When a death occurs in Nick's family, Jess, Schmidt and Winston travel with Nick to the Windy City to help him with the funeral preparations and meet his boisterous family members, including his mom, Bonnie ; his younger brother, Jamie ; and his Boston cousin, Bobby,.

Jess decides to throw Cece a surprise bachelorette party while Nick and Winston awkwardly take her fiance's, Shivrang, out for the night. Then, as Schmidt desperately tries to find a real girlfriend in time for the wedding in order to get a "plus one," he is forced to seek out his old girlfriend from his "fat Schmidt" college days.