When Caroline Lash arrives in Greenhead, Massachusetts, she falls head-over-heels for Van Whittaker. Born and raised in this picturesque coastal village, Van runs with the same crowd he did as a kid: his ex-girlfriend, Bailey; Augusta, who is old money, horsey and snobbish; and Fran, who is too fed up with boys to ever consider marrying one. Together, the group runs wild through the marshes, beaches and bars of Greenhead, drinking on houseboats and spending long afternoons sunbathing with their children. But when Bailey discovers that she is pregnant with Van’s baby, the delicate balance of the group’s friendship is thrown off. Soon Caroline is cast out of the circle. What she does next exposes long-held secrets and works the entire town of Greenhead into a lather. 

PINEAPPLE STREET follows three women in one wealthy Brooklyn clan. Darley, the eldest daughter in the well-connected old money Stockton family, followed her heart, trading her job and her inheritance for motherhood but giving up far too much in the process. Sasha, a middle-class New England girl, has married into the Brooklyn Heights family and finds herself cast as the arriviste outsider. And Georgiana, the baby of the family, has fallen in love with someone she can’t have and must decide what kind of person she wants to be.