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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.
01 - Pilot
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.
02 - All About Honesty
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.
03 - All About What You Really, Really Want
When Rose is told that she will have to repeat her freshman year of high school at the exclusive prep school she and Sage attend, Megan requests a meeting with the headmaster, Jacob Cassidy (recurring guest star DAVID GIUNTOLI - "Nip/Tuck," "Road Rules"). Jacob turns out to be young and handsome, and Megan is temporarily thrown by the flirtatious vibe between them, but quickly regains her composure and convinces him to give Rose another chance to bring her grades up. When Rose and Sage skip their tutoring session that evening to party, Megan follows them onto their friend's yacht and tries to lay down the law. Megan sees Will at the party, but she rebuffs his advances and encourages him to continue dating her sister, Lily, whom Megan has been avoiding since their fight at the fundraiser. Finally, Megan accepts a date with Jacob, never noticing that her best friend Charlie is jealous.
04 - All About the Power Position
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.
05 - All About Friends and Family
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 the pool party Rose and Sage are throwing. In an attempt to help repair the relationship between Megan and her sister, Lily, Rose convinces Megan she should invite Lily to the party. At first, Megan and Lily seem to be on the road to reconciliation, until Rose realizes her expensive bracelet is missing and Megan accuses Lily of stealing it. And Sage breaks out in hives after some jealous girlfriends spike her drink and Megan shuts the party down -- but not before LAUREN CONRAD ("The Hills") appears in a cameo role as a party guest. Plus, Charlie admits to Marco that he is in love with Megan and is jealous of her new relationships with Jacob and Will.
06 - All About Appearances
Megan suggests that Laurel use Rose and Sage in her upcoming marketing campaign as a way of bringing the family closer together. The twins are thrilled to be doing a shoot with top photographer Rocco Zaretti (guest star NIGEL BARKER - "America's Next Top Model"), but their relationship with Laurel is so dysfunctional that the shoot is a disaster. Laurel must face that her relationship with her granddaughters is not what she wants it to be, and the twins are disappointed that their fashion debut has been thwarted once again. Plus, Megan's happiness over her new romance with Jacob (recurring guest star DAVID GIUNTOLI) turns to hurt when she realizes he is still interested in an ex-girlfriend. And Charlie decides to pull back on his friendship with Megan rather than letting her go on taking him for granted.
07 - All About the Haves and Have-nots
Megan is concerned that Rose and Sage don't have enough extracurricular activities to get into Duke, so she arranges for them to volunteer with a charity that provides prom dresses to underprivileged 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 (guest star JOHN ALLEN NELSON - "24," "Vanished," "Baywatch") 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 -- that is, 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 Charlie.
08 - All About Defining Yourself
Megan has been compiling research on Laurel with the intention of presenting a book proposal to her, but Sage discovers Megan's notes and emails them to Laurel before Megan has a chance to explain. Megan is pleasantly surprised to find that Laurel likes the idea of a biography, but when Laurel takes over the project and hires an experienced ghostwriter, Megan feels dismissed. Continuing her research, Megan inadvertently discovers a shocking secret about Laurel's past. When Megan comes clean to Laurel about what she has learned, Laurel reacts by freezing Megan out. Meanwhile, Sage is sure her modeling career is about to kick into high gear when she meets with high-powered publicist Patricia Kingston (recurring guest star KATHY NAJIMY - "Numb3rs," "King of the Hill," "Veronica's Closet," "Sister Act 2"), but Patricia makes it clear she is only interested in representing Sage if Rose is also involved. Tension mounts between the twins when Rose rejects modeling in favor of her school work. And Charlie realizes that Mandy (recurring guest star ALICE GRECZYN - "Sex Drive," "Lincoln Heights," "Windfall"), the girl he has been casually dating, may be better suited for him than Megan ever was.
09 - All About Insecurities
Upset that Laurel is still giving her the cold shoulder, Megan is nonetheless excited that her college pal Caryn (guest star SARAH DREW - "Everwood") is coming to visit her in Palm Beach. When Caryn reveals that she's just been promoted from assistant to junior editor at The New Yorker magazine, Megan can't help but feel bad about her own stalled writing career. Trying to be helpful, Caryn suggests Megan write an exposé about the lives of the people she's met in Palm Beach, but Megan rejects the idea. When Sage and Rose's publicist (recurring guest star KATHY NAJIMY) learns that Rose and Sage have musical talent, she books them a gig performing at the opening of a hot new Miami nightclub, where the girls are thrilled to have a red carpet encounter with PEREZ HILTON (guest starring as himself). Finally, Will invites Megan and Caryn to a tennis match he has been hired to photograph, but Megan accidentally tells his boss (guest star ROBERT MAILHOUSE - "Without a Trace," "Sports Night") that Will is independently wealthy, which causes a rift in their friendship.
