What makes it awkward?

The Missing Claws: A Modern Story

When the bear has no claws.  Being a bear.  When no claws are sharp.  When the bear hugs.  That day when the girl with pigtails turns into a pig to disguise herself from the bear.  When liking the pig.  That sudden impulse where the bear kills the pig even though the bear has no claws.  That year when it is the year of the pig.  When the bear has no claws.   

This is the manner in which people are writing and talking these days.  I don't understand it.  I can't tell what people are trying to convey.  If they write "That awkward moment when you trip over.", what do they mean?  Tell me about that awkward moment.  What about it?  Why is it awkward?  Do you like it?  Do you hate it?  Have you forgotten the rest of the sentence?  

Here are some options:

"That awkward moment when you trip over is funny but when you dance I want to hide."

"Do you remember that awkward moment when you trip over at the start of the video?"

"I've always wondered why you insist on eating cake during that awkward moment when you trip over."