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The girls, Rose (Lucy Hale) and Sage (Ashley Newbrough), are beautiful, rebellious, and less-than-thrilled with their new tutor, but Megan is determined to win them over as she enjoys the perks of her new job: breathtaking private suite, gorgeous convertible, and live-in chef Marco (Allan Louis).Even the neighbors are fabulous in Palm Beach and Megan quickly catches the eye of Will (Brian Hallisay), the wealthy and attractive dilettante who lives on the estate next door and just happens to be dating Megan’s estranged sister, Lily (Kristina Apgar).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.
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.
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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.