This episode starts at night and the gang is at Anthony's. Dan is at the bar with a very good-looking woman, and he is yammering away in that tone of voice that instantly lets you know he is attempting to pick up a woman. It's the tone of voice all men adopt when we start talking about ourselves, that tone of voice that conveys a slight touch of bashfulness, almost as if talking about ourselves embarrasses us, but at the same time, we're proud of what we do and love life and are not afraid of a little introspection or self-analysis and are not afraid to seem just a little, yes, vulnerable sometimes. And, hey, sure Dan Rydell may seem like a completely self-assured big kahuna on Sports Night, but as he faux-reluctantly reveals to this woman, he had an unhappy childhood and didn't get the things he needed as a kid and what happens is "you come to rely on the love of three or four million strangers," and he looks soulfully at the woman at this last bit, and I have to say Dan is pretty good at this shtick, even nailing the recommended eye contact. I'm very impressed he didn't tack on something cheesy like "...or maybe all I need is the love of one beautiful stranger," but he probably realized that this woman looks too smart for that. "What happens when they go away?" she asks. Dan pauses, looks away, and says, "Well, you try to avoid that," and takes a sip of his drink. The woman looks over her shoulder and sees this creepy-looking extra standing there staring at them, not saying or doing anything. The woman says she has to go, because "the guy I came with looks like he's ready to go," like maybe Creepy Extra sent out some sort of vibe or something, making her look. Dan says, "I'm Dan Rydell," so I guess he didn't explain who he is or what he does after all, which would only make that "love of three or four million strangers" line seem pretty skanky to potential pickups. Luckily, the woman knows who he is and Dan says, "Thank you," but then admits he assumed she knew who he is. Uh oh! Careful, Dan! Your Vulnerable Sensitive Man is in danger of morphing into Drunken Braggart! Quick! Mention your love of Yeats! How much you love cooking! How your volunteerism at the Y is "all about the kids"! Hurry! Anything! Whew, not necessary. The woman says, "Abby Jacobs," and gives Dan her card and tells him he should call her, and she leaves, and Dan puts the card in his pocket and looks back over his shoulder at the departed Abby, clearly thinking, "Sweeeet."
At a table, Dana is working on a crossword puzzle, and she asks Casey's help on every single clue, and then he gives her the answer and she writes it down. "So what about this?" says Casey. "What?" says Dana. "Right here, right now?" says Casey. Jesus Jones! I love that song! If he name-checks the Soup Dragons too, I'm going to be freaked out. Dana has no idea what he's talking about. "Wouldn't this be considered a date?" says Casey. And, of course, she says no, and she explains The Dating Plan for him again and for any viewer who maybe had never watched an episode of Sports Night before. Judging by its ratings, I guess that's pretty much everyone in the world. Casey says his point is that if an outside observer, some "loner," were to see them in this bar, that observer would assume they were on a date. "He'd be wrong," says Dana. Casey says, "The loner's a fairly bright guy, he's known for his smarts." If that's the case, this loner would notice the woman doing a crossword puzzle, not the hallmark of a great date. Dana says, "The longer you wait, the longer you wait," which Casey interprets as meaning that he should get on with dating other women. HOW MANY TIMES can we watch this scene, which we have already seen about 100 million times as it consists of Casey arguing against the Dating Plan, Dana sticking to her guns, and Casey smiling and agreeing to it because it's what Dana wants? I swear, whenever the Dating Plan came up on this damn show, it was the only time I was glad the show was just half an hour long.
Oh, wait, the other time was when Jeremy goes into his Dorky Proclamation mode, as he is about to in this scene. Jeremy and Natalie walk up to the table and Jeremy says, "I am victorious," and Natalie confirms it. "Jeremy fixed the K-Y thing," says Natalie, and Jeremy hastily corrects her and says, "The Y2K thing," and cheap laughs aside, Sorkin, I do not buy Natalie making that mistake. Anyway, Dana tries to explain that they're bringing in a professional to look after that problem, which Jeremy says is not necessary, and Dana is of course really worried because "our entire organization runs on computers," and Jeremy says "yes" and giggles in that way that only computer geeks do, when someone mixes up "internet" and "ethernet" or some such egregious error. "What have you done?" says Dana. "I've done nothing less than face down the millennium and show it who's in charge," says Jeremy, and such annoying non-answers don't win him any points in my book. Dana asks him if he at least used a manual, and Jeremy makes this "Come on!" face and says, "Dana, this is my area!" and Natalie once again agrees. Dana says, "Listen, just because you're a nerd..." which was pretty funny, but J+N cut her off and explain that tomorrow they're running a test. "What kind of test?" says Dana. "A K-Y test," says Natalie, in a joke-rehashing that I DIDN'T BUY THE FIRST TIME you used it, Sorkin, seemingly hours ago. Jeremy corrects her again and explains to Dana that tomorrow he'll recalibrate the computers to believe it's January 1, 2000. You'd think a computer geek like Jeremy would know that computers don't believe anything, but I'll let that one slide. Jeremy says the test will prove the station is Y2K compatible and while we're on the subject, how annoying is it to be recapping this episode while we are STILL hearing references to "the new millennium" in conjunction with completely unrelated concepts, as though "the first Stanley Cup champs of the new millennium" or whatever are somehow even more special than any team that's won it in the past. And we're not through yet, because in a few months all the math geeks will remind us yet again that the new millennium doesn't actually start until 2001, as if it matters since the only reason we're hearing about it at all is because of society's tendency to arbitrarily attach significance to large round numbers, ESPECIALLY since it has only been 2,000 years since the estimated birth of a guy not everyone believes in anyway, like maybe I should have asked my Jewish friends their thoughts on this.