JENNY: 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.
As I saw all the girls that I knew becoming women,
it was like standing on a dock watching the ship sail away.
WINFREY: It was a crushing burden,
and all along he hoped that love what cure him.
JENNY: If I were loved deeply enough, it would save me.
WINFREY: In college he continued to keep up the front
that he was a regular guy, but he was secretly dressing as a woman,
hiding it from everyone who knew him.
JENNY: When I was in graduate school, I really was living this kind of double
life. I was living as a woman most of the time.
I met this wonderful woman, and we fell in love,
and what I'd always prayed for my whole life had come true.
I'd prayed, `Dear God, please make someone fall in love with me
so that I can stay a man.'
WINFREY: Deedie and Jim married.
His bride had no idea about Jim's secret life.
JENNY: I put all my female gear into the trash bag--skirts, clothes,
makeup, everything, and I put it out by the curb.
I walked back to my apartment as a man for what I hoped would be forever.
WINFREY: They moved to Maine and started a family.
Their lives were nearly complete until thoughts of being a woman
came crashing down on Jim again.
After 10 years of marriage, he realized he could no longer keep up
the facade and live as a man.
So Jim now faced the most difficult conversation of his life. Imagine this.
You take your vows, you say for better or for worse,
but nothing prepares you for this conversation.
His wife had no idea that this was coming.
He started taking female hormones which altered his emotions
and morphed his body. After a year, Jim completed the transition
with full sex change surgery.
But this transformation had a crucial cost.
So Jenny first shared this fascinating story with us two years ago,
and at that time Deedie did not want to reveal her identity
or appear on our show.
Today, for the first time, she is ready to tell her side of this intriguing tale.
Deedie, come on up. Come on up here. Hi.
DEEDIE: Hi.
WINFREY: How are you?
DEEDIE: I'm OK.
WINFREY: Nice to see you. Nice to see you.
Well, it's been two years since I met Jenny, who used to be Jim.
Are you still married?
DEEDIE: We are.
WINFREY: You are still married.
DEEDIE: See?
WINFREY: OK. You know, I do so many stories, and many of the things
that I do,
after a while in my brain, all seem to run together, but yours is distinct.
I have never forgotten you.
I was just in a conversation the other day with my friend Julia Roberts
and Mike Nichols.
We were all sitting around--I'm not trying to name-drop,
but really Julia watches the show every day.
And I was saying, `Did you see the day we had Jenny on?'
And she had seen, and we started talking about what happens
in a relationship like this,
and who stays and why?
Can you take us back, because I really wanted to talk to you then,
but I really do understand that you were still kind of reeling from it all.
DEEDIE: I was.
WINFREY: Can you take us to the day that Jim came to you and said,
`I want to be a woman'?
DEEDIE: I think that, you know, my first emotional
reactions were to be scared and to be sad.
I think that the reason we're still married is that she
is the same person, it's...
WINFREY: Yeah.
DEEDIE: ...just a different body.
And I think it's really hard to understand unless you're close
to somebody or experienced this or had known Jim before Jen.
WINFREY: Because Jen still acts like Jim.
DEEDIE: Exactly.
WINFREY: Except Jen is now a woman.
DEEDIE: Absolutely.
WINFREY: I can't believe you didn't say, `I'm outta here.'
DEEDIE: I think a lot of people felt that way.
I mean, in part, we're still married because of the life that we built together
that I still really care about.
WINFREY: So when you first heard it, you were--you didn't scream,
you didn't cry, you didn't say, `What the...'
DEEDIE: Oh, I cried. I cried.
WINFREY: You know?
DEEDIE: I cried.
WINFREY: For the sadness, yeah.
DEEDIE: For the sadness.
WINFREY: And the loss.
JENNY: We both cried.
DEEDIE: For the loss.
WINFREY: Grieving what...
WINFREY: ...what would have been...
DEEDIE: Right.
WINFREY: ...or could have been.
DEEDIE: Losing the...
WINFREY: The dream.
DEEDIE: Losing the dream, losing--I knew I was losing my husband.
WINFREY: The passage that struck me more than any other
in Jenny's powerful memoir, which is called "She's Not There,"
was the description of the last time the two of you made love together,
and in it you say, `We lay in bed after making love, lying back on our pillows,
the sheet covering us at the waist, Deedie was curled onto me,
but her head was resting on a female breast.
I felt something liquid on my ribs.
I leaned forward to see the tears flowing quietly from her face
and rolling down my body. I said, "It's OK."
She didn't say anything for a long time.
"It's just," she said at last, "each time we make love now,
I'm afraid it's going to be the last time."'
When I read that the first time, I just pictured you--I didn't know you
or what you looked like, but I pictured you there with your head
on his breast and how weird that would be if, you know,
you had never expected your husband to have a breast before.
DEEDIE: Well--and who does, right?
WINFREY: Yeah, yeah. And I say that, `weird,'
because you are not a lesbian.
WINFREY: And who does?
JENNY: Yeah.
DEEDIE: That's correct.
WINFREY: Yeah. And you still are not a lesbian.
DEEDIE: Nope. Nope.
WINFREY: And still are not a lesbian. So was that weird?
DEEDIE: Well, it's very weird. I mean, I remember Jen saying
to me at one point when we were in bed, I was curled on her shoulder,
and she said, `You know, this won't be so bad when there's a breast there,
will it?' And I said, `Yes, it will.'
JENNY: Yeah.
DEEDIE: I said, `I won't be here.'
WINFREY: So was that the last time you were intimate,
or are you still intimate? Can I ask that question?
DEEDIE: You can ask. No, we are not still intimate.
WINFREY: Because you're not a lesbian.
Now the question I think is whether or not,
then, you are still interested in women, or were you now...
JENNY: Yeah, I have to say I'm...
WINFREY: ...as a woman...
JENNY: ...curious about men now.
Somebody said to me something like, you know,
`Jenny, you just--you know, you spent, you know,
all this money on a new sports car.
Are you just going to leave it in the driveway?' But...
WINFREY: That's one way of looking at it. Yeah.
JENNY: But I have to--so I am curious about men,
but I'm--I'll--to be honest, I'm not looking, because
I'm so grateful for what I have.
And I'll tell you what, this family's been through enough.
So I'm--you know, I'm not looking.
WINFREY: You're not looking.
JENNY: No.
WINFREY: But if somebody came along...
JENNY: Well, I don't think so.
I don't think anybody's--I don't--well, I mean, the future is unknown, but I...
WINFREY: Yeah.
JENNY: ...can't imagine wanting to jeopardize...
WINFREY: So you're curious, but does...
JENNY: ...this family for that sense of curiosity.
WINFREY: OK, but does that mean you have not been with a man?
JENNY: No, it means--yeah, I've not been with anyone.
WINFREY: You--not...
DEEDIE: We're still married.
WINFREY: Well, I'm just asking.
DEEDIE: I know. I know.