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Definitions by HermanMelville

undercompensating 

Being modest, cheap, or the opposite of overcompensating. Using distractions to avoid undue attention to pockets that look like they got the mumps.
Guy 1:"why do women always go for underachievers, slackers, and losers?"

Guy 2: "They must know something we don't know about guys who are undercompensating..."

Guy1: "The worlds just not fair. Why can't we have it all?"