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.

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 is still unsure about her relationship with Matty, but after she attends the winter formal with Jake, she begins to re-think all of her choices.

An unexpected text brings Jenna's love drama into the spotlight.