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.

Charles: Hey, Rosa, are you ready to go streaking?
Rosa: What?
Charles: That's what my dad and I called getting blonde streaks in your hair. We used to do it to our ponytails on road trips. You just take a little lemon up top, and let the sun do the rest. We called it giving each other road head.
Rosa: You just said you called it going streaking.
Charles: It had a couple names.

Charles: Are you blackmailing me? I don't have any money, Hitchcock. I'm still paying my uncle's funeral bills. I rear-ended the hearse. It was a mess.

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.