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.

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.