
Jeremy: Natalie.
Natalie: Hello.
Jeremy: Just the woman I’m looking for.
Natalie: Coming out of the mouth of anyone but the guy I just broke up with, that’d make my day.
Jeremy: I broke up with you, but that seems neither here nor there. Can I talk to you a second?
Natalie: Yeah, I broke up with you there, Mr. “Obviously has a short-term memory loss with a myriad of other problems, which I won’t even go into, but thinks that he broke up with me because of the short-term memory loss, which is so obvious.”
Jeremy: No need to be so formal. I’ve seen you naked. Call me Jeremy.
-Sports Night 2x17 “Draft Day Part I”

Jeremy: You should really call technical support.
Natalie: I like it when you fix it. It’s so cute and nerdy. I could just lick you up.
Jeremy: This is a serious computer problem, I don’t want to fool around with this.
Natalie: What does “err” mean?
Jeremy: Call technical support.
Natalie: What does “err” mean?
Jeremy: It means a mistake.
Natalie: Is it Latin?
Jeremy: It’s English. It’s “E-R-R”. It means error. Call technical support.
Natalie: “Minus-1, SM Trunc”, what does it mean?
Jeremy: Natalie—
Natalie: Come on, just one.
Jeremy: It means the truncation indicator alone is wider than the specified width. It probably also indicates a “Minus-5 Type SCP” which is an invalid queue element.
Natalie: Okay. Then it says “Minus-15, out of range.” What does that mean?
Jeremy: It means it’s out of range.
Natalie: You’re not doing this right!
Jeremy: What the hell are we doing?
Natalie: Well I thought we were having phone sex, but I guess you just weren’t interested.
Jeremy: We were having phone sex?
Natalie: Well not phone sex, but whatever. We were having sex.
Jeremy: I didn’t even know.
Natalie: And frankly, it showed up in your performance.
Jeremy: I wasn’t having sex.
Natalie: I know that, Jeremy, I was sitting here having sex all by myself.
Jeremy: You were having sex.
Natalie: Yes.
Jeremy: Well I think maybe you’re not doing it right.
Natalie: Call technical support.
-Sports Night 1x12, “Smoky”

Jeremy: Natalie, listen to me. You’ve lost a lot of money to me tonight. You’re basically going to be living the rest of your life on a charitable grant from the Jeremy Goodwin foundation. Take the hundred bucks back and fold.
Natalie: Scared?
Jeremy: I’ve got a straight. You’ve got 3 sevens.
Natalie: You don’t have a straight.
Jeremy: Look at me. I’m not lying to you. I have a straight.
Natalie: How do you know I don’t have a big house?
Jeremy: A full house. Dan already folded the six you needed, and I have the other one. You don’t have a house of any sort. You don’t have a pup tent. You’ve got trip sevens, and I have a straight. I want you to trust me right now. I want you to say to yourself, “Yeah, I dated a string of jerks in my life. They were stupid, they were mean to me. But maybe this one’s different. Maybe I should take a chance and not adopt the ‘break up with him before he breaks my heart’ strategy.” I want you to remember that when I started liking you, I didn’t stop liking tennis. And I want you to know that I don’t think there’s a woman in the world that you need to be threatened by, no matter how glamorous you think she is. But mostly, I want you to trust me, just once, when I tell you that you have three sevens, and I have a straight.
-Sports Night 1x10 “Shoe Money Tonight”