In the break room, Jim looks at us innocently before turning away to crunch a potato chip. Going out, he meets Dwight coming in, and then goes right back in when Dwight yells at him for putting all of Dwight's stuff in the vending machine. "A dollar for a stapler, that's pretty good," Jim points out. Dwight refuses to play along, until Pam comes in and buys Dwight's pencil cup right in front of him. "I love these," she grins. Dwight admits defeat, and reaches for his wallet, but it is of course in slot J1. Jim hands Dwight a bag of nickels, and leaves him to the project that's probably going to take up the rest of his morning. I am so unsurprised that Jim was an Undeclared fan.
Michael comes into the bullpen, and everyone quizzes him about the mysterious field trip that's apparently happening that afternoon. Michael stays mum. Well, mum for Michael. Dual TH of Pam and Jim, reading off the memo that Michael sent telling them what to bring: "A swimsuit, a toothbrush, rubber-soled shoes, and a ski mask." Jim figures the camaraderie event will involve robbing a bank and then escaping through the sewers. "And brush[ing] our teeth," Pam laughs, flashing a set of choppers that show she's way ahead of Michael. As usual.
Stanley comes into Michael's office and gets him to admit that they're going on a booze cruise on Lake Wallenpaupack, which apparently actually exists. "In January?" Stanley asks disgustedly. A bit of the joy goes out of Michael's eyes as he says, "It's cheaper." And not frozen over? I don't know about Pennsylvania, but if you want to go out on a lake this time of year in Minnesota, you'll have to do it in a bus.
In a TH, Michael claims that the cruise isn't just a party, but a leadership seminar blah-blah-blah. And then in the conference room, he reveals to everyone what the plan is. Only Dwight seems excited. "It's a booze cruise," Michael adds, and that's Meredith on board too, so to speak. Ryan asks if he can skip the cruise in favor of studying for a test, and is told no. Kelly complains about having bought a swimsuit, which Michael says isn't his fault. By the way, who is the unfamiliar woman sitting at Michael's right hand? He introduces her as "Brenda Something" from Corporate. She looks a lot more "corporate" than "something." Michael delivers some content-free blather about leadership containing the word "ship" and him being the captain (complete with a dopey skipper's hat that he's just whipped out and popped onto his head, where it turns out to be too small for him), but they're ultimately all in the same boat.
Oscar THs about last year's theme, "Bowl Over The Competition," and leaves it to us to guess where they went. Roller-skating?
Michael asks what part of the ship sales would be. Misunderstanding and then disregarding Darryl's guess that sales is the sails, Michael calls them the furnace. The furnace? "How old is this ship?" Jim wonders. Michael wants to move on to the movie Titanic, which Jim and Pam amusingly pretend to never have heard of. Jim THs, "Michael stands in front of the boat and says the he's king of the world in the first hour or I give you my paycheck." Back in the conference room, Michael keeps going on about the engine room guys, "sweaty and grimy and singing their ethnic songs," which makes him reconsider that maybe the engine room is actually the warehouse. Darryl begins to take offense, and Brenda Something starts writing on her pad as Michael, realizing his little presentation is headed for the reef, says they'll talk about it on the boat.
As the DM crew board the boat on what looks like a very chilly evening, Michael tries to pump everyone up by singing the Gilligan's Island theme and assigning everyone roles: Pam's Mary Ann, Jim and his then-girlfriend Katy are the Professor and Ginger (respectively), Angela's Mrs. Howell, Kelly's a "native," Stanley's one of the Globetrotters, Michael himself is the Skipper, and Dwight is Gilligan. Except then, the boat's actual captain turns up, introducing himself as Captain Jack. Not that he's anything like the Captain Jack you're thinking of. Or that other one, for that matter. Captain Jack politely but firmly says he's the skipper of the boat, and of anyone who steps aboard it. Michael THs cluelessly about where a regional manager falls in the chain of command on a boat versus an office, and is then seen doing the "king of the world" thing before the boat's even clear of the dock. Jim grins at us, pointing at his watch. I'm not giving you my paycheck, Halpert.
