Charles: Oh, you're right. I'm gonna tell him. It might not be today. It might not be tomorrow. It definitely won't be later than tomorrow. So pretty much today or tomorrow then.

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.

Captain Holt: I was trying to shield you. Do you know how much stress I've been under lately? My husband says he hasn't seen me smile in weeks.
Sergeant Jeffords: How much did you smile before that?
Captain Holt: Constantly.

Jake: So, now that we are alone. I have to ask. Did you arrest a perp named Joe Uterus?
Amy: Oh my god, yes. I should have told you immediately. Perp name Hall of Fame, right?
Jake: Oh, yeah. First ballot. It was right up there with Sylvester Stools and Janet Stalkmuncher.

Captain Holt: Resume the drill, Timmy. And do not say or do anything a seven-year-old boy would not say or do. Feel free to consult the script I've prepared.
Sergeant Jeffords: Okay, but it's a little stilted. "I am feeling trepidation at the prospect of a parent-less existence." No kid talks like that.
Captain Holt: Those lines were lifted verbatim from my childhood diary.