Paul, Lauren's boyfriend from the previous school year, arrives back in the city and the sparks begin to fly once again between the two. This inspires a fit of jealousy in Jackson and he starts spying on the couple. Also, Winnie meets Prince Nicholas of ""Lichtenberg,"" who is enamored with her and asks her on a date. But before she goes, Ashley, Mr. Elliot and Ms. Dupre give Winnie lessons on the proper way to act around royalty.

Through Jackson, Lauren gets a modeling job with renowned fashion photographer Derek Donovan. But Jackson may have cause to regret it when Lauren appears to be on the verge of a career as a model which will take her away from the Academy. Meanwhile, Winnie and Ashley try selling ""Broadway Girl"" cosmetics. At first they can't sell a thing, then they recruit Christian as a salesman. Suddenly women can't get enough of their product.

In Ms. Dupre's drama class, Jackson and Ashley have to kiss for a scene. While practicing the exercise, they find they really enjoy it! But the two soon realize that even though they have a great physical attraction for each other, they may not be right for a more serious relationship. Meanwhile, Christian doesn't want to go to the dentist for his painful toothache, and after he's sent to ""Dr. Giggles,"" it looks like his apprehension may have been justified.