Dave McGuiness is about to propose to his longtime girlfriend, but before he does he'll embark on an epic journey across South Chicago to discover whether or not he's ready for a life of marriage.
Beth LackeKaren RossReggie NewtonAlJohn GawlikHankJody WilsonAlice McGuinessMichael FallsMarvin Renaldi Sr.Arlene CooneyMrs. Ross
Kellie MadisonAmyPeter BiagiSecurity Guard
Megan FrancesWoman at Party
Dava KrauseAggie
Phillip Edward Van LearBuddyCherise FlemingCarla