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Awkward Day noun An antiholiday, Awkward Day is a heinous day filled with insecurity, vulnerability, and tension, created to highlight the newness of a romantic relationship and to test the living shit out of it. If you make it through Awkward Day, your relationship has legs. Good news is that it only lasts one day, if that long. Bad news is that it’s tedious and you might not have that new boyfriend by the end of it. ↗