Privileged - Season 1 (2008)

Megan becomes disturbed when she finds an adult DVD in Rose's book bag in which she plans to use as practice for sex with her boyfriend Max, and Megan is further unnerved when she learns that Rose is not a virgin. Megan then decides to go on a date with Jacob, but becomes worried when he may ask her to spend the night. Meanwhile, Sage meets Lily at her beauty salon and asks her out to lunch to dig up any dirt on Megan to use to her own advantage.

When Laurel goes out of town, she asks Megan to chaperon a pool-party that the girls are hosting. Rose convinces Megan to invite her sister, Lily, to the party. Charlie confesses his love for Megan to Marco. At the pool party, Megan is forced to deal with underage drinking and the possibility that Lily may have stolen one of Rose's diamond tennis bracelets.

In an effort to bond Laurel with her granddaughters, Megan suggests that Laurel use the twins in a new advertising campaign for her cosmetics company. The plan backfires when Laurel announces that the girls would miss several weeks of school for a European photo shoot, preventing Megan from tutoring them properly. Deciding that his feelings for Megan are hindering him, Charlie begins distancing himself from Megan, but will not explain his actions. Meanwhile, Megan discovers that she is not the only woman in Jacob's life.

Megan has a run-in with her estranged father whom she decides to make an effort to reconcile by inviting him over at the mansion for dinner. But Arthur Smith inadvertently brings along Lily which brings up more tension since she and Megan are still not speaking to one another. Meanwhile, Megan has Sage and Rose do some charity work by having them design some evening gowns for a local school, in which Sage decides to take some issues over the designs in her own hands. Elsewhere, Megan has an argument with Charlie when she finds out that he told her father that she was ...

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 ...

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 ...

Megan becomes more neurotic and uncomfortable when her eccentric and estranged mother Shelby, whom she hasn't seen in 16 years, suddenly shows up to visit Arthur. Megan instead confides in Charlie about her problems, which makes Will feel left out and a little jealous over Megan's friendliness with Charlie. Megan also learns that Lily has eloped with her punk boyfriend, which makes Megan feel that she's losing control even more. Meanwhile, Rose asks Marco to help set up Sage with the sous chief Louis, while Sage makes a bet with Rami the doorman to try to set up Rose ...

Hoping to spend more time with Luis, Sage and Rose plan a charity dinner for Cuban refugees. Megan comes clean to her mother about her feelings of abandonment. Charlie returns to school, spurning jealousy from Mandy when he seeks Megan's help. Megan learns that Lily has been arrested.

Megan seeks to aid her sister, and in so doing learns why Lily is in jail. Will offers to bail Lily out, but both Arthur and Megan refuse saying that Lily should learn a lesson by staying in jail for her long history of making the same dumb mistakes and getting involved with the wrong people. Shelby secretly meets with Will behind Megan's back to ask for his assistance, and he agrees to help... only to find out later what Shelby's real reason is. Meanwhioe, Rose helps Sage pick out a lavish gift for Luis to further get his attention, but neither sister foresees his ...

Will introduces Megan to his parents. Rose's new boyfriend, Zachary, discovers a picture of her partying with Pete Wentz.

When Charlie announces that he will be leaving down to go back to college in San Diego, Megan's natural neurotic reaction is that she fears she will never see her best friend again. Then one evening during planning for a going away party for Charlie that his girlfriend, Mandy, planning, Charlie kisses Megan and expresses that he loves her which fills her with conflicting emotions, and fills Will with anger and jealousy. Meanwhile, Sage tells Louis that she happens to be a virgin, and gets a surprise when he tells her the same about him, and in an attempt to understand...

Rose tells Sage the truth about who their grandfather is, causing a confrontation between Laurel and the twins. Laurel gets more bad luck when Elyse Valencour, Miles Franklin's daughter, brings a lawsuit against her for emotional distress against her father when she informs her that Miles has been hospitalized from a fatal heart attack. Sage also confides in Rose that she feels indirectly responsible for their parents death years earlier. Meanwhile, Will's father decides to start a new magazine and Megan wants to contribute to the first issue. But Megan and Will soon ...

While Marco and Keith plan for their upcoming commitment wedding, Rose and Sage's sisterly relationship takes a bad turn when Rose decides to ditch their annual plans for spring break and go someplace on her own, in which Sage becomes upset. Zachary too feels that Rose is maturing rather quickly, and worries about the future of their relationship. Sage has relationship problems herself when Luis tells her that he does not believe in gay marriages and refuses to attend Marco and Keith's ceremony. Elsewhere, Will and Megan have a fight over their creative differences ...