Now that the cruise is underway, everyone is in the reception-hall-looking space belowdecks, Captain Jack gets everyone's attention to try to do the safety briefing. Except that he has to share the floor with Michael, also wearing his own captain's hat. Captain Jack says he's also the "party captain," and Michael says he is too. He tries to take over, until Captain Jack points out that there are other passengers besides the ones from Dunder Mifflin on the boat. Captain Jack needs to back up a bit; Michael is still struggling with the concept of other people besides Michael being on the planet.
Jim and Katy sit at a table, across from Pam and Roy, as Katy observes that they're at the cool table. She is apparently unaware that saying it makes it immediately not true. But Roy laughs. It turns out that his high school and Katy's were in the same athletic conference, and Katy goes into a cheer from her high-school days. Yes, she's an ex-cheerleader. There's always that danger when you date a hot girl, you know. Mine, I hasten to assure you, was in danceline. Jim looks across at Pam with a helpless shrug like, "What are you going to do?" "Mock you mercilessly without saying a word," appears to be Pam's answer.
Elsewhere, Brenda Something asks when Michael is going to start his presentation. Michael heads over to his group to try and ad-lib about life preservers, but Captain Jack puts an end to that with a limbo announcement. He asks who wants to hold his stick, which somehow fails to elicit a "that's what she said" from an off-his-game Michael. Dwight pushes Meredith aside to try to win that honor, so Captain Jack decides to get rid of Dwight by offering to let him steer the ship.
From behind a ship's wheel on the foredeck, Dwight brags about the time he got to help fly a plane when he was four. That's great, Dwight, but try doing that post-9/11. Or, indeed, getting on a plane at all. Or within half a mile of an airport.
Down below, limbo time is over, and it's time for the dance contest. Michael wants to do his presentation first, but Captain Jack kiboshes that. Michael tries to make the best of it by taking over the dance floor and babbling about dance as a concept, as if he's saying anything about anything. Not that his words are any more embarrassing than his movements, which appear to have been choreographed by a blind epileptic. Everyone looks on in varying degrees of horror, particularly the Dunder Mifflin contingent. "Sometimes you just have to be the boss of dancing," he panting-heads afterward.
Dwight sings a sea chantey at the helm, as the camera pans up to the boat's real pilot, above and behind him on the nice, warm, enclosed bridge. He doesn't appear aware of Dwight's existence. Angela comes to ask Dwight back in. "Do you want us to run aground, woman?" Dwight asks. Angela goes back inside without bothering to respond.
It's now the snorkel-shot stage of the party. Pam tries to pull Roy away, but Roy would rather watch Darryl drink. So Pam goes out on the deck with Jim instead. She says she doesn't understand Roy sometimes. Only sometimes? There's a long pause while Jim tries to think of a response, until Pam asks what it's like dating a cheerleader. Jim doesn't have an answer for that either. His face gets serious, like he's about to say something. But before he can, Pam gets cold and decides to heads back inside. Jim thinks, "Not as cold as my feet."
Inside at the bar, Jim is quietly giving himself a well-deserved mental beating while to him, Captain Jack is being nice enough to ask Michael what the presentation is about. Michael babbles about his boat analogy, which Captain Jack says is stupid, and Michael says Captain Jack clearly knows nothing about leadership. So Captain Jack mentions his Desert Storm experience. Dwight (apparently relieved from helm duty) tells Captain Jack that he should be the motivational speaker. In case you think this is an accidental slight on Michael, Dwight goes out of his way to compliment Captain Jack's delegation skills by mentioning that he got to steer the ship for the last hour. Captain Jack actually looks a little guilty for some mysterious reason.
