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.

After Rose is told that she must repeat her freshman year of high school due to poor grades, Megan visits the headmaster and tries to get her a second chance. However, a connection sparks between the headmaster and Megan and she later accepts a date with him - causing Charlie to feel jealous.

Megan is shocked when she finds an adult DVD in Rose's bookbag, but even more shocked when Rose reveals that she is not a virgin and is planning on having sex with her current boyfriend. Meanwhile, Sage invites Lily out to a restaurant to dig up dirt on Megan and the two end up drinking together, something that infuriates Megan. Finally, Megan is worried when she thinks that Jacob might be losing interest in her.

Laurel gives Megan the task of chaperoning the twins' pool party, thus forcing her to cancel plans for a spa weekend with Jacob. Meanwhile, Charlie confesses to Marco that he is in love with Megan, and Megan is convinced by Rose to invite Lily to the pool party.

Megan's relationship issues with the opposite sex reach a new level when she realizes that Jacob is still interested in his ex-girlfriend and Charlie decides to put the brakes on their friendship. Meanwhile, Laurel is persuaded by Megan to include Sage and Rose in her marketing campaign.

Megan finally decides to reunite with her father and invites him over for dinner at the mansion. Meanwhile, Lily is caught by Sage in a compromising position, and Charlie and Megan's friendship may be over after the two have a major confrontation.

Megan discovers surprising information about Laurel's past. Meanwhile, Sage and Rose get a publicist to help them with their fame and popularity.

Sage and Rose's publicist gets them gigs at the opening of a hot nightclub, where Rose sings and Sage plays the guitar.

Megan and Will finally take action on their feelings for each other and begin dating.

Megan decides to punish Rose for planning to cheat on her final by grounding her. Meanwhile, Laurel rekindles an old flame, Charlie has doubts about living with Mandy, and Marco gets a new partner in the kitchen.

Just as she's finally beginning to adjust to having a relationship with her father, Megan receives an unexpected visit from her mother. Meanwhile, Sage fights her feelings for Luis, and Will finds it difficult to comprehend Megan's family issues.

Megan finally confronts her mother without any sugarcoating about how she really feels about being abandoned. Meanwhile, Sage and Rose plan a charity event for Cuban refugees as an excuse for Sage to spend more time with Luis. Also, Charlie goes back to school, but Mandy becomes jealous when she learns that he will be studying with Megan. Finally, Megan learns that Lily is being held in prison.

Upon learning that Lily is in prison, Megan rushes to her aid and discovers the reasoning behind her sister's imprisonment. Nonetheless, Will offers to bail Lily out, but Arthur refuses the help as a means to teach his daughter a lesson. Meanwhile, Rose aids Sage in picking out an expensive gift for Luis, but his reaction is nothing like what the twins had anticipated.

Will encourages Megan to distance herself from her family's problems and introduces her to his parents. Meanwhile, Rose and Zachary encounter a bump in their relationship when he discovers a picture of her, Sage, and Pete Wentz hanging out at a nightclub.

Megan and Charlie share a kiss, Sage is afraid that Luis will not like that she is a virgin, and Rose is approached by Miles' daughter.

Rose tells Sage the truth about who their grandfather is, causing a confrontation between Laurel and the twins. Meanwhile, Will's dad decides to start a new magazine and Megan wants to contribute to the first issue, but the editor-in-chief is much harder to please than she anticipated. Also, Marco goes to drastic measures to win Keith back.

In the first season finale, as Marco and Keith plan for their wedding, Rose and Sage's relationship takes a bad turn when Rose decides to ditch their annual plans for spring break and Sage becomes upset. Zachary too feels that Rose is changing rather quickly, and worries about the future of their relationship. Meanwhile, Megan and Lily discover that Arthur is drinking again and that Shelby wants him to give her another chance. Also, Will and Megan have a fight and break up.