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 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 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 (JoAnna Garcia) is concerned that Rose (Lucy Kate Hale) and Sage (Ashley Newbrough) 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 (guest star John Allen Nelson, “24”) and invites him to dinner at the estate. Megan asks Marco (Allan Louis) to prepare dinner for two, but when Lily (Kristina Apgar), Will (Brian Hallisay), 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 (Michael Cassidy). Liz Friedlander directed the episode written by David Babcock.
Megan discovers surprising information about Laurel's past. Meanwhile, Sage and Rose get a publicist to help them with their fame and popularity.
Upset that Laurel (Anne Archer) is still giving her the cold shoulder, Megan (JoAnna Garcia) is nonetheless excited that her college pal Caryn (guest star Sarah Drew) 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 expose about the lives of the people she's met in Palm Beach, but Megan rejects the idea. When Sage and Rose's publicist (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 (Brian Hallisay) invites Megan and Caryn to a tennis match he has been hired to photograph, but Megan accidentally tells his boss (guest star Robert Mailhouse) that Will is independently wealthy, causing a rift in their friendship.
Megan and Will finally begin dating, but the relationship faces early challenges when Megan discovers that Will is dating other women at the same time. Meanwhile, Rose begins to go to extreme measures to maintain good grades after doing badly on an English exam.
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 is getting used to having a relationship with her father, Arthur (guest star John Allan Nelson), Megan (JoAnna Garcia) is thrown for a loop by the return of her mother, Shelby (guest star Lawrence), 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 Lily (Kristina Apgar, who does not appear in the episode) impulsively ran off and got married to a man Megan can't stand. Will (Brian Hallisay) finds it hard to understand Megan's complicated family issues, and is jealous that Megan seems to prefer discussing her problems with Charlie (Michael Cassidy). Meanwhile, Sage (Ashley Newbrough) denies that she is attracted to Luis (guest star Ignacio Serricchio), so Rose (Lucy Kate Hale) and Marco (Allan Louis) come up with a scheme to make Sage admit her true feelings. Sage turns the tables on Rose by setting up a date for her with Zachary (guest star David Franco, "Greek"), a boy Rose already likes. Ron Lagomarsino directed the episode written by Rina Mimoun & David Babcock.
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.
After learning that her sister Lily (Kristina Apgar) is in jail, Megan (JoAnna Garcia) 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 (Brian Hallisay) along when she relays the bad news about Lily to her parents, Arthur (guest star John Allen Nelson) and Shelby (guest star Sharon Lawrence), and although Will offers to pay Lily’s bail, 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 has to 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. Meanwhile, Rose (Lucy Kate Hale) helps Sage (Ashley Newbrough) pick out an expensive gift for Luis (guest star Ignacio Serricchio) and they are baffled by his reaction.
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.