Frasier tells Roz about his family's adventure on the Millenial New Year... Chez Henri, where they planned to spend it, burned down, so they drove toward Sun Valley in Martin's Winnebago, for a party thrown by a wine club friend. Hijinks ensue en route, starting when a drowsy Niles boards the wrong Winnebago at a truck stop.
At Cafe Nervosa, Frasier runs into his unrequited high school crush and former prom queen, Lorna Lynley (Smart). The courtship gives Frasier a chance to live up the high school glory days that he never had.
Frasier plans to introduce himself to a beautiful woman he has seen at the opera, but brings Martin along to the opera so as not to look lonely. The woman's mother takes a shine to Martin, and he pretends to be gay to deflect her advances. Frasier makes his overture, and Emily comes to his apartment for a nightcap, bringing along her uncle, Edward, as a date for Martin.
When Roz takes a vacation, Frasier hires Mary, a producer fresh out of of training, to fill in for the week. Soon, Mary starts taking over Frasier's show, but Frasier is hesitant to say anything because she's black. Meanwhile, Niles shows off his new kick-boxing skills with disastrous results.
Frasier begins to think that Niles' new girlfriend may be slightly manipulative, a suspicion that is brought to the forefront when Niles suddenly announces he wants to run against Frasier to be the prestigious Corkmaster of their wine club.
Frasier and Roz share a room at a broadcasting conference, which is notorious for being a meet market. However, both strikeout miserably and return to the room dejected. The combined effects of both their recent dating dry spells and their respective new looks (Frasier has beard stubble and Roz tries on a blonde wig) cause them to seek each other for companionship. Martin takes on a stakeout job at Donny's request, but Niles has his concerns.
Frasier's show is pulled off the air for a week, supposedly to give a new talk show a try, but Frasier has figured out the real reason: leverage against him in his contract negotiations with the station. Thinking two can play that game, Bebe lines up a one-week guest spot on AM Seattle, a morning TV talk show, for him and Roz. When Roz shows up on Monday with a raging fever, Bebe steps in as his co-host. They're such a hit that the TV station wants them on a permanent basis, which fame-struck Bebe desperately wants while Frasier wrestles with decision. Meanwhile, ...
Frasier learns that comely neighbor Regan Shaw has recently become available again, but is shy about approaching her because his previous encounters with her resulted in him looking foolish. Meanwhile, Donnie is looking for someone to organize his bachelor party, but balks when Frasier offers, due to his stuffy perception. Out to prove he can be "just one of the guys", Frasier auditions a stripper for the event, only to become handcuffed to her. Unable to get them off, he desperately tries to hide his predicament from both Daphne, who is against a raunchy bachelor ...
Part One of Two. Daphne's wedding is approaching and Niles becomes even more apprehensive when he and Mel decide to take a trip together. He feels it is too early in the relationship to go away with her but, after a therapy session with Frasier, decides to take the risk. While the two are away, Daphne finally tells Frasier that she may have feelings for Niles. Upon his return, much to the shock of the rest of the family, Niles announces that he and Mel eloped and are now husband and wife, leaving Daphne devastated.
Part Two of Two. It is the night before Daphne and Donny's wedding and her entire family, as well as Frasier, Martin, Roz and Niles have arrived at the Wayside Inn, where the wedding is to take place. As much as he tries, Niles realizes that he is nowhere near over Daphne at all and he decides to lay it all on the line and tell Daphne how he feels once and for all.
After Niles and Daphne run out on her wedding, they return to do the honorable thing and face their jilted lovers. Donnie and Mel each seek some sort of revenge: Donnie sues Daphne, and then threatens to sue Frasier as well for his part in the affair; Mel promises Niles his divorce, but only after he agrees to put in some public appearances with her as newlyweds.
The tension of Donnie's lawsuit and Mel's demand that Niles and Daphne not be seen in public together (which nixes their planned first date) erupts in a major fight among Frasier, Niles and Daphne. Frasier vows never again to meddle in their affairs, but comes up with a plan to help smooth things over.
Frasier uses his father as a pawn in order to date the attractive owner of a home for senior citizens. Niles and Daphne plan a picnic during which to watch a meteor shower, but are accidentally separated at the crucial moment.
Frasier adopts the role of cultural mentor to Todd Peterson, a Silicon Valley billionaire who's just become the station's new owner. Unfortunately, Peterson simply copies Frasier's tastes - and worse, gets all the credit. Meanwhile, Mel makes fresh demands upon Niles before agreeing to their divorce.
Frasier hires a butler to take over for Daphne's housekeeping duties, now that she is Niles' girlfriend. However, Mel continues to forbid them to be seen in public, and when she unexpectedly shows up at a party at Frasier's house and ruins Niles and Daphne's planned evening out, it proves to be the last straw.
Frasier hires an attractive lawyer, Abigail Michaels, to handle his lawsuit with Donnie, but he suddenly drops the lawsuit. To celebrate, the Cranes all take Abby out to dinner, where they happen to run into Donnie. He explains that he dropped the case because he has become engaged to a client of his, but Daphne fears that he might just be on the rebound, and checks in on him for closure...at his wedding ceremony. Meanwhile, Frasier's budding relationship with Abby is going great, except for the exorbitant legal bill she charged him for her minimal services.
Roz introduces Frasier to her new boyfriend, Luke, and the two men hit it off as well. When she catches Luke cheating on her, she dumps him. Frasier, however, hides his continuing friendship with him while supporting Roz during her heartbreak. Then when Roz gets back together with Luke, she hides that fact from Frasier as well.
Frasier butters up the local morning TV host to let him co-host the Seattle Christmas parade with her, but when she comes down with food poisoning (from his cooking, perhaps?), he learns that Dr. Mary will be his new partner.