Making the transition from friends to lovers is probably difficult enough without having a socially conscious mother like the hero of this book and a penniless, and eccentric family like the heroine. The secondary characters in this book include smugglers, traitors, and a relative who’s a little too original for most people’s tastes. But you also have a kind-hearted (but not saccharine-sweet) heroine, and a hero who comes up with seventeen different plans to make sure the love of his life doesn’t get away.

Ada Westlake, whose family has fallen on hard times, finds a purse filled with coins in one of her orchard trees. Since Ada believes this is money that a smuggler has left hidden there, she is reluctant to spend any of it, much to the irritation of her widowed sister-in-law Jane, who resents the family’s current situation. If it were up to Jane, the purse of coins would be spent on suitable gowns and decorations, but Ada is determined to find where the money came from and she begins a search for the smugglers.

Meanwhile, Charles Ashford, Viscount Ashmead, is recovering from his latest dealings with Ada. He has known the Westlake family forever and his repeated proposals to Ada always end in heated confrontations, with Ada demanding he never again ask her to marry him. Ada refuses to accept the proposal of a friend like Charles since she believes it’s kindness rather than love that leads him to make an her offer. Plus Charles’s mother, Lady Ashmead, is not sympathetic to Ada. She is determined to see her son married well, and not to someone like Ada, who is penniless and has a sister who’s got a few screws loose. Ada agrees in theory, but when she sees Charles with the very wealthy and suitable (despite her lisp) marriage prospect Lady Esther, she begins to have second thoughts.

Ada’s sister, Tess Westlake isn’t crazy, she’s just creative. She has danced ballet (in the fountain) and sung arias (when no one expected her to) and at the moment, she’s devoting her creative energy to writing her masterpiece, Sebastian and the Sea Goddess. The moment Tess meets reputed smuggler Leo Tobin, who also happens to be Charles’s half-brother, she has found her Sebastian, and the reader is in for a sweet, if a little unusual, secondary romance. Charles and Leo are not only half-brothers, they are true friends, despite Lady Ashmead’s continued attempts to pretend Leo doesn’t even exist. During the course of the book, Charles is nursing some physical injuries, resulting from rather strange circumstances he’s reluctant to discuss, but which don’t prevent him from watching over his beloved “addled Ada.”

Miss Westlake’s Windfall is a book packed with interesting characters, including Charles’s beloved dog, Tally, who ends up going into labor at the most inconvenient place. Only when it is dealing with Tess’s play does the book go a bit overboard. Otherwise, the secondary characters (and there are enough of them that they might have been ill-defined in less-skilled hands), are well rounded and really contribute to the story. Characters are not treated cruelly, i.e., just because Lady Esther is not destined to marry Charles doesn’t mean she ends up being odious. Something else I liked was the humor in this book, including how Ada goes from being ignored because she’s penniless to having proposals the moment it’s known she has a fortune in her hands.

If you’ve ever shied away from Regency Romances because you have a preconceived notion of what type of book they are, I’d recommend you give Miss Westlake’s Windfall a try. While it’s a Regency through and through, from the title to the language used, it’s a delightful story of two lifelong friends who are a little afraid of rejection from the person who matters the most to each of them. I think you’ll enjoy this very sweet book, and meanwhile, I’m off to hunt for Ms. Metzger’s backlist.