When Rose (Lucy Kate Hale) is told that she will have to repeat her freshman year of high school at the exclusive prep school she and Sage (Ashley Newbrough) attend, Megan (JoAnna Garcia) requests a meeting with the headmaster, Jacob Cassidy (guest star David Giuntoli). Jacob turns out to be young and handsome, and Megan is temporarily thrown by the flirtatious vibe between them, but quickly regains her composure and convinces him to give Rose another chance to bring her grades up. When Rose and Sage skip their tutoring session that evening to party, Megan follows them onto their friend’s yacht and tries to lay down the law. Megan sees Will (Brian Hallisay) at the party, but she rebuffs his advances and encourages him to continue dating her sister, Lily (Kristina Apgar), whom Megan has been avoiding since their fight at the fund-raiser. Finally, Megan accepts a date with Jacob, never noticing that her best friend Charlie (Michael Cassidy) is jealous.