Back at the table, Katy says she'd like to be engaged. Well, let's hope she meets a nice man soon, then. She asks how Pam got engaged. "I've been engaged for three years, and there's no end in sight," Pam says, a touch bitterly. "So you don't want to ask my advice." Because that advice would be, "Duck out of any serious interactions with the guy who really loves you."
Captain Jack is trying to keep up with Michael's analogy, asking Jim who he would save if the building were on fire. Jim looks across the room to where Pam is laughing, and lies that he would save the customer. Michael likes that, but Captain Jack says Jim is only sucking up. A drunk Roy drapes himself over Captain Jack's shoulder, and asks if he ever almost died. Captain Jack says he did, and married his first wife as soon as he got back to shore. Jim, meanwhile, has decided to make his move, as he purposefully heads down the aisle towards where Pam and Katy are sitting. Which of them will he talk to first? Unfortunately, he pauses just long enough to tell us he'd save the receptionist. And that makes him too late, because Roy has jumped up on the bandstand and commandeered the mic. He tells Pam they should set a date: June 10. Pam happily goes up and kisses Roy while everyone claps and cheers, especially Katy. Jim just sinks into a seat. If fortune favors the brave, clearly the converse is also true.
Back from the ads, there's still a celebratory vibe. Michael tries to take credit as Roy's motivation, but Roy says it was Captain Jack. Captain Jack offers to marry them as captain of the vessel, and of course Michael offers to marry them as regional manager. Pam declines, since he wants her parents to be there. Very diplomatic of her.
Later, everyone's slow-dancing. Jim and Katy are watching Pam and Roy from outside through a window, and she asks if he thinks that'll ever be them. Jim flatly says no, and breaks up with her on the spot.
Captain Jack shows Meredith his ready room, if you know what I mean, and Meredith clearly does.
Meanwhile, Michael is getting seasick. Dwight tells Michael that Captain Jack says to look at the moon when that happens. "Captain Jack's a fart-face," Michael says before puking onto the floor. Seeing that a shocked Brenda Something has just arrived, he blames it on medication. "Vomicillin," he claims. Finally he gets up and takes over the microphone. In Captain Jack's absence, he goes public with his "sinking ship" metaphor, which is not good because nobody except the Dunder Mifflin employees realize that he's just being Michael, and he's starting a panic. Kevin tries and fails to stop a guy who grabs a life jacket and dives out the window. Captain Jack returns, stripped down to a t-shirt. Meredith is also back, wearing a life jacket with nothing underneath. Where's Michael's digital camera?
Cut to Michael, out on the upper deck with his hands plastic-cuffed to the deck rail. "Boat's not as corporate-friendly as advertised," he grumbles at us Michael blames the other passenger for jumping overboard. "If he had just waited and listened to what I had to say, he would be motivated right now and not all wet." Michael gives himself too much credit; everyone would have jumped overboard rather than listen to one of his full speeches.
Jim gets tired of pouting in the same room as Katy, and gets up to leave. See, this is why you don't break up on a cruise, unless you have access to the lifeboats. Jim goes to visit Michael in the brig. "Captain Jack has a problem with authority," Michael tells him. "Cause you announced that his ship was sinking?" Jim wonders. Michael says that at least Jim had a good night, since his friend got engaged. Jim says she already was engaged. "Roy said the first one didn't count," Michael clarifies. "That's...great," Jim pouts. He confesses that he "used to have a big thing for Pam." Michael is totally blown away by that, of course. "I usually have a radar for stuff like that." He makes sure to mention that he made out with Jan, and says Pam is cute. Jim adds, "Really funny, and warm, and...anyway." Michael tells Jim not to give up. "Engaged ain't married," he encourages. Jim considers that and Michael repeats his sentence, the one motivational thing he's managed to say all night. From the fake wheel on the deck below, Dwight tells Michael not to worry, as he's taking them to shore. "It's a fake wheel, dummy," Michael calls down. So much for nautical analogies.