This story goes beyond the normal transgendered narrative to include more of the feelings and impressions of those around the subject. James Boylan, a Colby professor, became Jenny Boylan, a Colby professor, at the late age of 41. She already had a wife, two kids, a close friendship with writer Richard Russo, and a whole life history as a man. Jenny relates why she came to her decision to actually have surgery to become physically female, and how it affected those around her. She is lucky to have not only a strong writing ability, but friends who share her skills. Sections of this book are just email conversations between her [then him] and Richard Russo, talking about some of the more complex issues of the transgendered transformation -- while Jenny felt that she was becoming what she always had been on the inside, her friends and her wife were having a tougher time saying goodbye to Jim.
A good deal of this book is also wrapped up in describing Jenny’s childhood as James, what his sexual and gender identity was like, what his family was like, how he grew up. Notably missing is his sister who was hostile to his transformation and she does not appear in the book except towards the end as someone who was not supportive and with whom Jenny had broken off contact. In retrospect, her absence from Jenny’s childhood is somewhat palpable. At the time you don’t notice it. The book contains many lively anecdotes and a small amount of female brand fetishization [who cares what brand of makeup you wear? girls do, I guess] which reads as more ironic than annoying.