When Kylie learns of a bullied fan looking for a prom date, she plans to surprise him as his date, but her quest hits a huge obstacle at the airport.

Kylie finally makes it to her first prom and gives dateless fan, Albert, the surprise of his life; Kylie plays wingman and coaches Jordyn through a blind date despite Jordyn's concerns of bringing an outsider into the group.

After struggling with her squad's boundaries, Kylie has to draw the line between friend and boss as a CEO; Kylie and Jordyn attempt to launch a sting operation when her brand's reputation is hit with a flood of fake lip kits.

Kylie struggles to keep her private life out of the public eye after running into a certain ex-boyfriend at a major music festival; she hits a low point when every move she makes goes viral.

Kylie and her Glam Squad must deliver an iconic look for the celebrity-filled Met Gala as a special guest of Versace. After a wild weekend on the East Coast, Jordyn wonders if she's living her own life, or getting lost in Kylie's.

After an emotional visit with a young fan, Jordyn is forced to come to terms with the recent death of her father; Kylie is inspired and prompted to strengthen her bond with Caitlyn.

Kylie, Jordyn and Kris travel to Peru on a charity mission; when Kylie's spontaneous lifestyle doesn't fare well with Kris Jenner's demanding itinerary, they have to reconcile their differences.

Kylie and Jordyn continue their trip in Peru while exploring their friendship and future; the guidance of a shaman reading and a commitment ceremony leads Kylie and Jordyn into the next chapter of their lives.