Kourtney Kardashian’s Most Outrageous Moments: From Wild Parties To Jaw-Dropping Fashion Choices!
(Kourtney Kardashian’s Most Outrageous Moments: From Wild Parties To Jaw-Dropping Fashion Choices! /Image Credits:Page Six)

During the first season of "KUWTK," Kourtney's nude photos leaked after Kim stole them and put them in her purse as a prank.Kim's purse was stolen, and when she realized that meant her pictures could leak, she panicked. The family called in the FBI for help since Kourtney was underage when the photos were taken, and in the end, they never surfaced.Khloe supposedly reenacted her arrest outside of a club in 2007 for the "KUWTK" cameras, according to a book called "Kardashian Dynasty." The show also followed Khloe the morning she went to jail after violating probation, including the famous scene when Kris Jenner told Kim to stop taking selfies in the car because her "sister's going to jail."On what is remembered as one of the most iconic episodes in the second season of the show, Kim hit Khloe with her purse and said, "Don't be f---ing rude," after an argument involving a Bentley.

In the first season of "KUWTK," Kim posed for Playboy for the first time and brought mom Kris along with her for support. At the time, her decision to pose for the magazine came as a surprise.Despite the fact that Caitlyn Jenner voiced her concerns about the older sisters participating, Kim, Kourtney, and Khloe snuck off to Mexico to model for Ashley Paige swimwear. They had a blast, but their secret didn't stay a secret for long. In 2009, Khloe married Lamar just one month after they started dating.At the time, Kardashian's family was shocked to find out she was taking such a huge step so early on in their relationship, but they quickly pulled it together for her big day.

Kourtney Kardashian’s Most Outrageous Moments: From Wild Parties To Jaw-Dropping Fashion Choices!
(Kourtney Kardashian’s Most Outrageous Moments: From Wild Parties To Jaw-Dropping Fashion Choices! /Image Credits:Showbiz Cheat Sheet)

Later, the newlyweds scored their own spin-off reality show on E!, "Khloe and Lamar."We witnessed Kourtney's entire journey during her pregnancy with Mason, including his birth.Kourtney surprised viewers and her entire family by finishing her delivery by pulling Mason out. This wasn't her last time doing it either — we also saw that when Kourtney was giving birth to Penelope.When the two were living together in Miami, Kim's psoriasis got much worse and she read online that breast milk helped with the red spots.What started as Kim taking a bit of Kourtney's breast milk that was in the fridge, turned into much more when Kim thought that it was working and needed more.

Kourtney finally got wind of the fact that Kim was taking her breast milk and decided to directly squirt her breast milk onto Kim's psoriasis.  KOURTNEY Kardashian shared a never-before-seen throwback photo with pals including Nicole Richie from her wild party days.The 42-year-old took a walk down memory lane while posting the snap on Sunday night.In the Instagram Story photo, Kourtney posed alongside a large group of friends that included Nicole, 40, and friends names Katie and Melissa.Both Kourtney and Nicole appeared to be sporting fake tans, while the Keeping Up With the Kardashians alum donned a big grin as she wore an orange tank top.

Kourtney Kardashian’s Most Outrageous Moments: From Wild Parties To Jaw-Dropping Fashion Choices!
(Kourtney Kardashian’s Most Outrageous Moments: From Wild Parties To Jaw-Dropping Fashion Choices! /Image Credits:Closer magazine,Daily Mail)

Meanwhile, Nicole appeared happy as she wore a white tank top and posed in between  Katie and Melissa.Kourtney tagged her three friends in the post, though admitted: “I don’t know what year this is or who half these people are…”Nicole and Kourtney were good friends in the early 2000s, while Khloe Kardashian even worked as the actress' personal assistant. Back in October 2020, Khloe reflected on the gig while appearing on the Emergency Contact podcast.More recently, a TikTok user shared her theory that Kourtney is pregnant based on a recent Instagram Story post.