Angelika and Jake

In September 2007, Oprah met Angelika and Jake, young adults who said they were born in the wrong body. These transgender youths began transitioning to their new genders at a young age.

Oprah also met Dr. Marci Bowers, a biological man who became a woman late in life. Even after transitioning to the opposite sex, Dr. Bowers remains married to her wife of more than 20 years.

At the end of the show, Oprah still had unanswered questions. "This was a conversation that could have gone on for hours," she says. "We're picking up where we left off talking to men, fathers and husbands who, after many years of marriage, decided to live as women."

Having a transgender spouse may be a deal breaker for some wives...but not as many as you may think. About 25,000 women responded to an poll that asked, "Would you stay with your husband if he told you he wanted to live as a woman?" More than 10 percent of you said you would stay married.
Oprah reads Zachary's letter.

Wives aren't the only ones affected by this life-changing decision. Many men who become women are also fathers. Oprah says she was inspired to meet the families of these men after receiving a letter from Zachary, the 13-year-old son of Jenny Boylan. Jenny was known as Jim before her sex-change operation.

In the letter, Zachary writes, "Sometimes it's true that I wish I had a regular father, but only because I don't really remember what it was like to have a normal family. Sometimes it's hard to have a family that is different, but most of the time, I think I'm the luckiest kid on earth. I know people from lots of different kinds of families, but no matter how different they are, they really are all just people. My goal is that someday everybody will be treated with love."

"That's my goal, too," Oprah says.
Don (left) transitioned into a woman named Denise (right).

Back in 2003, the Brunner family blended right in on their tree-lined suburban street. Don and Fran were high school sweethearts who married after college and started a family. To friends and neighbors, they seemed like an all-American couple.

Then, everything changed. Don, the man of the house, decided to become a woman named Denise.

Friends and family were shocked by the decision, Denise says. "My closest friends said they had no hint because I had to hide it so well," she says. "I had to try to do the most masculine things to keep that stuff suppressed."

In high school, when Denise was still living as Don, she says she wrestled and played football. As an adult, she worked as a plumber and coached football in her free time. "I did everything possible to keep my feminine side in check by trying to be super macho," Denise says.

The only person who knew Denise was struggling with a secret was her wife, Fran. "She came out to me in college that she liked to wear women's underwear," Fran says. "Then, it progressed to more than just the underwear. I figured once we got married, everything would go away. ... I thought that I could change her."
Fran married Don years before she found out he was transgender.

The couple got married a year after college, but Don's attraction to feminine things didn't fade.

Fran says she used to find bras, dresses, underwear and blouses that belonged to Don while putting away the laundry. "[I would] get upset and throw everything out that I found," she says. At times, Fran says she also felt resentful toward her husband.

While living as Don, Denise says cross-dressing eased the pain she felt inside and made her feel like she was finally home. "[Being transgender] is such an alien feeling and so hard to explain to somebody unless you're there, but you just don't feel like you fit in your own body," she says. "When I was able to dress at those times, you feel more yourself."

At first, Denise says she only wore women's clothes at home. Then, after joining a transgender support group, she began going out as her natural self.

Denise says living a secret life began to take a toll on her mental and physical health. "I was getting migraines three or four times a month. My blood pressure was going sky-high," she says. "I was getting more and more tense, and I felt I was a time bomb ready to explode."

Suicidal thoughts began to haunt the father of three. Denise says she gave herself two choices—kill herself or become the woman she truly was.

After living as a man for more than 40 years, Denise says she began taking female hormones without her family's knowledge. "I realized I was risking my marriage, losing my kids, possibly being thrown out on the street, but I knew that's what I had to do," she says. "I just couldn't live life the way I was anymore."
Fran, Denise and Oprah

Denise said goodbye to Don just a few years ago, but she says she's always been the woman you see today. "I've always been Denise inside," she says. "The way I look at it is I finally took my Halloween costume off."

Fran also had to say goodbye to Don, but she says she never considered leaving her spouse. "I wanted the family to remain in a stable family," Fran says. "I had three children, and I needed to make sure we had a stable, loving home, and we had that. The person [I married] didn't change...just the packaging."

