On Saturday, February 6, Caitlyn uploaded a 15-minute clip to her YouTube channel, in which her youngest daughter did up her face during a candid chat.
"This is the highlight of my life," Kylie said, "It's the highlight of mine!" Caitlyn replied.
"We've been talking about this for forever," the 23-year-old explained. "We saved this special moment for you guys because this is going to be the first time that I ever do my dad's makeup."
"You’ve been doing your makeup longer than anyone I can imagine," Kylie said, adding that Caitlyn was "good" at glamming up to go out.
"I was doing makeup 30 years before you were born," Caitlyn joked.
The intimate moment was monumental for the both of them and their tight bond. "I mean, I was 65 years old before I finally came through this. It's like I had to raise everybody else and I had such a life and finally, it was my time to be me and live my life," the Olympian said.
"I didn't think I could do it," expressed Caitlyn, who came out as transgender in 2015. "And then I did it and you guys have been my best friends."
"Sometimes people get really confused when Kendall and I still call you dad," Kylie commented. "I know we had a talk a few years ago, and you were okay with us still calling you dad. How do you feel about that now?"
"It was one of the best decisions I made," Caitlyn replied. "And sometimes this community can be pretty tough, especially when it comes to pronouns and everybody's got an opinion, and on and on and on. But I really felt from the beginning that I got to do it my way that works for me, and everybody out there has to do it their way, which works for them.
"Some people say 'Oh, you're the mother.' No I'm not — I'm the dad, and I've been the dad the whole way. I will be their father until the day they die, or I die."
Caitlyn added that her children were always "so good" adjusting to their father's new pronouns and said, "My dad — she."
Caitlyn talked with Kylie about how she found out she was passionate about sports at a "very young" age and that "changed [her] as a person."
"And you, at a very young age, you found it in makeup," she related to her daughter. "I mean you just loved it, I always remember you obsessed over makeup."
However, Caitlyn wasn’t always sure that Kylie Cosmetics would be a success when Kylie decided to turn her makeup hobby into a career when she was 17.
"I remember you used to yell at me for watching all these YouTube videos!" Kylie recalled. The makeup mogul added that her daughter, Stormi, is not as interested in makeup but is athletic.
"I love that," Caitlyn remarked, as Kylie finished her look — which was made exclusively with Kylie Cosmetics and Kylie Skin products. "Not bad for 71," she joked.