After Miss Wilhelmina Radcliff’s father lost the family fortune in a poor investment decision, she finds herself banished from the fashionable set within New York society and directly into the wallflower section. Taking on work as a social secretary in order to help with family expenses, she spends her time penning out invitations to all the most sought-after events, wondering if her life will ever improve. While languishing one evening at a ball given by one of the esteemed New York patriarchs, Wilhelmina is appalled to discover that Mr. Edgar Wanamaker, her oldest and dearest friend, and the first gentleman to offer her a marriage proposal, has shown up at the ball unexpectedly, having been absent from New York ever since she rejected his offer years before.

Miss Permilia Griswold, the wallflower behind "The Quill" gossip column, knows everything that goes on in the ballrooms of New York. When she overhears a threat against the estimable Mr. Asher Rutherford, she's determined to warn him. Away from society's spotlight, Asher and Permilia discover there's more going on behind the scenes than they anticipated.

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.

After years of hiding her true nature, Miss Temperance Flowerdew is finally enjoying freedom outside of the shadow of her relations, so the last thing she expected on her way to work was to be grabbed off the street by a stranger and put on a train bound for Chicago. When Mr. Gilbert Cavendish is called upon to rescue a missing woman, he follows the trail to Chicago only to discover that the woman is his good friend, Temperance. Before they can discover who was behind her abduction, they're spotted alone together by a New York society matron, putting their reputations at risk. Even though Gilbert is willing to propose marriage, Temperance is determined not to lose her newfound independence. But when the misunderstanding in Chicago escalates into a threat on her life, accepting Gilbert's help in solving the mystery may lead to more than she ever could have dreamed.