10 - All About Overcompensating
Megan has a great date with Will but breaks off their relationship when she can't deal with the fact that he is also dating several other women. Will wins her back by promising to date her exclusively, but when he gets a job offer that will take him out of the country for several months, Megan is unsure what to do. Laurel asks Megan to uncover information the man with whom Laurel had a secret affair years ago. When Rose gets a "D" (a terrible grade) on her English exam, she decides to cheat on her upcoming History test. Sage tries to talk Rose out of cheating, but ultimately comes up with a plan to make sure Rose won't get caught. Megan discovers what the girls are doing and races to the school to try to stop Rose before it's too late.
11 - All About Love, Actually
Laurel makes a trip to Santa Barbara to see her old flame Miles (guest star MICHAEL NOURI - "Damages," "The O.C."), and is surprised when he shows up at her doorstep in Palm Beach a few days later. Miles quickly realizes that Laurel's business and family come first. Megan and Will's new status as a couple gets off to a rocky start when Will announces he has accepted a job that will take him to Brazil for six months. Meanwhile, Megan prevents Rose from cheating on her final and grounds her as punishment. Rose accepts being grounded, but is furious when she learns that Sage was the one who told Megan about the plan to cheat. Charlie has second thoughts about moving in with his girlfriend, Mandy (recurring guest star ALICE GRECZYN). Finally, Charlie's cousin Luis (recurring guest star IGNACIO SERRICCHIO - "Ghost Whisperer," "General Hospital") gets a job working in the kitchen with Marco and Sage decides to "torture" him with her demands.
12 - All About The Ripple Effect
Just as she is getting used to having a relationship with her father, Arthur (recurring guest star JOHN ALLEN NELSON), Megan is thrown for a loop by the return of her mother, Shelby (guest star SHARON LAWRENCE - "NYPD Blue"), who abandoned the family when Megan was a child. Megan finds it hard to control her anger toward Shelby, but Arthur makes it clear that he wants Megan to forgive the mistakes made by both her parents in the past. To make matters worse, Megan learns that her sister impulsively ran off and got married to a man Megan can't stand. Will finds it hard to understand Megan's complicated family issues, and is jealous that Megan seems to prefer discussing her problems with Charlie. Meanwhile, Sage denies that she is attracted to Luis (recurring guest star IGNACIO SERRICCHIO), so Rose and Marco come up with a scheme to make Sage admit her true feelings. Sage turns the tables on Rose by setting her up on a date with Zachary (recurring guest star DAVID FRANCO - "Greek"), a boy Rose already likes.
13 - All About What Lies Beneath
Megan is upset when Shelby (recurring guest star SHARON LAWRENCE) tells her that Will is a playboy who will never commit. Megan finally confronts Shelby and lets out all her anger over being abandoned. As an excuse for Sage to spend more time with Luis (recurring guest star IGNACIO SERRICCHIO), Rose comes up with the idea of throwing an elaborate charity dinner, complete with a synchronized swim team to tell the story of Cuban refugees. However, the plan backfires when Luis reveals he is not of Cuban descent. Meanwhile, Marco's boyfriend, Keith (recurring guest star DAVID MONAHAN - "Crossing Jordan," "Dawson's Creek"), encourages Marco to quit his job and open his own café, but they end up arguing about their future together. Charlie decides to go back to school, but his girlfriend, Mandy (recurring guest star ALICE GRECZYN) turns manipulative when she learns he'll be spending study time with Megan. Finally, Megan is shocked to get a phone call telling her that her sister, Lily, is in jail.
14 - All About Tough Love
After learning that Lily is in jail, Megan rushes to be with her and find out why she was arrested. Lily insists she knew nothing about the backpack full of drugs found in her hotel room, but her new husband is missing and she needs $25,000 for bail. Megan takes Will along when she relays the bad news about Lily to her parents, Arthur (recurring guest star JOHN ALLEN NELSON), and Shelby (recurring guest star SHARON LAWRENCE). Will offers to pay Lily's bail, but Arthur decides that Lily needs to be frightened into cleaning up her life, and refuses to let anyone bail her out. A heartbroken Megan has to tell Lily that she must remain in jail. Later, Shelby arranges a secret meeting with Will and convinces him to give her the bail money, leading to an argument with Megan and a shock for everyone over Shelby's actions. Plus, Rose helps Sage pick out an expensive gift for Luis (recurring guest star IGNACIO SERRICCHIO) and they are baffled by his reaction.
