Nearly two years ago, Bruce Jenner sat down with Diane Sawyer for an interview on 20/20 in which he revealed he was transgender. It’s been a wild two years since then. Jenner introduced Caitlyn to the world when she appeared on the cover of Vanity Fair, had her continuing evolution documented in a reality series on E!, and oscillated between being a champion for and a force against the very community she considered herself a part of. To put it gently, Jenner’s journey as an unofficial spokesperson of the trans community has not been smooth.
Now, several days before the release of her new memoir, called The Secrets of My Life, Caitlyn Jenner and Sawyer have reunited, taking it back to where it all began. Where does Jenner, 67, see herself now, two years later? Here’s what we learned.
1. She doesn’t regret saying goodbye to Bruce.
The first question Jenner faced? How she feels two years after coming out. “Happy, peaceful, peace in my soul … all of that confusion has left me,” said Jenner. When Sawyer pressed her further, asking if there was ever any doubt in her mind about embracing her feminine side, she insisted there was none.
“I did the right thing,” Jenner stated, noting that she doesn’t miss Bruce at all. “Not even close!” she laughed, adding that when she was Bruce, she’d look in the mirror and feel anxious. But as Caitlyn? “I’m excited about the day. For so many years, I isolated myself — I couldn’t care less about the next day. Now I do.”
2. She uses her public outings as a way to change the narrative around the trans community — and lets it continue to change her too.
Sawyer followed Jenner on a trip to the grocery store, where she was swamped with well-wishers and selfie-seekers. Jenner explained she uses these encounters as an opportunity to make friends and give them a positive experience. “This may be their only encounter with a trans person, and I want it to be a good one,” Jenner said, adding she sometimes takes up to 40 selfies in a day. Still, she wonders what her fans are really thinking.
“I had a guy actually ask me for a selfie, and he said, ‘Bruce, can you give me a selfie?’ Nobody has called me that in two years,” Jenner recounted. “I looked at him and said, ‘No problem.’ I want him to walk away saying, ‘Caitlyn Jenner is so nice,’ that trans people are approachable, and they’re a vital part of our society.”
3. She’d pose for that Vanity Fair cover all over again.
According to 20/20, Jenner’s Vanity Fair cover was seen by over 3 billion people around the world — and she’d gladly slip into that bustier again, even though some members of her family thought “it was a little too much.”
“From my standpoint, I had suffered for 65 years, OK?” Jenner said. “To have a beautiful shot of my authentic self was important, and the shock value.” When asked if that was intentional, Jenner admitted it was, but not for the reasons we might think. “I wanted to end the old Bruce, my old life — and that picture did it.”
— VANITY FAIR (@VanityFair) June 1, 2015
4. She’s still not sure what her peers thought of her at the ESPY Awards.
When Jenner attended the 2015 ESPY Awards to accept the Arthur Ashe Award for Courage, she did so in front of 6,000 people, many of whom were athletic superstars like LeBron James and Derek Jeter. Even though she had the full support of her family behind her, she was uncomfortable about her appearance.
“These are my peers — I’d been to the ESPYs plenty of times, [but] I was scared to go,” she said, adding that she was sure everyone was thinking, “What a freak!
“And I still wonder about that,” Jenner continued. “Some guys can accept it, some guys can’t.”
So what got her through the night? Thinking about the thousands of transgender people who are bullied every day … and how 40 percent of the community attempts suicide at some point in their life.
5. She often wore a bra and panties under Bruce’s suits — and put it in her will that she wanted to be buried in women’s clothing.
Bruce Jenner frequently gave motivational speeches to corporations, where he’d tell the audience things like “Dare to take risks” and “Life has got to be an adventure, or it’s nothing.” Jenner can still recite the sayings verbatim today, but she admitted to Sawyer she often wore a bra and panties under her suits.
“I had my little suit on, I would walk off the stage, and I would feel like a liar,” she confessed. And though she had started taking female hormones years ago and quit, she still had it put in her will that she wanted to be dressed in women’s clothing for her funeral.
“If I go, when I’m buried … yeah, I want to be dressed as her, because that’s the way I was going to heaven,” Jenner said quietly, then with a little smirk added, “Yeah, I’d kind of shock everyone when they came to see the casket.”
6. She’s still optimistic about changing the world, but is a little more realistic about it — and the role she plays.
When Caitlyn Jenner first stepped into the public eye and started speaking out about LGBTQ rights, she became more controversial — largely because of her views surrounding the LGBTQ community. Those views, along with her political stance, didn’t sit quite right with the LGBTQ crowd. As Jenner put it, “I was hoping then — there was a lot of hope there. Have I in the last two years had a bigger dose of reality? Absolutely.”
There’s no denying Jenner’s influence has had a positive effect — 20/20 points out that thanks to Jenner’s bravery, the number of people who publicly identify as transgender has jumped from 700,000 to an estimated 1.4 million. But when Jenner came out, she’d never met another transgender person. So how could she possibly become a spokesperson for a group of people who were so far removed from who she was?
“I feel it and I see it,” Jenner told Sawyer. “At the beginning of this whole thing, yes, I knew absolutely nothing. Yes, I made mistakes. On some subjects I was insensitive because honestly, I didn’t know any better. It’s tough to take 65 years of being Bruce, and then, like [snaps her fingers], overnight everything changes. At first you don’t know how to handle it.”
