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 is concerned that Rose and Sage 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 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 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.

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 is now dating her irresponsible punk boyfriend again.

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 romance with Megan work when his work plans change.

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 with her old boyfriend Zack.

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. Meanwhile, Rose helps Sage pick out a lavish gift for Luis to further get his attention, but neither sister foresees his reaction, while at the same time, Rose finds a love poem and assumes that her nebish classmate Zack wrote it for her.

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 Arthur is in denial about the situation and Lily is angry and hurt that she didn't even get to see her mother. When a picture of Rose and Sage with bassist Pete Wentz of the band Fallout Boy at a nightclub upsets Rose's boyfriend Zach, 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 and Josephine, and feels guilty for involving Will with her own dysfunctional family, but Will surprises Megan with a declaration of his true feelings for her.

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 her better, invites her to his church. Also, Rose confides in Zack that she is not a virgin, and he reveals the same about him... And a twist comes when Rose gets a visit from Elyse, the daughter of Miles Franklin where she confides the secret that Miles is her late mother's natural father.

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 meet the editor-in-chief, David Besser, whom is much harder to please than anticipated. However, the strain on both Will and Megan for the same job puts a strain on their relationship. Elsewhere, Marco goes to drastic measures to win Keith back when he finds him living with his best friend Jennifer who wants to get romantically together with Keith to start a family.

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 over Will's job and Megan's mental ability to be independent. Also, Megan finally finishes her biography about Laurel who approves it for publishing.