When Denise first began transitioning, Fran says she was a little uncomfortable with public displays of affection. "I was a little leery about it—about people marking me as a lesbian—and of people staring and getting the looks, the disgusted looks," she says. "You just come to the realization that, you know, that's their problem. Not mine."

Both Fran and Denise say their 27-year marriage is stronger than ever. "If you asked me 10 years ago, did I marry my soul mate? I would tell you that I married somebody that I love and that loves me back, but I didn't feel that I had my soul mate," Denise says. "You ask me today, did I marry my soul mate? And I will absolutely, positively, say yes. That's not because she stayed with me. It's just that we've gotten on such a higher plane of a relationship than I think we've ever been."

Though she's only been using mascara and curlers for a few years, Denise says she's felt feminine since kindergarten.

"I knew something was up, but I didn't have a name for it," she says. "I couldn't really say that I wanted to be a woman, but I didn't want to go out and play in the sand box. I wanted to play in the kitchen with the other girls. I didn't want to go out on the jungle gym. I wanted to be inside doing hair and makeup."

At age 14 or 16, Denise says she finally told herself, "You know what? I need to be a woman. I want to be a woman."

"Why not just gay?" Oprah asks.

"It's totally different," Denise says. "Sex is between the legs. Gender's between the ears."

Even though she's taking female hormones, Denise says she's never been interested in having sexual relationships with men. "I'm not sure if that's because I'm in a committed relationship and I have already somebody that loves me dearly, or if it's truly where my sexuality is," she says. "I don't know that. I'm not exploring it because I'm in a committed relationship. We're happily married."
Alyssa, Scott and Jessica

For the past few years, Denise and Fran's three children, Alyssa, Scott and Jessica, have watched their father slowly become a woman.

Jessica, the oldest, says she was the first to find out about her dad's decision to transition. "We had prom coming up, and I needed somewhere to get my nails done. Denise mentioned something to me, 'Oh, I know where you should go.' And I was like, 'What?'" Jessica says. "It kind of threw me for a minute. Afterwards, she sat me down and explained to me that she was transgender."

After Denise explained the situation to Scott, her only son, Scott says his first thoughts were of his family. "My fear was that [my parents] were going to break up," he says. "She's still my dad. We still do the same things. I like seeing her as happy as she is. I love it."

Alyssa, the youngest, had the most trouble accepting her father's transformation. "I miss my daddy," she says. "I was daddy's little girl. ... I felt really betrayed. I felt like she lied to me for 15 years of my life." Over time, Alyssa says she's realized that her father, who she calls "D" in public, has always loved her and never meant to hurt her.

Denise says, no matter what, she'll always be a father to her children. "I love my kids no matter how I am," she says. "My love for all of them has never changed. As I said, I had my Halloween costume on. I've taken it off, but nothing else has changed."
Denise chats with her neighbors.

After years of being afraid to go out in public as a woman, Denise now lives openly in her community. She says that friends, neighbors and strangers have been supportive of her decision.

"Our whole community—from the teachers, the principals, the coaches, our friends, the officials in town—have been outrageously supportive," she says. "I'm not naive. I know there was some tongue wagging behind our backs and everything else, but I have a great community. I'll tell you, 99 percent of them are with me."

Before beginning her transition, Denise went door to door letting her neighbors know there were going to be some "changes" in the neighborhood. "First thing I thought was, they're selling their house, they're moving, something like that," says Mike, a friend who lives a few doors down. "Then Don proceeded to tell me, 'I'm going to change into a woman, and [my] name is going to be Denise.' And I said, 'Whatever. It's great. Good.'"

Mike says one of the only changes is that now Denise shops with his wife instead of him.

Denise still remembers the day she told her friends, the O'Malleys, about her decision to live as a woman. "I was doing some work in their house when I went over to my buddy John, and I said, 'John, I have something to tell you. John, I'm a transsexual, and I'm going to be transitioning within the next couple of months,'" Denise says. "He looked at me, square in the eyes, came over and gave me a big hug...which to this day, I'll never forget."