7. She’s no longer a fan of Donald Trump.
It’s no secret Jenner is Republican and that she voted for Donald Trump, but it seems like her allegiance may have changed — at least where Trump is concerned. When Sawyer asked her about it, Jenner said, “This administration for me was extremely, extremely disappointing. Here’s the deal breaker with the Republican Party. And the deal breaker is, you mess with my community, I’m coming after you.”
As Jenner said in previous clips shared on Good Morning America, “When it comes to all equality issues, for the entire LGBT community, what we need is federal guidance. Just like the previous administration said that it was OK to serve as a trans person in the military. We have frontline people, OK? I’m talking Marines, trans guys, on the frontline, fighting for our country. I’m trying to get, especially the Republican Party, to make a change.”
When Sawyer pressed her on the issue, Jenner admitted she went to Trump’s inauguration, and revealed he invited her to play golf with him when they chatted at a cocktail party. “At the time I thought it was a pretty good idea, but since Title IX, it’s not a good idea. And so I won’t be playing golf with him.”
8. She has no regrets about gender reassignment surgery — and doesn’t want to ever talk about it again.
While taking female hormones helped to quiet her inner chatter and dissipate her depression, Jenner admits she’s lucky she had the money to change her overall appearance, altering her jawline, forehead, and breasts. Now that she’s one of the 12 percent of trans women who get gender reassignment surgery, she wrote about its success and how liberating it was in her new book, but she insists it didn’t change who she was before or after she had it.
“I wasn’t less of a woman the day before I had the surgery than I was the day after I had the surgery, because that did not define who I am as a human being,” Jenner stated, adding she has no regrets about it. However, she says it’s a subject people shouldn’t ask about.
“This book is about honesty, but that doesn’t mean that in the future that I have to talk about it — that I’m going to dwell,” she said. “The media may, but I am not going to dwell on that subject. And I would make a suggestion to all people out there, don’t ask the question. It’s not an appropriate question to ask any trans person.”
9. She regrets not being a better parent to her children.
Jenner (who has six biological children) shared family videos and pictures with Sawyer, before she confessed, “I just kind of dropped out of society, and also I dropped out as a parent.” Her four older kids — Burt, Cassandra, Brandon, and Brody — didn’t see her for about a decade before she popped up on Keeping Up With the Kardashians, and she noted that while some remain close, others are a bit more distant. “I have to admit I’ll sit here and wonder, is it because of me transitioning or is it because their life is so busy that they don’t call all the time?” Jenner asked. “But every parent goes through that.”
Still, Jenner can admit her failings as a parent, and she points to her absence as the reason why God may take issue with her when her time is up. “This is a lesson for every parent — children can accept when you change your gender, but they’ll never forget all the times Dad wasn’t there. There’s no excuse for not being a good parent, no matter how many problems you have. No excuse for that.”
And though they were present for her first interview with Sawyer, the Jenner kids declined to be interviewed this time around, sharing only this statement: “We love our father and have deep admiration for her bravery. Every family has unique milestones, but we can honestly say Caitlyn’s gender transition has brought our family closer.”
10. She and Kris Kardashian don’t talk that often.
Sounds like any friendliness between the exes is now gone. When Sawyer asks Jenner what her relationships are like with her ex-wives, she simply said, “Do I talk to obviously the last one, Kris, all the time? No, she’s obviously moved on. I’ve certainly moved on. But we’re fine with each other.”
11. She doesn’t see a companion in her future.
When Jenner’s older sister Pam joined in on the fun, she said she wants to see Caitlyn in a relationship … but Caitlyn isn’t so sure. “I honestly do not see dating in my future,” she admitted. “I have not been approached; I’ve never been out on a date. I just have a lot of friends.”
When Sawyer tells her that doesn’t heal loneliness, Jenner tells her, “My life revolves around my kids, and they’ll be in my life until the day I die.”
12. She’s a closet hoarder.
Jenner took Sawyer on a tour of her closet and pulled out clothes that were reminiscent of her history. “I can’t get rid of it because it represents something from my past,” she confessed. When Sawyer teased her for her vast collection of sunglasses, Jenner slipped on a particular pair with a smile. “These are very old. I think actually … I stole these from Kris — a long time ago.”
13. She doesn’t believe trans acceptance will be achieved in this lifetime.
Now that she’s come through the fire of two very public years of her transition journey, Jenner told Sawyer she wants to focus on raising money for her charity and fighting for transgender rights, focusing on helping trans women of color who face terrible unemployment rates. When asked if we’ll see equality for trans people in either of their lifetimes, Jenner isn’t optimistic.
“No, I don’t think we’ll ever see full acceptance,” she replied. “Is it going to get better? I hope so. And I hope that I’m part of that. I want to fight this fight. And I’m playing in the fourth quarter of life. And I don’t have that many years left.”
14. She believes her dad would be proud of her.
Though her father and brother have long since passed, Jenner dedicated her book to the two of them. Why? “They’re the only two in my family who have never heard this story,” she says. And even though she thinks her father would have trouble with her coming out as transgender, she still believes he’d come to accept her and knows he’s proud of her.
“I’m sure he’s looking down on me watching all of this,” she said. “He’s buried in Arlington Cemetery in Washington, D.C., there with all his Army buddies, looking down and saying, ‘Go Caitlyn!’”
Jenner’s memoir, The Secrets of My Life, comes out April 25.
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