Privileged

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 to go out 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 is concerned that Rose and Sage don't have enough extra-curricular activities to get into Duke, so she arranges for them to volunteer with a charity that provides prom dresses to under-privileged girls. Rose and Sage make a mess of the dresses they are supposed to alter, but they fix the problem in their own unique style. Meanwhile, Megan decides the time has come to reconnect with her estranged father and invites him to dinner at the estate. Megan asks Marco to prepare dinner for two, but when Lily, Will, Rose and Sage also show up for dinner, the party goes surprisingly well until Sage catches Lily in an embarrassing situation. Megan comes to a new understanding with her dad, but later that night, she has a nasty confrontation with her best friend Charlie.

Megan tells Laurel she wants to write a biography about her, but Laurel wants to hire a ghost writer to write the book which makes Megan feel left out. But later, Megan investigates and learns a dark secret from Laurel's past. Meanwhile, Rose and Sage have different goals when Sage hires a publicist, named Patty Kingston, to boost their fame careers when Rose thinks school is more important.

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 becomes more uncertain about where she stands in her growing romance with Will when he claims to have dated a lot more that she has, So, Megan asks Charlie's latest girlfriend, Mandy, to set her up on a blind date with one of her co-workers. Meanwhile, Rose gets a 'D' on her English exam and plots to keep herself from failing her upcoming history exam by stealing a copy of the test, and Sage devises a crafty plan so Rose will not get caught. Elsewhere, Laurel confides in Megan about her long-lost romance with her one-time boss, while Megan also learns that Lily is now dating her irresponsible punk boyfriend again.

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.