Megan Smith, a recent graduate from Yale University unable to find success in the journalism field, accepts a job offer from Laurel Limoges - tutoring her two snobby, stuck-up billionaire twin granddaughters with the hopes of getting them into Duke University.

Megan is ecstatic to be attending a gala event of the rich and famous, where Laurel introduces her to several influential individuals. However, the event turns sour when Megan gets into a heated argument with her sister Lily, Rose spots her ex-boyfriend with another girl, and Megan has to rescue both Rose and Sage after the two get caught driving without a license.

Megan is thrilled when her former college roommate Caryn visits and updates her on her present career, which prompts Megan to think about her own life and where it might lead. She also confides in Caryn about her interest in Will, who has taken a job as an assistant photographer for a magazine editor, and who is not aware of his wealthy background. Meanwhile, Rose and Sage's publicist books them for their first gig as a singing act at a prestigious nightclub where Sage becomes jealous that Rose will eclipse her in the spotlight.

Megan decides to punish Rose after learning that she tried to cheat on her history exam by grounding her, which is not an easy thing to carry out when Rose takes her punishment a little too seriously. Meanwhile, Laurel travels to Santa Barbara, California to rekindle with an old flame, named Miles Franklin, who follows her back to Florida. Charlie has doubts about living with Mandy at his place. Also, the family chef, Marco, gets a new partner in the kitchen: Charlie's cousin, Louis, whom clashes with the demanding and snobbish Sage. Elsewhere, Will tries to make his romance with Megan work when his work plans change.