Freddie finds himself attracted to the beautiful woman who has opened a bakery down the street – and who is putting a serious dent into his dessert business. There's only one problem: Chris asks her out first, and seems to be really falling for her. Meanwhile, Allison decides to send her resume around to drum up job offers, with sorry results.

In an attempt to kiss up to Dr. Celia Adams, the beautiful dean of her medical school, Sofia suggests that Freddie's restaurant be the location for a fundraiser. Freddie turns on the charm to Celia, leading to them sleeping together. While at first upset, Sofia becomes amused when she concludes that Celia is only using Freddie as a 'boy toy.' When she happily shares this with Freddie, and also tells him that he is way out of his league, Freddie is determined to prove her wrong.

After finding out that Chris used his share of Freddie's restaurant as collateral for his own failed restaurant venture, Freddie insists that Chris ask his wealthy grandfather, Carl, for money to pay off the debt. Carl is displeased with Chris' slacker lifestyle and impressed with Freddie's work ethic, so he makes Chris work as his chauffeur to teach him a lesson about money and responsibility. When Chris feels humiliated, he pushes back, and the result is that grandfather pays off the loan but takes Chris's trust fund and condo in return. So Chris ends up homeless at Freddie's already crowded apartment.