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Jane is thrilled when her middle school crush, Nick, asks her to the Winter Formal, until she realizes the event is the same evening as an important company preview party that Gray told her to plan.
Nick sees Jane's best friend Billy and It-girl Lulu kissing. Jane must juggle an evening at the winter formal and the fashion runway.
Nick hopes Jane can make it to his baseball game, but the wedding dress drama may complicate that. Jane wants to go with Nick; India insists Jane go with her for a business trip.
Jane meets Beau (Oded Fehr) and is shocked to learn Gray is still married to him.
Jane comes to the aid of a stressed-out Jeremy, who's intent on wooing a demanding fashion editor with high expectations that could help or hurt his career.Jeremy must design a wedding dress for famous socialite Charlotte Whitmore (Autumn Reeser) who's marrying a prince; well, not a prince actually.Jane has the perfect dress, but India takes credit for it, even though the design has special meaning for Jane.Jane, India, and Beau's assistant Christopher (Brandon Jones) end up at a hotel bar together, where Jane opens up about her feelings for Nick.While camping, Lulu and Nick complain about their relationships with Jane and Billy, respectively. Ben goes to Donovan Decker looking around for Jane and finds out that Jane's job isn't an internship like he thought.
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At Donovan Decker, Jane discovers a world full of fashion challenges working for Gray Chandler Murray (Andie Mac Dowell) and tackles them with the help of her co-workers, Jeremy Jones (Rowley Dennis), India Jourdain (India de Beaufort), Carter (Ser'Darius Blain) and Birdie (Brooke Lyons).