My mom has really long hair, until recently it was down around her ankle but cut it to her waste and donated it. But when it was long people would always say to her "Did you know you have really long hair?" I am not kiding.
I have a pair of Misfits shoes like these [link] and once, when I was wearing them, some girl thought the logo was for Slipknot or some equally dire band. I playfully poked fun at her, but I could already taste the backwash.
I think use of the words 'fail', 'win', 'lulz' etc. are generally indicative of a lack of individuality. Not because the terms are used so often, but because the context in which the terms seem to be most inserted pushes them as some sort of patronizing chastisement. They seem to be the internet equivalent of subtly putting yourself on a pedestal for saying something hardly original, or 'win', so to speak.