Jane Quimby is juggling life as a high school student and as an assistant.
Meanwhile, Nick leverages his knowledge of Billy's secret relationship with Lulu to get advice on approaching Jane. When Nick asks her to the Winter Formal, Jane thinks life couldn't get any better. But when she realizes the Winter Formal is the same night as the Spring Preview Party, her two perfect nights become her worst nightmare.
Jane is feeling on top of the world when Gray gifts her with the use of a real Birkin bag to commend her for a job well done. Jane thinks she finally has this job under control when Gray gives her the task of running the private trunk show at Gray's house. But with India feeling the pains of jealousy of Gray's new "favorite" stealing the preview party spotlight, she is determined to show Gray and the company what a failure Jane can really be.
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?.
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.
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.
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.
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?.
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.
Now that Ben is onto Jane's secret, her dream job looks like it could be coming to an end quickly. But with Fashion Week finally here, Gray and the Donovan Decker team are counting on her more than ever - especially when the mole rears their ugly head again. How can Jane let everyone down and let go of her dream? But if she goes, how would she be able to explain herself to Ben? This is one fashion problem that doesn't have a quick fix.
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 stops by the Donavan Decker offices to spruce up Gray's office.
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?.
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.
