Top Definition
n. a life that's seemingly hopeless, a neverending epic fail. Those who lead a Trail of Fail are often emo teenagers or nerdy 40-year-olds who live with their mothers.
My life is a Trail of Fail. I woke up, stubbed my toe, burned my breakfast, found out that my bike was stolen, was dumped by my girlfriend and it's not even noon yet.
by emoboi0716 December 06, 2009

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