Kris Jenner has endured her fair share of complicated relationships, from navigating interactions with OJ Simpson in the wake of Nicole Brown Simpson's murder to understanding the needs of her longtime partner, Bruce Jenner, after he became Caitlyn.
In an appearance on the March 1 edition of "Ellen," the momager opened up about both topics.
Kris admitted she and her friends regretted missing signals from Nicole that might have suggested, as Ellen put it, "I am in trouble and I need to get away from this guy."
The reality star, who said she'd known OJ since she was 17, pointed out that she and his late wife were due to have lunch the day after Nicole ended up being killed.
"She said she wanted to show me some things and talk about what was in her safe. And so now unfortunately it all makes sense that that's probably what she wanted to reveal to me that next day," Kris recalled. "Which broke my heart because I will always feel horrible that I didn't pay enough attention."
As for Caitlyn, Kris made it clear she's determined to offer her support, even though "it's confusing" to hear that her ex-husband, now a woman, wants to be with men.
"But you know, I think that I really want her to be happy and be really comfortable in all the things where she says she wasn't her true authentic self for most of her life and knew when she was 4 that she felt like that," said Kris.
"So you don't want somebody to be miserable or in pain or anything like that. I think for me, just getting used to that, you know I am human and I have my feelings and I try and it's baby steps. And it's the mourning of somebody that you feel you are never going to be with or see again."
She added that Caitlyn herself has obviously been dealing privately with her own transformation much longer than Kris and their daughters have.
"I said to her when this first happened, 'You are so excited you have to wait for the rest of us to catch up,'" said the reality star. "Like, we haven't had as many drinks as you, like when you are at a party and every else is smashed and you are, like, just getting started."
After calling it quits in 2013, the Jenners were officially divorced last year. And while Kris has said she harbored some bitterness over how things ended, she and Caitlyn began to rebuild their friendship last summer.
"I think that someone following their dream is truly inspirational to a lot of people," Kris said after Caitlyn took her new identity public with a cover spread in Vanity Fair. "You have to do what makes you happy."