In the series premiere of "Awkward", 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.
Jenna gets her cast off, but her shirt comes with it. An unwanted photo op gives everyone a chance to voice their opinion - on the most intimate of subjects. Will anyone come to her rescue and wake her up from this nightmare?
Jenna and Matty's relationship is heating up in private, but in public she's still his secret. Will a party at Lissa's be their first PDA, or will an unexpected hot-tub visitor ruin everything?
A Homecoming bonfire gives everyone license to misbehave, and Jenna contemplates the ultimate decision: to DTR (define the relationship) with Matty or not DTR.
Jenna's big accident is a distant memory, and she actually starts to feel normal again until a strange stalker brings her suicide stigma back to life. Jenna even starts to wonder if her "that girl" reputation is preventing Matty from seeing her as girlfriend material or. does he already have one?
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.
When Lacey's BFF Ally comes to town, they decide to "help" Jenna throw a rager. The next day, a forgetful and hungover Jenna struggles to reconstruct the events of the wild night and find out who she kissed.
Jenna's sixteenth birthday isn't very sweet as she suffers one embarrassing experience after the next. Jenna is still reeling from the aftermath of her house party and dealing with the repercussions of everyone she's alienated. After failing her driving test and getting humiliated in the school cafeteria, Jenna wonders if she can repair her relationships with Matty and Tamara.
Jenna feels like she and Matty are actually on solid ground for the first time when he asks her out on their first real date. But, when Tamara reveals her suspicion that Matty wrote Jenna's care-frontation letter, Jenna starts to question everything about her romance with Matty.
As the night of winter formal approaches, someone shares the carefrontation letter with the whole student body, and Jenna must make a difficult decision.