Jenna Hamilton finds out that getting the boy of her dreams isn't all it's cracked up to be. When a mysterious letter leads to a misunderstanding of epic proportions, Jenna realizes that her new stigma might be her ticket to social visibility.

It's time Jenna can finally get her cast off, but an accident results in her exposing herself. With pictures now circulating around the school, Jenna must deal with everyone's mixed opinions. Jenna is hopeful Matty will rescue her from her nightmare.

Matt invites Jenna to a party, making her wonder if he's ready to make their relationship public. Meanwhile, she also starts to realize that she might have more in common with Jake.

Tamara becomes happily involved in her first sex scandal after contracting pink eye while making out in a hot tub. Also: Jenna tries to define her relationship with Matty.

Jenna gets a strange stalker, and worries that her reputation is keeping Matty from seeing her as girlfriend material.

Jenna mingles with the mean girls at an elite charity event. Later, things get even more awkward when she runs into Matty and Jake.

A mock DUI event is held at the school, and Jenna gets cast as the victim. Meanwhile, Jake and Matty vie for her attention.

Jenna throws a wild bash, with help from her mom and her mom's best friend. The next day, a hungover Jenna struggles to reconstruct the events of the night, which ended with a kiss.

Jenna turns 16, but her birthday celebration doesn't go as planned after she fails her driving test and is forced to deal with repercussions from everyone she's alienated.

Matty asks Jenna out on their first official date, but a revelation has Jenna questioning everything about their romance.

Matty and Jenna have barbecue with Jenna's parents, and they discuss the upcoming formal dance. Matty doesn't actually ask Jenna to the dance, but does ask her what color dress she will be wearing. Later, while still not asking her to the dance, he asks her if she is a limo girl or not. Jenna sees several boys going to great lengths to make a "big ask," by dressing up as apes, popping out of coffins, etc. Jake asks Jenna to the dance by giving her a mix CD, which has "Will you go to the dance with me?" printed on it. She tells him that she can't go with him because she already has a date. Matty and Jake talk about the Formal, and Jake tells Matty about being turned down by Jenna. Matty almost tells Jake about going with Jenna, but chickens out, and later asks Jenna if it would be okay if they skip the Formal (because he doesn't want to hurt Jake, but he doesn't tell Jenna that). Meanwhile, Sadie manages to steal Jenna's file, with the letter in it. Jenna is surprised to be nominated for Sophomore Princess, but then discovers that the ballot has her letter printed on the back of it. Jenna decides that she deserves more than Matty has offered, and tells him that she won't go out with him that night, to the Formal, or anywhere.

As the night of winter formal approaches, someone shares the carefrontation letter with the whole student body, and Jenna must make a difficult decision.