A guy who wears old fashion clothes, and whips around in his car. A skertboy has much class and a way with the ladies, but tends to fool around often. You'll find a skertboy smoking a cigar by the log cabin.
" man dude you were whipping around the corner, youre such a skertboy".
" slow down, stop cheefing the cigar so hard skertboy".
Means literally anything you want it to mean. Ambiguous but nonetheless, the skerpiest word of all time. Commonly also used as skerpy derpy, skerpiest, mmmm
12 step recovery jargon referring to someone new who talks about how great life is, now that they'resober. Usually meaning that the person is out of touch with reality.
The new guy seems pretty happy for a dude who has no job, no money and no family. He must be on a pink cloud.