Anna-Kat's eighth birthday is approaching and she confronts her parents with the promise they made to her when she was five: that on said birthday she would be allowed to walk two blocks by herself. When she is allowed to do this, word gets out and Katie is branded a neglectful mother by her rival housewives.
Meanwhile, Greg is increasingly concerned by how close Taylor and her boyfriend Eyo have been getting, and Katie is enraged at Cooper Bradford hanging out around their house and being a terrible influence on Oliver, so he decides to spy on her with Cooper's drone, and she decides to force him to do chores around the house to deter him from coming over.
Tropes:
- A Day in the Limelight: After a number of minor appearances, Cooper is much more prominent here and even gets to deliver a Shaming the Mob speech at the episode's climax (which works because nobody wants to cross his uber-rich parents).
- Birthday Episode: Anna-Kat turns 8 years old.
- Education Mama: Katie is deliberately tough on Cooper because she dislikes how spoiled he is and she wants to get him to stop coming over. What she doesn't expect is that Cooper thrives under the structure and discipline she has imposed on him that he's been lacking all his life and starts to take to her.
- Gone Horribly Right: Katie doesn't expect Cooper to actually like doing all the chores she forces him to do, but it works out in the end when he speaks up to defend her from all the other Westport housewives.
- Spoiled Brat: This is the first episode that gives us a clear impression of just how spoiled Cooper is.
