Recently, however, their typically breezy conversations took a decidedly more personal turn, when the former Olympian opened up to them about his gender transition.
“I tried to explain to them that. ... ‘As much of your upbringing was her much as it was the he side, that I will always be there. I’m not going anywhere,’” Jenner told ABC’s Diane Sawyer in an exclusive interview that aired Friday in a special edition of “20/20.”
During the interview, Jenner referred to himself using male pronouns and ABC News has chosen to follow his lead, though he also referred to himself as “Bruce” and “her.”
Still, Jenner’s openness was met by his kids with tears, concern and love. There were also questions, including, ‘Should we still call you ‘Dad’?”
"Those are the only ones I’m concerned with and… I can’t let myself hurt them,” Jenner said.
Jenner has six biological children: Burt and Cassandra with his first wife Chrystie Scott, Brandon and Brody with his second wife Linda Thompson, and Kendall and Kylie with his third wife Kris Jenner. Jenner also played an integral role in raising Kris’s four children from her first marriage, Kourtney, Kim, Khloe and Robert Kardashian.
Each had a different reaction:
Burt: Jenner’s eldest was supportive, but he also admitted that he’s struggled with the news. “It’s hard for me. He’s always answered his phone, you know, ‘What are you doin’ big guy?’ ‘Well, nothin’ big guy!’” he said. “And now, you know, do I ever-- would you ever call a female ‘big guy’? No you would not.”
Cassandra: Cassandra met her father’s admission with concern. Worried that she was losing the parent she knew, she felt “huge relief” when Jenner said that she should still call him “dad.” “Dad said… ‘It’s not that I’m trying to dress up like a woman. It’s that I’ve spent my whole life dressing like a man,’” she recalled. “I just held his hand and I cried with him and I just told him how proud of him I was and how inspired I was.”
Brandon: Brandon, Jenner’s third-born and an expectant father himself, was the first child Jenner told that he was struggling with gender identity.
“Brandon is kind of like our little Gandhi,” Jenner explained. “He’s got this soul that’s just wonderful.”
Brandon understands the transition might not be “easy,” and he and his siblings are rallying around their dad. “There’s a thread throughout his whole life of, you know, a life that he was longing to live, really. And, you know, when you’re that close with somebody, you see little clues, you know, no matter what,” he said. “I feel like I’m getting an upgraded version of my dad, of a parent.”
“I’m just honored and more proud than ever to be a part of the family,” Brandon said.
Brody: Jenner admitted that he wasn’t always a very attentive father, especially in the years when he was struggling most with his gender identity, which is when Brody was a young child. Brody, his fourth child, took that especially hard. Having this conversation, Brody said, really helped him better understand what was going on during those years. “The first thing I thought was just like, 'It finally makes sense,’” he said.
Kendall and Kylie: Jenner’s youngest two actually caught their father trying on in a dress well before he talked to them about his gender transition. “They had their computer on that security mode, so any time someone walked in the room, the camera turned on because Kendall thought Kylie was stealing clothes from her,” Jenner explained. “They came home and turned on their computer and ‘oh my God.’” However, the Olympian’s discussion about the transition was still a tearful one. “They are very protective of me,” Jenner explained. “They don’t want anybody to hurt dad."
In a joint statement to ABC News, Kendall and Kylie Jenner said, “We love our dad very much as he is an amazing father. We couldn’t ask for a better dad. He has the biggest heart and all we want for him is to be happy. If he’s happy, we’re happy.”
The Kardashians: Kim, who also once caught Jenner in a dress, was the first of the Kardashian children to know. After she initially brushed him off, the reality TV star became much more understanding after her husband, Kanye West, discussed with her the importance of being true to one’s self.
“They were talking about it and he says to Kim, ‘Look, I can be married to the most beautiful woman in the world, and I am. I can have the most beautiful little daughter in the world. I have that. But I’m nothing if I can’t be me ... if I can’t be true to myself they don’t mean anything,’ … and since then, Kimberly has been by far the most accepting, and the easiest to talk to,” Jenner said.
She’s also encouraged Jenner to really embrace his new image. “[She said], ‘Girl, you gotta rock it baby. You gotta look good! If you’re doing this thing, I’m helping you. You’re representing the family. You gotta look really good,’” Jenner said.
Also in Jenner’s camp is Kourtney, though she did have questions about what to tell her three small children about Jenner’s new life.
And of all the Kardashians, Khloe has had the toughest time with Jenner’s transition. “She’s had a lot of losses in her life,” he said, citing the death of Khloe’s father and the breakup of her marriage. “She feels likes there’s this massive… ‘my whole life is falling apart,’ you know, ‘it’s my dad,’ and I try to explain… but I’m not going anywhere. I’m still going to be there for you."
When reached by ABC News for this report, Kim Kardashian declined to comment. Kourtney, Khloe and Rob Kardashian did not respond to ABC News’ requests for comment.
ABC News also reached out to Kris Jenner for this report, but she declined to comment.