Scandalous photos of Kourtney and Kim resurface, which makes Kim both scared and humiliated, as she already feels like she really screwed up with her sex tape.

Khloé and Kourtney find out that a homeless man called Shorty is living behind their store D-A-S-H, and they decide to help him out by cleaning his appearance up.

Kourtney, Kim and Khloé are about to leave to Las Vegas when Kourtney has a pregnancy scare. Meanwhile, Kendall & Kylie ask their dad for a puppy, and he says no, but Kris goes behind his back and buys them a puppy anyway, which makes him upset, as he feels like Kris never lets him make decisions.

The family remembers Robert Kardashian on his death anniversary. Khloé doesn't deal with his anniversary well and gets drunk. She is then arrested for a DUI.

Playboy magazine contacts Kris, asking her to tell Kim that they want her to be on the cover of their December 2007 issue. Kim is at first hesitant, but at Kris' urge, Kim poses for Playboy. Kris thinks that Kim is complaining over the photoshoot too much and Kim thinks that Kris doesn't know how hard it is to pose nude, so Kim "plays" manager for a day by setting her mom up for a nude photoshoot, which Kris surprisingly handles well.

Kourtney, Kim and Khloé go to Mexico for a Girls Gone Wild photo shoot without telling Bruce, as they are afraid that he will disapprove. He finds out and leaves his son Brody Jenner to babysit Kylie and Kendall while he goes to Mexico to confront them.

Kim "fires" Kris from being her manager after using racy pictures of her which she really didn't want to be used. Meanwhile, Kris hires a nanny named Bree, who isn't as appropriate and decent of a nanny as she thought she would be. Kim later takes Kris back as her manager, after forgiving her for her mistake.

Bruce Jenner and Kris Jenner celebrate their anniversary. Kim Kardashian appears on The Tyra Banks Show.