This phrase describes a situation, one can have an "awkward ashley" moment. This situation usually involves long periods of silence after someone makes a comment or does something that creates possible tension and nervousness for all involved. Often times one can interject their own name into the phrase, i.e. "Awkward Jane", however it has been found that "Awkward Ashley" flows much easier for 92% of the population.
You tell a story and no one laughs. This is an "Awkward Ashley" moment.
You make an non-PC comment and everyone is silent. This is an "Awkward Ashley" moment.
You show up to a party uninvited but felt that it was ok because you knew most of the people there and the host doesn't acknowledge your presence. This is an "Awkward Ashley" moment.
You get the idea..