his shirt up to reveal a tie around his torso.
- Holt assigns Jake to the records room since he didn't brief him about his plan and the perp got away (despite Jake giving him Hazelnut).
- After explaining a breakthrough with the Morgenthau case, Jake stands up for a fist bump and reveals he's only wearing a Speedo from the waist down. Embarrassing Jake again, Holt calls the squad to the records room.
- During their stakeout with Amy, Jake mentions Holt catching the Disco Strangler and then asks why it took him so long to get his first command. Holt reveals to them that it's because he's gay.
- After Holt relays his story, Jake apologizes for being a jackass.
- In the middle of catching the perp, Jake blurts out he finally realized Holt wanted him to wear a tie so that they'd look like a team.
- Holt wonders why Jake looks uncomfortable. It turns out, he's still wearing the Speedo underneath his trousers.
- Jake arrives at the precinct with Holt waiting for him at his desk. Not only does he reprimand Jake for being late, he also points out a lot of his downfalls (sloppy paperwork, messy locker, etc.) and tells Jake to get his act together.
- After mentioning that he and Jake would take Terry's minivan, Jake tells him he doesn't need back-up then Holt corrects him that it isn't back-up, it's babysitting.
- Holt left for the stakeout without Jake. Jake explained it was because he had to put on his minivan disguise. He again scolds Jake for his lack of being serious. Their conversation ends when Jake spots the tagger beside their vehicle.
- Jake talks to Holt about Trevor and his relationship with his father. Holt effectively makes Jake realize he has to arrest Trevor and then Jake says yes when Holt asks him if he needs back-up.
- After Deputy Commissioner Podolski threatens to make Jake's life miserable for arresting his son, Holt steps up in Jake's defense.
- Before Holt starts the morning briefing, Jake is shown to have slept inside a tent in the briefing room. When Holt points out he's not in uniform, Jake pats him and says, "baby steps".
- Holt approaches Jake's desk and before he says anything, Jake tries to guess what he was about to say and states two opposites then concludes that he isn't getting better at reading Holt's expression.
- Announcing that his slump is over after he enters Holt's office, Jake takes a selfie with Holt. Jake then explains that he figured out the case because his mind just rebooted and he was inspired by one of his old cases. Holt gives him a smile.
- Holt gives Jake a pep talk that all talented detectives have their ups and downs to which Jake picks up immediately and says that Holt cannot take back that Hold said he thinks he's talented.
- It turns out, the rabbit's foot Holt gave was only to mess with Jake. Jake takes it that he and Holt are becoming homies.
- Jake says he's gonna regret teaching Holt the "bup-bup-bup-bup" thing when he interrupts him while he was trying to explain himself.
- Jake takes full blame on taking the squad into a crime scene while inebriated. Holt's happy he's learning to be a part of the team.
- Jake and Holt have a bet on whether or not Jake can steal Holt's Medal of Valor by midnight. If Jake loses, he has to do five weekends with no overtime but if Jake wins, Holt does his paper work and publicly announce that he's an amazing detective/genius.
- After Holt agrees to the bet, Jake says, "there's the robot I fell in love with".
- Holt catches Jake hiding in his ceiling which leads to Holt hiding his medal in a safe in a locked cabinet.
- While Jake distracts Holt from entering his office, he comments that Holt has beautiful eyes.
- Holt again catches Jake while he's stuffing pigeons in Holt's air conditioning vent.
- Jake suggest they forget about the bet when Holt catches him in the break room with his keys.
- In the interrogation room where Jake is handcuffed for scaling the building with a blowtorch, Jake explains his plan to Holt. Holt says he's impressed with Jake's plan.
- Holt tells Jake not to call him "cap'n" before Jake relays the story on Dustin Whitman's arrest.
- Jake asks how Holt looks the same even after sleeping in his office. Holt tells him his hair is a mess.
- Holt looks impressed as Jake own up to his mistake and tries to make it up to everyone.
- Holt explains to Jake that while it seemed that the 70s were amazing, it was not a pleasant time with all the prejudice and discrimination.
- Holt makes Jake drink the raw egg yolks Amy gave him since Jake insisted they weren't a hangover cure.
- Jake tells Holt that he punched Jimmy Brogan and Holt gets mad and sends him home.
- It turns out Jake had reason to punch Brogan and it was Amy who had to tell it to Holt. It is revealed Jake punched Brogan because he called Holt a "homo".
- As Amy reads Brogan's article to Jake, Holt interrupts and tells them that Brogan wouldn't know a legit cop if he punched him in the face and Jake smiles infinitesimally.
- Holt immediately figures out Jake is looking for an excuse to not attend Amy's Thanksgiving party.
- Jake works a case with Holt since he agreed to give Jake any open case that would come up.
- Jake gives up after multiple times of getting nothing exciting after saying "punch it!" numerous times. When Jake starts calling out Holt, he steps on the gas, effectively cutting off what Jake was about to say.
- Jake gaves both of them a character to play, Bart Barley and Gerald Jimes. Holt doesn't play along but when they're trying to break a fight he shouts Jimes' backstory that Jake came up with. Jake looks surprised and amused in the background.
- Holt lectures Jake about making a new family with new traditions but Jake brushes him off. By the end of the episode, Jake realizes what Holt said and refers to the 99 as his family in his toast.
- After Holt receives death threats, Jake is assigned to look after Holt where he is in complete control of Holt's movements for his safety.
- Jake gives Holt multiple Secret Service codenames: Stone Eagle, Cold Mountain, and Ice Veins.
- Jake catches Holt leaving the precinct and Holt tells him he only chose Jake as his security escort because the threat isn't real and that Jake wouldn't have any problem breaking rules.
- Jake successfully gets Holt in a safehouse and he handcuffs himself to Holt.
- In the safe house, Holt and Jake engage in various activities to pass the time: Eating, Playing a Wii, and almost watching Safe House.
- After figuring out Holt texted Boyle instead of his husband, Jake changes Holt's code name to Bad Boy.
- Jake knows Holt's tell when he's lying: the corner of his mouth moves.
- Holt insists that Jake, Boyle, and the rest of the squad shouldn't get involved because he should be dealing on it alone, Jake convinces him that he needs the squad.
- Before going to the rail yard, Jake knows he can't convince Holt not to come so he settles on telling Holt to stick with him. Holt simply replies with, "Oh. Goodie."
- Jake tells Holt it was an honor to boss him around and then asks him what cute nickname he calls his husband, Holt replies with "Kevin".
- After Haimes is taken down, Holt compliments Terry and Jake about their nice work. Jake teases him, saying, "Captain, you're doing it. You're emoting."
- Holt tells Jake that he was right for a second time about convincing him to include the team. Jake once again attempts the wave with Holt, and after a few moments, Holt gives in.
- Holt notes Jake's weakness in dealing with Math and offers that the department can provide a math tutor for him. Jake can't detect whether Holt was joking or not.
- Holt helps Jake keep count while doing his push-ups
- Jake continues to point out the lack of emotion in Holt's face.
- Jake mentions how Holt will be happy to know that Terry punched him in the face several times. Holt agrees and says that it does make him happy. Jake walks away after a comment about being candid, Holt smiles to himself.
- Jake says that most humans say "Hello" at the beginning of a conversation. Before Holt dismisses them, Jake starts talking only to be cut off by Holt telling them, "Goodbye". Jake says, "It's learning," as Amy pulls him away.
- Holt talks some sense into Jake while he's complaining about Holt supporting Amy's decision to take the job in Major Crimes.