Members of the Old School Crew contact Kris: they want her to be a cheerleader. Kris is worried about auditioning, especially after a knee injury. Meanwhile, Khloé has a woman-to-woman talk with Kendall, with help from Kim, Kourtney, and Kylie.
Kim and Kourtney, worried about Khloé being single, start an online-dating profile for her. Khloé gets angry but goes along with the speed dates. Meanwhile, Bruce teaches Kendall about doing chores and earning her own money but Kendall hires a handyman and takes the money and the credit for his work.
Kim battles against Kourtney and Khloé after she purchases a Bentley. Kris gets drunk with a friend and gets a tattoo. Bruce experiences a mid-life crisis.
Bruce thinks a family ski-trip to Colorado will ease some of the family chaos, but first it intensifies his midlife crisis as he spends time with guys who are Rob's age. Meanwhile, the family gangs up on Kim, claiming she's not joining in the family quality time. Kim, feeling hurt, leaves Colorado, but an apology message from Khloé persuades her to return. The clan enjoys the rest of their vacation together.
Kim shoots a sexy calendar for Reggie, but Kris distributes it for public sale. Kim gets back at her mom by selling the nude poster from Season 1. Bruce hopes to inspire Kourtney and Khloé, and earn their respect, by taking them to one of his motivational speeches.
When the girls visit New Orleans for a charity pool tournament organized by Reggie, they meet a family devastated by Hurricane Katrina. Meanwhile, Kris' cousin CiCi crashes Bruce's plans for a romantic weekend.
