Jane Quimby is juggling life as a high school student and as an assistant.
Jane must juggle two of the most important nights of her life at the same time.
Competition to be number one at school and at work has Jane running in circles.
Billy and Lulu come clean about their relationship, but their friends react with disapproval. Meanwhile, Jane and Jeremy must impress a top fashion editor who's visiting the office.
Jane gets to go to Paris to deliver a special book to Gray, but her task requires help from Lulu. Elsewhere, Billy's brother tries to rope Billy into doing something that's illegal.
Jane is told to uncover the next teenage fashion trend, so she does research at her school. Meanwhile, Billy makes some personal style changes, which displeases Jane.
Jane's job becomes a nightmare when she is assigned to keep tabs on an uncontrollable young model.
The Donovan Decker crew is under pressure to come up with perfection.
Jane must abandon her camping plans and instead accompany India on a business trip to Los Angeles. Meanwhile, the school camping trip goes on without her, but it does not go well for those in attendance.
Jane prepares for Fashion Week and her coworkers lean on her, but she may have to bail on them since Ben now knows about her secret. Elsewhere, Billy has to face the consequences of aiding his brother's illegal activities.
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.
Jane gets a taste of the lime-light when a major movie star considers working with Donovan Decker.
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.
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.
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.
Once in awhile people get a second chance and for the Quimby family they are getting them in spades. After a faux date with Eli for her birthday, Jane finally gets the opportunity to go on a real date, while Ben gets a second chance of a lifetime when a minor league baseball scout wants him to try out for a coveted spot. With Dakota's proposal hanging in the air, Kate must decide on if she should give marriage a second chance or will she allow her commitment issues to scare her off again. But if Kate says yes, what does that mean for Jane and Ben? Will their second chance with their mother be over with her heading back to Colorado for marital bliss?
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.