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 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.