In the late '90s, Jim Boylan was many things: a college English professor, the author of several novels, a husband with a loving wife named Deedie and a father to two young sons. But Boylan was also living with a deep secret: Ever since childhood, Boylan had thoughts of living as her truly authentic female self.
"I was Jimmy when I was a little kid, but I knew that I was a girl. Even as a child, I did have a sense of my soul as being female," the author says.
As powerful as this sense was, no one knew that Boylan felt that way -- not even his wife. After 10 years of marriage, however, Boylan realized he could no longer keep up the façade of living as a man. Through difficult conversations with Deedie, Boylan made the decision to transition to presenting and living as a woman, completed gender confirmation surgery and began living as Jenny. The couple remained married, and in 2005, Jenny appeared on "The Oprah Winfrey Show" along with Deedie to tell their story.
"My first emotional reactions were to be scared and to be sad," Deedie admitted back then. "In part, we're still married because of the life that we built together, that I still really care about."
"Are you still intimate?" Oprah asked. "Can I ask that question?"
"You can ask," Deedie said. "No, we're not still intimate."
Along the same lines, Jenny explained that she was still working through her own feelings about intimacy in general. "I'm curious about men now," she said. "But, to be honest, I'm not looking. I'm so grateful for what I have. I'll tell you what, this family's been through enough, so I'm not looking."
"And we're still married," Deedie added.
It's now been 10 years since Deedie and Jenny spoke with Oprah for that poignant show. "Oprah: Where Are They Now -- Extra" recently caught up with Jenny to find out what life has been life since their appearance.
"Deedie and I are celebrating 27 years of marriage this very year," Jenny says in the above video. "That means 12 years as husband-and-wife, and 15 years as wife-and-wife."
Looking back at "The Oprah Show," Jenny acknowledges that the couple's relationship appeared to be in a very different state than it is now. "Deedie's and my relationship was in a fairly vulnerable place. It wasn't that we doubted each other, but we just didn't know what was going to happen," Jenny explains. "Now... I can say that Deedie and I have essentially returned to each other. I would certainly describe our relationship as intimate and that there is love at the center of everything we do."
The Boylan's sons are now college students -- one is a drama major and the other is studying engineering -- and Jenny believes that her transition has been a positive influence on her children's lives.
"I feel sometimes as if having a father who became a woman enabled my sons, in turn, to become better men," she says. "They learned something about the value of living an authentic life."
Jenny is still an English professor, and is also the national co-chair of GLAAD as well as a contributing opinion writer for The New York Times. Her latest book is "Stuck in the Middle with You: A Memoir of Parenting in Three Genders."
"Oprah: Where Are They Now -- Extra" is a web-based spinoff of OWN's "Oprah: Where Are They Now?", which airs Sundays at 9 p.m. ET.