15 - All About The Big Picture
When Megan tells Will that her mother has disappeared again, along with his money, Will suggests that it's time for Megan to separate herself from her family's problems. However, Megan is heartsick that her father (recurring guest star JOHN ALLEN NELSON) is in denial about the situation and Lily is angry and hurt that she didn't even get to see her mother. When Rose's boyfriend, Zach (recurring guest star DAVID FRANCO), gets upset after seeing a picture of Rose and Sage at a nightclub with bassist PETE WENTZ of the band Fallout Boy, Sage has to admit that her pursuit of fame is taking a big toll on their social lives. Meanwhile, Laurel gives Marco the money to start his own restaurant, but he realizes that isn't what he really wants. Finally, Megan meets Will's parents, Elliot (recurring guest star STEVEN CULP - "Desperate Housewives") and Josephine (guest star MARY PAGE KELLER - "Commander in Chief"), and feels guilty for involving Will with her own dysfunctional family. But Will surprises Megan with a declaration of his true feelings for her.
16 - All About Confessions
Megan is surprised to hear that Charlie has been accepted to UCSD (University of California, San Diego) and is moving to California. She takes him out to celebration his good news, and he shocks her by kissing her and admitting he has been in love with her for years. When Megan tells Will what happened, he is so upset that he ruins Charlie's good-bye party by confronting Charlie and starting a fist fight. Meanwhile, Rose is approached by the daughter of Miles (guest star MICHAEL NOURI), Elyse (guest star ELAINE HENDRIX - "Joan of Arcadia"), who reveals to Rose that Miles is the girls' real grandfather. Sage worries that Luis (recurring guest star IGNACIO SERRICCHIO) will be disappointed that she is a virgin, but is surprised to learn that he is deeply religious and does not believe in pre-marital sex. Luis invites Sage to church, which brings up her grief about her parents' death and leads to a startling confession.
17 - All About Betrayal
Megan is thrilled when Will tells her that his father (recurring guest star STEVEN CULP) is starting a new magazine based on Megan and Will's idea. Eager to pitch ideas for the first issue, Megan and Will soon find the magazine's new editor-in-chief, David Besser (guest star ROBERT BUCKLEY - "Lipstick Jungle"), is not easy to please. When Marco decides to win Keith (recurring guest star DAVID MONOHAN) back and shows up unannounced at his house, he discovers Keith is now involved with his longtime friend Jennifer (guest star JENNIFER ELISE COX - "The Brady Bunch Movie," "Six Feet Under," "10 Items of Less"). Marco takes dramatic action to keep his true love from slipping away. Meanwhile, Rose tells Sage the shocking news that Miles is their real grandfather. The twins tell Megan what they know, then confront Laurel with the truth. During all the family drama, Rose knows that Sage is keeping something from her and when Sage finally confesses her own personal secret, it causes a profound change in the twin's relationship.
18 - All About a Brand New You!
As Marco and Keith (recurring guest star DAVID MONOHAN) prepare for their wedding, with the help of a wedding planner, Olivia (guest star KATHY GRIFFIN - "My Life on the 'D' List," "Suddenly Susan"), Megan discovers that her father, Arthur (recurring guest star JOHN ALLEN NELSON), is drinking again. Megan and Lily lovingly tell their father how worried they are, but are unaware that he has received a letter from their mother asking him to let her explain in person why she left. Sage is upset when Rose reveals she plans to go on a wilderness trip over spring break, instead of going with Sage on their annual spa vacation, and Zach (recurring guest star DAVID FRANCO) worries that Rose is changing and won't be interested in him much longer. In addition to being upset with Rose, Sage is shocked when Luis (recurring guest star IGNACIO SERRICCHIO) tells her he doesn't believe in gay marriage and refuses to attend Marco's wedding. Meanwhile, Megan gives Laurel the first draft of Laurel's biography and is relieved when Laurel loves it. Megan and Will have a fight and all of their repressed issues come out; consequently, they decide to break up. Attending the wedding alone, Megan meets Simon (guest star JULIAN MORRIS - "ER"), a college friend of Keith's, and, when Will calls her the next morning to apologize, she is unsure what to do.