When it comes to matchmaking, the obvious choice doesn't always lead to love. Will the third time be the charm? Orphaned at sixteen, Emma Fitzsimmons lives at the London finishing school her late father, George, arranged for her to attend. With no prospects for marriage but having experience as a bookkeeper at her father's hat shop, Emma decides to pursue a position as an accomptant. But who will hire a woman in 1802 London? Her roommate's brother, Thomas Welllingham, inherited his father's import company and quickly expanded operations to include a way to transport goods across Great Britain. Convinced someone is embezzling from Wellingham Imports, he solicits advice from his banker, Sir William Burroughs. Charged with Emma's financial welfare, Sir William recommends Thomas hire her to audit his books. Thomas does so, arranging for her to work at his manor in Chiswick and be a companion to his sister Christiana. And he may have just the man for Emma. Todd Vandermeer, a wealthy broker with the East India Company, has decided to marry. His apparent low birth and excessive height make courting awkward, although once he meets Emma, he's sure she's the one for him. Emma's best friend Deborah, a midwife at a home for unwed mothers, may be a better choice, though. The tall, willowy woman has an unfortunate past that may prove too much to overcome, although not in a way she expects. Emma's new landlords, an older couple who are rather overt in their affection for one another, seem intent on introducing her to the wealthy Gregory Grandby. With a reputation as a rake, Gregory has already made his choice in a future wife, a young lady who is rather good at keeping secrets—especially him. With one couple having found love despite their class differences and three couples looking to find love, one banker is determined to see it all work out in his favor. Or will it be the butler who prevails in the epic Regency "The Promise of a Gentleman?"

First comes matchmaking, then comes marriage, and then comes a baby carriage ... well, usually. Life in 1802 London throbs with great expectations and unlimited potential. A house under renovation reveals its secrets, and newlyweds Gregory and Christiana embark on a wedding trip to Italy, determined to keep their secret. Thomas Wellingham's import business grows faster than he can manage with his brash and brave new wife Emma as head accountant. Wellingham's best friend, Todd Vandermeer, accepts his offer of employment despite concerns about the viability of Wellingham Imports. His wife, Deborah, is expecting their first child, after all, and he needs the position. Now that he's completed his life's work seeing to the renovations of every townhouse his wife owns, James Simpson is ready for a new job—that of father. Having informed Sophia he would like an heir, he's rather surprised to discover his plans for a family aren't so far-fetched. But can she abide a late-in-life pregnancy and the possibility of heartbreak should it all go wrong? A single night will prove fateful for all their futures as Emma is forced to take on a role she has only played a few times—that of midwife. Can best friends and family remain so when life doesn't quite get it right? Are romance and marriage compatible, reconcilable? Perhaps, but only if they can overcome The Pride of a Gentleman.