Anne & Gilbert is a musical based on the Anne of Green Gables series of books by Lucy Maud Montgomery. The show was based on the books Anne of Avonlea and Anne of the Island, and adapted by Jeff Hochhauser, Nancy White, and Bob Johnston.
The show closely follows that of the books on which it was based, suffering only a handful of alterations and a number of cuts for length. The first act is comprised entirely of Anne of Avonlea, while the second act is based on Anne of the Island.
During the course of the first act, Gilbert Blythe gives up the position of Avonlea Schoolmaster for Anne Shirley, allowing her to stay close to home to care for her adopted mother. It is revealed that almost all of Avonlea knows that Gilbert is deeply in love with Anne, and she with him, although Anne will not admit it. In return for the kindness he has done her, Anne agrees to a wager with Gil; he will propose to her at some day of his choosing, and if she says no he will never ask again. After some time, Anne's best friend Diana Barry becomes engaged to her beau, Fred Wright and at the end of the first act, marries him. Gilbert takes advantage of his wager with Anne and proposes to her following the wedding, but she rejects him. He vows never to propose again. Through a series of fortuitous events, Anne is finally able to follow her dreams and go to Redmond University.
The second act opens with Anne of the Island, introducing several new friends for Anne. Meanwhile Anne falls in love with a millionaire named Royal Gardner much to the dismay of her adopted mother Marilla Cuthbert and Diana back home in Avonlea. Although she toys with the idea of marrying him, she finally decides that she does not truly love him and rejects his proposal. Roy storms off and is not seen again. Gilbert, who is paying his way through University with odd jobs, happens to be at the restaurant where Anne and Roy are as a waiter. He gives Anne an early birthday gift in the form of three letters her parents left behind before they passed away. As she reads the letters she begins to realize that she truly can love somebody, and finally finds the love she's had for Gilbert all along.
The show ends with Anne proposing to Gilbert back home in Avonlea for the summer, as the entire town and several friends from Redmond look on.