Jane Quimby (Erica Dasher) is a quirky teen with an eclectic chic fashion sense, who lands a job at a hip fashion house when they mistake her for an adult. Torn between her love of fashion and the need to finish high school, Jane conceals her true age to assist the demanding, but talented Gray Chandler Murray (Andie MacDowell), who travels the world in search of the next big style trend. Jane quickly learns that working for a successful executive in the cutthroat world of fashion is not as glamorous as she once thought. But with help from her best friend Billy Nutter (Nicholas Roux), Jane tries to keep up appearances as she toggles between two lives and guard her secret. Even with Billy’s support, will Jane’s ruse be a passing fad, or will she be able to fashion a career in the design business? With the school play's future in the lurch because of her, Jane decides to do something very unselfish - giving the play her well earned bonus check from Donovan Decker so the show can go on. But with the play back on, and getting some much needed help from the Donovan and Decker crew on the costumes, Jane feels like she may have given up more than just some money for this play. The Harrods and Donovan Decker deal looks bleak when the Harrods team demands to get Jeremy's designs. With little to go on, Gray gives Jane the task of going to London to find Jeremy and persuade him to come back. Now all alone in London, Jane heads out to find Jeremy and save the day. Meanwhile Billy tries to repair things with Zoe, only to have his relationship with Jane get in the way - again. Jane and Billy volunteer in backstage work for the Cinderella play, starring Zoe and Nick. Kate gives away the dress that Jane made to Zoe, leaving Jane without a dress to wear for her first official date with Eli. Ben gets a chance to play a minor league baseball in Ohio. Jane and Eli's date gets a complicated, with the buyer of the dress made by Donovan Decker appearing in the same restaurant as Jane, with Jane wearing the same exact dress previously labeled as the "backup dress". Kate accepts Dakota's proposal and heads out to Colorado. Jane is left alone in the house since Ben and Kate went on their own journeys. Love is in the air, but needs a little help to get going and Jane is determined to help her friends out. Billy is caught off guard when Zoe invites him to meet her parents and he isn’t so sure he is ready to take that step. Kate, on the other hand, decides to help Gray take the next step with her love life by setting up an online dating profile for her. Mortified by her mother’s actions, Jane must now try to put a stop to the online dating scheme before Gray finds out and fires her for sure. Meanwhile, Rita decides to finally fight for Ben - but is she up for taking on life-long mean girl Amanda? Jane's mother, Kate, is back and full of wild stories but no real answers of why she left and hasn't been in touch. Jane is excited for her to be there, seeing it as a chance to finally get to know the mother she only dreamed about. Ben, on the other hand, sees Kate's arrival as nothing but trouble and ultimately only disappointment for Jane when Kate disappears again. Meanwhile, Billy starts to wonder about Zoe when things start to seem off about her.