When Jim Boylan was 6 years old, he knew he was different from other boys because he often dreamed of being a girl. During his teens, Jim tried to fit in, and after college, he moved to New York to become a writer. At that time, he started dressing as a woman, hiding it from everyone who knew him. Jim continued the facade until he met a woman and fell in love. They eventually got married, but his bride had no idea about Jim’s secret life. Then, after 10 years of marriage, Jim’s thoughts of becoming a woman returned. After a tearful discussion with his wife, Jim decided to fully transition and have sex reassignment surgery. He also changed his name to Jenny.
In 2005, Oprah spoke with Jenny and her wife, Deedie, about their relationship and Jenny’s transition. “My first emotional reactions were to be scared and to be sad,” Deedie told Oprah. Now, for the first time in 10 years, Jenny shares an exclusive update with Oprah: Where Are They Now? producers. “Deedie and I are celebrating 27 years of marriage this very year,” Jenny says. “That means 12 years as husband and wife, and 15 years as wife and wife.” In the video above, Jenny, the author of Stuck in the Middle With You and the children’s book series Falcon Quinn, reveals how she and Deedie made their marriage work, and opens up about how her transition helped make their sons better men.