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 24, 2011
Get the That awkward moment when mug.
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
Get the That awkward moment when.. mug.
How you start you sentence when you're about to recall an event or occurence that was funny, embarassing or awkward. Usually the moment you are recalling is something that has embarassed many.
the awkward moment when... you fart during a business conference and try to cover it up with a cough, but realise immediately and without need to confer, that everyone around you knows you just farted.

The awkward moment when... you make a black joke seconds before realising you are standing next to a black guy.

The awkward moment when... you say bye to someone then you both continue walking in the same direction.
by Bottom Face May 29, 2011
Get the the awkward moment when... mug.
A meme-y phrase that was extremely popular back around 2012 due to its versatility. Modern usage is more or less the same, but it is now commonly replaced with the newer phrase "that feeling when".
That awkward moment when you change your Facebook status to ‘single’ and your ex likes it.
by UwUltimateDoge February 29, 2020
Get the That awkward moment when mug.