Awekwardsome 

A person, place, thing, or event that is simultaneously awesome and awkward.

- Hey Mike, I heard your ex shit her pants at the party last night. That's hilarious, in a messed up kind of way.
- Yeah, it was awekwardsome.

Awekwardsome by Adamzmin Hoobley October 15, 2009

Awkwardometer

The mental gauge one uses to sense how awkward a situation is. Like a speedometer but gauges awkwardness.

Person A: Why did Jim ask that girl out? It's obvious she thinks he's a huge tool.
Person B: Yeah that was really weird.
Person A: He has no awkwardometer.

Awkwardometer by Manderson April 1, 2008

awkwarsome 

when a situation with an awesome friend suddenly becomes hilariously awkward

The conversation I was having started out good but became totally awkwarsome

awkwarsome by Rian Dee-hawn April 26, 2010

awkwardsome 

A person, a pet, a situation, a photograph or an idea that is both awkward and awesome.

"Did you see that TV clip about a donkey parasailing at a beach in Mexico? Awkwardsome!"

overheard at a watercooler on Madison Avenue in Manhattan on March 31, 2011

awkwardsome by PRwiz101 April 21, 2011