Philip mistakes Will for Carlton accidentally several times and offers to pay for Will's Homecoming dance expenses, causing Will to become paranoid that he is becoming exactly like Carlton and totally living off of Uncle Phil's help and money. Will decides to secretly get a job at a pirate-themed restaurant to pay for the Homecoming expenses himself. Will excitedly tells the news to Uncle Phil, who then grounds him for "not telling the truth" for his missing basketball practices, sleeping in class, and skipping school. Ashley knows about this, and takes the family to the restaurant Will works for. Due to the costume, Uncle Phil originally doesn't recognize Will, who tries to get away with some insults. When Uncle Phil tells the pirate server (Will) about how rude he is being, Will takes the costume off. In the end they make up once Uncle Phil realizes why Will wanted to get a job, and Will realizes it is okay to get help from Uncle Phil to succeed. Meanwhile, Carlton has to put up with Ashley's friend Tina after she sees him in a swimsuit. She follows him around until she sees Will in the costume.