After several establishing shots of the water, twee downtown Capeside, and the exterior of the Icehouse, we see Joey bussing tables as Pacey "Fabio" Witter, Jen "Miss Cochon-iality" Lindley and Dawson discuss the upcoming "Windjammer Days"; the Bride of Flash will be judging a contest, and "the station" has allowed Dawson to "cover it." Well, the shadow of his head will cover the proceedings in darkness, but that can't be what they meant. Jen asks what Windjammer Days are, and Dawson explains that it's an annual event put on by the yacht club to reel in the season's last tourists before the town shuts down for the season. Knowing what comes later, it's interesting to note that while Jen and Dawson sit on their asses as Joey waits on them, Pacey tries to make her job marginally easier by handing his empty french fry basket to her before she has to reach for it. Of course, Katie Holmes then gingerly sets it on her tray with an unease that makes it perfectly clear she's never worked in food service, but never mind. For Jen's benefit, Joey elaborates on Dawson's description: "It's a blue-blooded tradition that celebrates the grand achievement of being born rich, the culmination of which is this asinine formal dinner held at the yacht club where some young nubile whose daddy owns the bank is crowned Miss Windjammer." I must interrupt at this point and say that you can really tell this episode aired before we were recapping the show; they'd never throw in a gimme like logjammer -- I mean "windjammer" -- now. But Joey isn't finished: "It's the most archaic display of ageism, racism and sexism known to man." I don't think "archaic" is the word you mean if you're going to name all those other -isms explicitly, but whatever. Pacey wants to know if the contest includes a swimsuit competition, and Dawson says he doesn't think so. Pacey suggests that he could be "like, one of those guys who warms up the girls before they go onstage." Ha! Pacey would make a good fluffer. Jen chuckles very frat-boyishly and Joey sternly replies, "It's not a porno, Pacey." Jen wryly announces that her mother used to enter Jen "in these disgusting 'Little Miss' pageants before I was old enough to protest." Dawson says, "Let me guess: You twirled the baton?" Is that what the kids are calling it nowadays? Jen suddenly gets all snitty and demands, "Meaning...?" Dawson shrugs and smirks, "Nothing. You should enter." Jen snorts, "Yeah." Dawson insists, "No, I mean, seriously, I mean, you're beautiful. I mean, nobody can dispute that." Joey, standing between Dawson and Jen, glares at Dawson for a beat and then moves off, sighing loudly; naturally, he doesn't notice, but Jen does. Dawson goes on: "I can totally picture you strolling past the judges flashing that million-dollar smile of yours." Jen, having watched Joey slink off, turns back to Dawson and says, "I'm afraid that my baton-twirling days are over." Dawson informs her that first prize is five thousand dollars and a trip to New York. Pacey exhales like, "That's a spicy meatball!"
Getting up, Jen suggests, "Why don't you enter, Dawson? I'm sure you have some inspired ideas on how to achieve world peace." Dawson makes some unfunny remark about "tap-dancing pumps," and Jen moseys off. Pacey sits in her vacated seat and comments, "Hm. Backhanded insults disguised as compliments. That's really a novel approach to winning back a woman's affections." And what might a "backhanded insult" be? A legitimate compliment? Don't mind me, I'm just a third wheel, here. Dawson claims that he thought he'd give it a shot, since he's already tried everything else. Pacey states the obvious: "Why don't you just get over it, man? She has!" Dawson's voice gets all squeaky as he protests, "I think I have gotten over it, I just...winning her back has evolved into some bizarre hobby."