Tess is 21 when she moves to the Big Apple from her Ohio town. She finds a sweet gig as a waitress, and she does a good job. Eventually, she starts to learn about spirits and wine, and she makes plans to bartend one day. Tess is blown away by the licentious living of the restaurant employees, and although they think of her as a prude, they eventually welcome her and she begins to experiment with their behavior.
Tess makes friends with Jake and Simone, a strange family, basically, because Simone actually raised Jake from youth. Tess has a serious crush on Jake, and Simone allows the relationship, so Tess and Jake become partners. Eventually, Tess discovers more about their relationship, that they have matching tattoos, that Simone raised Jake as a child, and Tess becomes jealous.
Suddenly, the prestigious restaurant is closed by the city health inspectors without warning, and Tess accidentally learns in the manager's office that Simone and Jake are taking a whole month of vacation without her. They are going to France, which makes Tess very jealous, and in a fit of emotion, she blacks out drinking and confronts them.
The confrontation is of no avail, because Simone and Jake can see that she clearly becoming zealous and drunk, so they just ignore her. When they see each other next, Tess is openly hostile. In her frustration, she decides to offer her boss sex for a raise, and it works. Instead, he transfers her away after having sex with her, and she quits and takes a job at a local liquor store as a wine clerk.