"I was Nicole Richie's assistant and you were Jonathan Cheban's assistant and we met five faces ago," Khloé quipped, referencing cosmetic procedures.
Khloé, who appeared on Monday's podcast — which features interview with celebrities and the people who have stood by them through all of life's ups and downs — alongside best friend Malika Haqq, said that she didn't work for Richie for "long."
"I went to school with her," Khloé explained. "She was one of my best friends growing up and we were just really, really close and then when she started doing Simple Life — I think it was after Simple Life — she just needed some help and I just needed a job."
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The Good American founder had always been familiar with reality shows, but said she never really thought about actually doing one herself until the idea came along. "Kourtney [Kardashian] did Filthy Rich: Cattle Drive prior ... and Kim [Kardashian] was obsessed with The Real World, but I didn't think about it, and I think that's the beauty of it," Khloé said of KUWTK.
She shared that she and her family had no expectations for the E! reality show and were shocked at how successful it turned out to be.
"We were told we were a show filler and to not get comfortable. There wasn't any pressure because it was like, they don't think we're gonna last, so let's have fun with it," Khloé said.
She explained that life changed drastically for her and her family after season 3, when she and Kourtney, 41, filmed their spinoff, Kourtney and Khloé Take Miami. "It was the first time we couldn't really go a lot of places and it was more paparazzi and fans," Khloé remembered.
Reflecting back on that time period, Haqq, 37, said things drastically changed: "It wasn't until they started filming more and moving around more that I was like, 'Wait, she's not in [Dash] with me anymore, she really cannot be here all the time' and she was like, 'Come work with me.' And I ended up running around the world with her."
Now — over a decade later — the show is coming to an end.
"It's devastating for all of us," Khloé told Huck and co-host Melissa Gray Washington.
"The day it happened, Malika and I were talking throughout the day, because you don't have to be a main character — you're still a part of this journey from day one, even if you were in the first episode or not. You have been you Simon, you Malika, you guys have been our family. You're on this journey with us and just for any chapter to end, that doesn't mean everything is ending for good. That just means there's room for another chapter to open."
"It's sad, but we've been doing this for 15 years. We get two weeks off a year. It's exhausting. We're all in a different place in our lives and some of us need a nap," Khloé continued.
She said that while she thinks ending the show is a good decision, the idea still gives her anxiety. "It's hard because I'm not good with change, but that doesn't mean I don't need a break. I'm also sometimes afraid to take the break. I know it's good. It hits me in waves — like today, I've been nauseous all day and I know I have anxiety."
Haqq echoed similar sentiments, saying: "It's a flood of emotions."
"I have a s--- ton of memories and I never would have thought I would have gotten with my best friend. There's a lot to be thankful for. [But] I have such anxiety. This has been the most consistent thing that I've known over the last 14 years," Haqq said.
In an Instagram post, Kim Kardashian West shared a heartfelt statement on behalf of herself, family matriarch Kris Jenner; sisters Kourtney Kardashian, Khloé, Kylie Jenner and Kendall Jenner; brother Rob Kardashian; and Kourtney's ex, Scott Disick.
"To our amazing fans - It is with heavy hearts that we’ve made the difficult decision as a family to say goodbye to Keeping Up with the Kardashians," the statement began. "After what will be 14 years, 20 seasons, hundreds of episodes and numerous spin-off shows, we are beyond grateful to all of you who’ve watched us for all of these years – through the good times, the bad times, the happiness, the tears, and the many relationships and children. We’ll forever cherish the wonderful memories and countless people we’ve met along the way."
The family thanked "the thousands of individuals and businesses that have been a part of this experience and, most importantly, a very special thank you to Ryan Seacrest for believing in us, E! for being our partner, and our production team at Bunim/Murray, who’ve spent countless hours documenting our lives."
Despite the massive life change, Haqq is excited for Khloé to start a new chapter. Haqq explained that she feels Khloé doesn't know her "true potential" and will find it once she allows herself to "tap into some of those unique areas that she'll flourish in."
The pair also looked back on their years-long friendship, which started when they were just 15. At the time, Haqq was dating Khloé's guy friend and the two met when the reality star stopped by his house to drop something off.
"[We] talked for two hours and I was like I love this girl," Haqq said.
"Malika and I are really good at knowing, like, okay we might hang out with a borrowed friend, but they're not like your ride or dies. You have to know who you're doing a feature with and who you're doing a f---ing duet with. And Malika and I are doing a f---ing album," Khloé said.
Throughout the show, fans have been able to see Khloé and Haqq's friendship evolve, including both becoming mothers in recent years. Khloé and Tristan Thompson welcomed daughter True in April 2018, and Haqq gave birth in March to son Ace, whom she shares with rapper O.T. Genasis.
"I'm always on her line," Haqq said of asking Khloé for parenting advice. "It's a lot of coaching, but I think us having babies together, which is something I always pictured, is amazing because our kids love each other."
Khloé added: "And we get to have mommy wine nights!"