Charles: I'm so sorry, I just got some bad news. My sister was gonna go with me to an engagement party but she had to cancel.
Rosa: So go alone. Maybe you'll meet some new bag.
Charles: It's my ex-wife Eleanor's engagement party. I can't go alone. I'm worried it might seem a little pathetic.
Rosa: Yeah, if only you could've gone with your sister.

Rosa: Dude, why are you going to your ex-wife's engagement party at all?
Charles: She and her fiance, Hercules, are also my landlords. I mean, it's not like I can avoid them. I live in their basement.

Captain Holt: Interesting. I will attempt to cooperate with you. Under these new circumstances.
Madeline Wuntch: Don't sweet-talk me, Holt.
Captain Holt: I gave it my best shot. Let's begin.

Gina: Jake, I am so scared that man is about to make a huge mistake, RE: his vas deferens.

Jake: I know, he made me promise to not let him get that surgery. And it wasn't just the drugs. He doesn't want this. As his friend, it's my job to stop him. [screams] Sorry, Terry turned my spine into a loose stack of pebbles.

Captain Holt: And since my arrival, violent crime has gone down by 17.3%, as you can see here.
Madeline Wuntch: Two-toned graphs? You think you can distract me from the precinct's problems with a flashy presentation? Same old Ray Holt. All sizzle, no steak.

Captain Holt: We were doomed the minute she slithered into the precinct. It's funny. When we first met, we had some good times.
[flashback:]
Captain Holt: Looks like we both want that stapler.
Madeline Wuntch: Seems that way based on what happened.
[Holt and Wuntch chuckle]

[flashback:]
Captain Holt: Madeline. Would you care for a drink?
Madeline Wuntch: I'd love one.
Captain Holt: I'm sure you can tell I'm quite drunk. I've had a couple to build up the nerve. I think we both know what I'm about to say.
Madeline Wuntch: Raymond, I don't think we need to say anything. [undresses]
Captain Holt: I'm gay. That's what I was going to tell you.
Madeline Wuntch: Well, then.
[present:]
Captain Holt: She sabotaged my career because I refused to bed her.

Sergeant Jeffords: Have you seen this man around DRK MLK?
Woman: Oh, I don't go there. They don't allow babies in there.
Jake: What is wrong with them? All I drank when I was a baby was chocolate milk.

Amy: Excuse me, captain, I don't want to say that I saved the day, but I will because I did. So... The letter of recommendation she wrote for you 25 years ago.
Captain Holt: Where'd you get this?
Amy: I just went down to one police plaza and applied some of my signature Amy charm.
Gina: And then when you wouldn't stop, they just gave it to you?
Amy: More or less.

Amy: You're just gonna let her fail us?
Captain Holt: I'm sorry about your precious grade, Santiago, but this isn't about you.
Amy: Don't "this isn't about you" me! I'm "this isn't about you"-ing you!

Captain Holt: I attempted to cajole her but she rebuffed me. I'm not a man of unlimited cajoling.
Amy: Well, you better become one because I need you in command. This precinct needs you in command. Cajole up, captain.

Rosa: Here's what's about to happen. We're gonna go to this terrible party, I'm gonna laugh at all your jokes, gonna talk about your medal of valor, and I'm gonna make you look like a Jamaican God of rhythm.
Charles: Sebastian from the little mermaid.
Rosa: Also, tomorrow, I'm gonna help you find a new apartment. You can't live in your ex-wife's basement anymore.
Charles: Wow! Respect, mon. I'm gonna read you my toast in the car.
Rosa: You're giving a toast?
Charles: More like we're giving a toast.

Sergeant Jeffords: Jake, I have to tell you something.
Jake: Oh, boy.
Sergeant Jeffords: I am a little conflicted about having a vasectomy.
Jake: Really? Is that why you threw an EKG machine at the doctor?
Sergeant Jeffords: I'm sorry I thought of you as a work friend. You're here, man. You're a friend friend. You made Terry get real with himself and his genitals. Your tiny head has a big heart inside it.
Jake: I know that's scientifically wrong, but thanks, sarge.

Jake: Hey, Rosa, just who I was looking for. Quick question, can I have your friend Katie's phone number? I want to ask her out.
Rosa: No, I don't mix personal and professional. You're never getting her number.
Jake: Never like, "we're never gonna have a black President" never? 'Cause that happened.
Rosa: A real never. Like if you ever ask me about this again, you're never gonna be able to eat without a straw.
Jake: Yeah, okay, well you are on the wrong side of history, my friend.