As Oscar makes his way through the parking lot, he beckons the camera guys over. Earnestly, he tells them he knows they saw him with the Senator on Halloween but asks them for maturity and discretion. Oscar explains that he is truly in love for the first time. Just then, the camera moves to reveal Kevin - he's heard it all. Kevin drops his ice cream in shock as Oscar looks miserably at the camera, silently cursing his bad luck.
Andy discovers that his family is in the middle of a meltdown: his dad has blown all their money and taken off to Argentina with a younger woman. Pam and Jim are quite impressed at how well Andy's doing with damage control, remaining cool and competent. In the hush of the stairwell, Oscar begs Kevin to keep mum about what he knows. Oscar explains that he needs time to sort this out in a responsible manner. Kevin admires the sentiment, but claims he can make no promises. Pam gets off the phone with Iris Black, a radio DJ who's looking to interview someone from Dunder Mifflin. Dwight, feeling particularly passionate about local business issues, volunteers for the job. He believes the media can make you famous, and famous people can sell anything.
Meredith strolls into Andy's office, casually asking him about his handsome brother who's currently in a downward spiral with booze. Andy informs her he's in a rehab center in New Mexico, and Meredith leaves his office disappointed. Meanwhile, Dwight is driving everyone insane as he loudly performs his extensive vocal warm-ups for the radio show. In the conference room, Erin, Oscar and Darryl are helping Andy sort out his mother's legal issues. Although Andy should sell his family's boat for the huge profit, he can't bear parting with it - it's the heart and soul of his family. Darryl does the math and figures out that if Andy sells everything but the boat, his mom can only keep afloat for six months. Seeing no other way, Andy goes to call his lawyer and tell him to go head with the selling of the boat. Off camera, he cries a little.
The radio station calls to inform the office that the interview is off. Nellie gets up to tell Dwight, but Jim stops her. It's the perfect opportunity for an epic Dwight prank. Pam, Jim, Nellie and Darryl set up camp in the conference room where Nellie pretends to be Iris Black. She calls Dwight, who's eagerly awaiting the big call in the break room. At her desk, Erin puts in a set of gruesome false teeth to try to cheer up Andy. However, Andy is too depressed even for Erin's cute antics. Angela, frustrated with Kevin that he didn't order a set of forms, tells him that this doesn't surprise her. In fact, nothing he does ever surprises her. Unable to contain himself, Kevin is absolutely gleeful that he finally does have a bit of information that would surprise Angela. Oscar, panicking at Kevin's creepy smile, gives him a look, and Kevin covers by saying that he has to go the bathroom. Oscar muses that that was actually a valid cover; Kevin is often seen running out of elevators, meetings, even cars, shouting that he has to go to the bathroom.
Andy can't shake the loss of the boat: his dad never let him sail it, and now that Andy's finally the man of the family, he has to sell the boat and will never get a chance to sail it. Erin convinces Andy to drive to Connecticut with her and go for a sunset sail before the boat is sold. Still on the phone, Dwight's convinced he's giving Iris Black the interview of her career. Nellie, as Iris, instructs Dwight to take off his shirt and his pants because the buttons and zippers are interfering with the call connection; Pam and Jim giggle with glee. When Angela gets off the phone with her husband, she vents to Oscar about how exhausted the Senator is with his campaign: he's up against a dirty man, and he's really trying to push back. Kevin can barely handle all the unintentional innuendos Angela is throwing out there. Shrieking with laughter, he leaves his desk. Oscar realizes he's in big, big trouble.
To alleviate his Kevin problem, Oscar approaches Toby with the company's accounting issues, citing Kevin as the problem. Toby infers that Kevin's gambling has returned and tells Oscar he'll probably need to send Kevin home until an investigation can be done. An overjoyed Kevin thinks he's getting called to Toby because he's getting a promotion, particularly because then he'd get his own office and avoid accidentally spilling Oscar's secret. Oscar now feels guilty and admits to Toby that the numbers he gave him were false: he set up Kevin because he was being vindictive. Back in the conference room, Nellie does her best to anger Dwight by asking him about Dunder Mifflin's toxic paper. She's bolstered by Pam doing an impressive smoker-lady-voice cameo as Sondra Mick, a foreman of Dunder Mifflin's upstate New York paper mill. Jim runs into Dwight, grabbing him by the shoulders and telling him to fix things immediately because the stock price is imploding!
Nellie is milking Dwight's disastrous on-air performance for all it's worth, announcing that since the interview, the company's share price has fallen A grief-stricken Dwight, down to a tank top and his underwear, sits in the break room (with Kevin in the background munching on chips, also inexplicably in his underwear). Nellie (as Iris) asks for Dwight's resignation, but a panicked Dwight blames the entire ordeal on CEO David Wallace. In Connecticut, Andy and Erin try to take the gorgeous boat out for a spin, but a rude, prickly dockhand is already loading the boat. Andy tries to hoist the mainsail, but is rebuked repeatedly with a slap on the arm, just like Andy's father used to do. Andy and Erin end up having a picnic on the boat, but Andy's still upset that he's never gotten a chance to sail it. Standing up for himself, Andy informs the crewman that he's sailing the boat to the Bahamas. Showing Erin around the boat, Andy uncovers Walt, his alcoholic brother, hungover in the booze closet, claiming to be getting his first relapse out of the way. A light bulb clicks, and Andy excitedly invites Walt to sail with him to the Bahamas.
At the office, Nellie's on a roll, informing Dwight that the police have surrounded David Wallace's home and that, in his despair, Wallace has taken a mailman hostage. Dwight is sweaty and disheveled, and he decides to conference in Wallace to try to put a stop to all this. Dwight gets Wallace on the phone, assures him he's always believed in him, and tries to convince him to let the mailman go. Obviously, Wallace has no clue what Dwight is talking about and asks him not to call his cell anymore. Jim, Pam, Nellie and now Phyllis are dying with laughter in the other room. As Dwight finally ends the call and steps out of the break room, he's met with applause from the staff. They start chanting Dwight's name, still laughing about their amazing prank.
Unfortunate timing brings Senator Lipton to the office. Oscar is extremely panicky, and Angela cannot help but notice. When she presses him about it, Kevin steps in and changes the subject, assuring everyone that Senator Lipton is in the middle of an important election and they all need to support him. Off camera, Oscar is relieved at Kevin's class, but we learn that Kevin has simply forgotten about the affair for a second! And now he's remembered and he can't stop laughing. At the harbor, Erin watches Andy sail away, leaving her behind. To the camera, she admits she would have loved to go with him on this romantic, spur-of-the-moment trip - except he didn't ask her to come. Later at the office, a smitten Pete asks Erin to grab a drink with him and his friends. He promises her a night of idiocy courtesy of his friend Flipper, and Erin agrees.