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Jane Quimby está haciendo malabarismos con la vida como una estudiante de secundaria y como asistente.

Jane es lanzada en un bucle cuando Gray le asigna la tarea de última hora de obtener la nueva línea de accesorios lista para la fiesta preliminar de primavera. Jane está bastante segura de que tiene algo más de lo que puede masticar, pero con Jeremy buscando hacer las paces, los dos equipos de seguimiento para garantizar la línea es la que los críticos y los compradores no se olviden pronto. Mientras tanto, Nick se aprovecha de su conocimiento de la relación secreta de Billy con Lulu para obtener asesoramiento para acercarse a Jane. Cuando Nick la invita al baile de Invierno , Jane piensa que la vida no podía ser mejor. Pero cuando se da cuenta de que el baile de Invierno es la misma noche que la fiesta preliminar de primavera, sus dos noches perfectas se convertirán en su peor pesadilla.

Jane se siente en la cima del mundo cuando Gray la premia con el uso de un auténtico bolso Birkin en recompensa por un trabajo bien hecho. Jane piensa que por fin tiene ese trabajo bajo control cuando Gray le da la tarea de dirigir la exhibición itinerante privada en la casa de Gray. Pero con India sintiendo los dolores por los celos de la nueva favorita de Gray, robar el centro de atención de la fiesta previa, ella está decidida a mostrar a Gray y a la empresa el fallo que puede ser realmente Jane. Mientras tanto, se calienta la competencia entre Jane y Lulu en la escuela cuando se les dice que están empatadas en el primer lugar de la clase.

Now that Billy and Lulu have decided to take their relationship public, Billy must tell Jane. Feeling betrayed and lied to, Jane doesn’t take the news of the high school’s new “It” couple well. But now with the news out there and neither group of friends seeming very supportive of it, can Billy and Lulu withstand the peer pressure? And has Jane truly lost her one true ally in the social shark tank that is high school? Meanwhile, Jeremy and Jane are given the impossible task to present the new fashion line to top fashion magazine editor Miyoko Sato and make a good impression when she visits the Donovan Decker offices.

Jane is over-the-moon with anticipation when Gray tells her she will be boarding a flight to Paris the following night to bring her the coveted Donovan Decker Lookbook, which holds all the secrets, inspirations and ideas for the fashion company. When Jane is tasked with secretly securing the Lookbook until she leaves, she will do anything to hold onto it and make the flight to Paris, even if that means she has to turn to her nemesis and best friend’s girlfriend, Lulu for help. Meanwhile, Billy’s brother Tommy, has a new criminal scheme that he wants Billy to help him with.

When she questions India’s presentation in front of Gray, Jane is tasked to do her own research to find out what high school students are really looking for in the fashion world. Determined to prove that teenagers are about finding out who they are and not changing just to fit some mold, Jane hits the hallways of her school to prove her point. But when her classmates are less then helpful, Jane starts to worry that she won’t be able to pull the presentation off. Meanwhile, Billy tries a new look to gain a little bit more respect, much to Jane’s chagrin.

When Donovan Decker lands unpredictable teen supermodel Piper Grace as the face of their new line, Jane is the one tasked to keep her under control until the photo shoot. What first seemed like an easy job quickly becomes Jane’s nightmare when Piper lives up to all of the hype. Meanwhile, Ben gets tired of Jane’s behavior and decides to lay down the law and ground her.

The Donovan Decker crew is under pressure to come up with the perfect wedding dress for socialite Charlotte Whitmore after her rejection of the original dress. With all hands on deck pulling an all nighter and Jeremy’s job on the line, tensions are high in the office. Wanting to impress Jeremy and save-the-day, India takes credit for Jane’s wedding dress design. But with the design holding special meaning to Jane, she isn’t going to let the betrayal go idly by. Can Jane prove that the design is hers, and better yet – will Donovan Decker be able to pull off the perfect wedding dress? Meanwhile, Jane sets up a night out with Billy and Nick so the two guys can get to know each other better.

Jane is looking forward to the school camping trip as a way to finally get some quality time with Nick. But now with Ben acting as chaperone, her weekend may be a little less perfect. Then, her weekend gets totally uprooted when India requests that Jane go with her to Los Angeles to help pick the new Donovan Decker store location. So instead of spending time with Nick, Jane is now stuck with India – leaving Nick in the lurch, yet again. Meanwhile, the school camping trip is anything but fun for Ben, Billy, Lulu and Nick.

The aftermath of what Billy did with his brother has legal consequences that lead him to get called before a judge... Lulu's father. Ben knows Jane's secret and Jane might stop everything.

Jane is scrambling to get a handle on both her personal and professional life. With Billy returning from juvie, Jane is nervous about how things were left and what that means now for the two best friends. But, she doesn’t have too much time to think about it because with India now gone from Donovan Decker, Gray is leaning on Jane more than ever. Jane starts to wonder if she may have a shot at the job, with a little encouragement from Jeremy, but some stiff competition might be standing in her way. Interior designer Martyn Lawrence-Bullard (from Bravo’s “Million Dollar Decorators”) stops by the Donavan Decker offices to spruce up Gray’s office. Meanwhile, Ben tries his best to keep Jane’s secret safe even though it is affecting his new relationship with Rita.

It’s bad enough that the Donovan Decker team has to win the approval of India to clinch the coveted new Harrod’s fashion line, but now they have to also dazzle movie star Aiden Redmond – the new celebrity face of the retail chain. With his Hollywood looks and charm, it is only a matter of time before the whole team is smitten. Now with access to one of Hollywood’s top leading men, will all the fame and celebrity get the best of Jane? Meanwhile, Billy is still struggling to fit back into daily life of high school and his new reputation.

It’s Jane’s big day – her birthday, but everyone seems to have forgotten – or so she thinks. Unbeknownst to her, Ben and Billy have grand plans to surprise Jane with a surprise birthday party. But their party plans start to unravel as Jane’s hurt feelings and a work situation get in the way. In the end, it isn’t a birthday party that gives Jane the surprise of her life. Meanwhile, India puts the pressure on Jeremy to get information on Gray.

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.

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 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.

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.

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.