Niles and Frasier plot to rescue their prep school from bankruptcy with the help of Martin’s wealthy new girlfriend.

The Crane brothers are saddened by the news that Bryce Academy, their beloved alma mater, is on the brink of closing. In a last-ditch effort to save the school, Frasier and Niles host a fundraiser at Frasier’s condo. Although all of their rich friends are tapped out, their spirits rise when philanthropist Penelope Janvier walks in.

Before they can speak with Penelope, she leaves the party, though Martin informs them that Penelope asked him out to dinner. The following night, Frasier and Niles are thrilled when Martin’s date lasts for five hours. Their excitement is short-lived, however, when Martin brings home Estelle, a waitress he met at a coffee shop after dropping off Penelope.

Suddenly, Martin happily finds himself juggling two girlfriends at the same time. Eager to press their case with Penelope, the brothers invite themselves to a party she’s asked Martin to attend. Once there, Martin decides to dump Penelope for Estelle. Frasier scrambles to secure a donation from Penelope before Martin breaks up with her. Eventually, Penelope learns about Estelle, and both women drop Martin. But, true to her word, Penelope gives Frasier a check – for a measly $50!