Working as a paid companion may be quite commonplace, but Miss Gertrude Cadwalader's eccentric employer makes her job unpredictable, to say the least. She finds herself carrying out an array of highly unusual tasks, including wearing peculiar outfits and returning items the woman pilfered. But when the wealthy Mrs. Sinclair catches Gertrude sneaking around the Sinclair yacht with some of the missing items in her possession, she immediately jumps to the wrong conclusion.

Shipping magnate Harrison Sinclair is caught in the middle of a misunderstanding between his mother and Gertrude, but he can't help coming to his friend's defense. Even as he hopes their friendship might become something more, Harrison is unprepared for the outlandish escapades that seem to follow the lovely, anything-but-ordinary Gertrude at every turn.