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Jane is thrilled when her middle school crush, Nick, asks her to the Winter Formal, until she realizes the event is the same evening as an important company preview party that Gray told her to plan.Nick sees Jane's best friend Billy and It-girl Lulu kissing. Jane must juggle an evening at the winter formal and the fashion runway.Jane and Lulu learn that they are tied to become class valedictorian.
Jane, India, and Beau's assistant Christopher (Brandon Jones) end up at a hotel bar together, where Jane opens up about her feelings for Nick.
While camping, Lulu and Nick complain about their relationships with Jane and Billy, respectively. Ben goes to Donovan Decker looking around for Jane and finds out that Jane's job isn't an internship like he thought.
At Donovan Decker, Jane discovers a world full of fashion challenges working for Gray Chandler Murray (Andie Mac Dowell) and tackles them with the help of her co-workers, Jeremy Jones (Rowley Dennis), India Jourdain (India de Beaufort), Carter (Ser'Darius Blain) and Birdie (Brooke Lyons).
Jane tries to be the best at her job and her school, juggling the everyday challenges of high school and the world of fashion.
However, India is wrongfully accused by Jane of being the mole, Gray overhears this and fires India on the spot.
Things are tense and awkward with Nick and Jane after Billy reveals to her that Nick kissed Lulu on the camping trip; Nick and Jane break up.
Jane Quimby, a high-school student applying for an internship, is mistaken for a qualified adult applicant and is hired by Gray Chandler Murray, a high maintenance fashion designer.
She must now juggle her life as a high school student, a fashion designer and as the breadwinner living with her unemployed older brother.
But when she loses it somewhere in the city, it turns into a mad-dash hunt against the clock.