Megan is offered a job by Laurel as a live-in tutor to her twin granddaughters, Rose and Sage. The teens are less than thrilled about their new tutor, but Megan is determined to make the new situation work. With the job comes several perks: a private suite, a new car and even a live-in chef.
Megan is thrilled when she is invited to Palm Beach by Laurel for an exclusive social event. There, she is introduced to several influential people. However, when Laurel points out a girl that is inappropriately dressed, Megan is horrified to see that it is her sister Lily and immediately lies about knowing her. Meanwhile, when Lily meets Will, she and Megan get into a very public argument.
When Rose learns she has to repeat her freshman year of high school, Megan sets up a meeting with the headmaster, Jacob Cassidy. Megan is shocked when the headmaster turns out to be young and handsome, which throws her off initially but she soon regains her composure and convinces him to give Rose another chance. However, things change when Rose and Sage skip their tutoring session to party.
Megan's modesty comes front and center when she discovers that Rose's bookbag contains an adult DVD, and Rose announces that she is not a virgin. Later, Megan fears that Jacob no longer is interested in her, and Sage asks Lily to join her for dinner so she can find out more about Megan.
Megan has to cancel her plans with Jacob when Laurel asks her to chaperone the pool party Rose and Sage are throwing. Meanwhile, Charlie admits to Marco that he is in love with Megan.
Megan comes up with the idea of having Laurel use Rose and Sage in a marketing campaign in order to bring the family together. The twins are thrilled to be involved in a shoot with photographer Rocco Zaretti, but the shoot does not go smoothly. Meanwhile, Megan's new relationship with Jacob is put on the line when she begins to think he's still in love with his ex-girlfriend.
Megan worries that Rose and Sage do not have enough extra-curricular activities to get into Duke, so she sets them up for a volunteer program at a charity. Meanwhile, Megan decides to reconnect with her estranged father.
Laurel takes over when Megan decides to write a biography about her, and removes Meghan's name for that of a ghostwriter. But Megan trudges on and discovers a secret about Laurel's past while doing research. Elsewhere, Sage talks with a publicist about a modeling career, and Charlie believes Mandy is better for him than Megan.
Megan reflects on her faltering career as a writer after her college friend, Caryn, pays Megan a visit and shares the news of her promotion at The New Yorker. Meanwhile, Sage and Rose get a performing gig at a Miami nightclub thanks to their publicist, where they meet Perez Hilton. Also, Megan strains her relationship with Will after he invites her and Caryn to a tennis match he is photographing.
Megan and Will have a great time on their date together, but they end up breaking up when she learns he is also dating other women. Meanwhile, Laurel asks Megan to investigate Miles; and Rose gets a D on her English exam, leading her to decide to cheat on her History exam.
As Laurel heads to Santa Barbara to visit Miles, Megan and Will's relationship hits a bump when Will takes a job that will require him to spend six months in Brazil. Meanwhile, Charlie debates moving in with his girlfriend.
While awaiting a visit from her dad, Megan's estranged mother stops in, who abandoned the family years earlier. Meanwhile, Megan turns to Charlie for advice on family matters, which makes Will jealous. Sage, who keeps denying her feelings for Luis, sets up Rose on a date.
Megan becomes upset when Shelby says Will is a playboy who will never commit to just one person. In order to get Sage to spend more time with Luis, Rose puts together a large charity dinner, but not everything goes as planned. Meanwhile, Keith tries to convince Marco to quit his job and open a cafe; Charlie goes back to school, but his girlfriend is upset to learn he will be spending more time with Megan; and Megan is shocked to receive a call that her sister Lily is in jail.
After getting a call that her sister Lily is in jail, Megan rushes out to find why she was arrested. Will goes with Megan to deliver the bad news about Lily's arrest to her parents where they decide to not post bail in order to teach her a lesson. Meanwhile, Rose helps Sage buy a gift for Luis.
Megan informs Will that once again her mother has left town, and took all her money. Meanwhile, Rose's boyfriend is angered when she is seen in a picture with Pete Wentz of "Fall Out Boy." Also, Laurel gives Marco money so he can open up a restaurant.
Will tells Megan that his father has agreed to start a new magazine based on Megan and Will's idea. However, they find that the magazine's new editor-in-chief, David Besser, is difficult to work with. When Marco tries to win Keith back by showing up at his house, he finds that Keith is now involved with Jennifer. Meanwhile, Rose tells Sage that Miles is their real grandfather, and confront Laurel with the truth. During the family drama, Sage confesses her own secret, which changes the twin's relationship forever.
Will's father uses his and Megan's idea for a magazine, but discover that pleasing the editor-in-chief is hard to do. Marco learns that Keith has renewed a relationship with an old friend, as he was hoping to win him back. Rose tells Sage that Miles is her real grandfather, and she and Megan confront Laurel. Sage reveals her own secret which dramatically effects her relationship with Rose.
As Marco and Keith get ready for their wedding with the help of Olivia, Megan learns that her father has taken up drinking again, unaware that he received a letter from her mother. Sage becomes upset after Rose reveals she is going on a wilderness trip over Spring Break instead of their annual spa vacation.