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.
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Also known as: S Club 7 effect
When a multitude of people mishear one after another.
Person 1: I am not a sailor.
Person 2: Ask Leila?
Person 3: Escalator?
Person 4: S Club 7?
Person 1: Wow, what a trail of fail