To have chocked, to have had made it close but never having made it all the way, to have continually come up short, to have lost in an often comical way. In reference to the Chicago Cubs of the MLB. Past tense of cub.
A sugar cubbie is a clean cut, good looking male under the age of 30, who has a healthy bank account that he uses to spoil his women. Sugar cubbies are often sought out by attractive women in their 30s, often referred to as pumas, not quite old enough to be a cougar, but a cougar in training.