50 Most iconic Keeping Up With the Kardashians moments

36. Kim goes on date with her bodyguard

Pre-Kanye, Kim was fully in the dating scene on KUWTK. And in the season 5 episode “The Bodyguard,” she starts crushing on her Australian bodyguard Shengo. The pair flirt for a bit before ending one night with a kiss, but it’s all over the next morning when Kim comes to her senses and tells him they should keep things professional.

37. Kim accuses Jonathan of leaking her information

You can never be too careful with your private information when you’re a super famous person, so when Kim suspects BFF Jonathan of leaking stuff, it turns into a whole mess. On Kourtney and Khloe Take the Hamptons, the duo is headed to the Jersey Shore when Kim, along with her sisters, smell something fishy about Jonathan.

But when she confronts him, he’s unsurprisingly hurt and embarrassed, assuring her he would never do such a thing.

38. Kris gets a pet monkey

Throwing it back to one of the earlier episodes, Kim receives a monkey from her daughters after feeling lonely with them growing up. The season 3 episode “Leaving the Nest” shows Kris dressing, feeding, and chasing around the monkey while realizing how much work taking care of her really is.

39. Kim and her assistant Steph part ways

After five years of being Kim’s assistant, Stephanie Shepherd makes it clear to Kourtney that she’s just not as fulfilled as she once was. And surprisingly, Kim is understanding and agrees it’s time for their professional relationship to end.

In the season 14 episode “Trimester Trouble,” Kim recalls to her friend Allison Statter what happened, explaining, “”I said, ‘I love you a lot, like a sister, and this conversation is really hard for me to have. But I just think that you’ve outgrown your position here.'” Steph still hangs out with the family frequently.

40. Scott and Khloé prank Kris over paintings

In the season 15 episode “The Art of the Prank,” Khloé is upset with her mom when she art-shames her. So when KoKo informs Scott of what’s going on, they naturally come up with a prank to get back at the momager. The pair decide to make their own paintings and convince Kris that they’re by a famous artist. It fully works.