At the station, Frasier discovers that Roz had a one night stand…with Bulldog. When Bulldog comes in later, he tries to be subtle about asking Roz for a date, until he realizes that Frasier knows. Roz is taken aback, however, when Bulldog asks that they have dinner together first, like a real couple. When Bulldog leaves, Roz is flabbergasted and tells Frasier that she needs to end things immediately. Bulldog pops into the studio and is holding a notice that he has been fired. In disbelief, he loses control of his emotions. Finally, he embraces Roz and says, "At least I have a wonderful girlfriend." Roz looks helplessly over his shoulder at Frasier.
That evening, Frasier finds Daphne's lost engagement ring, much to her delight. Daphne and Donny are very happy together, and things are going very well between Martin and his girlfriend, Bonnie. Frasier has started dating Faye, who is also at his place, but he keeps referring to her accidentally as Cassandra, his old girlfriend. While the three happy couples are hanging out together, Niles bounds in with his peppy new girlfriend, Kit, whom he met in Café Nervosa. Kit is young and fun and energetic and child-like, and Niles is exhausted but beaming from a night of bar-hopping and dancing at clubs. Kit announces to everyone that Niles is taking her to France to visit Eurodisney, and Niles says "Apparently, it's so kitsch that it's actually cool." Kit inadvertently insults Faye's cooking, and while Kit is out on the balcony having a cigarette, Frasier confides to Niles that he doesn't see him and Kit having anything in common. Niles grows defensive, accuses Frasier of being jealous, calls him a "buzz-kill" and then storms off with Kit.
The next day, at Café Nervosa, Roz confesses to Frasier that she is definitely going to break things off with Bulldog, and that she is meeting him there to do that very thing. Frasier calls Faye and leaves a message, accidentally calling her "Cassandra" again. The two of them observe Niles in a corner of Café Nervosa, and Roz says that Niles actually looks happy. Frasier acknowledges that she's right, and decides to give him his blessing on Kit. Meanwhile, Bulldog walks in, hands Roz a stuffed bulldog, and declares that this must be his lucky week. Just as Roz is opening her mouth to tell him it's over, Bulldog informs her that he's met a "hot chick" that morning and that the two of them are flying to Hawaii together. Roz screams, "I was about to dump you! and Bulldog simply laughs and tells her to try to get over him as he leaves. Noel was sitting there behind a newspaper the entire time, observing this. Martin pops in and informs Frasier that he broke things off with Bonnie. The reason being, Bonnie's dog humped Eddie in the park. Frasier laughs and Martin gets angry, saying that's exactly why he dumped Bonnie, and leaves Faye walks in then, and greets Frasier. She's a little miffed at having gotten his message and been called "Cassandra" again, but believes it when Frasier reiterates that "Cassandra" is his aunt. Just after she goes to the rest room, Cassandra, Frasier's old girlfriend, walks into Café Nervosa and tells Frasier that she's met a great guy, harbors no ill will towards him, and is very happy. She's about to hug him when Faye gets back; Frasier breaks off the hug before it can happen and ends up injuring her. Roz helps hustle Cassandra out of the café before she can be formally introduced to Faye. Faye leaves momentarily to feed the meter, and meanwhile, Niles comes over and Frasier tells him that he likes Kit after all. Niles says, "Really? Then please take her!" He explains that he's exhausted from trying to keep up with all her activities, including rollerblading. Kit is working there, and Niles goes over to tell her that he wants to talk with her later. Kit jokes, "You're not going to break up with me, are you?" sees Niles face, and drops her tray of beverages and other items. She totally freaks out at Niles in front of everyone before jetting out of Café Nervosa. As Frasier and Niles clean up the mess, Faye walks back in, and at the same time, so does Cassandra. Frasier watches helplessly as Faye introduces herself, and hurls himself towards the two of them too late. Faye finally knows who Frasier's "Cassandra" really is.
The final scene depicts Niles, Frasier, and Martin sitting at the bar, all lamenting their dating woes. Frasier suggests psychoanalysis for himself and for Niles, but Martin assesses each of them instead, concluding that Frasier should stay with hot girlfriend #1, Niles is just starting to date (25 years later than normal) and for him, "Lady humped Eddie" and that's that. They end up reluctantly taking Martin's suggestion and gather around the bar pianist and sing "Goldfinger."