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. Walter is reluctantly in search of a wife for the sake of his unruly motherless children. What he wasn't expecting was Miss Brinley, who turns his quest for a new wife into a complete and utter debacle. The more time they spend together throughout the Newport Season, the harder it is for Gwendolyn to find Walter a wife when she realizes his perfect match might be … her.