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It is a situation that falls in between both categories of awkwardness and awfulness creating something known as awkful.
I have to make sandwiches with my boss, it is going to be so awkful
Awkful by Fragileharp July 24, 2019
Related Words

Awkfunctional 

A big dysfunctional family that has many birth problems and many plot twists.
Wow our family is too Awkfunctional.
Awkfunctional by swagg699 June 22, 2014
Awkun for the drink, homie.
Awkun by Oun March 7, 2009
A portmanteau of awkward and awful; something that is both awkward and awful.
It's going to be awkful to discuss the sex-ridden book in Mr. Smith's English class, he is a 82 year old man you know.
Awkful by Scott Warshire September 11, 2007
an amalgam of awesome and fun
did you bring out the slip 'n slide on the weekend and fill the hose with beer? THAT WAS AWFUN.
awfun by mlp September 18, 2008
An adjective used to describe a situation that is either awfully awkward or awkwardly awful. This must be a situation in which both words are necessary, but also a situation wherein one cannot be bothered to use them both. Thus, "awkful" was born.
In a word, awkful.
awkful by PLLbiiiiiitch March 15, 2011