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.

Khloé goes to New York to host a fashion show and becomes interested in moving there to open a second D-A-S-H store. Kim's focus on her career forces her to choose between it and Reggie.

Khloé gets excited when she thinks she's pregnant, but it turns out that she isn't. When Kim lies to everyone to get out of doing things, Kris and Bruce get upset, but she may learn a lesson when she lies to Kendall and Kylie.

Dog-non-lover Kim finds herself taking in, and loving, a stray Chihuahua until she must give up "Princess" because of medical problems. Bruce pressures Rob to move out of the house, and he gets a job developing his own skin-care line with Kourtney's help.