When Joan first met her husband, she fell for him immediately. "It was that storybook romance that you hear about," Joan says. Both doctors, Joan thought she had found the man she would spend the rest of her life with. They married in the spring of 1993 and have three children—but Joan's husband had a secret.

About two years into their marriage, Joan stumbled upon a box in her basement. "It was full of women's clothing. A lot of women's clothing. It was everything. It was undergarments, and it was shirts and blouses and pants and skirts. The whole bit. Stockings, shoes—expensive shoes."

Knowing the clothes weren't hers, Joan confronted her husband—and he admitted they were his. "[He] had said, ''Well, you know, it's nothing bad. It's not harmful, and it's really not cheating on you. I just want to reassure you from that viewpoint, and it's harmless. But if it upsets you that much, it's gone. That's okay. I don't need to do this,'" Joan says.

Joan believed her husband when he said he would stop cross-dressing. "I was so uninformed," she said. "I was very ignorant about this topic. And so to me it represented a choice—I thought this was something that could be controlled."
Sydney talks about her transition

Although Joan's husband tried to stop cross-dressing, he says his feminine side could not be suppressed. After 12 years of marriage, he made a life-altering decision—to transition into a woman and rename herself Sydney. "I just knew that I was a girl, and it's a hard thing to describe to someone," Sydney says. "It was a pretty deep secret for me."

Sydney says for years she wasn't sure how to label herself. "When I was in high school and very early university I had boyfriends, very superficially. They were like crushes—nothing serious ever happened. And I thought if I feel these feelings, maybe I'm gay. Because that was the framework that society was able to support at the time."

As time went on, Sydney says she realized that she was attracted to women. "So I thought, well, I'm obviously not a gay man. What am I?"
Joan says she misses the man she married.

Although Joan and Sydney are still married, Joan says she misses the man she fell in love with. "You know, once Sydney transitioned, that was it. My husband never came back. It makes me sad. It still does," Joan says. "It's not that my husband's left. My husband's still here. It is a really weird thing. You can't really close a chapter and move on. It's the same story. ... The character hasn't changed. But how they look and how the act and how they sound is really different."

Joan says she once had thoughts of leaving Sydney—but not because of the cross-dressing. "It was because of the lack of truthfulness," she says.

Over time, Joan says she finally got past the betrayal. "I think enough time has passed where I can certainly understand the reasons behind it and I think I can look at it with more compassion."
Chloe talks about her transgender parent.

While confessing her true identity to Joan was just a first step for Sydney, she also had to tell her three children. "I think it was actually very easy a few years ago because they had no clue there was a problem," Joan says.

Instead of calling Sydney mom or dad, they refer to her as mada. "She wanted us to start thinking about a name that sounded like mommy and daddy," says 9-year-old Chloe. "I thought of mommy and daddy, like mom and dada, and I kind of just mixed them together."

Though the adjustment for the children seemed relatively painless, Chloe admits a classmate did make fun of her. "I'm worried they're going to do it again," she says. "I don't like being made fun of."

Ethan, Joan and Sydney's son, says he wishes he had a dad like the other 7-year-olds. "I like being the same as everybody else," he says. "I don't want to be different."

Joan believes her children have handled Sydney's transition well, but she's concerned about the future. "Now as they're getting older, I think they're starting to get that there are some issues," Joan says. "I think once they get even older than this, other issues will come up that we have no clue about."
Sydney and Oprah talk about acceptance.

As Joan and the children come to terms with their new life, things are still difficult for Sydney. "It really got to the stage where I really didn't want to transition," she says. "I didn't want to be someone that was going to be marginalized or pathologized."

Growing up, Sydney says there was little acceptance and understanding of transgender individuals. "Our world is very well set up for a man to be a man," Sydney says. "When someone does a gender transition, there's no real good language or framework around that. There's no system set up to support that in a major way within society. It's still seen as such a rare thing, but it's not that rare."

Oprah applauds Sydney and all the guests for helping to educate society on acceptance. "By opening your lives to us ... you are opening even wider the hearts and minds of those people who are watching."

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