After dreaming about a former girlfriend, Lana, while in bed with his current girlfriend, Claire, on their vacation in Belize (picked up from the season eight finale "Cranes Go Caribbean"), Frasier begins to wonder if he is in a relationship with the wrong woman. Breaking up is hard to do, but particularly hard for Frasier as he cannot shake his feelings but at the same time feels that Claire is the "perfect woman" for him - that, and his family just loves her. He is not alone with his thoughts however, as his ex-wife Lilith and ex-girlfriend Diane pay him a "visit" of sorts.
An hour-long opening to the ninth season, "Don Juan In Hell" is easily one of the best episodes of Frasier of the eleven year series. Opening with the Cranes in Belize and ending with a very odd twist of events, the first half of "Don Juan In Hell" is absolutely hilarious - Frasier goes through relationship trials and tribulations, Niles finds a new way to be quirky, Martin is not afraid to tell Frasier what he thinks, and Roz gets used for "man bait."