50 Most iconic Keeping Up With the Kardashians moments

16. Kris proposes to Kim

After getting the approval to propose to Kim, Kris seemingly gets cold feet for a moment when the two get into a fight. However, the season 6 episode “The Proposal” shows the former basketball player pulling through and popping the question to the reality star in her bedroom with rose petals. Cute, but obviously the relationship doesn’t last long.

17. Kendall’s sweet 16

One episode later, the family have another reason to celebrate. Kendall and the gang party it up for her birthday in “Kendall’s Sweet 16,” complete with a performance from Tyga. A 14-year-old Kylie meets the “Rack City” rapper for the first time at the bash, which led to the two eventually dating a few years later.

18. Oprah’s Interview

For one of their first major interviews, the Kardashians are visited by Oprah Winfrey in the season 7 episode “Kardashian Therapy: Part 1.” The members of the crew are interviewed together and one-on-one, getting some insane exposure in the media.

19. Kim and Kanye start dating

After a couple silly relationships, Kim finally finds her forever man in Kanye. In the season 7 episode “Sometimes You Need to Adjust: Part 2,” Rob calls Kim and Kourtney to ask about the rapper’s new song “Cold,” in which one verse goes, “And I’ll admit, I had fell in love with Kim / Around the same time she had fell in love with him.”

Though Kim remains coy on their relationship, she brings ‘Ye along to New York with the crew for the grand opening of Scott’s restaurant, marking the official start of their romance.

20. Tristan is caught cheating again

As if Tristan cheating on Khloé the first time wasn’t shocking enough, the family finds out in season 16 episode “Treachery” that he was involved in an alleged kiss with Jordyn Woods, Kylie’s then-best friend. The crew is understandably heartbroken over the news as they try and get all the info from Jordyn. Spoiler alert: She doesn’t tell them much.