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.