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Upon learning that Lily is in prison, Megan rushes to her aid and discovers the reasoning behind her sister's imprisonment.Nonetheless, Will offers to bail Lily out, but Arthur refuses the help as a means to teach his daughter a lesson.Meanwhile, Lily is caught by Sage in a compromising position, and Charlie and Megan's friendship may be over after the two have a major confrontation.Sage and Rose's publicist gets them gigs at the opening of a hot nightclub, where Rose sings and Sage plays the guitar.
Meanwhile, Laurel rekindles an old flame, Charlie has doubts about living with Mandy, and Marco gets a new partner in the kitchen.
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.
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.
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.