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 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 (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).

Megan (JoAnna Garcia) has been compiling research on Laurel (Anne Archer) with the intention of presenting a book proposal to her, but Sage (Ashley Newbrough) 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 (guest star Najimy), but Patricia makes it clear she is only interested in representing Sage if Rose (Lucy Kate Hale) is also involved. Tension mounts between the twins when Rose rejects modeling in favor of her school work. Charlie (Michael Cassidy) realizes that Mandy (guest star Alice Greczyn), the girl he has been casually dating, may be better suited for him than Megan ever was. Allan Louis and Brian Hallisay also star. Paul Lazarus directed the episode written by Jenny Lynn.

Upset that Laurel is still giving her the cold shoulder, Megan 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. 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) that Will is independently wealthy, causing a rift in their friendship. Allan Louis also stars.

Megan (JoAnna Garcia) has a great date with Will (Brian Hallisay) 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 (Anne Archer) asks Megan to uncover information about Miles, the man with whom Laurel had a secret affair years ago. When Rose (Lucy Kate Hale) gets a “D” on her English exam, she decides to cheat on her upcoming History test. Sage (Ashley Newbrough) tries to talk Rose out of cheating, but ends up coming 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. Michael Cassidy, Allan Louis and Kristina Apgar also star. Norm Buckley directed the episode written by Michael Reisz.

Laurel (Anne Archer) makes a trip to Santa Barbra to see her old flame Miles (guest star Michael Nouri, "Damages"), and is surprised when he shows up at her doorstep in Palm Beach a few days later, but Miles quickly realizes that Laurel’s business and family come first. Megan (JoAnna Garcia) and Will’s (Brian Hallisay) 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 (Lucy Kate Hale) from cheating on her final and grounds her as punishment. Rose accepts being grounded, but is furious when she learns that Sage (Ashley Newbrough) was the one who told Megan about the plan to cheat. Charlie has second thoughts about moving in with his girlfriend Mandy (guest star Alice Greczyn). Finally, Charlie’s cousin Luis (guest star Ignacio Serricchio, “General Hospital”) gets a job working in the kitchen with Marco (Allan Louis) and Sage decides to torture him with her demands. Michael Engler directed the episode written by Margaux Froley.

Just as she's finally beginning to adjust to having a relationship with her father, Megan receives an unexpected visit from her mother. Meanwhile, Sage fights her feelings for Luis, and Will finds it difficult to comprehend Megan's family issues.

Megan (Joanna Garcia) is upset when Shelby (guest star Sharon Lawrence) tells her that Will (Brian Hallisay) 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 (Ashley Newbrough) to spend more time with Luis (guest star Ignacio Serricchio), Rose (Lucy Kate Hale) 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 (Allan Louis) boyfriend Keith (guest star David Monahan) encourages Marco to quit his job and open his own cafe, but they end up arguing about their future together. Charlie (Michael Cassidy) decides to go back to school, but his girlfriend Mandy (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 (Kristina Apgar, who does not appear in the episode) is in jail. Liz Friedlander directed the episode written by Anna Fricke.

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. Michael Cassidy and Allan Louis also star. David Paymer directed the episode written by Rina Mimoun & Christopher Fife (#113).

When Megan (JoAnna Garcia) tells Will (Brian Hallisay) 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 Arthur (guest star John Allen Nelson) is in denial about the situation and Lily (Kristina Apgar) is angry and hurt that she didn't even get to see her mother. When a picture of Rose (Lucy Kate Hale) and Sage (Ashley Newbrough) with bassist Pete Wentz of the band Fallout Boy at a nightclub upsets Rose's boyfriend Zach (guest star David Franco), Sage has to admit that her pursuit of fame is taking a big toll on their social lives. Meanwhile, Laurel (Anne Archer) gives Marco (Allan Louis) the money to start his own restaurant, but he realizes that isn't what he really wants. Finally, Megan meets Will's parents, Elliot (Steven Culp, "Desperate Housewives") and Josephine (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. Michael Schultz directed the episode written by Natasha Gaty.

Megan (JoAnna Garcia) is surprised to hear that Charlie (Michael Cassidy) has been accepted to UCSD 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 (Brian Hallisay) what happened, he is so upset that he ruins Charlie's goodbye party by confronting Charlie and starting a fist fight. Meanwhile, Rose (Lucy Kate Hale) is approached by Miles' daughter, Elyse (guest star Elaine Hendrix), who reveals to Rose that Miles is the girls' real grandfather. Sage (Ashley Newbrough) worries that Luis (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. Kristina Apgar also stars. David Paymer directed the episode written by Jenny Lynn.

Megan (JoAnna Garcia) is thrilled when Will (Brian Hallisay) tells her that his father (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 (Robert Buckley), is not easy to please. When Marco (Allan Louis) decides to win Keith (guest star David Monohan) back and shows up unannounced at his house, he discovers Keith is now involved with his longtime friend Jennifer (Jennifer Elise Cox). Marco takes dramatic action to keep his true love from slipping away. Meanwhile, Rose (Lucy Kate Hale) tells Sage (Ashley Newbrough) the shocking news that Miles is their real grandfather. The twins tell Megan what they know, then confront Laurel (Anne Archer) 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. Ron Lagomarsino directed the episode written by Scott Weinger & David Babcock.

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. Also, Will and Megan have a fight and break up.