When Miss Charlotte Wilson asks God for a husband, she decides He must want her to pursue Mr. Hamilton Beckett, the catch of the season. The only problem? She's never actually met Hamilton. Fortunately, one of her oldest and dearest friends, Mr. Henry St. James - who has returned to New York after a two-year absence - does know Hamilton. Much to Henry's chagrin, Charlotte immediately ropes him into helping her meet Hamilton. However, none of her plans to catch Hamilton's eye go as she expected, and she is even more confused when her old feelings for Henry begin to resurrect themselves.

Miss Gwendolyn Brinley accepted a temporary paid companion position for the Newport summer season, believing it would be a lark to spend the summer in America's most exclusive town. She suddenly finds her summer turning anything but amusing when her employer expects her to take over responsibilities as an assistant matchmaker. Tasked with the daunting prospect of attaining advantageous matches for her clients, Gwendolyn soon finds herself in the company of Mr. Walter Townsend, the catch of the Season, but a gentleman Gwendolyn finds beyond annoying.

Miss Harriet Peabody dreams of the day she can open up a shop selling refashioned gowns to independent working women like herself. Unfortunately, when an errand for her millinery shop job goes sadly awry due to a difficult customer, she finds herself out of an income. Mr. Oliver Addleshaw is on the verge of his biggest business deal yet, when he learns his potential partner prefers to deal with men who are settled down and wed. 

Miss Isadora Delafield may be an heiress, but her life is far from carefree. When her mother begins pressuring her to marry an elderly and uncouth duke, she escapes from the high-society world she's always known and finds herself to be an unlikely candidate for a housekeeper position in rural Pennsylvania. Mr. Ian MacKenzie is known for his savvy business sense and has built his reputation and fortune completely on his own merits. But when his adopted parents are in need of a new housekeeper and Isadora is thrown into his path, he's unexpectedly charmed by her unconventional manner.

After her father lost the family's fortune, Wilhelmina was cast out of the fashionable set and banished to the wallflower section. Taking a position as a social secretary to help support her family, she's mostly come to terms with her new status. But when her old friend Edgar returns to New York society for the first time since she rejected his marriage proposal, she's newly ashamed at how far she's fallen—and how hastily she dismissed him years ago. Her strategy is to avoid a face-to-face encounter at all costs, but he seems to have other plans.