Frasier and his family are still with Claire (Patricia Clarkson) in Belize. Niles and Martin think Claire is wonderful (although Daphne resents this), but Frasier is troubled by a dream he had about Lana (Jean Smart), and wonders if he is with the right woman. On returning to Seattle, he meets a man (Brian Kerwin) at a lost luggage office who is torn between two women, and who asks Frasier's advice as a psychiatrist. Frasier says he must consider whom he would spend the rest of his life with, prompting him to choose his ex-wife over his new woman. This sets Frasier thinking, and on returning to his apartment he finds Claire and breaks up with her, to the indignation of the rest of his family (and also Daphne, surprisingly). He then attends Kirby's (Brian Klugman) graduation party with Roz, hoping to discuss his feelings with Lana, but is astonished when the man from the luggage office also turns up. It turns out that this man, Bob, is Kirby's father, who left Lana for his dental hygienist. Now he wants her back, acting on Frasier's advice. Lana throws him out, and then retires to her bedroom. Kirby begs Frasier to talk to her, and in the end he takes the honorable course by advising Lana to talk to Bob, since she clearly still has feelings for him. Returning home later in a state of distress, Frasier finds his family totally unsympathetic, and something Martin says particularly upsets him: "It's not easy coming up with happy talk every time you can't make it work with a woman." Frasier takes a drive by himself to think about this, and his thoughts manifest themselves on screen as a discussion between him, his former partners Diane (Shelley Long), ex-wives Lilith (Bebe Neuwirth), and Nanette Guzman (Dina Spybey), and even his late mother (Rita Wilson), as he searches for a reason why his relationships often fail. Before the search is over, he is confronted with a crowd consisting of "every woman [he] ever dated".

Martin is about to start a new job as a security guard, and the occasion dredges up memories of the fateful day years ago when he was shot. These memories appear in flashback: while out on patrol with his partner Frank (Tom Irwin), he pleads with Martin to pull into a convenience store so he could get a slushie. Martin ultimately gives in and pulls into the parking lot of a store that was being robbed. Martin walked in at the wrong time and got shot. Frasier has ordered a special congratulatory cake, which Roz delivers. Meanwhile, Niles has bought Daphne tickets to a Billy Joel concert for that evening, and she has bought him tickets to a festival of Mongolian throat-singing, also for that evening. This means they have to decide which to attend, so Niles offers Frasier the tickets to the throat-singing concert. Martin then points out that someone has to walk Eddie at 10pm, so as he prepares to leave for work, the others discuss (and argue) who should do this job. When Roz arrives with the cake, she finds herself drawn into the argument.

Frasier is celebrating two thousand editions of his show at KACL, with a guest appearance from Bill Gates, who ends up taking several calls about Microsoft products. Returning home afterward, Frasier opens a bedroom cupboard full of cassette tape recordings of his shows. Just after adding the two thousandth edition to his collection, he notices that one of the other cases is upside down, and on closer examination, finds that it contains a Hall & Oates tape. He calls in Niles, Martin and Daphne to find out who is responsible. Daphne confesses that she borrowed the tape and accidentally broke it. This prompts Frasier to broadcast an appeal to anyone who has a recording of the missing show. Niles becomes worried how the incomplete nature of his brother's collection is affecting him; staying in, sleeping late, not dressing. Frasier insists that he is quirky rather than obsessed. When station listener Tom (Adam Arkin) calls in to say he has a taped copy of the episode Frasier, he and Niles get a first-hand experience of fan obsession.

The Seattle radio airwaves have a new star psychiatrist: Dr. Zach (Chris Berg), a doctor from whom Frasier differs entirely. Dr. Zach's brand of radio is, as Frasier describes it, "suggestive smarmy sleaze", but it has become very popular. Kenny suggests Frasier emulate him a little to improve the ratings. Frasier prefers the idea of raising the advertising budget; Kenny disagrees. This prompts Frasier to contact his agent Bebe Glazer (Harriet Sansom Harris), but upon arriving at her office, he learns that her newest client is Dr. Zach himself. She passes Frasier on to her former assistant, Portia Sanders (Kristin Chenoweth), who has become a "full-fledged junior agent". Frasier refuses and storms out angrily, deciding to end his association with Bebe's agency. However, he finds Portia very persistent, determined to prove her abilities to him. Meanwhile, he is disappointed not to have any more offers from agents, so considers representing himself. Martin attempts to avoid a medical examination by asking Niles to write a prescription for him. Niles refuses to violate his ethics, so Martin devises a plan by which he hopes to force his hand.

Frasier discovers that Martin's supervisor at work, Rich (M. Emmet Walsh), is treating him badly, being unnecessarily bossy and disrespectful. It upsets Frasier to see his father in this situation, even though Martin insists that it does not bother him, because he respects the chain of command. Frasier decides to speak to the owner of the security company (Robert Picardo), who also happens to be Rich's son, and in order to ensure that their conversation remains confidential, he agrees to hire a bodyguard on a trial basis from the company. Unfortunately, this seems to do more harm than good, when Rich receives a reprimand from his son and assumes that Martin went over his head to complain. Meanwhile, Roz is boring everyone by talking endlessly about how well her relationship with Roger is going. It reaches the point where, no matter how obscure the topic of conversation, she can always turn it back to Roger. Eventually Niles, although he disapproves of his brother's meddling in Martin's business, agrees to help him solve the problem by confronting Rich, just to get away from listening to Roz. This backfires as they hide in the janitors closet to escape Martin's sight as they didn't want him to know. Martin and Rich discover them in the closet via security cameras and have a little good-matured ribbing about how their kids are always meddling in their lives. Martin gets back at Frasier and Niles for their meddling by calling them and, with Rich's help, gets "stuck" at the desk for five hours.

