In the first of three Valentine’s Day vignettes, Niles prepares for a date with the president of his wine club. While he waits for her to arrive at Frasier’s place, Niles’ last-minute effort to iron a proper crease in his trousers quickly escalates into a series of comic calamities which leave his pants scorched, his dinner in ruins and Frasier’s couch on fire.

Meanwhile, the station’s gorgeous publicity director Cassandra Stone asks Frasier out to dinner, but he’s not sure if it’s a business meeting or a bona fide date. Cassandra sends Frasier mixed signals all evening, until Frasier finds himself in bed with Cassandra – who promptly falls asleep on him.

Across town, a dateless Martin and Daphne go out to a restaurant together. Surrounded by happy Valentine’s Day couples, Daphne begins crying and admits she’s afraid she’ll end up alone. Martin’s attempts to console her work, but when a busboy refers to Martin as Daphne’s “father,” Martin sinks into a depression about growing older. This time, it’s Daphne who cheers up Martin, although they’re soon bickering again like an old married couple.