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This thesis explores different styles of creative nonfiction. I am attempt to examine on a more intimate level the human experience of awkwardness. I hope to catalogue my personal experiences of awkwardness. To accomplish this I explore the notion of awkwardness as a human experience in humorous terms that suggest serious consequences for the weight we tend to put on awkward situations. The overall arc of this collection is meant to fluctuate and retrace itself. I intentionally have multiple essays on similar subjects, such as those about romantic relationships and the dynamics of a mother-daughter relationship, because I want to highlight the complexity of those relationships and examine the so-called awkwardness on different levels.