Jake: That's so bitter. What's wrong with this chocolate milk?
Store Owner: Dark milk isn't chocolate milk. This is teat-to-mouth raw cow's milk. The bitterness of the chocolate brings out the sourness in the milk.
Jake: That's the worst part of both of those things.

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.

Jake: I would give you more details, but someone just came in to try and find her dalmatian coat.
Madeline Wuntch: Hello, Raymond.

Jake: How much could I possibly owe you? Fifty, sixty bucks?
Sergeant Jeffords: Two thousand, four hundred and thirty seven dollars.
Jake: Dollars?! Wait, of course dollars. Why was that the part I was surprised by?

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.

Jake: And our second option is surveillance footage of Detective Amy Santiago soliciting drugs using perfect grammar.
Amy: It's not that weird to say, "may I have some cocaine?"
Jake: It is.

Gina: Jake, why don't you just do the right thing and jump out a window? Captain Holt will never fire me if he knows I'm mourning the death of a close friend.

Jake: "Uh-oh, hope it doesn't get too sexual." Title of your sex tape. But seriously, what is taking so long. Also the title of your sex tape.

Sergeant Jeffords: We've got to make this place kid-friendly. No crime scene photos lying about.
Hitchcock: That's not a crime scene. That's a boudouir photo I'm having framed for my wife. That's me underneath the mask.

Jake: Captain, quick update. Another one of the Fulton Street Four was murdered here this morning.
Captain Holt: Huh. I'm surprised you're not celebrating inappropriately.
Jake: This is a crime scene and I'm a professional.
Captain Holt: You did it before I showed up?
Jake: Yep, that is exactly correct.

Captain Holt: Marcus, Detective Diaz, what a surprise. I didn't expect you for another nine and a half minutes.
Rosa: See, told you it was rude to be early. Well, let's cancel the entire evening and try again next year.

Captain Holt: Gina, you know I appreciate you, but you have to admit we're not exactly cut from the same cloth.
Gina: Apparently not. I am, of course, exotic silk, where you, sir, are snake skin.

Captain Holt: Wuntchtime is over. Boom! Did it. Had it both ways. No regrets.

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.

Sergeant Jeffords: Plus, the longer I stay out of my house today, the better. My brother-in-law, Zeke, is in town.
Captain Holt: Oh, I remember Zeke. Large gentleman. Calls you Tiny Terry.
Sergeant Jeffords: Also teensie Terry, Teeny Weeny Terry Berry, and Little Dumb Dumb. You know, it's that lack of effort on the last one that really gets me.