While late to the game I fell in love with Issa Rae’s webseries, Awkward Black Girl, for its honest and hilarious interrogation of race and race relations via the lens of some very typical situations. From her humble approach to her daring showcasing of other talents (i.e. her rapping skills) I felt endeared to her struggles with dating, co-workers, and friends each episode. Watching the web show with my best friend or my aunt made the ‘Awkward Black Girl’ experience less…awkward and more…laughable and okay. However, reactions to Ms. Rae’s big win at the Shorty Award reveals that being Black is still awkward for some.