For the first time, Oliver is happy to be one of the "poors" because his new girlfriend Gina is from Branford and dislikes stuck-up "Westport kids". But there's a problem - Oliver may able to hide his materialistic side, but Cooper is a dyed-in-the-wool blue blood, meaning that he and Gina clash instantly. Cooper insists that Oliver choose between them, and after Oliver chooses Gina, he goes to Katie in hopes of becoming less spoiled. Meanwhile, Greg tries to get Taylor and Trip to stop with the PDA in front of him, and Anna-Kat, now the only single Otto, tries to mold Franklin into a boyfriend.
- A Day in the Limelight: Cooper gets the episode's A-story as he attempts to reform (with the help of Katie) to be less of a Westport snob.
- Friend Versus Lover: For Oliver, with Cooper as the friend and Gina as the lover. Although Oliver chooses Gina, when Cooper asks for forgiveness Oliver is so moved that he practically begs Gina to let them resume being friends. (Gina, to her credit, does.)
- Inadvertent Entrance Cue: When Oliver is pretending to not be interested in money to impress Gina, he says "Westport's the worst! All people care about is showing off how rich they are!" Enter Cooper, showing off the custom-made Italian leather tote bag he charged to his black Amex.
- Puppy Love: Anna-Kat and Franklin are 8 or 9 years old when Anna-Kat decides Franklin is her "boyfriend".