Privileged

In the series premiere, based on the hit book How to Teach Filthy Rich Girls, Megan makes the transition from New York to Palm Beach, and takes on her new position with gusto. Hoping to upset Megan, Sage invites Megan's estranged sister, Lily (series star KRISTINA APGAR), to Laurel's fundraising event. One of the waiters at the event is Megan's best friend, Charlie (series star MICHAEL CASSIDY), who has been secretly in love with her for a long time. Despite her own complicated romantic and family relationships, Megan is committed to making a difference in the lives of her two headstrong students as she navigates the treacherous waters of high society in Palm Beach.

Megan is thrilled when Laurel invites her to a glamorous Palm Beach social event and introduces her to several influential people. When Laurel points out a young woman who is inappropriately dressed, Megan is shocked to realize it's her sister, Lily, and lies to Laurel about knowing her. Later, when Lily connects with Will and she and Megan get into a loud, public argument, Laurel realizes that Megan lied to her about knowing Lily. Meanwhile, Rose is devastated that her ex-boyfriend, Max (guest star ANDREW J. WEST) is at the party with another girl, and Megan and Sage argue over how to help Rose deal with the situation. Finally, Megan offers to help the daughter of one of Laurel's important business contacts with her application to Yale, but has to leave the girl hanging to rescue Rose and Sage from being arrested for driving without a license.

Megan meets with Rose's headmaster, Jacob Cassidy (recurring guest star DAVID GIUNTOLI), and is disarmed by his age and good looks. Plus, the twins skip tutoring for a yacht party.

Megan is shocked to discover an adult DVD in Rose's book bag and even more shocked when Rose reveals she is not a virgin. Rose admits she is planning to have sex with her current boyfriend, Max (recurring guest star ANDREW J. WEST), and doesn't understand why Megan seems so uptight about sexual issues. Megan's insecurities also show up during a date with Jacob (recurring guest star DAVID GIUNTOLI) and she fears he is losing interest in her. Meanwhile, Sage invites Lily out to a restaurant in order to dig up dirt on Megan, and Megan is furious when she finds out that Lily and Sage were drinking together.

Megan is forced to cancel her plans for a spa weekend with Jacob (recurring guest star DAVID GIUNTOLI) when Laurel demands she act as chaperone for Rose and Sage's pool party.

A photo shoot with Rose and Sage for Laurel's upcoming marketing campaign with top photographer Rocco Zaretti (guest star NIGEL BARKER - "America's Next Top Model") is a disaster.

Megan reconnects with her estranged father (guest star JOHN ALLEN NELSON - "24") and asks Marco to prepare dinner for two at the estate. Lily, Will, Rose and Sage also show up.

Megan learns a secret about Laurel's past. Sage meets with publicist Patricia Kingston (guest star KATHY NAJIMY - "Numb3rs"), but she is only interested if Rose is also involved.

The twins encounter blogger PEREZ HILTON on the red carpet at a club and SARAH DREW ("Everwood") guest stars as Megan's best friend from Yale, Caryn.

Megan has a great date with Will but can't deal with the fact that he is also dating other women. When Rose gets a bad grade on an exam, she decides to cheat on her next test.

Will and Megan's new romance is threatened when Will plans to accept a job in Brazil. Sage "tortures" Charlie's cousin, Luis (IGNACIO SERRICCHIO), who gets a job in the kitchen.

Megan's mother, Shelby (guest star SHARON LAWRENCE - "NYPD Blue"), who abandoned the family when Megan was a child, returns. Will is jealous when Megan turns to Charlie for advice.

Megan confronts her mother, Shelby (SHARON LAWRENCE), Rose and Sage throw an elaborate charity dinner and Marco's boyfriend, Keith (DAVID MONAHAN), pushes Marco to quit his job.

Megan wants Lily out of jail, but her father (JOHN ALLEN NELSON) thinks Lily should be left there to learn a lesson. Shelby (SHARON LAWRENCE) later asks Will for the bail money.

Rose's boyfriend, Zach (DAVID FRANCO), gets upset after seeing a picture of Rose and Sage with bassist PETE WENTZ of the band Fallout Boy. Megan meets Will's parents.

Charlie surprises Megan by admitting he has been in love with her for years. Will reacts badly to the news. And Rose gets some surprising news of her own.

The twins confront Laurel with their shocking news. Rose knows Sage is keeping something from her and when Sage finally confesses her secret, it changes their relationship.

In the season finale, Brenda and Fritz's wedding plans are interrupted as both are called in to work on investigations. FRANCES STERNHAGEN, BARRY CORBIN and AMY SEDARIS guest star.