Rosa: Wow. You really are an idiot.
Jake: Um, exsqueeze me?

Jake: We're gonna kidnap a cop. But not just any cop it needs to be someone so high-ranking that it sends shockwaves through the system, but not important enough that their absence negatively impacts the NYPD in any way.
Captain C.J. Jason Stentley: Who you guys thinking?
Amy: We're clearly all looking at you.
Captain C.J. Jason Stentley: Oh, God. Am I in charge of the meeting? Dismissed. Dismissed.

Trudy Judy: There's just one problem. I don't have the car. I already handed it off to a fence.
Doug Judy: Oh, Trudy Judy, you screwed me.

Jake: Hey, you made it.
Amy: Yeah.
Jake: We finally got all the Lambda Nus back into holding.
Amy: Who are the Lambda Nus? Doesn't matter. I'll read your notes later.
Jake: I didn't take any notes.
Amy: What the hell, Jake? Do you even love me?
Jake: Says the woman who never once sent me flowers. Never mind.

Jake: And this is rock bottom.
[On the other side of the two-way mirror:]
Madeline Wuntch: Oh, Raymond. This is sad. He's the one you think of like a son, right? Or are you closer to Santiago? Not that it matters. They're both equally going to prison.

Captain Holt: Quote: "The bird that leaves the nest too soon plummets to its death on the concrete below." Captain Raymond Holt, immediately afterwards.

Madeline Wuntch: The only way to get you to trust me is if you thought I was betraying Holt.
Jake: Yeah!
Madeline Wuntch: And now I have access to all your personal correspondence-
Jake: All right!
Madeline Wuntch: Including all stingray authorizations. It's over, Kelly. You're done.
John Kelly: Okay. You may have won this round, Madeline, but you're gonna live to regret it. You are both so gonna live to regret it.
Jake: I agree with what was just said.
Madeline Wuntch: Hey, Jake? I'm just gonna hold this down.
Jake: Yeah, sounds good.

Captain Holt: So what's your plan? Not with chess, with your life moving forward.
Gina: I mean, I could do basically anything. I could come up with a new form of cryptocurrency called GinaCoin, make millions. Could write a YA novel about literally anything, I think, and make millions. I could discover a new type of melon, make millions.

Jenna Pazhley: Don't let her go. You guys, I used to have this boyfriend, Jason, then we broke up 'cause I got drunk at Spring Fling and passed out in a bush, and he took too long to find me, and now he's gone and it's like, there's no one to find me when I pass out in a bush.
Jake: I'm not sure that totally applies here.
Rosa: No, she's right. I can't let Jocelyn go. Can you handle this without me?
Jake: Yeah, it's under control. Go get Jocelyn back. Jocelyn Pryce.

Amy: Why is the FDNY in our cop bar?
Rob Dulubnik: We needed a new place, since our bar, O'Brien's, burned down.
Charles: You couldn't put that out?
Rosa: They probably started it. Most arsonists turn out to be firefighters.
Rob Dulubnik: That's not true, though it is very common, and definitely what happened in this case.

John Kelly: Oh, come on, Madeline. There's no need to gloat. Though, it does feel good. Gloaty, gloat, gloat.
Captain Holt: I knew I never should have trusted you.
Madeline Wuntch: Yes, obviously not, you dum-dum. John, you're gonna wanna remember this. Why don't you snap a photo of him?
John Kelly: Oh, yeah. Yeah.
Madeline Wuntch: Why don't you get in there with him?
John Kelly: Oh, why the heck not? My kids just got me a digital picture frame.
Madeline Wuntch: All right, everybody say, "Nine-Nine."
John Kelly: Nine-Nine.
Madeline Wuntch: Mm. Raymond, I love the scowl, but could you slump your shoulders a bit more? Remember you're a man who just lost everything.

Captain Holt: Check it out. His footprint. Gotcha.
Jake: [whispers] I am Raymond Holt and my brain is rock hard.
Captain Holt: I'm not going to say that.
Jake: Smart. Saving it for a bigger moment in front of a bunch of people. Can't wait!

Gina: Charles, weirdly, you're kind of the person I'm the closest to here. Don't say why.
Charles: Because I was your brother and your lover? Sorry, I can't control my tongue around you.
Gina: All right, well, here.
Charles: The Boyle family mother dough starter! I'll think of you every time I handle her.
Gina: Oh, man. You know, I never really understood the logic behind the two of us. But I love you and I'm gonna miss you.
Charles: I'm gonna miss you too, Gina.

Captain Holt: Wait, the LACMI server isn't wired to the Internet. It's supposed to be offline. How are they accessing it?
Sergeant Knox: They must be going through a physical AP.
Jake: Again, these guys don't get computers like you and I, so-
Sergeant Knox: It's not a remote connection. The hacker's inside the building.

Jake: Look, sir, I've explained this. Wuntch is the only one that can get close to Kelly. We need her.
Captain Holt: Okay. The worm pile stays.