When Reginald "Cool" Coolidge's ex-fiancee Charli pulls into the gas station where he works, he realizes that he still loves her after three years apart. There's just one problem: Charli is marrying another man in 36 hours.

Fueled by cheap whiskey, greed and hatred, Willie teams up once again with his angry little sidekick, Marcus, to knock off a Chicago charity on Christmas Eve.

Philippe, a French-American writer living in Manhattan, decides to take on ten relationship-challenged men to help them learn the art of seduction.