Frasier has become fed up with the way the modern world treats good Samaritans. His son Freddie comes to visit and one night, while driving home, Frasier stops to help a woman stuck in the rain, only to discover that she is a prostitute.
Frasier and Roz set his father Martin up with her mother Joanna on a "blind date". Afterwards, Martin announces that he never wants to see her again while Joanna cannot wait to see Martin a second time. It all comes to a head when Frasier invites Roz and Joanna over to watch the Superbowl, but Martin has invited Bonnie, a waitress from McGinty's, whom he is interested in dating.
Frasier's old bartender at Cheers in Boston, Woody, shows up in Seattle to visit his old friend. Things turn bad after their first night reunion when Frasier realizes that he has moved on with his life and left Woody in the past.
Three different act long stories following Frasier, Daphne, Niles and Martin on Valentine's Day. Niles prepares for a date at Frasier's apartment, but ends up lighting the apartment on fire. Martin and Daphne, both dateless, head out for dinner. Frasier is confused as to whether or not his date with Cassandra, a promotional manager at KACL is just a business meeting or actually a date.
Niles' and Maris' divorce proceedings heat up and Niles hires Roz's ex-boyfriend Donny Douglas, a cut-throat lawyer who soon has Maris' legal team on the ropes. However, when Maris claims that Niles was in love with another woman through their marriage, Niles fears he may have to come clean about his crush on Daphne.
Niles, still reeling from Daphne and Donny's new relationship, wins Maris' old cottage in the woods from the divorce. In an attempt to win Daphne from Donny, he invites Roz and Donny up to the cabin in hopes that their old relationship might spark some new feelings.
Frasier and Niles decide to host a dinner party at Frasier's apartment. It becomes more complicated than either of them could have imagined and it leads them to think that maybe the brothers are spending too much of their time together.
With the divorce with Maris finally settled, Niles moves back into his luxurious apartment in the Montana. But when the tenant Frasier chose to let the apartment comes under attack, Niles is subject to severe scrutiny from the Montana Board, who tell Niles that they are considering kicking him out of the building once and for all. In an attempt to wrangle the support of the Board back to his side, Niles decides to throw a dinner party for the members, but with disastrous results.
Frasier and Niles' long time competitiveness is reawakened at a silence auction where the two spend eight thousand dollars for a lunch with three Nobel Prize winners. Determined to find the root of the fierce competition, the two remember an old IQ test they took to which they never found out the results. The brothers dig through their childhood papers and find the IQ test. Now the only question is which one of them has the higher points?
Frasier's radio show is doing well in its ratings, and KACL has decided that another show in the same genre would do well. They ask Frasier to hire another doctor to fill the slot and he is immediately taken with an intelligent woman named Dr. Nora. Frasier is suddenly shocked to realize that Dr. Nora is not all that she appeared to be.
Fraiser has begun dating Cassandra Stone, the beautiful woman whom he spent Valentine's Day with. Everything is going well until Faye Moskowitz comes back to town and Frasier remembers how much he enjoyed spending time with her. He begins to date both women but soon discovers the prestigious dating level is not all it is cracked up to be.
Martin sees Donny buying an engagement ring for Daphne and, while relaying the information to Frasier, accidentally tells the bride-to-be herself. When Niles finds out, he is absolutely devastated. The next day, Daphne comes to Niles' office saying that she had a vision that she should not marry Donny and that the man of her dreams is waiting for her somewhere.
Part One of Two. In the wake of Daphne's engagement to Donny, Niles becomes frequently distant, leading Martin and Frasier to believe that he has run back to his ex-wife Maris. Meanwhile, Martin begins dating Bonny the waitress, and as his relationship with Faye deepens, Frasier begins having Fruedian slips, continuously referring to her as Cassandra, the woman Frasier was dating before Faye.
Part Two of Two. Niles has started dating Kit, a wild waitress from Cafe Nervosa. Frasier becomes increasingly worried about Niles when he begins to adopt Kit's wild, free-spirited approach to life. Meanwhile, Martin is upset with Bonny when her dog, Lady, begins dominating Eddie and Frasier is even more worried about his situation with Faye when Cassandra begins popping back into his life.
Daphne complains about her mother's pushiness in planning her wedding. Frasier makes a Freudian slip that leads her to think that he and Martin are offering to pay for her wedding, which she joyfully accepts. Before long, Frasier becomes even more domineering than her mother. Niles, depressed about Daphne's impending nuptials, decides to try a dating service and is elated to be matched with an attractive blonde named Sabrina. But Frasier learns from Donny that the service in question is actually a call girl ring.
Frasier is repeatedly made the butt of phone pranks by KACL's new comedy team, "Carlos and the Chicken." When the team announces a contest for a covert photo of Frasier's hindquarters, he decides to retaliate by composing an oration, a move ridiculed by his family and friends.
After losing his job at KACL, Bulldog is delivering pizzas. Seeing how well he gets along with Alice, Roz offers him a job as a babysitter. After a while, she finds that he is driving away her dates so he can declare his own feelings for her. Martin, pressured by his sons, makes arrangements for his own burial.
No one at the station can stand the owner's airhead daughter, Poppy, but Niles finds himself taken with her. Frasier finds a half-naked woman in his apartment, and she introduces herself as his new neighbor. Both brothers start dating, but a misunderstanding leads both of them to conclude that they are competing for the same woman.
The rift between Martin and his sons' tastes is bridged when they find they are all fans of "The Antique Roadshow." The boys have a great time watching it on TV, and when the Roadshow comes to Seattle, they all go. Martin takes along an old family heirloom, a rather ugly pewter clock. Frasier and Niles are stunned to hear that it was originally made for the Romanovs (the Russian royal dynasty). Believing the clock is a link to their own royal blood, Frasier and Niles launch an investigation into its origins.
A minor fender-bender sends Frasier to the hospital. While waiting, Niles hears the name of Maris's plastic surgeon, Mel Karnofsky, and decides to confront him about a billing error. An annoying man bores Frasier into leaving the office, and the man uses Frasier's name to jump the line. Niles is surprised to find that Mel is actually a woman, with whom he has a lot in common. The man at the hospital dies suddenly, and Frasier is mistakenly thought dead for a day. He takes it as a wake-up call, doing his best to live live to the fullest every day. Niles doesn't have ...
Lilith and Frederick come to Seattle for Thanksgiving dinner with the Cranes. Frederick maneuvers Frasier and Lilith into spending an evening together, and they begin to suspect that he is trying to get them back together. Or is he just trying to guilt them into buying him a moped?
On his birthday, Frasier is seized with crippling back pain. Niles wonders if he's stressed, and while recovering at home, Frasier muses aloud about why he's unhappy. One reason is that he's still single, and he will miss Daphne's companionship after she gets married. Daphne, overhearing, misunderstands him to mean that he has feelings for her. Frasier resolves the confusion, but while he's doped up on painkillers, lets slip to Daphne the truth about Niles's feelings for her.
Daphne is unsure how to deal with Niles's feelings for her. Roz assures her there's nothing to worry about: Niles has a girlfriend now, and she's engaged to Donny. However, Niles has a meeting with Maris to console her over the loss of a friend, a meeting that he keeps secret from Mel. Frasier lets slip the secret, and Mel angrily breaks up with Niles, making Daphne very nervous. Frasier's Christmas party competes with one thrown by his rival neighbor, Cam Winston.