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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
Urban Dictionary Merch
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
Related Words
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

Awful Awful Challenge 

The act of masturbating while taking a shit.
Man, I was doing the Awful Awful Challenge after I ate Taco Bell last night.
Awful Awful Challenge by AN0SEater December 21, 2020

Awfully hot Coffee pot

Something hot that you’d drop on someone.
”That’s an awfully hot coffee pot/ Should I drop it on Donald Trump? Probably not.” -Eminem BET cypher 2017.

Gawds Awful Towers 

A game on Roblox that is a spin off of JToH and is filled to the brim with irony and top-tier shitty jokes.
Person 1: Bro what are you playin on roblox?

Person 2: I'm playin Gawds Awful Towers ok

Person 1: bruh

awfultunity 

I had an awfultunity to play Tony Hawk Ride.
awfultunity by lobert124 April 25, 2010
More from Urban Dictionary
In sales terms, a whale is a prospect that is significantly larger than an organization’s average customer.

Whales are large and extremely difficult to close. Due to their immense size, they are highly sought-after.

A whale is typically identified at first by a whale hunter on the sales team, but often requires cross-discipline participation in order to close; this includes assistance from operations, engineering, creative, client success, and business development teams.
"Shit...the sales director chewed me out on the sales call this morning. He's totally pissed that I have nothing in my pipeline. I've been focused on this one whale for so long that I haven't had time to prospect for normal-sized deals."
Whale by FQ_GFY February 3, 2020
Word of the Day on September 21, 2026

Concrete cowboy 

A guy who thinks he's a country kinda guy, but in reality lives a comfortable city / suburban life.
Eugene: Look at that dude in the cowboy hat!
Todd: He's just a concrete cowboy.
Word of the Day on September 20, 2026
any hard liquor that is cheap & potent.. eg. relska, popov, potters, evan williams, kamchatka, fireball, rumpleminze, southern comfort, everclear
hey let's get a drink of that?

go ahead
*takes drink* ugh wtf is that?

everclear & bepsi
fucking hobo loko eeessshh
hobo loko by d i z k o 2 0 8 September 14, 2026
Word of the Day on September 19, 2026

God Shot 

A chance happening with profound meaning, an unexpected blessing, a "sign".
Dr. Drew on Celebrity Rehab said "All of a sudden what had been just another Hollywood proposal became for him an unexpected blessing, an opportunity for growth. In drug recovery language, that's called a "God shot."
God Shot by Imogen1564 February 25, 2011
Word of the Day on September 18, 2026
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