Charles: Was it a mistake, Sarge? Or was it a stroke of brilliance?
Sergeant Jeffords: What are you talking about?
Charles: Look, you're a good actor. You could even be a great one. But you're too gentle. Life hasn't kicked you around enough.
Sergeant Jeffords: I mean, I grew up poor, and my father was emotionally abusive.
Charles: It's not enough. You needed to be rejected by me, a man you admire so much.
Sergeant Jeffords: What?

Sergeant Jeffords: So we have good news, and we have bad news.
Charles: My Nana always said, "Bad news first because the good news is probably a lie." Fun fact: she made me cry a lot.

Sergeant Jeffords: Boyle! Were you dreaming about Jake again?
Charles: Why did you wake me up?! I told you never to wake me up!

Charles: Is the equipment secure?
Jake: Check.
Charles: Weapon loaded?
Jake: Check.
Charles: Did you have breakfast?
Jake: What? That's not on the checklist.
Charles: I added it because I care about you.
Jake: No, I did not have breakfast.
Charles: Unacceptable. Look in your pocket.
Jake: Hey, there's little chocolate chips in this.
Charles: Yeah, I'm not an idiot. I know how to trick my best friend into eating his fiber.

Charles: I want to send someone into holding, undercover as a perp, to see if they can get him to open up.
Sergeant Jeffords: Why don't you do it? You're always going on about your acting abilities and that time you played Annie.
Charles: I'm an adult man, Sarge. I didn't play Annie. I was in "Annie." I played Miss Hannigan.

Charles: Hey, Captain, Sarge, I have a case I want to discuss with you.
Captain Holt: You want to talk about work in the break room? That's highly unorthodox, but I suppose we can give it a try.
Charles: Okay, so I have a perp-
Captain Holt: I'm sorry, this is insane. Let's talk in my office.

Jake: Ames, super important question. Which one of these shirts should I wear to dinner with your mom tonight?
Rosa: Those are exactly the same.
Jake: I have a signature look, Rosa.