Winston: A-ha! You see this whole time, y'all thought you were having breakfast with Winston, but it turns out y'all been sitting with James Wonder. I'm talking about my alias. See, I'm thinking about applying for undercover work.
Jess: That sounds incredibly dangerous.
Winston: Well, not if I go deep enough into my undercover character. I've been practicing on y'all unknowin' asses. I combined the names of my favorite singers... Stevie Wonder and James Blunt. And I put those together to create a different name as my alias, James Wonder.
Jess: I'm worried you're not the undercover type of guy. I feel like if you had the ability to pretend to be someone else, you would have made that decision a long time ago. I feel like that sounded harsh, but it's only 'cause I care about you.

Winston: Jess, you don't want to talk at a funeral. I've tried that once.
[flashback:]
Winston: What kind of dummy fixes a washing machine using a knife? [points to casket] This kind of dummy!
[present:]
Winston: It did not go well.

Winston: Joanie... [chuckles] I don't want to lie to you, so I'm not... There's shells all in these eggs.

Camilla: Are you really gonna let her get away with this? You must know how this makes me feel. You've clearly been dumped many times.
Winston: Why do people keep saying that?
Camilla: You ordered a Shirley Temple.
Winston: It's a virgin Denzel.

Winston: Look, this might not be the right time to say this, you guys, but, uh, should we take a straw poll on this whole Cosby thing?

Winston: Here's what I was thinking, okay? If we want to win this concert, we play something cool, like "Eye of the Tiger."
Girl: What's "Eye of the Tiger"?
Winston: "Eye of the Tiger" is the greatest song ever written. It's so cool, it ended the Cold War.
Jess: That's not even a little bit true.

Winston: So, um... your place or mine?
Shelby: [laughs]
Winston: What are we laughing at?
Shelby: How much I'm not going home with you tonight. [laughs] You show up after two years, out of the blue, and all you do is talk about yourself. You don't even let me get a word in edgewise.
Winston: Why did you agree to let me take you out for drinks?
Shelby: Winston, you took me out for a drink at the place where I work! Here's your bill. Thanks for the water.
Winston: Man, I told you to get yourself whatever you wanted. You chose water.

Woman: This sangria is amazing, Winston.
Winston: My grandmother's recipe, so I can't take credit for that. But seriously, Tia, you don't want a man who has fancier underpants than you.
Shelby: I keep trying to tell her that.
Tia: It's true.
Winston: You want to have the fanciest drawers in the relationship. Boom.

Winston: Okay, this is a good segue. [sighs] Um, can I talk to you about something that's kind of tough?
Nick: Yeah, man, shoot.
Winston: [reading] "The subject of this talk is the debt of money between us. I feel that..."
Nick: Oh, man! I thought this was about something serious. You set that up like it was about something different. This is about the poker? Oh, I'll pay you your money. Relax.
Winston: "If I am reading this section, then I can only assume you have told me to relax.
Nick: You wrote that?
Winston: "Let me assure you I am very relaxed, although I have good reason not to be, as you owe me a very large sum."
Nick: I will pay you the money, you clown.
Winston: "I am aware that we're both broke, one of us embarrassingly so. Points to Nick. I have recently tumbled down the socioeconomic ladder and have hit rock bottom, where you, Nick Miller, have been waiting patiently for the past 15 years. But I want that money. Give me my money. I really mean it. It's my money. You owe me that money, so give me my money."
Nick: Seriously. Are you finished?
Winston: "Where is the money, dude?"
Nick: You wrote "dude"?
Winston: "But I am not without pity. I am willing to just call it an even $200."

Winston: Whoa, whoa! Why you taking back your lamp?
Nick: I think you just answered that when you called it my lamp.
Winston: No, man. Squatters' rights.
Nick: What's wrong? You still afraid of the dark?
Winston: What? No. Dude.
Nick: 'Cause, if you are, I'll leave this behind.
Winston: Nick, first of all, I'm not afraid of the dark. But if I were afraid of the dark, that would be a totally rational, adaptive evolutionary response.
Nick: Good night, Winston.
Winston: That's ridiculous. I'm not afraid of the dark.
Nick: Good night, sweetheart. [ghoulish] Unless the monsters get you. [closes door; opens door again to scream]