Kenny announces to Frasier and Roz that some recent research into KACL listeners shows that Frasier's average listener is an older gentleman who keeps the radio on for company. He suggests Frasier reach out to the youth, by appearing on Teen Scene; Frasier, who appeared once before on that show, refuses initially, but when approached for an autograph by a young woman working for a hospice, he reluctantly consents. The representative of the Teen Scene panel whom he meets first, Emily, seems very intelligent and pleasant. Things change drastically when the show starts, and the panel asks Frasier numerous probing questions about his personal life. Fortunately, Kirby Gardner, who went to the same school as the panel members, is on hand to help out by providing Frasier with embarrassing information about the trio, and Frasier enacts his revenge against Teen Scene, embarrassing all three of them. Meanwhile, Niles decides to steal a street sign with Daphne's name on it as a romantic gesture. Daphne discovers that Martin kissed a woman named Peg (Lindsay Crouse) at a work party, and although he insists that it was nothing special, he spends a few days waiting by the telephone in case she calls.

Frederick is due to compete in the National Spelling Championship, and Frasier has been training him very thoroughly, even in stance and diet. Frederick does extremely well in the spelling bee, and is crowned National Champion. However, the parents of the runner-up notice an anomaly when watching the recording: it seems that Frasier was unconsciously mouthing the letters of the final word as Frederick spelled it out. The trophy is then reawarded to the runner-up, Warren Clayton, but Frederick and Frasier are still invited to the finalists' banquet, where they are subjected to taunts and accusations of cheating. Frederick will not tolerate his father being called a cheater, and challenges Warren to a rematch.

Frasier, Martin, Niles and Daphne are in Boston for a conference that Frasier and Niles will attend. They encounter Frasier's old friend Cliff Clavin (John Ratzenberger) at the airport bar, who thinks Frasier is in town for his retirement party before he moves to Florida, and end up going along to the party with him before dinner. The only ones not in attendance are Sam (who is using the bar for a Red Sox reunion party), Woody (who is out with his wife Kelly and their child), Rebecca, and Diane (the latter two aren't mentioned). Martin hits it off with fellow beer lover Norm Peterson (George Wendt). Both are able to correctly figure out the other's preferred method of beer consumption by their handshake, and they swap beer stories. Daphne meets Cliff, and takes all of his erroneous trivial facts and stories at face value. Niles is the only person not having a good time; he has to prepare an introduction for Frasier's speech, and must continually postpone a dinner reservation at a fancy restaurant. Niles's mood changes, though, when Carla (Rhea Perlman) begins telling him of all the pranks and jokes that she and the others used to play on Frasier. Eventually, Cliff confides in Frasier, saying that he does not believe any of his supposed friends actually care that he plans to leave town. When Cliff leaves for a walk around the block, Frasier shares this news, and inspires everyone to deliver speeches in Cliff's honor. Everything is going well... until Carla, after years of frustration at Cliff's chatter, snaps. She goes on a long rant, discussing how joyous she is that he is finally leaving, and claims that the past few years of her life would have been more enjoyable had she been "covered in open sores and thrown into a pit of starving rats!" Upon hearing this, Cliff pauses... and announces that only a true friend would make such a wonderful, humorous speech. He decides that he cannot leave such good friends, and opts to stay in Boston! This naturally infuriates Carla, who tries to shoot Cliff with a speargun he received as a present while the others try their best to restrain her.

Frasier's show has been picked up by a station in Spokane, and he excitedly announces that he and Roz have been invited there by the station to do their first show from Spokane. Once off air, he also learns from Roz that she and Roger have broken up. Frasier wants to help, but Roz says she is OK about it. Once in Spokane, Frasier appears at a press conference to introduce himself and Roz to the local media. During this conference the reporters are obnoxious and condescending as they say that he will probably never be able to live up to local icon Neil Sullivan (affectionately known as Sully by the locals). When Sully (Bill Hayes) arrives to make a final appearance and to wish Frasier luck the reporters give a dramatic final send-off. Things do not go too smoothly during Frasier's show either; every caller wants him to go back to Seattle, with some deciding to boycott the station until Sully comes back on the air. Frasier is determined to show the local audience his brand of therapy can help, and so convinces Roz to call in with a problem. Originally Roz improvises and says she is afraid of the dark. But Frasier delves deeper into the problem and this soon develops into him resolving Roz's feeling of loss and emptiness over the break-up with Roger. Meanwhile, Martin, Niles and Daphne work together to try to build a TV table. Earlier in the episode when Martin expresses his desire to build the TV table, Niles recalls his childhood hatred of building things with Martin as Martin was never any good. But in a turn of events Daphne is the real bossy one and not only upsets Niles but Martin also.