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.
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.
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.
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.
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.
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.
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.
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.
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.
Things change drastically when the show starts, and the panel asks Frasier numerous probing questions about his personal life.
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.
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.
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).
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.
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!"