Caitlyn Jenner on deciding not to live a lie, what she learned: Part 2

After 65 years of living as a man, Jenner talks about her decision to transition and the public stumbles she made after coming out as transgender.
7:12 | 04/22/17

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Transcript for Caitlyn Jenner on deciding not to live a lie, what she learned: Part 2
I am transgender. Reporter: In the two years since our interview so many young people said they felt safe enough to come forward. The estimate of transgender Americans has now climbed from 700,000 to 1.4 million. What Bruce was saying just really hit home for a lot of the struggles I felt. It makes me feel safe. They're being accepted. This shows me that I can be accepted. This is something I always I would just take to my grave, because no one needed to know. And I didn't know there were others out there in the world that were like me. Reporter: And like the little boy who lived in tarrytown, new York, 60 years ago. And had never even heard the word transgender. But at the age of 8 or 9, Bruce Jenner says he knew with certainty he was happier sneaking out in his sister or mother's clothes. I ate a lot of wheaties. Reporter: A secret living inside the olympic icon on the wheaties box. And a secret still hidden when giving all those motivational speeches to corporate executives, dressed in a suit, but underneath often wearing a bra and pantyhose. I had my little suit on. I would walk off the stage, and I would feel like a liar. "You've just got no guts." Gamble. Gamble your best shot in life. Dare to take risks. Dare to take risks. Life has got to be a great adventure or it's nothing. Steal. Steal every moment of happiness. Live every day as if it's your last -- because we never know when that day is going to come. Reporter: He fell into a severe depression. He started taking female hormones and felt better, but then lost his nerve and stopped. Deciding instead to put an instruction in his will for the day he died. Yeah. Reporter: That that was going to be part of your will, to be buried. Yeah, it was. I thought that most of my life. I said, "If I -- if I go and when I'm buried," yeah, I wanted to be dressed as her, because that's the way I was going to heaven. I would say I'd kind of shock everybody when they come and visit the casket. Reporter: Through the decades, wishing he could be as brave as the other younger pioneers coming forward. I am a woman. I live my life as a woman. My mom has her first child who's a girl. We didn't know anything about this. I was assigned boy at birth. You know inside what you are. Reporter: She says it's harder to get your bearings at the age of 65 after a lifetime of secrets. At the time she decided to come out, she'd never even met another transgender person. In the beginning she was euphoric. Caitlyn! Caitlyn! Reporter: But so uninformed, she was about to hit all the land mines. She was asked the hardest part of being a woman. Figuring out what to wear. Reporter: On "Ellen," she seems hesitant when asked about marriage equality. That word marriage is really that that important to you, I can go with it. It's funny, you're a little not on board with it. No, I'm on board. Reporter: She now says she is 100% on board. But there was also her reality show, which tackled some serious issues in the transgender world, but mixed in a lot of makeup, clothes, wine and the tone-deaf problems of privilege. So many Paparazzis. Reporter: She complained about Paparazzi, while her community faces homelessness and violence. Not talking about Paparazzi but talking about survival. Survival. Reporter: The question I think was -- and I'm going to go -- Okay, hit me hard. Reporter: The question was do you really feel what they're living? I feel it. And I see it. At the beginning of this whole thing, yes, I -- I knew absolutely nothing. Yes, I made mistakes. On some subjects, I think I was insensitive, honestly, because I just didn't know any better. It's tough to take 65 years of being Bruce and then, like, overnight everything changes. At first, you -- you don't know how to handle it. Reporter: Some people in the transgender community were so angry they shouted her down in the streets. Do you have any idea what's really happening out here? You are an insult. I am not representing you. I am representing myself. Don't you Touch her! Reporter: At the same time, internet trolls attacked her for being transgender. Just brutal, brutal. It's like you don't even go there anymore. Reporter: What's the kindest thing anyone's said? "I love you." People who have thought about suicide and said they wouldn't do it. Reporter: Did she save lives? Absolutely. Reporter: Kids? Absolutely she saved lives. Reporter: This is professor Jenny Boylan at Barnard college who has written the defining memoirs of being transgender. She's also a member of the board of glad and appeared on the Cait Jenner reality show. She says we underestimate what it was for Caitlyn to begin this new life so isolated. And how much did she know and not know? She didn't know anything. I know some people roll their eyes at Caitlyn. And I would ask them if they have ever had to do anything this hard as Cait had to do, and I would ask them if they have gotten everything right the first time. Reporter: And out in the country, almost overnight, a lot of Americans were grappling with so many new ideas. Gender fluidity, gender neutral pronouns. Have you heard of gender neutral pronouns? Yeah, like they, or them. I've heard of Z, or zir? Z? Okay. Reporter: We counted 58 gender options on facbeook. Kids aren't surprised. Genderqueer, and I know intersex. Gender fluid, I've heard of that. Reporter: But grown-ups? Can you name any other gender identities? No. Two for sure. That's way too many. Reporter: Professor Boylan sensed for some Americans this was building into a kind of backlash. The fear is that the world is becoming an unstable place and that if there's -- if there's anything that we can depend on, it's that there are men and that there are women. Reporter: And the trigger was the presidential election year. This is why trump might win. This is exactly why. It's the Lunacy that's going on in colleges these days. You're supposed to walk up to someone and say, "Hi, nice to meet you, what pronoun should I use for your name?" Reporter: The dating app tinder announced a new feature this week which gives users 37 different gender identity options. It's called, "Why Democrats lost the election."

This transcript has been automatically generated and may not be 100% accurate.

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