As they age, men look for increasingly younger matches. The median 31 year-old guy, for instance, sets his allowable match age range from 22 to 35---nine years younger, but only four years older, than himself. This behaviour leads to a foolish imbalance in the internet dating world: most guys send most of their messages to women hardly out of their teens, while many perfectly good looking and interesting women within their thirties and forties go unwritten. This article analyzes this phenomenon in detail.