Roz arranges a blind date for Frasier with her friend Sharon (Jen Campbell), a former professional golfer. They meet and are immediately attracted, until Bulldog enters. He disparages golf, so Sharon challenges him to a game. They leave together and quickly become an item, much to Roz's anger. Bulldog is then heartbroken when Sharon dumps him over the phone shortly before his show.

Frasier has a recurring erotic dream in which he wakes up in bed, hears the shower running and is shocked when the person who emerges is KACL’s food critic, Gil Chesterton (Edward Hibbert). He struggles to work out the meaning of the dream, eventually concluding that his show did not provide him with the challenge he needed, so his subconscious provided a problem for him to work out.

Frasier is about to spend a week in Aspen at a psychiatrists' convention, and he asks Niles to stand in for him at KACL. While making way for Bulldog in the studio, Niles meets basketball player Reggie McLemore (Lorenzo Newton), who’s having a slump. Niles gives him two minutes' worth of advice in the corridor, and later that day Martin sees Reggie win a game for the Sonics on television. Niles is hailed as a hero in Seattle, and given VIP tickets to the next game, but he soon discovers that it was not his psychiatric expertise that Reggie believes helped him; it was his hair.

After a trip to the cinema, Martin complains that Frasier paid for the tickets when they had initially agreed that Martin would. The two of them decide that the next time they go out, Martin will pay. So when Daphne says she is cooking sheep's head soup for dinner, the three of them head off to Le Cigare Volante instead. After another argument about money, Martin refuses to pay, but he later tries to make it up by buying a painting from the restaurant. Niles and Frasier had effusively praised the painting so as not to offend the maître d', though in reality they disliked it.

During a slow day on his show at KACL, Frasier decides to tell a story about the aftermath of Eddie's recent trip to the vet. Eddie is not himself: he has lost his appetite, he is not sleeping, and seems generally listless. The vet says he is physically fine, so Martin worries that he may be depressed, and Daphne suggests taking him to a dog psychiatrist (Zeljko Ivanek), to the chagrin of Frasier and Niles. The diagnosis is that Eddie senses depression elsewhere in the family, so they are encouraged to act positively when around him.

While out driving, Frasier and Niles discover Roz collecting litter on the side of the road with a group of other people. She explains it is community service for a speeding offence, and she chose this option rather than visiting a retirement home, due to her fear of ageing. Frasier persuades her to confront her fear, but while playing checkers with the elderly Mr. Krantz, he dies mid-game. Frasier insists she persevere, but while reading to another resident, Mr. Gouldenstein, he dies as well. Frasier accompanies her to her next visit, where he meets a blind man named Norman (James Earl Jones), who is a fan of his.

At a benefit for the Seattle Theatre Ensemble, Frasier is approached by three attractive women in the course of the evening, and each one gives him her number. He therefore finds himself with a three-day weekend coming up and a date on each day. On the first date, Frasier claims to be a dog-lover and a vegetarian to impress his date, but Martin and Sherry come back early and reveal his deception. The following evening, Sherry accidentally reveals to the second date that Frasier had a date with a different woman the previous night. Martin has broken up with Sherry, and she calls by to drop something off, just before Frasier's third date arrives. Despite his worry that Sherry will wreck this date, Frasier tries to understand why Martin broke up with her, and finds out that it was due to Martin's guilt over falling in love with someone else other than his late wife.