Bruce and Kris Jenner celebrate their anniversary. Kim buys them a stripper pole as a gift, the youngest Jenner plays on it. Kim appears on The Tyra Banks Show. Kourtney deals with a relationship drama.

Kim and Kris, her manager, argue over the publication of some of Kim's racy pictures. Meanwhile, Kris hires a nanny, Bree, who isn't as appropriate and nanny-decent as she hoped.

Kourtney, Kim and Khloé go to Mexico for a Girls Gone Wild photo shoot without telling Bruce, afraid that he would disapprove. When he finds out, he leaves his son Brody Jenner to look after Kylie and Kendall while he heads to Mexico to confront them. Unfortunately, leaving Brody with his daughters creates even more chaos.

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 hesitant at first, but Kris encourages her. To show Kris what a difficult decision it is, Kim proposing trading places and plays Kris' manager and setting her mom up for a semi-nude shoot. Kim gets the skimpiest outfit she can. Kris's best picture is her topless, in an American flag towel/blanket. Kris enjoys the shoot, surprising Kim.

The family remembers Robert Kardashian on his death anniversary. Khloé, not dealing well with the anniversary, gets drunk and ends up arrested for a DUI.

Kourtney, Kim and Khloé are about to leave for Las Vegas when Kourtney has a pregnancy scare. Meanwhile, Kendall and Kylie ask their dad for a puppy, which causes a disagreement between their parents.

Rob gets set up on a date but catches his sisters spying on him. Khloé and Kourtney find out that a homeless man, Shorty, is living behind their store D-A-S-H, and clean up his appearance.