A dating blogger who writes under the pen name Luckless, goes viral for a post about a bad date with a single sports agent. When Winnie's boss offers her, her own column, she has no choice but to keep dating him for content.

Just before he and Madelyn McKay, his BFF since college freshman year, are to head off to Milwaukee to spend Christmas with his long widowed mother Kate Spencer and his army soldier brother Aiden Spencer, hard working and talented Manhattan lawyer Hugo Spencer, facing his regular year end review, issues an ultimatum to his boss, George Vogel, for a position as partner in the new year, he looking for a job elsewhere otherwise, such forthrightness about himself unusual for Hugo. Vogel admits that...

Set in a separate storyline not related to the "Trailer Park Boys" Television show, but with the same lovable characters. The boys get arrested for robbing an ATM machine and spend 18 months in jail. When the get out, they decide to pull off "The Big Dirty" which is to steal a large amount of coins because they are untraceable and quit their life of crime forever.