look up any word, like cunt:
 
1.
A shickley would be any situation that a teenager would be put in that contains decisions that a teenger should not be making and stresses one out! Usually contains life-altering changes.
You have to chose between your best friend or a girl. You have been placed in a shickley.

"Man what am i gonna do? This in one big shickley"
by Gilligan January 26, 2005