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1.
A phrase that prefaces a Facebook status update that uses the word awkward in the same way most people use the word irony (read: incorrectly). Essentially, "awkward moments" are never awkward.
Person A: That awkward moment when you realize you will die alone
Person B: That's not awkward, that's sad and soul crushing.

As you can see, Person B is well read and has a firm grasp on the definition of the word awkward and that awkward moment when, Person A on the other hand is a sad plebeian who hasn't come to such realizations.
by Lexicomane December 23, 2011
 
2.
The phrase used when someone is tryign to find a reason to post something completley stupid on facebook

The phrase can also be used to send a message to someone.
1. That awkward moment when.. your brushing you teeth and you manage to get toothpaste in your eye.
2. That awkward moment when you ex girlfriend relizes you had been cheating on her when you were going out.
by whatyoutalkingabout October 30, 2011
 
3.
An introductory phrase commonly followed by a situation that is dubbed awkward.
That awkward moment when little kids talk trash online.
by anonymously clever September 22, 2013