Following on from where last season's finale left off, Niles and Daphne drive off in the Winnebago, but decide to go back and face the music. They tell Donny and Mel that they are in love with each other and naturally Donny and Mel are upset.

Niles is forced to postpone his first romantic date with Daphne due to his marriage obligations with Mel. He has to attend their phony wedding reception and act happy about it so Mel can grant him the divorce. During the party, Mel tells him he can't be seen in public with Daphne while they're still officially married. This comes as a great turn off for Daphne, who thinks Niles is taking Mel's side on the whole thing. Frasier, now threatened to be sued by Donny for revealing to Daphne how Niles felt about her, decides he's done too much harm to the story and no longer wants anything to do with it. But Frasier Crane is Frasier Crane, and he can't help himself. With some help of Martin, he convinces Daphne to go out with him while Martin takes Niles out. They take the two to the roof, where Frasier set a dinner table and a very romantic environment. Just because they can't be seen in public doesn't mean they can't have their romantic dinner.

When Frasier's car breaks down, he and Roz decide to take the bus. There, Frasier spots an attractive woman whom he tries to start a conversation with, but unfortunately he slips and falls and the woman leaves the bus. But Frasier won't give up so easily: he overheard her conversation with a friend and now he knows her name and job, so he goes after her. She works in a retirement home, where Frasier takes his father to, pretending they're interested in having Martin live there. Frasier scores his date, but spends the entire time worrying about his father when Miranda tells him his father filled an application â- later to be discovered that it was only done so Martin could play poker with the residents. Meanwhile, Niles and Daphne are separated during their romantic dinner on the roof when Niles gets locked in the hall.

Frasier tries to make a good impression on the new station owner and ends up becoming his mentor. The guy is a young Sillicon Valley billionaire who has more money than society expertise, and seeks from Frasier the help he needs to enter the high society lifestyle without embarrassing himself. But Frasier sees his dream job go down the drain when Todd starts copying everything about him, his clothes, his furniture etc. Frasier then decides that perhaps he should be the one changing styles, but doesn't find anything that relates to him as much as his old furniture. Lastly, Frasier receives the worst news of all, Architectural Digest is doing a cover story on Todd's apartment. Meanwhile, Niles struggles to be a royal pain in the ass in front of Mel's society friends, as a part of her deal to give him the divorce, but his bad behavior actually brings good results and only makes him look even better for her friends.

Frasier hires an authentic English butler after his original boss passes away, achieving one of his many fancy dreams. Ferguson is great with the Cranes, and it doesn't take him long to start giving his opinions on the family routine. First he gives hints to Frasier on how he can charm opera board members and perhaps even get invited to join them. After that he warns Daphne about employee/employer relationships and how the social barrier is never broken. He helps Frasier organize a fancy dinner party, and Mel unexpectedly shows up, ruining once more Niles and Daphne's plans of being together. When Mel agrees on spending New Year's with some friends in the company of Niles, he draws the line and breaks up the entire marriage scam they were carrying on. Mel is devastated, and Daphne, relieved. Seeing that true love between boss and help can exist, Ferguson resigns to chase after someone he cared deeply, but never had the courage to do anything due to the social barriers.

Frasier starts dating the lawyer who is defending Daphne and him against Donny's lawsuit.

Frasier makes friends with Roz's new boyfriend, but when they break up Frasier hides from Roz that he's still hanging out with the guy. Roz gets back together with Luke and feels ashamed to tell Frasier about it since he was so supportive when they broke up. They keep the circle of secrets until they both get locked in Luke's closet and witness Luke making out with another girl. They both feel bad for lying to each other and accidentally get pushed out of the closet when Roz inflates Luke's boat. Meanwhile, Martin is mad at Niles because Niles put Eddie in a kennel while he was away instead of taking him to his house as planned.

Frasier learns that Dr. Mary will be his co-host for the annual Christmas parade.

Frasier is delighted to hear that he's been awarded a lifetime achievement award, but freaks out after he receives flowers from his mentor with a card that doesn't say exactly what he hoped. Moments before the awards dinner, Frasier goes down to his mentor's office and confronts him about the reason he wrote what he did in the card, and soon beings a ride of self-analysis and looks back on his life, wondering why he feels so empty despite all his achievements. Meanwhile, Martin tries to reassure Niles he's just as good a psychiatrist as Frasier, even though he's not receiving any awards, and Roz wonders why Daphne is putting on so much weight.

Freddy returns and Frasier takes him and Martin on a camping trip.

Frasier and Niles decide to enter an auto repair class after they embarrass themselves in front of their respective dates when their car breaks down and the women show more knowledge on engines than them. After falling behind on the course, they start to study frantically, until Roz suggests they simple coast the course. Of course the two take it too seriously and get kicked out of class. Meanwhile, Martin is overprotective of Roz's new puppy, which creates a conflict between them.

Niles and Frasier accidentally hire a bad actor for a play.

Two different scenarios of Frasier's Valentine's Day unfold: in the first he meets a beautiful artist; in the second he stays home alone. Meanwhile, Niles and Daphne either intend to fly to Hawaii or to stay home because of Niles' allergies.

Frasier intercedes to save station manager Kenny's marriage.

When Frasier, Niles and Martin go to a sonic's game, Niles is chosen at half time to make a basket to win a prize. Niles makes the basket on a fluke and gloats in his new glory. This disturbs Frasier, because he knows that Niles couldn't make the basket again.

Roz asks Frasier to narrate her space documentary.

Frasier and Niles look for a wealthy person to donate money to their closing prep school. Martin starts to date a very wealthy woman and the Crane brothers want to ask her for a donation. However, Martin finds ways to screw up the arrangement by dating multiple women at the same time.

Now that Frasier has landed a segment on Gil's gastronomic show about wine, he's ready to resign the Wine Club, just as Niles takes over the presidency duties. When no member from the club calls in his show, Frasier fears Niles is plotting against him in a vindictive sort of way, which is proven to be true when he finds out Niles forbid the members to call Frasier's show. The two start a fight and it takes Martin to yell at them in front of everybody so they will peace up again. Lastly, they get so embarrassed that they both quit the wine club and start their own. Meanwhile, Martin struggles with his new, hard-working physical therapist, Frederica.

When Daphne returns from her weight loss class, she realizes Niles didn't notice that she had gained weight because of how he remembered her being the last seven years. Meanwhile, Roz writes a children's book based on a story her mother used to tell her, but finds out it is already a book and a movie.

Frasier catches his mentor in a bathrobe with Roz. Niles doesn't believe Daphne is psychic, so she calls a spookologist.

Frasier must take Lana to her surprise birthday party, but he takes interest in Claire.

Lana promises to set up Frasier with Claire if he tutors Kirby, Lana's teenage son. Kirby agrees to study hard if Frasier can get him a date with Roz.

Niles becomes jealous when Daphne meets a dog lover. Lana becomes interested in Frasier when she tries to close a house sale. Martin meets a mystery woman.

Frasier is horrified when he learns Martin, Niles and Daphne are going to accompany him on his trip to Belize with Claire.